1,2:5,6-Di-O-iso­propyl­idene-3-C-methyl-α-d-allo­furan­ose

Forezi, L. da S.M.; Silva, M.M.P.; Santos, F. da C.; Ferreira, V.F.; Souza, M.C.B.V. de

doi:10.1107/S1600536813022447

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1512

doi:10.1107/S1600536813022447

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1,2:5,6-Di-O-isopropylidene-3-C-methyl-α-D-allofuranose

Luana da Silva Magalhães Forezi,^a Marcos Moitrel Pequeno Silva,^b Fernanda da Costa Santos,^a ^* Vitor Francisco Ferreira ^a and Maria Cecília Bastos Vieira de Souza ^a

^aDepartamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Niterói – RJ, CEP 24020-150, Brazil, and ^bDepartamento de Química Inorgânica, Instituto de Química, Universidade Federal Fluminense, Niterói – RJ, CEP 24020-150, Brazil
^*Correspondence e-mail: fernand@vm.uff.br

(Received 16 May 2013; accepted 9 August 2013; online 7 September 2013)

The title carbohydrate, C₁₃H₂₂O₆, is a derivative of D-glycose, in which the furanosidic and isopropylidene rings are in twisted conformations. The mean plane of the furanosidic ring makes a dihedral angle of 70.32 (18)° with the mean plane of the fused isopropylidene ring. The methyl groups in the other isopropylidene ring are disordered over two sets of sites, with an occupancy ratio of 0.74 (6):0.26 (6). In the crystal, molecules are linked by O—H⋯O hydrogen bonds into chains with graph-set notation C(5) along [100]. Weak C—H⋯O interactions also occur.

Related literature

For background information on this class of compound, see: Bio et al. (2004 ); Canuto et al. (2007 ); Mane et al. (2008 ); Yoneda et al. (2011 ). For details of ring-puckering calculations, see: Cremer & Pople (1975 ). Graph-set notation for the description of hydrogen-bonding motifs is given by Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₂₂O₆
M_r = 274.3
Triclinic, P 1
a = 5.503 (4) Å
b = 8.113 (1) Å
c = 9.122 (2) Å
α = 99.65 (2)°
β = 103.69 (3)°
γ = 98.86 (2)°
V = 382.0 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.14 × 0.11 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
9589 measured reflections
2758 independent reflections
2107 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.130
S = 1.04
2758 reflections
181 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack x calculated using 872 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons & Flack, 2004 ). There is insufficient information present to define handedness

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4ⁱ	0.82	2.28	3.022 (4)	152
C1—H1⋯O2ⁱⁱ	0.98	2.58	3.218 (5)	123
C2—H2⋯O6ⁱⁱⁱ	0.98	2.54	3.504 (5)	167
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) x, y, z+1.

Data collection: COLLECT (Nonius, 2004 ); cell refinement: DIRAX/LSQ (Duisenberg, 1992 ); data reduction: EVALCCD (Duisenberg et al., 2003 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813022447/pk2484sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813022447/pk2484Isup2.hkl

checkCIF report

Comment top

The structural modification of carbohydrates has been extensively explored for improvement of their pharmacology properties (Bio et al., 2004; Canuto et al. (2007); Mane et al. 2008; Yoneda et al. 2011). As ongoing research in developing potentially new drugs, we report here the structure of 1,2:5,6-Di-O-isopropylidene-3-C-methyl-α-D-allofuranose.

In the title molecule (Fig. 1), the torsion angle formed by atoms O4, C1, C2, O2 is 101.6 (3)° and that formed by O1, C1, C2, C3, is -130.8 (3)°.

The structure exhibits disorder in a isopropylidene group (atoms C71A, C72A, C71B and C72B) over two positions. Rings A (O1,C1,C2,O2,C8) and B (C1,C2,C3,C4,O4) adopt a twisted conformation, with ring-puckering parameters q2 = 0.223 (5) Å, ϕ2 = 277 (1)°; q2 = 0.376 (5) Å, ϕ2 = 89.8 (6)°, respectively. Ring C (O5,C5,C6,O6,C7) also shows a twist conformation, with ring-puckering parameters q2 = 0.404 (3) Å, ϕ2 = 196.021 (1)° (Cremer & Pople, 1975).

In the crystal packing, molecules are linked by O—H···O hydrogen bonds into chains with graph-set notation C(5) along [100] (Bernstein et al., 1995). There are also short C—H···O interactions that form a C(7) chain motif along [001] direction (Fig. 2).

Related literature top

For background information on this class of compound, see: Bio et al. (2004); Canuto et al. (2007); Mane et al. (2008); Yoneda et al. (2011). For details of ring-puckering calculations, see: Cremer & Pople (1975). Graph-set notation for the description of hydrogen-bonding motifs is given by Bernstein et al. (1995).

Experimental top

The reaction for obtaining the title compound was taken under nitrogen in a tritubulate vessel. To it, 2.64 ml (3.95 mmol) of methyl magnesium bromide 3 M diluted in THF (7.9 mmol, 2 eq) was added. Then, under vigorous stirring and in a ice bath, 3.96 mmol (1.02 g) diluted in dry THF was poured into the solution. The reaction took place for 5 h in room temperature. After finishing the reaction, it was slowly added dropwise 10 ml of distilled water and 1 g of Celite, filtering the resultant product in a Celite layer. The THF solvent was removed by heat. The aqueous phase was extracted with CH₂Cl₂ (3 × 30 ml) and the product washed with distilled water (3 × 20 ml), dried with MgSO₄ anhydrous and the solvent eliminated on a vacuum rotator evaporator apparatus. The solid was recrystallized in hexane and the yellow solid product was obtained with 72% yield. (m.p. = 104–105°C) (Bio et al., 2004).

Computing details top

Data collection: COLLECT (Nonius, 2004); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. Ellipsoid plot representation of the molecular structure of compound I with displacement ellipsoids drawn at the 30% probability level. Atoms C71A/B and C72A/B are disordered with fractional occupancies of 0.74 (6):0.26 (6) for the A and B components, respectively.
	Fig. 2. A packing diagram of (I), viewed approximately down the b axis. Hydrogen-bonds are shown by dashed lines.

1,2:5,6-Di-O-isopropylidene-3-C-methyl-α-D-allofuranose top

Crystal data top

C₁₃H₂₂O₆	Z = 1
M_r = 274.3	F(000) = 148
Triclinic, P1	D_x = 1.192 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.503 (4) Å	Cell parameters from 3284 reflections
b = 8.113 (1) Å	θ = 3.1–27.5°
c = 9.122 (2) Å	µ = 0.09 mm⁻¹
α = 99.65 (2)°	T = 293 K
β = 103.69 (3)°	Prism, colourless
γ = 98.86 (2)°	0.14 × 0.11 × 0.08 mm
V = 382.0 (3) Å³

Data collection top

Nonius KappaCCD diffractometer	2107 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	R_int = 0.043
Graphite monochromator	θ_max = 25.7°, θ_min = 3.1°
Detector resolution: 9 pixels mm^-1	h = −6→6
CCD rotation images, thick slices scans	k = −9→9
9589 measured reflections	l = −11→11
2758 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0729P)² + 0.0707P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.046	(Δ/σ)_max < 0.001
wR(F²) = 0.130	Δρ_max = 0.21 e Å⁻³
S = 1.04	Δρ_min = −0.24 e Å⁻³
2758 reflections	Extinction correction: SHELXL2013 (Sheldrick, 2013)
181 parameters	Extinction coefficient: 0.20 (3)
8 restraints	Absolute structure: Flack x calculated using 872 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004). There is insufficient information present to define handedness.
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: −0.2 (5)

Crystal data top

C₁₃H₂₂O₆	γ = 98.86 (2)°
M_r = 274.3	V = 382.0 (3) Å³
Triclinic, P1	Z = 1
a = 5.503 (4) Å	Mo Kα radiation
b = 8.113 (1) Å	µ = 0.09 mm⁻¹
c = 9.122 (2) Å	T = 293 K
α = 99.65 (2)°	0.14 × 0.11 × 0.08 mm
β = 103.69 (3)°

Data collection top

Nonius KappaCCD diffractometer	2107 reflections with I > 2σ(I)
9589 measured reflections	R_int = 0.043
2758 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.130	Δρ_max = 0.21 e Å⁻³
S = 1.04	Δρ_min = −0.24 e Å⁻³
2758 reflections	Absolute structure: Flack x calculated using 872 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004). There is insufficient information present to define handedness.
181 parameters	Absolute structure parameter: −0.2 (5)
8 restraints

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)
O1	0.2339 (6)	−0.0979 (4)	0.6028 (5)	0.0646 (10)
O2	−0.0659 (5)	0.0519 (3)	0.6425 (3)	0.0456 (8)
O3	−0.0994 (5)	0.3540 (4)	0.5720 (3)	0.0434 (7)
H3	−0.2119	0.2677	0.5383	0.065*
O4	0.3788 (5)	0.1260 (4)	0.4944 (3)	0.0446 (7)
O5	0.0585 (6)	0.3883 (5)	0.2656 (4)	0.0633 (10)
O6	0.2663 (8)	0.3148 (8)	0.0861 (5)	0.1016 (17)
C1	0.3517 (7)	0.0751 (5)	0.6312 (5)	0.0394 (9)
H1	0.5169	0.0992	0.7088	0.047*
C2	0.1689 (7)	0.1724 (5)	0.6883 (4)	0.0357 (9)
H2	0.2256	0.2197	0.7997	0.054*
C3	0.1409 (6)	0.3087 (5)	0.5930 (4)	0.0327 (9)
C4	0.1819 (7)	0.2156 (5)	0.4429 (5)	0.0397 (9)
H4	0.0255	0.1324	0.3853	0.048*
C5	0.2672 (8)	0.3188 (6)	0.3367 (5)	0.0486 (11)
H5	0.4124	0.411	0.3948	0.058*
C6	0.3295 (12)	0.2203 (10)	0.2017 (6)	0.0787 (18)
H6A	0.5092	0.2151	0.2255	0.094*
H6B	0.2282	0.1051	0.1701	0.094*
C7	0.0949 (10)	0.4150 (9)	0.1214 (6)	0.0727 (17)
C71A	0.222 (7)	0.598 (3)	0.144 (3)	0.149 (7)	0.74 (6)
H71A	0.0946	0.6662	0.1244	0.223*	0.74 (6)
H71C	0.3259	0.6077	0.0732	0.223*	0.74 (6)
H71B	0.3279	0.6382	0.2478	0.223*	0.74 (6)
C72A	−0.147 (3)	0.345 (4)	−0.0032 (17)	0.116 (6)	0.74 (6)
H72A	−0.1074	0.3085	−0.099	0.174*	0.74 (6)
H72B	−0.2456	0.4326	−0.0132	0.174*	0.74 (6)
H72C	−0.2427	0.2503	0.0222	0.174*	0.74 (6)
C71B	0.204 (18)	0.595 (8)	0.107 (11)	0.149 (7)	0.26 (6)
H71D	0.1085	0.6732	0.145	0.223*	0.26 (6)
H71E	0.1935	0.5954	0.0005	0.223*	0.26 (6)
H71F	0.3798	0.6279	0.1663	0.223*	0.26 (6)
C72B	−0.180 (6)	0.404 (11)	0.027 (6)	0.116 (6)	0.26 (6)
H72D	−0.1971	0.3568	−0.0794	0.174*	0.26 (6)
H72E	−0.2186	0.5155	0.0375	0.174*	0.26 (6)
H72F	−0.2952	0.3311	0.0647	0.174*	0.26 (6)
C8	−0.0148 (8)	−0.1149 (6)	0.6267 (6)	0.0517 (12)
C81	−0.2032 (11)	−0.2263 (8)	0.4845 (8)	0.0820 (17)
H81A	−0.1132	−0.2828	0.4198	0.123*
H81B	−0.3017	−0.1573	0.429	0.123*
H81C	−0.3152	−0.31	0.5137	0.123*
C82	−0.0177 (13)	−0.1798 (8)	0.7692 (8)	0.0823 (18)
H82A	0.1478	−0.2012	0.8139	0.123*
H82C	−0.1428	−0.2839	0.7441	0.123*
H82B	−0.0598	−0.0963	0.8418	0.123*
C9	0.3413 (8)	0.4681 (5)	0.6694 (5)	0.0454 (10)
H9C	0.3209	0.5524	0.6076	0.068*
H9B	0.5079	0.4417	0.6796	0.068*
H9A	0.3227	0.5117	0.7699	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0496 (18)	0.0411 (18)	0.120 (3)	0.0181 (14)	0.0450 (19)	0.0236 (18)
O2	0.0326 (14)	0.0361 (15)	0.079 (2)	0.0128 (12)	0.0242 (13)	0.0242 (14)
O3	0.0304 (14)	0.0420 (16)	0.0656 (19)	0.0149 (12)	0.0176 (13)	0.0193 (14)
O4	0.0368 (14)	0.0536 (17)	0.0531 (17)	0.0194 (13)	0.0218 (12)	0.0149 (14)
O5	0.066 (2)	0.102 (3)	0.0433 (17)	0.0418 (19)	0.0250 (15)	0.0373 (17)
O6	0.079 (3)	0.203 (5)	0.059 (2)	0.070 (3)	0.039 (2)	0.056 (3)
C1	0.031 (2)	0.043 (2)	0.052 (2)	0.0133 (17)	0.0156 (17)	0.0175 (19)
C2	0.0308 (19)	0.041 (2)	0.040 (2)	0.0105 (16)	0.0139 (16)	0.0117 (17)
C3	0.0270 (18)	0.037 (2)	0.038 (2)	0.0114 (16)	0.0119 (15)	0.0107 (17)
C4	0.0302 (19)	0.048 (2)	0.041 (2)	0.0087 (17)	0.0079 (16)	0.0101 (18)
C5	0.039 (2)	0.070 (3)	0.042 (2)	0.014 (2)	0.0138 (19)	0.021 (2)
C6	0.078 (4)	0.122 (5)	0.061 (3)	0.045 (4)	0.038 (3)	0.037 (3)
C7	0.055 (3)	0.132 (5)	0.045 (3)	0.030 (3)	0.019 (2)	0.037 (3)
C71A	0.239 (13)	0.140 (8)	0.076 (15)	0.001 (8)	0.059 (11)	0.059 (8)
C72A	0.057 (5)	0.26 (2)	0.048 (6)	0.069 (7)	0.023 (4)	0.033 (8)
C71B	0.239 (13)	0.140 (8)	0.076 (15)	0.001 (8)	0.059 (11)	0.059 (8)
C72B	0.057 (5)	0.26 (2)	0.048 (6)	0.069 (7)	0.023 (4)	0.033 (8)
C8	0.043 (2)	0.041 (2)	0.083 (3)	0.017 (2)	0.031 (2)	0.021 (2)
C81	0.066 (4)	0.056 (3)	0.115 (5)	0.002 (3)	0.025 (3)	0.005 (3)
C82	0.097 (4)	0.073 (4)	0.112 (5)	0.041 (3)	0.055 (4)	0.056 (4)
C9	0.043 (2)	0.038 (2)	0.056 (2)	0.0101 (18)	0.0146 (18)	0.0080 (18)

Geometric parameters (Å, º) top

O1—C1	1.405 (5)	C7—C71B	1.53 (3)
O1—C8	1.426 (5)	C7—C72B	1.53 (2)
O2—C8	1.415 (5)	C71A—H71A	0.96
O2—C2	1.421 (5)	C71A—H71C	0.96
O3—C3	1.405 (4)	C71A—H71B	0.96
O3—H3	0.82	C72A—H72A	0.96
O4—C1	1.412 (5)	C72A—H72B	0.96
O4—C4	1.428 (5)	C72A—H72C	0.96
O5—C7	1.422 (6)	C71B—H71D	0.96
O5—C5	1.423 (5)	C71B—H71E	0.96
O6—C7	1.395 (8)	C71B—H71F	0.96
O6—C6	1.415 (8)	C72B—H72D	0.96
C1—C2	1.504 (5)	C72B—H72E	0.96
C1—H1	0.98	C72B—H72F	0.96
C2—C3	1.521 (5)	C8—C82	1.485 (8)
C2—H2	0.98	C8—C81	1.503 (8)
C3—C9	1.506 (6)	C81—H81A	0.96
C3—C4	1.532 (6)	C81—H81B	0.96
C4—C5	1.493 (5)	C81—H81C	0.96
C4—H4	0.98	C82—H82A	0.96
C5—C6	1.492 (7)	C82—H82C	0.96
C5—H5	0.98	C82—H82B	0.96
C6—H6A	0.97	C9—H9C	0.96
C6—H6B	0.97	C9—H9B	0.96
C7—C72A	1.489 (12)	C9—H9A	0.96
C7—C71A	1.502 (16)

C1—O1—C8	110.7 (3)	O5—C7—C72B	102 (2)
C8—O2—C2	109.1 (3)	C71B—C7—C72B	97 (2)
C3—O3—H3	109.5	C7—C71A—H71A	109.5
C1—O4—C4	109.0 (3)	C7—C71A—H71C	109.5
C7—O5—C5	106.9 (4)	H71A—C71A—H71C	109.5
C7—O6—C6	109.5 (4)	C7—C71A—H71B	109.5
O1—C1—O4	111.8 (4)	H71A—C71A—H71B	109.5
O1—C1—C2	105.2 (3)	H71C—C71A—H71B	109.5
O4—C1—C2	106.8 (3)	C7—C72A—H72A	109.5
O1—C1—H1	110.9	C7—C72A—H72B	109.5
O4—C1—H1	110.9	H72A—C72A—H72B	109.5
C2—C1—H1	110.9	C7—C72A—H72C	109.5
O2—C2—C1	104.0 (3)	H72A—C72A—H72C	109.5
O2—C2—C3	108.0 (3)	H72B—C72A—H72C	109.5
C1—C2—C3	105.1 (3)	C7—C71B—H71D	109.5
O2—C2—H2	113	C7—C71B—H71E	109.5
C1—C2—H2	113	H71D—C71B—H71E	109.5
C3—C2—H2	113	C7—C71B—H71F	109.5
O3—C3—C9	107.8 (3)	H71D—C71B—H71F	109.5
O3—C3—C2	112.6 (3)	H71E—C71B—H71F	109.5
C9—C3—C2	110.7 (3)	C7—C72B—H72D	109.5
O3—C3—C4	112.9 (3)	C7—C72B—H72E	109.5
C9—C3—C4	112.8 (3)	H72D—C72B—H72E	109.5
C2—C3—C4	100.0 (3)	C7—C72B—H72F	109.5
O4—C4—C5	107.2 (3)	H72D—C72B—H72F	109.5
O4—C4—C3	103.8 (3)	H72E—C72B—H72F	109.5
C5—C4—C3	118.7 (3)	O2—C8—O1	105.1 (3)
O4—C4—H4	108.9	O2—C8—C82	110.5 (4)
C5—C4—H4	108.9	O1—C8—C82	110.4 (4)
C3—C4—H4	108.9	O2—C8—C81	108.5 (4)
O5—C5—C6	102.8 (4)	O1—C8—C81	108.6 (4)
O5—C5—C4	108.1 (3)	C82—C8—C81	113.3 (5)
C6—C5—C4	115.4 (4)	C8—C81—H81A	109.5
O5—C5—H5	110.1	C8—C81—H81B	109.5
C6—C5—H5	110.1	H81A—C81—H81B	109.5
C4—C5—H5	110.1	C8—C81—H81C	109.5
O6—C6—C5	103.3 (5)	H81A—C81—H81C	109.5
O6—C6—H6A	111.1	H81B—C81—H81C	109.5
C5—C6—H6A	111.1	C8—C82—H82A	109.5
O6—C6—H6B	111.1	C8—C82—H82C	109.5
C5—C6—H6B	111.1	H82A—C82—H82C	109.5
H6A—C6—H6B	109.1	C8—C82—H82B	109.5
O6—C7—O5	106.7 (4)	H82A—C82—H82B	109.5
O6—C7—C72A	105.2 (14)	H82C—C82—H82B	109.5
O5—C7—C72A	110.0 (8)	C3—C9—H9C	109.5
O6—C7—C71A	107.4 (16)	C3—C9—H9B	109.5
O5—C7—C71A	107.9 (12)	H9C—C9—H9B	109.5
C72A—C7—C71A	118.9 (19)	C3—C9—H9A	109.5
O6—C7—C71B	106 (5)	H9C—C9—H9A	109.5
O5—C7—C71B	119 (4)	H9B—C9—H9A	109.5
O6—C7—C72B	127 (3)

C8—O1—C1—O4	−111.3 (4)	C7—O5—C5—C4	−153.6 (4)
C8—O1—C1—C2	4.3 (5)	O4—C4—C5—O5	171.2 (4)
C4—O4—C1—O1	100.8 (3)	C3—C4—C5—O5	−71.9 (4)
C4—O4—C1—C2	−13.8 (4)	O4—C4—C5—C6	56.8 (5)
C8—O2—C2—C1	24.8 (4)	C3—C4—C5—C6	173.7 (4)
C8—O2—C2—C3	136.1 (3)	C7—O6—C6—C5	−21.4 (7)
O1—C1—C2—O2	−17.4 (4)	O5—C5—C6—O6	31.7 (6)
O4—C1—C2—O2	101.6 (3)	C4—C5—C6—O6	149.1 (4)
O1—C1—C2—C3	−130.8 (3)	C6—O6—C7—O5	2.5 (7)
O4—C1—C2—C3	−11.8 (4)	C6—O6—C7—C72A	−114.4 (10)
O2—C2—C3—O3	39.9 (4)	C6—O6—C7—C71A	118.0 (13)
C1—C2—C3—O3	150.4 (3)	C6—O6—C7—C71B	130 (3)
O2—C2—C3—C9	160.6 (3)	C6—O6—C7—C72B	−117 (3)
C1—C2—C3—C9	−88.8 (4)	C5—O5—C7—O6	18.7 (6)
O2—C2—C3—C4	−80.2 (3)	C5—O5—C7—C72A	132.4 (15)
C1—C2—C3—C4	30.3 (4)	C5—O5—C7—C71A	−96.4 (17)
C1—O4—C4—C5	160.1 (3)	C5—O5—C7—C71B	−101 (5)
C1—O4—C4—C3	33.7 (4)	C5—O5—C7—C72B	154 (3)
O3—C3—C4—O4	−158.5 (3)	C2—O2—C8—O1	−22.4 (5)
C9—C3—C4—O4	78.9 (4)	C2—O2—C8—C82	96.6 (5)
C2—C3—C4—O4	−38.6 (3)	C2—O2—C8—C81	−138.5 (4)
O3—C3—C4—C5	82.7 (4)	C1—O1—C8—O2	10.6 (5)
C9—C3—C4—C5	−39.8 (4)	C1—O1—C8—C82	−108.5 (5)
C2—C3—C4—C5	−157.4 (3)	C1—O1—C8—C81	126.6 (4)
C7—O5—C5—C6	−31.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	2.28	3.022 (4)	152
C1—H1···O2ⁱⁱ	0.98	2.58	3.218 (5)	123
C2—H2···O6ⁱⁱⁱ	0.98	2.54	3.504 (5)	167

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	2.28	3.022 (4)	151.6
C1—H1···O2ⁱⁱ	0.98	2.58	3.218 (5)	123.1
C2—H2···O6ⁱⁱⁱ	0.98	2.54	3.504 (5)	166.8

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

Acknowledgements

This work was supported by the Brazilian agencies FAPERJ, CAPES and CNPq, and by the X-ray diffraction laboratory LDRX-UFF for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 35, 1555–1573. CrossRef Web of Science Google Scholar
Bio, M. M., Xu, F., Waters, M., Williams, J. M., Savary, K. A., Cowden, C. J., Yang, C., Buck, E., Song, Z. J., Tschaen, D., Volante, R. P., Reamer, R. A. & Grabowski, E. J. J. (2004). J. Org. Chem. 69, 6257–6266. Web of Science CrossRef PubMed CAS Google Scholar
Canuto, C. V. B. S., Gomes, C. R. B., Marques, I. P., Faro, L. V., Santos, F. C., Frugulhetti, I. C. P. P., Souza, T. M. L., Cunha, A. C., Romeiro, G. A., Ferreira, V. F. & Souza, M. C. B. V. (2007). Lett. Drug. Des. Discov. 4, 404–409. CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92–96. CrossRef CAS Web of Science IUCr Journals Google Scholar
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220–229. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mane, R. S., Kumar, K. S. A. & Dhavale, D. D. (2008). J. Org. Chem. 73, 3284–3287. Web of Science CrossRef PubMed CAS Google Scholar
Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2013). SHELXL2013. University of Göttingen, Germany. Google Scholar
Yoneda, J. D., Velloso, M. H. R., Leal, K. Z., Azeredo, R. B. V., Sugiura, M., Albuquerque, M. G., Santos, F. C., Souza, M. C. B. V., Cunha, A. C., Seidl, P. R., Alencastro, R. B. & Ferreira, V. F. (2011). J. Mol. Struct. 985, 1–4. Web of Science CrossRef CAS Google Scholar