Crystal structure of 5-O-benzoyl-2,3-O-iso­propyl­idene-d-ribono-1,4-lactone

Bortoluzzi, A.J.; Silveira, G.P.; Sá, M.M.

doi:10.1107/S2056989017002043

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 73| Part 3| March 2017| Pages 407-409

https://doi.org/10.1107/S2056989017002043

Open

access

Crystal structure of 5-O-benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

Adailton J. Bortoluzzi,^a ^* Gustavo P. Silveira ^b and Marcus M. Sá ^a

^aDepto. de Química - Universidade Federal de Santa Catarina, 88040-900 – Florianópolis, Santa Catarina, Brazil, and ^bDepartamento de Química Orgânica - Instituto de Química, Universidade Federal do Rio Grande do Sul, 91501-970 – Porto Alegre, Rio Grande do Sul, Brazil
^*Correspondence e-mail: adailton.bortoluzzi@ufsc.br

Edited by G. Smith, Queensland University of Technology, Australia (Received 7 December 2016; accepted 8 February 2017; online 17 February 2017)

In the title compound, C₁₅H₁₆O₆, obtained from the acylation reaction between 2,3-O-isopropylidene-D-ribono-1,4-lactone and benzoyl chloride, the known absolute configuration for the lactone moiety of the ester substituent has been confirmed. The five-membered rings of the bicyclic lactone–dioxolane moiety both show envelope conformations and form a dihedral angle of 19.82 (7)° between the lactone ring and the benzene ring. In the crystal, molecules of the acylated sugar are linked by very weak intermolecular C—H⋯O interactions, forming a three-dimensional network.

Keywords: crystal structure; absolute configuration; D-ribono-1,4-lactone; fused five-membered ring system.

CCDC reference: 1531628

1. Chemical context

Aldonolactones are modified sugars with the anomeric center in its higher oxidation state. They have been widely employed as versatile chiral pools for the synthesis of biologically important molecules due to their abundance from sustainable resources as well as their low cost (Corma et al., 2007 ; Han et al., 1993 ; Silveira et al., 2015 ). However, the chemical complexity associated with most carbohydrates, which is mainly due to the subtle differences in the reactivity of similar hydroxyl groups and the simultaneous existence of tautomeric species in equilibrium, may lead to unexpected transformations such as rearrangements and functional group migrations (Baggett et al., 1985 ; Sá et al., 2008 ). Therefore, the synthesis of new carbohydrate-based molecules often relies on single crystal X-ray analysis for correct structural and conformational assignments (Booth et al., 2009 ; Czugler & Pintér, 2011 ; Sales & Silveira, 2015 ). In a continuation of our research on the chemistry of carbohydrates (Bortoluzzi et al., 2011 ; Cardoso et al., 2015 ; Sá et al., 2002 , 2008; Sebrão et al., 2011 ), we describe herein the crystal structure of 5-O-benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone, C₁₅H₁₆O₆, (I).

2. Structural commentary

Compound (I) (Fig. 1) has three chiral centers with the absolute configuration determined as C2(R),C3(S),C4(R) [Flack factor 0.05 (3) for 1078 quotients (Parsons et al., 2013 )], which is consistent with the known configuration for the lactone ring (Sá et al., 2008; Sales & Silveira, 2015). Both five-membered rings of the bicyclic lactone-dioxolane moiety show envelope conformations. However, the dioxolane ring adopts a more regular envelope conformation, comparing the puckering parameters for O3 [Q(2) = 0.3141 (15) Å, φ(2) = 284.5 (3)°] with those for C3 [Q(2) = 0.2261 (17) Å, φ(2) = 121.9 (4)°], but this ring is slightly twisted about the C1—C2 bond. This is indicated by the comparative torsion angles C13—O2—C2—C3 for the dioxolane ring and C4—O4—C1—C2 of the lactone ring of 1.55 (18) and 6.87 (16)°, respectively. The dihedral angle between the mean plane of the benzene ring and that of the ester group (O6/C6/O5/C5) is 16.59 (9)°. All bond lengths and angles observed for (I) are within the expected range for organic compounds (Bruno et al., 2004 ).

Figure 1
The molecular structure of (I)

, with the atom-labeling scheme. Displacement ellipsoids are shown at the 40% probability level.

3. Supramolecular features

The molecules of (I) are stacked along the crystallographic a axis. Several weak C—H⋯O interactions (Table 1, Fig. 2) are observed in the crystal, forming an intricate three-dimensional network.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	1.00	2.52	3.2381 (19)	128
C8—H8⋯O3ⁱⁱ	0.95	2.65	3.4951 (19)	148
C12—H12⋯O4ⁱⁱⁱ	0.95	2.66	3.4682 (19)	143
C15—H15A⋯O6^iv	0.98	2.59	3.551 (2)	166
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ .

Figure 2
Weak C—H⋯O contacts around the independent molecule.

4. Database survey

A search in the current version of the Cambridge Structural Database (Version 5.37, November 2016; Groom et al., 2016 ) for structures containing a bicyclic lactone-dioxolane moiety revealed only seven entries (refcodes: JOBJOZ, OCAVOE, VAXCAA, VENBAS, YISHAJ, YISHAK01 and YISHOX), which are related to articles published from 1991 to 2012.

5. Synthesis and crystallization

5-O-Benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone (I) was prepared in quantitative yield through the acylation of 2,3-O-isopropylidene-D-ribono-1,4-lactone (II) with benzoyl chloride in pyridine followed by aqueous work-up and purification according to the reported method (Sá et al., 2002). The two-step preparation of (I) is shown in the reaction scheme (Fig. 3). Slow crystallization from ethanol solution furnished single crystals (m.p. 371–372 K), allowing structural elucidation by X-ray crystallographic techniques. The absolute configuration for (I) was established by refinement of the Flack parameter and is in complete agreement with previous assignments made on the basis of hydrogen- and carbon-NMR shifts for the starting D-ribono-1,4-lactones (II) and (III), and on the homogeneity of the reaction product.

Figure 3
Reaction scheme for the synthesis of compound (I)

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in idealized positions and allowed to ride with C—H distances of 0.95 Å (CH_Ar), 1.00 Å (CH), 0.99 Å (CH₂) or 0.98 Å (CH₃) with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C_methyl).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₆O₆
M_r	292.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	200
a, b, c (Å)	5.7574 (1), 12.5703 (3), 20.1888 (4)
V (Å³)	1461.11 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.87
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.682, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	12424, 2655, 2635
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.068, 1.02
No. of reflections	2655
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.10
Absolute structure	Flack x determined using 1078 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013)
Absolute structure parameter	0.05 (3)
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008 ), SHELXL2012 (Sheldrick, 2015 ), PLATON (Spek, 2009 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1531628

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2056989017002043/zs2372sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017002043/zs2372Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989017002043/zs2372Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S2056989017002043/zs2372Isup4.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

5-O-Benzoyl-2,3-O-isopropylidene-D-ribono-1,4-lactone top

Crystal data top

C₁₅H₁₆O₆	D_x = 1.329 Mg m⁻³
M_r = 292.28	Melting point = 371–372 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
a = 5.7574 (1) Å	Cell parameters from 9982 reflections
b = 12.5703 (3) Å	θ = 4.1–68.1°
c = 20.1888 (4) Å	µ = 0.87 mm⁻¹
V = 1461.11 (5) Å³	T = 200 K
Z = 4	Irregular block, colourless
F(000) = 616	0.20 × 0.18 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	2635 reflections with I > 2σ(I)
Radiation source: Cu IµS microfocus X-ray source	R_int = 0.024
φ and ω scans	θ_max = 68.1°, θ_min = 4.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→6
T_min = 0.682, T_max = 0.753	k = −14→14
12424 measured reflections	l = −24→24
2655 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.044P)² + 0.1285P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.024	(Δ/σ)_max < 0.001
wR(F²) = 0.068	Δρ_max = 0.13 e Å⁻³
S = 1.02	Δρ_min = −0.10 e Å⁻³
2655 reflections	Extinction correction: SHELXL2012 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
193 parameters	Extinction coefficient: 0.0059 (7)
0 restraints	Absolute structure: Flack x determined using 1078 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.05 (3)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O5	0.67330 (19)	0.01217 (8)	0.65402 (5)	0.0398 (3)
O3	0.72276 (19)	0.09129 (8)	0.85566 (5)	0.0350 (3)
O4	1.0094 (2)	0.11588 (10)	0.73280 (5)	0.0461 (3)
O1	0.9394 (4)	0.28572 (11)	0.70948 (7)	0.0756 (5)
O2	0.5870 (3)	0.24630 (9)	0.81330 (6)	0.0514 (3)
O6	0.8024 (2)	−0.07705 (9)	0.56539 (6)	0.0476 (3)
C10	0.1551 (3)	0.15260 (14)	0.47990 (11)	0.0540 (4)
H10	0.0393	0.1887	0.4550	0.065*
C9	0.3372 (4)	0.10297 (15)	0.44780 (9)	0.0537 (5)
H9	0.3466	0.1057	0.4009	0.064*
C8	0.5059 (3)	0.04941 (12)	0.48336 (8)	0.0433 (4)
H8	0.6298	0.0146	0.4611	0.052*
C7	0.4921 (3)	0.04704 (11)	0.55213 (7)	0.0344 (3)
C6	0.6721 (3)	−0.01296 (11)	0.58914 (7)	0.0338 (3)
C5	0.8325 (3)	−0.04652 (12)	0.69549 (8)	0.0408 (4)
H5A	0.9779	−0.0620	0.6712	0.049*
H5B	0.7620	−0.1147	0.7096	0.049*
C4	0.8814 (3)	0.02301 (12)	0.75469 (7)	0.0359 (3)
H4	0.9769	−0.0175	0.7875	0.043*
C3	0.6671 (3)	0.06717 (11)	0.78883 (7)	0.0325 (3)
H3	0.5274	0.0205	0.7842	0.039*
C13	0.5968 (3)	0.18470 (12)	0.87332 (7)	0.0321 (3)
C14	0.3543 (3)	0.15824 (18)	0.89603 (12)	0.0622 (6)
H14A	0.2719	0.1206	0.8606	0.093*
H14C	0.2713	0.2241	0.9068	0.093*
H14B	0.3621	0.1129	0.9355	0.093*
C1	0.8711 (4)	0.20229 (13)	0.73049 (7)	0.0451 (4)
C2	0.6335 (3)	0.17742 (12)	0.75949 (7)	0.0384 (4)
H2	0.5079	0.1791	0.7253	0.046*
C11	0.1417 (3)	0.14971 (15)	0.54823 (10)	0.0509 (4)
H11	0.0162	0.1837	0.5703	0.061*
C12	0.3101 (3)	0.09759 (13)	0.58439 (8)	0.0405 (3)
H12	0.3016	0.0963	0.6314	0.049*
C15	0.7316 (3)	0.24526 (13)	0.92440 (8)	0.0419 (4)
H15A	0.7527	0.2008	0.9638	0.063*
H15B	0.6464	0.3099	0.9365	0.063*
H15C	0.8837	0.2647	0.9063	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0462 (6)	0.0393 (5)	0.0339 (5)	0.0110 (5)	−0.0058 (4)	−0.0088 (4)
O3	0.0450 (5)	0.0325 (5)	0.0275 (5)	0.0074 (4)	0.0000 (4)	0.0018 (4)
O4	0.0451 (6)	0.0534 (7)	0.0399 (6)	−0.0117 (5)	0.0069 (5)	−0.0091 (5)
O1	0.1282 (15)	0.0489 (7)	0.0498 (7)	−0.0368 (9)	0.0041 (9)	0.0046 (6)
O2	0.0832 (9)	0.0372 (6)	0.0340 (5)	0.0233 (6)	−0.0032 (6)	−0.0011 (5)
O6	0.0554 (7)	0.0464 (6)	0.0410 (6)	0.0153 (5)	−0.0015 (5)	−0.0115 (5)
C10	0.0549 (10)	0.0435 (9)	0.0636 (11)	0.0005 (8)	−0.0154 (9)	0.0109 (8)
C9	0.0779 (13)	0.0430 (9)	0.0402 (8)	−0.0036 (9)	−0.0121 (9)	0.0041 (7)
C8	0.0576 (10)	0.0350 (8)	0.0374 (8)	0.0003 (7)	0.0002 (7)	−0.0051 (6)
C7	0.0386 (8)	0.0280 (7)	0.0365 (7)	−0.0043 (6)	−0.0002 (6)	−0.0029 (5)
C6	0.0385 (7)	0.0286 (7)	0.0343 (7)	−0.0032 (6)	0.0010 (6)	−0.0061 (5)
C5	0.0468 (9)	0.0370 (7)	0.0386 (8)	0.0107 (7)	−0.0064 (7)	−0.0072 (6)
C4	0.0393 (7)	0.0345 (7)	0.0338 (7)	0.0038 (6)	−0.0019 (6)	−0.0011 (6)
C3	0.0359 (7)	0.0308 (7)	0.0307 (7)	0.0005 (6)	−0.0015 (5)	0.0001 (5)
C13	0.0336 (7)	0.0314 (7)	0.0312 (6)	0.0042 (6)	0.0006 (6)	−0.0006 (5)
C14	0.0376 (9)	0.0652 (12)	0.0839 (14)	−0.0097 (9)	0.0146 (9)	−0.0254 (11)
C1	0.0713 (11)	0.0384 (8)	0.0257 (7)	−0.0142 (8)	−0.0022 (7)	−0.0031 (6)
C2	0.0534 (9)	0.0326 (7)	0.0291 (6)	0.0077 (7)	−0.0082 (7)	−0.0027 (6)
C11	0.0408 (9)	0.0483 (9)	0.0636 (11)	0.0046 (8)	0.0013 (8)	0.0053 (8)
C12	0.0375 (7)	0.0409 (8)	0.0430 (8)	−0.0017 (7)	0.0034 (7)	0.0017 (6)
C15	0.0400 (8)	0.0411 (8)	0.0445 (8)	0.0018 (7)	−0.0064 (7)	−0.0053 (7)

Geometric parameters (Å, º) top

O5—C6	1.3475 (17)	C5—H5A	0.9900
O5—C5	1.4440 (18)	C5—H5B	0.9900
O3—C3	1.4196 (17)	C4—C3	1.518 (2)
O3—C13	1.4253 (17)	C4—H4	1.0000
O4—C1	1.348 (2)	C3—C2	1.520 (2)
O4—C4	1.4496 (19)	C3—H3	1.0000
O1—C1	1.198 (2)	C13—C15	1.498 (2)
O2—C2	1.4148 (18)	C13—C14	1.507 (2)
O2—C13	1.4391 (17)	C14—H14A	0.9800
O6—C6	1.2008 (18)	C14—H14C	0.9800
C10—C9	1.381 (3)	C14—H14B	0.9800
C10—C11	1.382 (3)	C1—C2	1.520 (3)
C10—H10	0.9500	C2—H2	1.0000
C9—C8	1.383 (3)	C11—C12	1.379 (2)
C9—H9	0.9500	C11—H11	0.9500
C8—C7	1.391 (2)	C12—H12	0.9500
C8—H8	0.9500	C15—H15A	0.9800
C7—C12	1.388 (2)	C15—H15B	0.9800
C7—C6	1.484 (2)	C15—H15C	0.9800
C5—C4	1.507 (2)

C6—O5—C5	116.56 (11)	C4—C3—H3	113.4
C3—O3—C13	107.39 (10)	C2—C3—H3	113.4
C1—O4—C4	111.05 (12)	O3—C13—O2	104.63 (11)
C2—O2—C13	108.05 (11)	O3—C13—C15	109.11 (12)
C9—C10—C11	119.93 (17)	O2—C13—C15	109.05 (13)
C9—C10—H10	120.0	O3—C13—C14	111.45 (14)
C11—C10—H10	120.0	O2—C13—C14	109.80 (15)
C8—C9—C10	120.63 (17)	C15—C13—C14	112.49 (14)
C8—C9—H9	119.7	C13—C14—H14A	109.5
C10—C9—H9	119.7	C13—C14—H14C	109.5
C9—C8—C7	119.23 (17)	H14A—C14—H14C	109.5
C9—C8—H8	120.4	C13—C14—H14B	109.5
C7—C8—H8	120.4	H14A—C14—H14B	109.5
C12—C7—C8	120.13 (15)	H14C—C14—H14B	109.5
C12—C7—C6	121.59 (13)	O1—C1—O4	121.6 (2)
C8—C7—C6	118.26 (14)	O1—C1—C2	127.7 (2)
O6—C6—O5	122.84 (13)	O4—C1—C2	110.64 (12)
O6—C6—C7	125.20 (13)	O2—C2—C3	106.43 (11)
O5—C6—C7	111.96 (12)	O2—C2—C1	109.89 (14)
O5—C5—C4	106.38 (12)	C3—C2—C1	102.91 (13)
O5—C5—H5A	110.5	O2—C2—H2	112.4
C4—C5—H5A	110.5	C3—C2—H2	112.4
O5—C5—H5B	110.5	C1—C2—H2	112.4
C4—C5—H5B	110.5	C12—C11—C10	120.07 (18)
H5A—C5—H5B	108.6	C12—C11—H11	120.0
O4—C4—C5	108.68 (12)	C10—C11—H11	120.0
O4—C4—C3	104.91 (11)	C11—C12—C7	120.00 (16)
C5—C4—C3	114.84 (13)	C11—C12—H12	120.0
O4—C4—H4	109.4	C7—C12—H12	120.0
C5—C4—H4	109.4	C13—C15—H15A	109.5
C3—C4—H4	109.4	C13—C15—H15B	109.5
O3—C3—C4	109.02 (12)	H15A—C15—H15B	109.5
O3—C3—C2	101.79 (11)	C13—C15—H15C	109.5
C4—C3—C2	105.05 (12)	H15A—C15—H15C	109.5
O3—C3—H3	113.4	H15B—C15—H15C	109.5

C11—C10—C9—C8	0.5 (3)	C3—O3—C13—C15	−150.12 (12)
C10—C9—C8—C7	−0.8 (3)	C3—O3—C13—C14	85.06 (16)
C9—C8—C7—C12	0.3 (2)	C2—O2—C13—O3	18.81 (16)
C9—C8—C7—C6	178.64 (14)	C2—O2—C13—C15	135.43 (14)
C5—O5—C6—O6	−3.3 (2)	C2—O2—C13—C14	−100.90 (16)
C5—O5—C6—C7	176.29 (12)	C4—O4—C1—O1	−175.01 (14)
C12—C7—C6—O6	162.66 (16)	C4—O4—C1—C2	6.87 (16)
C8—C7—C6—O6	−15.7 (2)	C13—O2—C2—C3	1.55 (18)
C12—C7—C6—O5	−16.96 (19)	C13—O2—C2—C1	−109.21 (14)
C8—C7—C6—O5	164.70 (13)	O3—C3—C2—O2	−21.16 (17)
C6—O5—C5—C4	155.62 (13)	C4—C3—C2—O2	−134.80 (13)
C1—O4—C4—C5	104.04 (14)	O3—C3—C2—C1	94.39 (12)
C1—O4—C4—C3	−19.24 (15)	C4—C3—C2—C1	−19.24 (14)
O5—C5—C4—O4	−66.95 (15)	O1—C1—C2—O2	−56.6 (2)
O5—C5—C4—C3	50.16 (17)	O4—C1—C2—O2	121.41 (13)
C13—O3—C3—C4	144.09 (12)	O1—C1—C2—C3	−169.62 (16)
C13—O3—C3—C2	33.44 (14)	O4—C1—C2—C3	8.36 (15)
O4—C4—C3—O3	−84.91 (13)	C9—C10—C11—C12	0.2 (3)
C5—C4—C3—O3	155.85 (12)	C10—C11—C12—C7	−0.7 (3)
O4—C4—C3—C2	23.54 (14)	C8—C7—C12—C11	0.4 (2)
C5—C4—C3—C2	−95.70 (15)	C6—C7—C12—C11	−177.87 (15)
C3—O3—C13—O2	−33.54 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	1.00	2.52	3.2381 (19)	128
C5—H5B···O1ⁱ	0.99	2.68	3.139 (2)	108
C8—H8···O3ⁱⁱ	0.95	2.65	3.4951 (19)	148
C12—H12···O4ⁱⁱⁱ	0.95	2.66	3.4682 (19)	143
C15—H15A···O6^iv	0.98	2.59	3.551 (2)	166
C15—H15C···O6^v	0.98	2.75	3.497 (2)	134

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+3/2, −y, z−1/2; (iii) x−1, y, z; (iv) −x+3/2, −y, z+1/2; (v) −x+2, y+1/2, −z+3/2.

Funding information

Funding for this research was provided by: Financiadora de Estudos e ProjetosCoordenação de Aperfeiçoamento de Pessoal de Nível SuperiorConselho Nacional de Desenvolvimento Científico e Tecnológico

References

Baggett, N., Buchanan, J. G., Fatah, M. V., Lachut, C. H., McCullough, K. J. & Webber, J. M. (1985). J. Chem. Soc. Chem. Commun. pp. 1826–1827. CrossRef Web of Science Google Scholar
Booth, K. V., Jenkinson, S. F., Fleet, G. W. J. & Watkin, D. J. (2009). Acta Cryst. E65, o2199. CSD CrossRef IUCr Journals Google Scholar
Bortoluzzi, A. J., Sebrão, D., Sá, M. M. & Nascimento, M. G. (2011). Acta Cryst. E67, o2778. CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci. 44, 2133–2144. Web of Science CSD CrossRef PubMed CAS Google Scholar
Cardoso, H. M., Ribeiro, T. F., Sá, M. M., Sebrão, D., Nascimento, M. G. & Silveira, G. P. (2015). J. Braz. Chem. Soc. 26, 755–764. Google Scholar
Corma, A., Iborra, S. & Velty, A. (2007). Chem. Rev. 107, 2411–2502. Web of Science CrossRef PubMed CAS Google Scholar
Czugler, M. & Pintér, I. (2011). Carbohydr. Res. 346, 1610–1616. CSD CrossRef CAS PubMed Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Han, S.-Y., Joullié, M. M., Petasis, N. A., Bigorra, J., Corbera, J., Font, J. & Ortuño, R. M. (1993). Tetrahedron, 49, 349–362. CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sá, M. M., Silveira, G. P., Caro, M. S. B. & Ellena, J. (2008). J. Braz. Chem. Soc. 19, 18–23. Google Scholar
Sá, M. M., Silveira, G. P., Castilho, M. S., Pavão, F. & Oliva, G. (2002). Arkivoc, 8, 112–124. Google Scholar
Sales, E. S. & Silveira, G. P. (2015). J. Chem. Educ. 92, 1932–1937. CrossRef CAS Google Scholar
Sebrão, D., Sá, M. M. & Nascimento, M. da G. (2011). Process Biochem. 46, 551–556. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Silveira, G. P., Cardozo, H. M., Rossa, T. A. & Sá, M. M. (2015). Curr. Org. Synth. 12, 584–602. CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar