5-Azido-4-benz­yloxy-2-meth­oxy-6-methyl­perhydro­pyran-3-ol

Fun, H.-K.; Loh, W.-S.; Rai, S.; Shetty, P.; Isloor, A.M.

doi:10.1107/S1600536809028657

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1972

doi:10.1107/S1600536809028657

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5-Azido-4-benzyloxy-2-methoxy-6-methylperhydropyran-3-ol

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a Sankappa Rai,^b Prakash Shetty ^c and Arun M. Isloor ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSyngene International Ltd, Biocon Park, Plot Nos. 2 & 3, Bommasandra 4th Phase, Jigani Link Rd, Bangalore 560 100, India, ^cDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India, and ^dDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 20 July 2009; accepted 20 July 2009; online 25 July 2009)

In the title compound, C₁₄H₁₉N₃O₄, the perhydropyran ring adopts a chair conformation. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal packing, molecules are linked by O—H⋯O hydrogen bonds, forming infinite chains along [100].

Related literature

For background to D-perosamine, see: Jacquinet (2006 ). For the synthesis of D-perosamine, see: Krishna & Agrawal (2000 ). For metabolites, see: Grond et al. (2000 ). For ring conformations, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₄H₁₉N₃O₄
M_r = 293.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.6662 (2) Å
b = 15.3356 (8) Å
c = 20.9273 (12) Å
V = 1497.54 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.27 × 0.11 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.773, T_max = 0.980
13029 measured reflections
1742 independent reflections
1334 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.103
S = 1.09
1742 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O2ⁱ	0.88 (4)	1.91 (3)	2.757 (2)	161 (3)
O2—H1O2⋯O3ⁱ	0.88 (3)	2.49 (3)	3.063 (3)	124 (3)
C7—H7B⋯O2	0.97	2.58	3.180 (4)	120
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028657/ng2616sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028657/ng2616Isup2.hkl

checkCIF report

Comment top

4-Amino-4,6-dideoxy-D-mannose (D-perosamine) was first discovered in the polyene macrolide antibiotic perimycin and was later recognized to be present in the lipopolysaccharide (LPS) of Vivrio cholera (Jacquinet, 2006). Methyl 3-benzyloxy-4-azido-α-D-rhamnopyranoside is an important intermediate in the synthesis of D-perosamine (Krishna & Agrawal, 2000). Rhamnopyranosides were detected as metabolites from five different strains of Streptomycetes (Grond et al., 2000).

The bond lengths (Allen et al., 1987) and angles in the molecule (Fig. 1) are within normal ranges. The perhydropyran ring adopts a chair conformation. The puckering parameters (Cremer & Pople, 1975) are Q = 0.540 (3) Å; Θ = 8.0 (3)° and ϕ = 8.0 (2)°. Intramolecular C7—H7B···O2 hydrogen bonds formed a six-membered ring, producing an S(6) ring motif (Bernstein et al., 1995). The dihedral angle formed between the benzene (C1—C6) and perhydropyran (C8—C10/O4/C11/C12) rings is 57.32 (16)°.

In the crystal packing (Fig. 2), the molecules are linked by intermolecular O2—H1O2···O2 and O2—H1O2···O3 hydrogen bonds (Table 1) into an infinite one-dimensional chains along the [100] direction.

Related literature top

For background to D-perosamine, see: Jacquinet (2006). For the synthesis of D-perosamine, see: Krishna & Agrawal (2000). For metabolites, see: Grond et al. (2000). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

To a stirred mixture of methyl 3-benzyloxy-4-methoxysulfonyl-α-D-rhamnopyranoside (0.50 g, 1.4 mmol) in DMF (5.0 ml) was added sodium azide (0.18 g, 2.8 mmol). The reaction mixture was stirred further at room temperature for 12 h. TLC (30% EtOAc/hexane, Rf-0.5) analysis showed complete conversion. The reaction mixture was concentrated under vacuum and the residue was purified by column chromatography using 25% ethylacetate in petroleum ether to get pure product as colourless crystals (yield: 300.0 mg, 71%, M.p. 376–378 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. Intramolecular interaction is shown by dashed line.
	Fig. 2. The crystal packing of the title compound, viewed along a axis. Intermolecular hydrogen bonds are shown by dashed lines.

5-Azido-4-benzyloxy-2-methoxy-6-methylperhydropyran-3-ol top

Crystal data top

C₁₄H₁₉N₃O₄	F(000) = 624
M_r = 293.32	D_x = 1.301 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1880 reflections
a = 4.6662 (2) Å	θ = 2.4–29.9°
b = 15.3356 (8) Å	µ = 0.10 mm⁻¹
c = 20.9273 (12) Å	T = 100 K
V = 1497.54 (13) Å³	Block, colourless
Z = 4	0.27 × 0.11 × 0.08 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1742 independent reflections
Radiation source: fine-focus sealed tube	1334 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
T_min = 0.773, T_max = 0.980	k = −18→17
13029 measured reflections	l = −25→25

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0499P)²] where P = (F_o² + 2F_c²)/3
1742 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₁₉N₃O₄	V = 1497.54 (13) Å³
M_r = 293.32	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.6662 (2) Å	µ = 0.10 mm⁻¹
b = 15.3356 (8) Å	T = 100 K
c = 20.9273 (12) Å	0.27 × 0.11 × 0.08 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1742 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1334 reflections with I > 2σ(I)
T_min = 0.773, T_max = 0.980	R_int = 0.096
13029 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.23 e Å⁻³
1742 reflections	Δρ_min = −0.20 e Å⁻³
196 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.0881 (4)	0.40074 (13)	0.13521 (10)	0.0229 (5)
O2	0.0911 (5)	0.28256 (14)	0.02574 (11)	0.0251 (5)
O3	0.3176 (5)	0.39026 (14)	−0.06657 (9)	0.0236 (5)
O4	−0.0200 (5)	0.49881 (14)	−0.04434 (10)	0.0250 (5)
N1	0.3572 (6)	0.56890 (17)	0.10102 (12)	0.0260 (7)
N2	0.3482 (6)	0.56020 (18)	0.16023 (14)	0.0306 (7)
N3	0.3680 (9)	0.5600 (2)	0.21422 (15)	0.0537 (11)
C1	0.2228 (8)	0.2487 (2)	0.26646 (17)	0.0341 (9)
H1A	0.3517	0.2100	0.2479	0.041*
C2	0.1203 (8)	0.2318 (2)	0.32682 (17)	0.0389 (9)
H2A	0.1795	0.1820	0.3485	0.047*
C3	−0.0706 (8)	0.2888 (3)	0.35523 (17)	0.0379 (9)
H3A	−0.1405	0.2776	0.3960	0.045*
C4	−0.1561 (9)	0.3619 (2)	0.32269 (16)	0.0362 (9)
H4A	−0.2856	0.4003	0.3413	0.043*
C5	−0.0489 (8)	0.3786 (2)	0.26165 (16)	0.0314 (9)
H5A	−0.1051	0.4289	0.2402	0.038*
C6	0.1390 (7)	0.3216 (2)	0.23289 (15)	0.0245 (7)
C7	0.2586 (8)	0.3380 (2)	0.16733 (16)	0.0309 (9)
H7A	0.4541	0.3590	0.1708	0.037*
H7B	0.2607	0.2840	0.1431	0.037*
C8	0.1803 (7)	0.4219 (2)	0.07207 (14)	0.0209 (7)
H8A	0.3837	0.4073	0.0675	0.025*
C9	0.1415 (7)	0.51995 (19)	0.06387 (14)	0.0193 (7)
H9A	−0.0498	0.5361	0.0791	0.023*
C10	0.1727 (7)	0.5493 (2)	−0.00515 (14)	0.0215 (7)
H10A	0.3703	0.5397	−0.0193	0.026*
C11	0.0416 (7)	0.4086 (2)	−0.04432 (15)	0.0241 (8)
H11A	−0.0965	0.3794	−0.0723	0.029*
C12	0.0088 (7)	0.37161 (19)	0.02287 (15)	0.0214 (7)
H12A	−0.1941	0.3754	0.0347	0.026*
C13	0.3436 (8)	0.4054 (3)	−0.13393 (15)	0.0361 (9)
H13A	0.5309	0.3880	−0.1480	0.054*
H13B	0.3159	0.4662	−0.1427	0.054*
H13C	0.2012	0.3720	−0.1562	0.054*
C14	0.0949 (9)	0.6437 (2)	−0.01442 (16)	0.0364 (9)
H14A	0.1146	0.6588	−0.0587	0.055*
H14B	0.2203	0.6795	0.0107	0.055*
H14C	−0.0997	0.6530	−0.0012	0.055*
H1O2	−0.060 (8)	0.251 (2)	0.0151 (15)	0.028 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0225 (12)	0.0219 (12)	0.0243 (11)	0.0014 (10)	0.0055 (10)	0.0037 (10)
O2	0.0200 (12)	0.0185 (12)	0.0368 (13)	−0.0030 (11)	0.0015 (11)	−0.0055 (10)
O3	0.0222 (11)	0.0283 (13)	0.0205 (11)	0.0038 (11)	−0.0013 (10)	−0.0046 (10)
O4	0.0249 (12)	0.0218 (12)	0.0282 (12)	0.0030 (11)	−0.0041 (10)	−0.0033 (10)
N1	0.0301 (16)	0.0255 (17)	0.0224 (16)	−0.0079 (14)	0.0009 (14)	−0.0004 (12)
N2	0.0360 (17)	0.0250 (17)	0.0307 (19)	−0.0096 (14)	−0.0032 (15)	−0.0024 (13)
N3	0.084 (3)	0.049 (2)	0.0274 (18)	−0.028 (2)	−0.0075 (19)	−0.0015 (15)
C1	0.036 (2)	0.032 (2)	0.035 (2)	0.0072 (17)	0.0014 (17)	0.0053 (17)
C2	0.044 (2)	0.032 (2)	0.040 (2)	0.003 (2)	0.000 (2)	0.0127 (18)
C3	0.040 (2)	0.045 (2)	0.0295 (19)	−0.002 (2)	0.0026 (18)	0.0106 (18)
C4	0.040 (2)	0.036 (2)	0.0329 (19)	0.0034 (19)	0.0131 (19)	0.0041 (17)
C5	0.038 (2)	0.0257 (19)	0.0300 (19)	0.0002 (18)	0.0039 (18)	0.0061 (16)
C6	0.0246 (18)	0.0220 (18)	0.0267 (17)	−0.0019 (16)	−0.0029 (16)	0.0018 (15)
C7	0.0305 (19)	0.031 (2)	0.0315 (19)	0.0135 (17)	0.0029 (16)	0.0033 (16)
C8	0.0170 (16)	0.0213 (18)	0.0244 (17)	−0.0001 (15)	0.0013 (15)	0.0015 (14)
C9	0.0197 (16)	0.0150 (16)	0.0233 (16)	0.0001 (14)	0.0031 (15)	−0.0037 (13)
C10	0.0238 (17)	0.0185 (17)	0.0224 (16)	−0.0001 (15)	0.0005 (15)	−0.0037 (14)
C11	0.0224 (16)	0.0213 (18)	0.0286 (18)	−0.0019 (15)	−0.0045 (15)	−0.0047 (15)
C12	0.0153 (15)	0.0157 (16)	0.0333 (18)	0.0017 (14)	0.0013 (15)	−0.0062 (14)
C13	0.035 (2)	0.052 (2)	0.0214 (17)	0.004 (2)	−0.0043 (18)	−0.0014 (17)
C14	0.052 (2)	0.028 (2)	0.0291 (19)	0.0020 (19)	0.0024 (19)	0.0017 (16)

Geometric parameters (Å, º) top

O1—C7	1.418 (4)	C5—H5A	0.9300
O1—C8	1.427 (4)	C6—C7	1.502 (4)
O2—C12	1.420 (3)	C7—H7A	0.9700
O2—H1O2	0.88 (4)	C7—H7B	0.9700
O3—C11	1.398 (4)	C8—C12	1.515 (4)
O3—C13	1.434 (4)	C8—C9	1.524 (4)
O4—C11	1.412 (4)	C8—H8A	0.9800
O4—C10	1.443 (4)	C9—C10	1.520 (4)
N1—N2	1.247 (4)	C9—H9A	0.9800
N1—C9	1.477 (4)	C10—C14	1.505 (4)
N2—N3	1.134 (4)	C10—H10A	0.9800
C1—C2	1.375 (5)	C11—C12	1.524 (4)
C1—C6	1.376 (5)	C11—H11A	0.9800
C1—H1A	0.9300	C12—H12A	0.9800
C2—C3	1.382 (5)	C13—H13A	0.9600
C2—H2A	0.9300	C13—H13B	0.9600
C3—C4	1.371 (5)	C13—H13C	0.9600
C3—H3A	0.9300	C14—H14A	0.9600
C4—C5	1.396 (5)	C14—H14B	0.9600
C4—H4A	0.9300	C14—H14C	0.9600
C5—C6	1.378 (5)

C7—O1—C8	115.1 (2)	N1—C9—C10	106.5 (2)
C12—O2—H1O2	107 (2)	N1—C9—C8	111.2 (3)
C11—O3—C13	111.9 (2)	C10—C9—C8	112.8 (2)
C11—O4—C10	113.5 (2)	N1—C9—H9A	108.7
N2—N1—C9	116.5 (3)	C10—C9—H9A	108.7
N3—N2—N1	171.1 (4)	C8—C9—H9A	108.7
C2—C1—C6	121.5 (3)	O4—C10—C14	107.0 (3)
C2—C1—H1A	119.2	O4—C10—C9	108.8 (2)
C6—C1—H1A	119.2	C14—C10—C9	112.6 (3)
C1—C2—C3	120.0 (3)	O4—C10—H10A	109.5
C1—C2—H2A	120.0	C14—C10—H10A	109.5
C3—C2—H2A	120.0	C9—C10—H10A	109.5
C4—C3—C2	119.4 (3)	O3—C11—O4	112.6 (3)
C4—C3—H3A	120.3	O3—C11—C12	109.0 (3)
C2—C3—H3A	120.3	O4—C11—C12	110.2 (3)
C3—C4—C5	120.1 (3)	O3—C11—H11A	108.3
C3—C4—H4A	120.0	O4—C11—H11A	108.3
C5—C4—H4A	120.0	C12—C11—H11A	108.3
C6—C5—C4	120.7 (3)	O2—C12—C8	108.5 (2)
C6—C5—H5A	119.6	O2—C12—C11	111.7 (2)
C4—C5—H5A	119.6	C8—C12—C11	112.6 (3)
C1—C6—C5	118.3 (3)	O2—C12—H12A	107.9
C1—C6—C7	119.8 (3)	C8—C12—H12A	107.9
C5—C6—C7	121.9 (3)	C11—C12—H12A	107.9
O1—C7—C6	109.8 (3)	O3—C13—H13A	109.5
O1—C7—H7A	109.7	O3—C13—H13B	109.5
C6—C7—H7A	109.7	H13A—C13—H13B	109.5
O1—C7—H7B	109.7	O3—C13—H13C	109.5
C6—C7—H7B	109.7	H13A—C13—H13C	109.5
H7A—C7—H7B	108.2	H13B—C13—H13C	109.5
O1—C8—C12	110.8 (2)	C10—C14—H14A	109.5
O1—C8—C9	107.0 (2)	C10—C14—H14B	109.5
C12—C8—C9	111.3 (3)	H14A—C14—H14B	109.5
O1—C8—H8A	109.2	C10—C14—H14C	109.5
C12—C8—H8A	109.2	H14A—C14—H14C	109.5
C9—C8—H8A	109.2	H14B—C14—H14C	109.5

C9—N1—N2—N3	−177 (2)	C12—C8—C9—C10	−47.1 (4)
C6—C1—C2—C3	−0.2 (6)	C11—O4—C10—C14	175.5 (3)
C1—C2—C3—C4	0.0 (6)	C11—O4—C10—C9	−62.7 (3)
C2—C3—C4—C5	−0.5 (6)	N1—C9—C10—O4	176.0 (2)
C3—C4—C5—C6	1.2 (6)	C8—C9—C10—O4	53.7 (3)
C2—C1—C6—C5	0.9 (5)	N1—C9—C10—C14	−65.6 (3)
C2—C1—C6—C7	179.4 (3)	C8—C9—C10—C14	172.2 (3)
C4—C5—C6—C1	−1.4 (5)	C13—O3—C11—O4	−70.6 (3)
C4—C5—C6—C7	−179.8 (3)	C13—O3—C11—C12	166.9 (2)
C8—O1—C7—C6	−179.9 (3)	C10—O4—C11—O3	−59.5 (3)
C1—C6—C7—O1	163.7 (3)	C10—O4—C11—C12	62.4 (3)
C5—C6—C7—O1	−17.8 (5)	O1—C8—C12—O2	−71.0 (3)
C7—O1—C8—C12	98.3 (3)	C9—C8—C12—O2	170.1 (3)
C7—O1—C8—C9	−140.2 (3)	O1—C8—C12—C11	164.8 (2)
N2—N1—C9—C10	173.4 (3)	C9—C8—C12—C11	45.9 (3)
N2—N1—C9—C8	−63.3 (4)	O3—C11—C12—O2	−51.3 (3)
O1—C8—C9—N1	72.2 (3)	O4—C11—C12—O2	−175.3 (2)
C12—C8—C9—N1	−166.7 (2)	O3—C11—C12—C8	71.1 (3)
O1—C8—C9—C10	−168.2 (2)	O4—C11—C12—C8	−52.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O2ⁱ	0.88 (4)	1.91 (3)	2.757 (2)	161 (3)
O2—H1O2···O3ⁱ	0.88 (3)	2.49 (3)	3.063 (3)	124 (3)
C7—H7B···O2	0.97	2.58	3.180 (4)	120

Symmetry code: (i) x−1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉N₃O₄
M_r	293.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	4.6662 (2), 15.3356 (8), 20.9273 (12)
V (Å³)	1497.54 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.27 × 0.11 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.773, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	13029, 1742, 1334
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.103, 1.09
No. of reflections	1742
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O2ⁱ	0.88 (4)	1.91 (3)	2.757 (2)	161 (3)
O2—H1O2···O3ⁱ	0.88 (3)	2.49 (3)	3.063 (3)	124 (3)
C7—H7B···O2	0.9700	2.5800	3.180 (4)	120.00

Symmetry code: (i) x−1/2, −y+1/2, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks USM for a student assistantship.

References

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