Sodium p-toluenesulfinate tetra­hydrate

Betz, R.; Gerber, T.

doi:10.1107/S1600536811021738

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m898

doi:10.1107/S1600536811021738

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Sodium p-toluenesulfinate tetrahydrate

Richard Betz ^a ^* and Thomas Gerber ^a

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 31 May 2011; accepted 6 June 2011; online 11 June 2011)

The title compound, Na⁺·C₇H₇O₂S⁻·4H₂O, is the hydrate of the sodium salt of para-toluenesulfinic acid. The molecular geometry around the sulfur atom is tetrahedral with X–S–Y angles spanning a range of 102.23 (6)–110.04 (6)°. In the crystal, the water molecules connect the sodium cations into chains along the b axis via O—H⋯O hydrogen bonds. An intermolecular O—H⋯π interaction is also observed.

Related literature

For the crystal structure of sodium para-toluenesulfonate, see: Reinke & Rudershausen (1999 ). For details of graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

Na⁺·C₇H₇O₂S⁻·4H₂O
M_r = 250.24
Monoclinic, P 2₁ /c
a = 15.9432 (19) Å
b = 6.1825 (7) Å
c = 12.2668 (15) Å
β = 100.166 (5)°
V = 1190.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 200 K
0.53 × 0.39 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.826, T_max = 1.000
10741 measured reflections
2846 independent reflections
2554 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.087
S = 1.11
2846 reflections
162 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H31⋯O1	0.81 (1)	1.98 (1)	2.7885 (14)	173 (2)
O3—H32⋯O2ⁱ	0.81 (1)	2.02 (1)	2.8059 (16)	166 (2)
O4—H41⋯O2	0.80 (1)	2.16 (1)	2.9038 (15)	154 (2)
O4—H42⋯O3ⁱⁱ	0.81 (1)	1.99 (1)	2.7884 (15)	173 (2)
O5—H51⋯O1ⁱⁱⁱ	0.80 (1)	1.99 (1)	2.7760 (15)	167 (2)
O5—H52⋯O2^iv	0.80 (1)	2.16 (1)	2.9319 (15)	163 (2)
O6—H61⋯O1^v	0.80 (1)	2.21 (2)	2.9528 (17)	154 (2)
O6—H62⋯Cg^vi	0.79 (1)	2.89 (2)	3.3782 (17)	122 (2)
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z; (v) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vi) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021738/dn2695sup1.cif

Supporting information file. DOI: 10.1107/S1600536811021738/dn2695Isup2.cdx

Supporting information file. DOI: 10.1107/S1600536811021738/dn2695Isup4.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021738/dn2695Isup3.hkl

checkCIF report

Comment top

Multidentate ligands play a major role in the synthesis of coordination polymers and metal-organic framework compounds (MOFs). Especially derivatives of benzoic acid have found widespread use in this aspect and a variety of these coordination polymers have been characterized in solution and in the solid state. Owing to the desire to synthesize functionalized MOFs whose poresizes or even complete architectural set-ups might easily be influenced upon variation of external parameters such as pH value or the presence and concentration of molecules that might reside inside the pores of these MOFs, chelating ligands related to benzoic acid but with the ability to change their bonding behaviour are necessary. In this aspect, para-toluenesulfinic acid seemed of interest since it may act as neutral or anionic ligand, and even the sulfur atom may show donor action. In order to gather structural information to allow for the tailored synthesis of MOFs based on para-toluenesulfinic acid, we determined the crystal structure of its sodium salt. The crystal structure of the sodium salt of para-toluenesulfonic acid is apparent in the literature (Reinke & Rudershausen, 1999).

Taking into account the lone pair on the sulfur atom, the latter is present in a pseudo-tetrahedral molecular geometry. The X–S–Y angles span a range of 102.23 (6)–110.04 (6) °. The least-squares planes defined by the atoms of the aromatic system on the one hand and the SOO group on the other hand intersect at an angle of 64.47 (6) °. The sodium cation is coordinated by six water molecules (two of them symmetry-generated) of which two act as bridging ligands to the neighbouring sodium cation and thus foster the formation of a "sodium-acqua-polymer" chain along the crystallographic b axis (Fig. 2). The angles between two trans-orientated water molecules in the resultant [Na(H₂O)₆]⁺ octahedra were found adopting values between 163.96 (5) ° and 173.68 (4) °.

The crystal structure is dominated by hydrogen bonds. Except for one of the hydrogen atoms on one water molecule that is part of a O–H···π interaction, all of the water molecules take part in O–H···O hydrogen bonding. Each of the sulfinic acid group's O atoms acts as multifold acceptor. In terms of graph set analysis (Etter et al. (1990); Bernstein et al. (1995)), the description of the hydrogen bonding systems necessitates a DDDDDDDD descriptor on the unitary level. In total, the components of the crystal structure are connected to double layers perpendicular to the crystallographic a axis with the hydrophobic aromatic moieties forming the outer surfaces of these layers. π-Stacking is not a prominent feature of the crystal structure with the shortest distance between two aromatic systems found at 5.5359 (11) Å.

Related literature top

For the crystal structure of the para-toluenesulfonic acid sodium salt, see: Reinke & Rudershausen (1999). For details of graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

The compound was obtained commercially (KEG). Crystals suitable for the X-ray diffraction study were obtained upon free evaporation of an aqueous solution thereof.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level). Symmetry operators: ⁱ -x + 1, -y + 1, -z; ⁱⁱ -x + 1, -y + 2, -z. For reasons of clarity, only one of the sodium cations with its octahedral coordination of water molecules is depicted instead of the polymeric chain.
	Fig. 2. Polymeric chain of sodium cations and water molecules, viewed along [1 0 0].

Sodium p-toluenesulfinate tetrahydrate top

Crystal data top

Na⁺·C₇H₇O₂S⁻·4H₂O	F(000) = 528
M_r = 250.24	D_x = 1.397 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7792 reflections
a = 15.9432 (19) Å	θ = 2.6–27.4°
b = 6.1825 (7) Å	µ = 0.31 mm⁻¹
c = 12.2668 (15) Å	T = 200 K
β = 100.166 (5)°	Platelet, colourless
V = 1190.1 (2) Å³	0.53 × 0.39 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2846 independent reflections
Radiation source: fine-focus sealed tube	2554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 28.0°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −21→20
T_min = 0.826, T_max = 1.000	k = −5→8
10741 measured reflections	l = −16→16

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0378P)² + 0.535P] where P = (F_o² + 2F_c²)/3
2846 reflections	(Δ/σ)_max = 0.001
162 parameters	Δρ_max = 0.72 e Å⁻³
12 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

Na⁺·C₇H₇O₂S⁻·4H₂O	V = 1190.1 (2) Å³
M_r = 250.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.9432 (19) Å	µ = 0.31 mm⁻¹
b = 6.1825 (7) Å	T = 200 K
c = 12.2668 (15) Å	0.53 × 0.39 × 0.21 mm
β = 100.166 (5)°

Data collection top

Bruker APEXII CCD diffractometer	2846 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2554 reflections with I > 2σ(I)
T_min = 0.826, T_max = 1.000	R_int = 0.025
10741 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	12 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.72 e Å⁻³
2846 reflections	Δρ_min = −0.23 e Å⁻³
162 parameters

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

	x	y	z	U_iso*/U_eq
Na1	0.45418 (3)	0.75184 (9)	0.02242 (4)	0.02500 (14)
O3	0.39909 (7)	0.88972 (17)	0.17974 (9)	0.0287 (2)
H31	0.3681 (11)	0.796 (2)	0.1963 (17)	0.043*
H32	0.3672 (11)	0.990 (2)	0.1611 (16)	0.043*
O4	0.48457 (7)	0.41959 (17)	0.12242 (8)	0.0274 (2)
H41	0.4404 (8)	0.378 (3)	0.1373 (15)	0.041*
H42	0.5152 (10)	0.417 (3)	0.1824 (11)	0.041*
O5	0.59271 (7)	0.89815 (18)	0.06769 (9)	0.0293 (2)
H51	0.6176 (11)	0.927 (3)	0.1281 (11)	0.044*
H52	0.6263 (11)	0.846 (3)	0.0338 (14)	0.044*
O6	0.31527 (9)	0.6560 (3)	−0.07052 (11)	0.0501 (4)
H61	0.2992 (17)	0.711 (4)	−0.1295 (14)	0.075*
H62	0.2971 (16)	0.537 (2)	−0.072 (2)	0.075*
S1	0.25275 (2)	0.41422 (5)	0.14718 (3)	0.02338 (10)
O1	0.30441 (6)	0.54447 (17)	0.24003 (8)	0.0293 (2)
O2	0.31037 (7)	0.26401 (18)	0.09734 (9)	0.0342 (2)
C1	0.19547 (8)	0.2298 (2)	0.22163 (11)	0.0230 (3)
C2	0.17035 (9)	0.2961 (2)	0.31990 (12)	0.0280 (3)
H2	0.1867	0.4342	0.3504	0.034*
C3	0.12128 (9)	0.1588 (3)	0.37294 (12)	0.0306 (3)
H3	0.1042	0.2048	0.4396	0.037*
C4	0.09673 (8)	−0.0448 (2)	0.33007 (12)	0.0287 (3)
C5	0.12217 (9)	−0.1073 (2)	0.23143 (13)	0.0298 (3)
H5	0.1056	−0.2451	0.2006	0.036*
C6	0.17114 (9)	0.0278 (2)	0.17743 (12)	0.0271 (3)
H6	0.1879	−0.0178	0.1105	0.032*
C7	0.04458 (11)	−0.1935 (3)	0.38969 (15)	0.0422 (4)
H7A	0.0714	−0.2048	0.4678	0.063*
H7B	0.0416	−0.3372	0.3555	0.063*
H7C	−0.0131	−0.1349	0.3845	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0267 (3)	0.0233 (3)	0.0256 (3)	0.0000 (2)	0.0062 (2)	0.0000 (2)
O3	0.0328 (5)	0.0258 (5)	0.0283 (5)	−0.0027 (4)	0.0078 (4)	0.0004 (4)
O4	0.0267 (5)	0.0300 (5)	0.0259 (5)	−0.0014 (4)	0.0057 (4)	0.0009 (4)
O5	0.0277 (5)	0.0322 (6)	0.0275 (5)	−0.0005 (4)	0.0036 (4)	−0.0044 (4)
O6	0.0465 (7)	0.0606 (9)	0.0391 (6)	−0.0253 (7)	−0.0043 (5)	0.0124 (6)
S1	0.02337 (17)	0.02331 (18)	0.02327 (17)	−0.00030 (12)	0.00355 (12)	0.00159 (12)
O1	0.0332 (5)	0.0270 (5)	0.0266 (5)	−0.0075 (4)	0.0021 (4)	0.0002 (4)
O2	0.0374 (6)	0.0302 (5)	0.0403 (6)	−0.0011 (4)	0.0212 (5)	−0.0026 (4)
C1	0.0190 (6)	0.0247 (6)	0.0251 (6)	0.0006 (5)	0.0034 (5)	0.0016 (5)
C2	0.0284 (7)	0.0272 (7)	0.0291 (7)	−0.0020 (5)	0.0071 (5)	−0.0040 (5)
C3	0.0288 (7)	0.0365 (8)	0.0281 (7)	−0.0016 (6)	0.0093 (5)	−0.0014 (6)
C4	0.0210 (6)	0.0325 (7)	0.0325 (7)	−0.0016 (5)	0.0046 (5)	0.0046 (6)
C5	0.0261 (7)	0.0253 (7)	0.0377 (8)	−0.0026 (5)	0.0043 (6)	−0.0018 (6)
C6	0.0254 (6)	0.0276 (7)	0.0284 (6)	0.0000 (5)	0.0054 (5)	−0.0031 (5)
C7	0.0392 (9)	0.0421 (9)	0.0481 (9)	−0.0111 (7)	0.0153 (7)	0.0055 (8)

Geometric parameters (Å, º) top

Na1—O5	2.3604 (12)	S1—O2	1.5094 (11)
Na1—O6	2.3801 (13)	S1—O1	1.5142 (10)
Na1—O4	2.3977 (12)	S1—C1	1.8062 (14)
Na1—O3	2.4127 (12)	C1—C6	1.3893 (19)
Na1—O4ⁱ	2.4178 (12)	C1—C2	1.3971 (19)
Na1—O5ⁱⁱ	2.4843 (12)	C2—C3	1.391 (2)
Na1—Na1ⁱⁱ	3.4837 (11)	C2—H2	0.9500
O3—H31	0.810 (11)	C3—C4	1.394 (2)
O3—H32	0.807 (11)	C3—H3	0.9500
O4—Na1ⁱ	2.4178 (12)	C4—C5	1.397 (2)
O4—H41	0.801 (11)	C4—C7	1.512 (2)
O4—H42	0.809 (12)	C5—C6	1.389 (2)
O5—Na1ⁱⁱ	2.4843 (12)	C5—H5	0.9500
O5—H51	0.798 (11)	C6—H6	0.9500
O5—H52	0.802 (11)	C7—H7A	0.9800
O6—H61	0.799 (12)	C7—H7B	0.9800
O6—H62	0.792 (12)	C7—H7C	0.9800

O5—Na1—O6	163.96 (5)	Na1—O5—Na1ⁱⁱ	91.92 (4)
O5—Na1—O4	96.42 (4)	Na1—O5—H51	126.7 (14)
O6—Na1—O4	96.81 (5)	Na1ⁱⁱ—O5—H51	106.2 (15)
O5—Na1—O3	97.70 (4)	Na1—O5—H52	114.0 (14)
O6—Na1—O3	91.82 (5)	Na1ⁱⁱ—O5—H52	107.3 (15)
O4—Na1—O3	87.86 (4)	H51—O5—H52	107.7 (16)
O5—Na1—O4ⁱ	81.86 (4)	Na1—O6—H61	116.7 (19)
O6—Na1—O4ⁱ	90.07 (5)	Na1—O6—H62	123.4 (19)
O4—Na1—O4ⁱ	85.93 (4)	H61—O6—H62	108 (2)
O3—Na1—O4ⁱ	173.68 (4)	O2—S1—O1	110.04 (6)
O5—Na1—O5ⁱⁱ	88.08 (4)	O2—S1—C1	102.39 (6)
O6—Na1—O5ⁱⁱ	79.76 (5)	O1—S1—C1	102.23 (6)
O4—Na1—O5ⁱⁱ	172.58 (4)	C6—C1—C2	119.84 (13)
O3—Na1—O5ⁱⁱ	85.68 (4)	C6—C1—S1	120.09 (10)
O4ⁱ—Na1—O5ⁱⁱ	100.59 (4)	C2—C1—S1	119.91 (10)
O5—Na1—Na1ⁱⁱ	45.46 (3)	C3—C2—C1	119.68 (13)
O6—Na1—Na1ⁱⁱ	121.63 (4)	C3—C2—H2	120.2
O4—Na1—Na1ⁱⁱ	141.52 (4)	C1—C2—H2	120.2
O3—Na1—Na1ⁱⁱ	92.13 (3)	C2—C3—C4	121.22 (13)
O4ⁱ—Na1—Na1ⁱⁱ	92.01 (3)	C2—C3—H3	119.4
O5ⁱⁱ—Na1—Na1ⁱⁱ	42.62 (3)	C4—C3—H3	119.4
O5—Na1—Na1ⁱ	88.79 (3)	C3—C4—C5	118.14 (13)
O6—Na1—Na1ⁱ	94.68 (5)	C3—C4—C7	120.58 (14)
O4—Na1—Na1ⁱ	43.19 (3)	C5—C4—C7	121.27 (14)
O3—Na1—Na1ⁱ	131.04 (4)	C6—C5—C4	121.35 (14)
O4ⁱ—Na1—Na1ⁱ	42.74 (3)	C6—C5—H5	119.3
O5ⁱⁱ—Na1—Na1ⁱ	143.21 (4)	C4—C5—H5	119.3
Na1ⁱⁱ—Na1—Na1ⁱ	123.83 (3)	C5—C6—C1	119.76 (13)
Na1—O3—H31	105.8 (15)	C5—C6—H6	120.1
Na1—O3—H32	110.1 (14)	C1—C6—H6	120.1
H31—O3—H32	103.7 (16)	C4—C7—H7A	109.5
Na1—O4—Na1ⁱ	94.07 (4)	C4—C7—H7B	109.5
Na1—O4—H41	106.7 (14)	H7A—C7—H7B	109.5
Na1ⁱ—O4—H41	120.8 (14)	C4—C7—H7C	109.5
Na1—O4—H42	121.2 (14)	H7A—C7—H7C	109.5
Na1ⁱ—O4—H42	113.7 (14)	H7B—C7—H7C	109.5
H41—O4—H42	101.5 (16)

O5—Na1—O4—Na1ⁱ	−81.33 (4)	O1—S1—C1—C6	−151.45 (11)
O6—Na1—O4—Na1ⁱ	89.58 (5)	O2—S1—C1—C2	147.07 (12)
O3—Na1—O4—Na1ⁱ	−178.84 (4)	O1—S1—C1—C2	33.07 (12)
O4ⁱ—Na1—O4—Na1ⁱ	0.0	C6—C1—C2—C3	0.2 (2)
O5ⁱⁱ—Na1—O4—Na1ⁱ	151.6 (3)	S1—C1—C2—C3	175.65 (11)
Na1ⁱⁱ—Na1—O4—Na1ⁱ	−88.11 (6)	C1—C2—C3—C4	0.2 (2)
O6—Na1—O5—Na1ⁱⁱ	40.5 (2)	C2—C3—C4—C5	−0.5 (2)
O4—Na1—O5—Na1ⁱⁱ	−174.08 (4)	C2—C3—C4—C7	179.01 (14)
O3—Na1—O5—Na1ⁱⁱ	−85.38 (4)	C3—C4—C5—C6	0.5 (2)
O4ⁱ—Na1—O5—Na1ⁱⁱ	100.98 (4)	C7—C4—C5—C6	−179.03 (14)
O5ⁱⁱ—Na1—O5—Na1ⁱⁱ	0.0	C4—C5—C6—C1	−0.2 (2)
Na1ⁱ—Na1—O5—Na1ⁱⁱ	143.33 (4)	C2—C1—C6—C5	−0.2 (2)
O2—S1—C1—C6	−37.45 (12)	S1—C1—C6—C5	−175.66 (11)

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···O1	0.81 (1)	1.98 (1)	2.7885 (14)	173 (2)
O3—H32···O2ⁱⁱⁱ	0.81 (1)	2.02 (1)	2.8059 (16)	166 (2)
O4—H41···O2	0.80 (1)	2.16 (1)	2.9038 (15)	154 (2)
O4—H42···O3^iv	0.81 (1)	1.99 (1)	2.7884 (15)	173 (2)
O5—H51···O1^v	0.80 (1)	1.99 (1)	2.7760 (15)	167 (2)
O5—H52···O2ⁱ	0.80 (1)	2.16 (1)	2.9319 (15)	163 (2)
O6—H61···O1^vi	0.80 (1)	2.21 (2)	2.9528 (17)	154 (2)
O6—H62···Cg^vii	0.79 (1)	2.89 (2)	3.3782 (17)	122 (2)

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

Experimental details

Crystal data
Chemical formula	Na⁺·C₇H₇O₂S⁻·4H₂O
M_r	250.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	15.9432 (19), 6.1825 (7), 12.2668 (15)
β (°)	100.166 (5)
V (Å³)	1190.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.53 × 0.39 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.826, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10741, 2846, 2554
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.087, 1.11
No. of reflections	2846
No. of parameters	162
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.23

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···O1	0.810 (11)	1.983 (12)	2.7885 (14)	173.1 (19)
O3—H32···O2ⁱ	0.807 (11)	2.015 (12)	2.8059 (16)	166.4 (19)
O4—H41···O2	0.801 (11)	2.162 (13)	2.9038 (15)	154.1 (18)
O4—H42···O3ⁱⁱ	0.809 (12)	1.985 (12)	2.7884 (15)	172.7 (19)
O5—H51···O1ⁱⁱⁱ	0.798 (11)	1.994 (12)	2.7760 (15)	167 (2)
O5—H52···O2^iv	0.802 (11)	2.155 (12)	2.9319 (15)	163.3 (19)
O6—H61···O1^v	0.799 (12)	2.214 (15)	2.9528 (17)	154 (2)
O6—H62···Cg^vi	0.792 (12)	2.89 (2)	3.3782 (17)	122 (2)

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

Acknowledgements

The authors thank Mrs Jaci Neil-Schutte for helpful discussions.

References

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Volume 67| Part 7| July 2011| Page m898

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