Tetra­methyl­ammonium aqua­trichlorido­oxalatostannate(IV) monohydrate

Sow, Y.; Diop, L.; Molloy, K.C.; Kociok-Köhn, G.

doi:10.1107/S1600536813000895

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages m106-m107

doi:10.1107/S1600536813000895

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Tetramethylammonium aquatrichloridooxalatostannate(IV) monohydrate

Yaya Sow,^a ^* Libasse Diop,^a Kieran C. Molloy ^b and Gabriele Kociok-Köhn ^b

^aLaboratoire de Chimie Minerale et Analytique (LACHIMIA), Departement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bDepartment of Chemistry, University of Bath, Bath BA2 7AY, England
^*Correspondence e-mail: yayasow81@yahoo.fr

(Received 5 December 2012; accepted 9 January 2013; online 16 January 2013)

The Sn^IV atom in the title compound, [(CH₃)₄N][Sn(C₂O₄)Cl₃(H₂O)]·H₂O, obtained from the reaction between SnCl₄ and [(CH₃)₄N]₂C₂O₄·2H₂O, is six-coordinated by three Cl atoms, an O atom of a water molecule and two O atoms from an asymmetrically chelating oxalate anion. The environment around the Sn^IV atom is distorted octahedral. The anions are connected by the lattice water molecule through O—H⋯O hydrogen bonds, leading to a layered structure parallel to (010). The cations are located between these layers and besides Coulombic forces are connected to the anionic layers through weak C—H⋯O and C—H⋯Cl interactions.

Related literature

For background to halogentin(IV) chemistry, see: Hausen et al. (1986 ); Koutsantonis et al. (2003 ); Mahon et al. (2004 ); Patt-Siebel et al.(1986 ); Szymanska-Buzar et al. (2001 ); Tudela et al. (1986 ). For tin compounds containing an Sn—Cl bond in a cis- or trans-position, see: Fernandez et al. (2002 ); Hazell et al. (1998 ); Sow et al. (2010 ). For tin compounds containing carboxylate moieties, see: Ng & Kumar Das (1993 ); Xu et al. (2003 ).

Experimental

Crystal data

(C₄H₁₂N)[Sn(C₂O₄)Cl₃(H₂O)]·H₂O
M_r = 423.24
Monoclinic, P 2₁ /n
a = 7.2458 (1) Å
b = 22.2812 (2) Å
c = 9.6019 (1) Å
β = 98.015 (1)°
V = 1535.04 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.20 mm⁻¹
T = 150 K
0.15 × 0.15 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.734, T_max = 0.763
35849 measured reflections
4445 independent reflections
3855 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.062
S = 1.08
4445 reflections
175 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H50A⋯O6	0.86 (2)	1.66 (2)	2.511 (2)	173 (3)
O5—H50B⋯O4ⁱ	0.85 (2)	1.78 (2)	2.6120 (19)	168 (3)
O6—H60B⋯O3ⁱⁱ	0.84 (2)	1.99 (2)	2.792 (2)	160 (3)
O6—H60A⋯O3ⁱⁱⁱ	0.84 (2)	1.95 (2)	2.7840 (19)	172 (3)
O6—H60B⋯O4ⁱⁱ	0.84 (2)	2.47 (3)	2.993 (2)	122 (3)
C6—H6B⋯O6ⁱ	0.98	2.54	3.411 (3)	148
C6—H6A⋯Cl3^iv	0.98	2.91	3.762 (3)	146
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x-1, y, z; (iii) -x+2, -y, -z+2; (iv) x, y, z-1.

Data collection: COLLECT (Nonius, 1999 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813000895/wm2712sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000895/wm2712Isup2.hkl

checkCIF report

Comment top

Numerous crystal structures of SnX₄ adducts (X = halogen) containing tin(IV) in an octahedral environment have been reported up to date, e.g. Hausen et al. (1986); Koutsantonis et al. (2003); Mahon et al. (2004); Patt-Siebel et al. (1986); Szymanska-Buzar et al. (2001); Tudela et al. (1986). Our group has previously reported the crystal structure of ((n-C₃H₇)₂NH₂)₂[Sn(C₂O₄)Cl₄] which contains a chelating oxalate anion, and the environment of tin(IV) being likewise octahedral (Sow et al., 2010). In the context of our search for new SnX₄ adducts we report here the study of the reaction between ((CH₃)₄N)₂C₂O₄^.2H₂O and SnCl₄ which has yielded the title compound, ((CH₃)₄N)[Sn(C₂O₄)Cl₃(H₂O)]^.H₂O. While many SnX₄ adducts have been reported (see above), a complex with a [SnCl₃]-containing residue is reported here.

The octahedral geometry around the tin(IV) atom is defined by three Cl atoms, two oxygen atoms from the chelating oxalate anion and the oxygen atom of a water molecule (Fig. 1). The two oxygen atoms from the oxalate anion and two of the Cl atoms are in the equatorial plane while the remaining Cl atom and the oxygen atom of the H₂O molecule are in axial positions.

The [Sn(C₂O₄)Cl₃(H₂O)]^- anions are connected to the lattice water molecule through H—O—H···OH₂ hydrogen bonds. The water molecule bonded to the tin(IV) atom is also hydrogen-bonded to the O4 atom of a neighbour complex-anion. The lattice water molecule O6 is bonded to O3 and O4 of the same oxalate anion through a bifurcated hydrogen bond and to a O3 atom of a neighbouring oxalate anion, leading to a layered structure extending parallel to (010). The cations are located between the anionic planes (Figs. 2,3). In the crystal packing, C—H···O and C—H···Cl interactions between cations and anions are also observed (Table 1).

The angle O5—Sn—Cl3 [170.75°(5)] deviates from linearity. The two Sn—Cl bond lengths in the equatorial plane are very similar [Sn—Cl2 = 2.3598 (5), Sn—Cl1 = 2.3627 (5) Å], but different from the one trans to the water molecule [Sn—Cl3 = 2.3926 (5) Å], pointing to a weak trans-effect involving the latter. The Sn—O5 bond of 2.0781 (15) Å involving the water molecule is shorter than the Sn—O bonds distances involving the oxalate anion [Sn—O1 = 2.0980 (13); Sn—O2 = 2.1025 (13) Å], whereby these two last Sn—O distances are very close. The dimensions of Sn—O bonds and Sn—Cl bonds are in the range of Sn—O and Sn—Cl bonds reported for O₂SnCl₄ containing adducts with cis- or trans-geometry (Fernandez et al., 2002; Hazell et al., 1998; Sow et al., 2010).

The C—O distances [O1—C1 = 1.285 (2); O2—C2 = 1.288 (2) Å; O3—C1 = 1.219 (2) Å; O4—C2 = 1.223 (2) Å] are in the typical range of C—O and C═O bonds (Ng & Kumar Das, 1993; Xu et al., 2003).

Related literature top

For background to halogentin(IV) chemistry, see: Hausen et al. (1986); Koutsantonis et al. (2003); Mahon et al. (2004); Patt-Siebel et al.(1986); Szymanska-Buzar et al. (2001); Tudela et al. (1986). For tin compounds containing an Sn—Cl bond in a cis- or trans-position, see: Fernandez et al. (2002); Hazell et al. (1998); Sow et al. (2010). For tin compounds containing carboxylate moieties, see: Ng & Kumar Das (1993); Xu et al. (2003).

Experimental top

All chemicals were purchased from Aldrich (Germany) and used without any further purification. ((CH₃)₄N)₂C₂O₄^.2H₂O has been obtained on allowing ((CH₃)₄N)OH as a 20% water solution to react with oxalic acid in a 2:1 ratio. A powder is obtained after evaporation of water at 333 K. On allowing the oxalic acid salt to react with SnCl₄ in a 1:1 ratio in ethanol, a colorless solution is obtained, which gives, after slow solvent evaporation, crystals suitable for X-ray determination . The reaction equation of the title compound is: ((CH₃)₄N)₂C₂O₄^.2H₂O + SnCl₄ → ((CH₃)₄N)Cl + ((CH₃)₄N)[Sn(C₂O₄)Cl₃H₂O]^.H₂O

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The asymmetric unit showing the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The layered structure of the anions and the lattice water molecule parallel to (010). O—H···O hydrogen bonding interactions are shown as dashed lines.
	Fig. 3. The packing of the structure showing O—H···O hydrogen bonding interactions as dashed lines [C—H···O and C—H···Cl contacts are omitted for clarity].

Tetramethylammonium aquatrichloridooxalatostannate(IV) monohydrate top

Crystal data top

(C₄H₁₂N)[Sn(C₂O₄)Cl₃(H₂O)]·H₂O	F(000) = 832
M_r = 423.24	D_x = 1.831 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 29534 reflections
a = 7.2458 (1) Å	θ = 2.9–30.0°
b = 22.2812 (2) Å	µ = 2.20 mm⁻¹
c = 9.6019 (1) Å	T = 150 K
β = 98.015 (1)°	Irregular, colourless
V = 1535.04 (3) Å³	0.15 × 0.15 × 0.13 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	4445 independent reflections
Radiation source: fine-focus sealed tube	3855 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
461 1.3 degree images with ω scans	θ_max = 30.0°, θ_min = 4.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −10→10
T_min = 0.734, T_max = 0.763	k = −28→31
35849 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.062	w = 1/[σ²(F_o²) + (0.0322P)² + 0.5616P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
4445 reflections	Δρ_max = 0.92 e Å⁻³
175 parameters	Δρ_min = −0.79 e Å⁻³
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0124 (5)

Crystal data top

(C₄H₁₂N)[Sn(C₂O₄)Cl₃(H₂O)]·H₂O	V = 1535.04 (3) Å³
M_r = 423.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.2458 (1) Å	µ = 2.20 mm⁻¹
b = 22.2812 (2) Å	T = 150 K
c = 9.6019 (1) Å	0.15 × 0.15 × 0.13 mm
β = 98.015 (1)°

Data collection top

Nonius KappaCCD diffractometer	4445 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3855 reflections with I > 2σ(I)
T_min = 0.734, T_max = 0.763	R_int = 0.042
35849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	4 restraints
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.92 e Å⁻³
4445 reflections	Δρ_min = −0.79 e Å⁻³
175 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
Sn	0.834510 (17)	0.112222 (6)	0.679281 (12)	0.02693 (6)
Cl1	0.61541 (8)	0.13476 (3)	0.83233 (5)	0.03867 (12)
Cl2	0.66559 (8)	0.14793 (3)	0.46760 (5)	0.04369 (14)
Cl3	1.01222 (8)	0.20243 (2)	0.72319 (6)	0.04152 (13)
O5	0.7216 (2)	0.02693 (7)	0.64413 (15)	0.0372 (3)
O1	1.00588 (18)	0.07154 (6)	0.84708 (13)	0.0278 (3)
O3	1.2565 (2)	0.01364 (6)	0.89271 (13)	0.0310 (3)
O4	1.28776 (19)	0.01308 (7)	0.61246 (13)	0.0323 (3)
O2	1.04412 (18)	0.07556 (6)	0.57415 (13)	0.0285 (3)
O6	0.5915 (2)	−0.03357 (7)	0.82856 (15)	0.0320 (3)
N	1.0670 (2)	0.16827 (7)	0.20003 (17)	0.0298 (3)
C1	1.1444 (2)	0.04194 (8)	0.81171 (17)	0.0241 (3)
C2	1.1635 (3)	0.04294 (8)	0.65224 (18)	0.0249 (3)
C3	0.9820 (3)	0.10701 (9)	0.1966 (3)	0.0370 (5)
H3A	0.8911	0.1053	0.2632	0.055*
H3B	1.0798	0.0771	0.2228	0.055*
H3C	0.9192	0.0985	0.1015	0.055*
C4	0.9184 (4)	0.21327 (11)	0.1570 (3)	0.0561 (7)
H4A	0.8558	0.2036	0.0624	0.084*
H4B	0.9739	0.2534	0.1566	0.084*
H4C	0.8274	0.2125	0.2235	0.084*
C5	1.1603 (4)	0.18245 (13)	0.3445 (2)	0.0500 (6)
H5A	1.2132	0.2230	0.3458	0.075*
H5B	1.2601	0.1533	0.3721	0.075*
H5C	1.0689	0.1804	0.4106	0.075*
C6	1.2081 (4)	0.17066 (11)	0.0997 (3)	0.0491 (6)
H6A	1.1482	0.1599	0.0051	0.074*
H6B	1.3090	0.1423	0.1300	0.074*
H6C	1.2592	0.2113	0.0984	0.074*
H50B	0.703 (4)	0.0121 (13)	0.562 (2)	0.058 (8)*
H60B	0.481 (3)	−0.0227 (14)	0.829 (3)	0.057 (9)*
H60A	0.647 (4)	−0.0270 (13)	0.909 (2)	0.053 (8)*
H50A	0.668 (4)	0.0068 (12)	0.704 (3)	0.059 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.02791 (9)	0.02922 (8)	0.02369 (8)	0.00383 (4)	0.00368 (5)	0.00042 (4)
Cl1	0.0382 (3)	0.0436 (3)	0.0363 (3)	0.0062 (2)	0.0124 (2)	−0.0069 (2)
Cl2	0.0376 (3)	0.0596 (3)	0.0325 (3)	0.0146 (2)	0.0002 (2)	0.0094 (2)
Cl3	0.0423 (3)	0.0295 (2)	0.0520 (3)	−0.0019 (2)	0.0039 (2)	0.0029 (2)
O5	0.0468 (9)	0.0414 (8)	0.0256 (7)	−0.0136 (7)	0.0122 (6)	−0.0087 (6)
O1	0.0321 (7)	0.0308 (6)	0.0208 (6)	0.0045 (5)	0.0048 (5)	−0.0001 (5)
O3	0.0316 (7)	0.0376 (7)	0.0230 (6)	0.0047 (6)	0.0014 (5)	0.0034 (5)
O4	0.0291 (7)	0.0442 (8)	0.0230 (6)	0.0069 (6)	0.0018 (5)	−0.0051 (5)
O2	0.0287 (7)	0.0362 (7)	0.0209 (6)	0.0051 (5)	0.0040 (5)	0.0033 (5)
O6	0.0323 (8)	0.0396 (8)	0.0239 (7)	0.0062 (6)	0.0031 (6)	0.0003 (5)
N	0.0361 (9)	0.0254 (7)	0.0272 (8)	−0.0021 (6)	0.0018 (6)	−0.0007 (6)
C1	0.0268 (9)	0.0247 (8)	0.0205 (8)	−0.0031 (6)	0.0024 (7)	−0.0013 (6)
C2	0.0260 (9)	0.0281 (8)	0.0199 (8)	−0.0025 (7)	0.0014 (6)	−0.0014 (6)
C3	0.0409 (12)	0.0269 (9)	0.0445 (12)	−0.0048 (8)	0.0106 (10)	−0.0014 (8)
C4	0.0539 (15)	0.0325 (12)	0.0774 (19)	0.0084 (10)	−0.0061 (13)	0.0040 (11)
C5	0.0551 (15)	0.0598 (15)	0.0319 (11)	−0.0207 (12)	−0.0052 (10)	0.0029 (10)
C6	0.0646 (16)	0.0399 (12)	0.0477 (13)	−0.0152 (11)	0.0249 (12)	−0.0067 (10)

Geometric parameters (Å, º) top

Sn—O5	2.0781 (15)	N—C3	1.496 (2)
Sn—O1	2.0980 (13)	N—C6	1.500 (3)
Sn—O2	2.1025 (13)	C1—C2	1.557 (2)
Sn—Cl2	2.3598 (5)	C3—H3A	0.9800
Sn—Cl1	2.3627 (5)	C3—H3B	0.9800
Sn—Cl3	2.3926 (5)	C3—H3C	0.9800
O5—H50B	0.850 (17)	C4—H4A	0.9800
O5—H50A	0.859 (17)	C4—H4B	0.9800
O1—C1	1.285 (2)	C4—H4C	0.9800
O3—C1	1.219 (2)	C5—H5A	0.9800
O4—C2	1.223 (2)	C5—H5B	0.9800
O2—C2	1.288 (2)	C5—H5C	0.9800
O6—H60B	0.836 (17)	C6—H6A	0.9800
O6—H60A	0.836 (17)	C6—H6B	0.9800
N—C4	1.488 (3)	C6—H6C	0.9800
N—C5	1.490 (3)

O5—Sn—O1	84.67 (6)	O1—C1—C2	115.63 (15)
O5—Sn—O2	82.02 (6)	O4—C2—O2	126.11 (16)
O1—Sn—O2	79.11 (5)	O4—C2—C1	118.03 (16)
O5—Sn—Cl2	91.33 (5)	O2—C2—C1	115.85 (15)
O1—Sn—Cl2	170.93 (4)	N—C3—H3A	109.5
O2—Sn—Cl2	92.30 (4)	N—C3—H3B	109.5
O5—Sn—Cl1	90.68 (4)	H3A—C3—H3B	109.5
O1—Sn—Cl1	89.50 (4)	N—C3—H3C	109.5
O2—Sn—Cl1	166.95 (4)	H3A—C3—H3C	109.5
Cl2—Sn—Cl1	98.70 (2)	H3B—C3—H3C	109.5
O5—Sn—Cl3	170.75 (5)	N—C4—H4A	109.5
O1—Sn—Cl3	88.93 (4)	N—C4—H4B	109.5
O2—Sn—Cl3	90.23 (4)	H4A—C4—H4B	109.5
Cl2—Sn—Cl3	94.03 (2)	N—C4—H4C	109.5
Cl1—Sn—Cl3	95.95 (2)	H4A—C4—H4C	109.5
Sn—O5—H50B	121 (2)	H4B—C4—H4C	109.5
Sn—O5—H50A	125 (2)	N—C5—H5A	109.5
H50B—O5—H50A	113 (3)	N—C5—H5B	109.5
C1—O1—Sn	114.77 (11)	H5A—C5—H5B	109.5
C2—O2—Sn	114.29 (11)	N—C5—H5C	109.5
H60B—O6—H60A	107 (3)	H5A—C5—H5C	109.5
C4—N—C5	109.4 (2)	H5B—C5—H5C	109.5
C4—N—C3	109.18 (18)	N—C6—H6A	109.5
C5—N—C3	110.24 (17)	N—C6—H6B	109.5
C4—N—C6	109.2 (2)	H6A—C6—H6B	109.5
C5—N—C6	109.25 (18)	N—C6—H6C	109.5
C3—N—C6	109.49 (16)	H6A—C6—H6C	109.5
O3—C1—O1	124.90 (16)	H6B—C6—H6C	109.5
O3—C1—C2	119.47 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H50A···O6	0.86 (2)	1.66 (2)	2.511 (2)	173 (3)
O5—H50B···O4ⁱ	0.85 (2)	1.78 (2)	2.6120 (19)	168 (3)
O6—H60B···O3ⁱⁱ	0.84 (2)	1.99 (2)	2.792 (2)	160 (3)
O6—H60A···O3ⁱⁱⁱ	0.84 (2)	1.95 (2)	2.7840 (19)	172 (3)
O6—H60B···O4ⁱⁱ	0.84 (2)	2.47 (3)	2.993 (2)	122 (3)
C6—H6B···O6ⁱ	0.98	2.54	3.411 (3)	148
C6—H6A···Cl3^iv	0.98	2.91	3.762 (3)	146

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

Experimental details

Crystal data
Chemical formula	(C₄H₁₂N)[Sn(C₂O₄)Cl₃(H₂O)]·H₂O
M_r	423.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	7.2458 (1), 22.2812 (2), 9.6019 (1)
β (°)	98.015 (1)
V (Å³)	1535.04 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.20
Crystal size (mm)	0.15 × 0.15 × 0.13

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.734, 0.763
No. of measured, independent and observed [I > 2σ(I)] reflections	35849, 4445, 3855
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.062, 1.08
No. of reflections	4445
No. of parameters	175
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.79

Computer programs: COLLECT (Nonius, 1999), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H50A···O6	0.859 (17)	1.657 (18)	2.511 (2)	173 (3)
O5—H50B···O4ⁱ	0.850 (17)	1.775 (18)	2.6120 (19)	168 (3)
O6—H60B···O3ⁱⁱ	0.836 (17)	1.99 (2)	2.792 (2)	160 (3)
O6—H60A···O3ⁱⁱⁱ	0.836 (17)	1.954 (18)	2.7840 (19)	172 (3)
O6—H60B···O4ⁱⁱ	0.836 (17)	2.47 (3)	2.993 (2)	122 (3)
C6—H6B···O6ⁱ	0.98	2.54	3.411 (3)	147.7
C6—H6A···Cl3^iv	0.98	2.91	3.762 (3)	146.3

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

References

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Volume 69| Part 2| February 2013| Pages m106-m107

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