catena-Poly[[tetra­aqua­manganese(II)]-μ-5-carboxyl­ato-1-carboxyl­atomethyl-2-oxidopyridinium-κ2O5:O1]

Yuan, H.-Y.; Jiang, M.-X.; Feng, Y.-L.

doi:10.1107/S1600536811025967

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1036

doi:10.1107/S1600536811025967

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catena-Poly[[tetraaquamanganese(II)]-μ-5-carboxylato-1-carboxylatomethyl-2-oxidopyridinium-κ²O⁵:O¹]

Hong-Yan Yuan,^a Mei-Xiang Jiang ^a and Yun-Long Feng ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky37@zjnu.edu.cn

(Received 23 June 2011; accepted 30 June 2011; online 6 July 2011)

In the title coordination polymer, [Mn(C₈H₅NO₅)(H₂O)₄]_n, the Mn^II atom is coordinated by two carboxylate O atoms from two 5-carboxylato-1-carboxylatomethyl-2-oxidopyridinium (L²⁻) ligands and by four water molecules in a distorted octahedral geometry. The L²⁻ ligands bridge the Mn atoms into an infinite chain motif along [100]; the chains are further interlinked by O—H⋯O hydrogen bonds into a three-dimensional supramolecular net.

Related literature

For the use of ligands involving pyridyl and carboxylate groups in the construction of novel complexes, see: Zhang et al. (2003 ); Jiang et al. (2010 ); Yang et al. (2010 ).

Experimental

Crystal data

[Mn(C₈H₅NO₅)(H₂O)₄]
M_r = 322.13
Monoclinic, P 2₁ /n
a = 5.1537 (2) Å
b = 21.2008 (9) Å
c = 10.9727 (4) Å
β = 99.182 (2)°
V = 1183.54 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 293 K
0.21 × 0.18 × 0.13 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.787, T_max = 0.858
11341 measured reflections
2680 independent reflections
2217 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.075
S = 1.03
2680 reflections
196 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2ⁱ	0.86 (1)	1.83 (1)	2.6833 (18)	171 (2)
O1W—H1WA⋯O1ⁱ	0.86 (1)	2.67 (2)	3.307 (2)	132 (2)
O1W—H1WB⋯O5ⁱⁱ	0.84 (1)	2.43 (2)	3.071 (2)	134 (2)
O2W—H2WA⋯O3ⁱⁱⁱ	0.84 (1)	1.88 (1)	2.7006 (19)	165 (2)
O2W—H2WB⋯O1ⁱ	0.84 (1)	2.01 (1)	2.8249 (18)	165 (2)
O3W—H3WA⋯O5^iv	0.85 (1)	1.83 (1)	2.6733 (18)	176 (2)
O3W—H3WB⋯O2ⁱⁱ	0.85 (1)	1.94 (1)	2.7550 (18)	159 (2)
O4W—H4WA⋯O3W^v	0.83 (1)	2.13 (1)	2.911 (2)	158 (2)
O4W—H4WB⋯O5	0.84 (1)	2.00 (1)	2.7270 (18)	145 (2)
Symmetry codes: (i) x+1, y, z-1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) x+1, y, z.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025967/ng5191sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025967/ng5191Isup2.hkl

checkCIF report

Comment top

Versatile ligands involving pyridyl and carboxylate groups have been extensively employed to construct novel complexes owing to their various coordination modes (Zhang et al., 2003; Jiang et al., 2010; Yang et al., 2010). Herein, we report the synthesis and crystal structure of a new complex, [MnL(H₂O)₄]_n (I).

In the title complex, the Mn(II) atom is six-coordinated by two carboxylic O atoms from two L^2- ligands and four water molecules, leading to a distorted octahedral environment (Fig. 1). Each L^2- ligand adopts a terminal monodentate bridging coordination mode to interconnect with the Mn(II) atoms forming a one-dimensional infinite polymeric chain motif. The shortest distance between the neighbour Mn(II) centers is 10.97 Å (Fig. 2). Additionally, with the aid of O—H···O hydrogen bonds found between the coordinated water molecules and carboxylato groups, the adjacent one-dimensional chains are further interlinked into a three-dimensional network (Fig. 3).

Related literature top

For the use of ligands involving pyridyl and carboxylate groups have in the construction of novel complexes, see: Zhang et al. (2003); Jiang et al. (2010); Yang et al. (2010).

Experimental top

All the starting materials and solvents were obtained commercially and were used without further purification. H₂L(0.197 g, 1.0 mmol), MnSO₄.H₂O (0.169 g, 1.0 mmol), Na₂CO₃ (0.106 g, 1.0 mmol) were mixed in 15 ml distilled water. Then the mixture was transferred into a Parr Teflon-lined stainless steel vessel (25 ml) and heated to 433 K for 72 h. Then, the reactor was cooled to room temperature at a speed of 5 degrees per hour. Colorless single crystals of title complex were obtained by slow evaporation of the filtrate over a few days.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the Mn(II) coordination environment in the structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (1) x + 1,y,z - 1]
	Fig. 2. A ball-stick diagram showing the one-dimensional chain. All H atoms have been omitted for clarity.
	Fig. 3. A packing structure of (I). The O—H···O interactions are depicted by green dashed lines.

catena-Poly[[tetraaquamanganese(II)]-µ-5-carboxylato- 1-carboxylatomethyl-2-oxidopyridinium-κ²O⁵:O¹] top

Crystal data top

[Mn(C₈H₅NO₅)(H₂O)₄]	F(000) = 660
M_r = 322.13	D_x = 1.808 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4396 reflections
a = 5.1537 (2) Å	θ = 2.1–27.4°
b = 21.2008 (9) Å	µ = 1.16 mm⁻¹
c = 10.9727 (4) Å	T = 293 K
β = 99.182 (2)°	Block, colourless
V = 1183.54 (8) Å³	0.21 × 0.18 × 0.13 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	2680 independent reflections
Radiation source: fine-focus sealed tube	2217 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 27.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→5
T_min = 0.787, T_max = 0.858	k = −27→27
11341 measured reflections	l = −14→14

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) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0353P)²] where P = (F_o² + 2F_c²)/3
2680 reflections	(Δ/σ)_max = 0.001
196 parameters	Δρ_max = 0.35 e Å⁻³
12 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Mn(C₈H₅NO₅)(H₂O)₄]	V = 1183.54 (8) Å³
M_r = 322.13	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.1537 (2) Å	µ = 1.16 mm⁻¹
b = 21.2008 (9) Å	T = 293 K
c = 10.9727 (4) Å	0.21 × 0.18 × 0.13 mm
β = 99.182 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	2680 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2217 reflections with I > 2σ(I)
T_min = 0.787, T_max = 0.858	R_int = 0.075
11341 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	12 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.35 e Å⁻³
2680 reflections	Δρ_min = −0.32 e Å⁻³
196 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
Mn1	0.82965 (5)	0.166986 (13)	0.24426 (2)	0.02401 (10)
O1W	0.9758 (3)	0.21539 (7)	0.08980 (12)	0.0362 (3)
H1WA	1.082 (4)	0.1969 (8)	0.0482 (18)	0.043*
H1WB	1.035 (4)	0.2513 (6)	0.1101 (19)	0.043*
O1	0.5110 (2)	0.12706 (7)	1.11849 (10)	0.0319 (3)
O2	0.2636 (3)	0.15549 (6)	0.94224 (11)	0.0339 (3)
O2W	1.0809 (3)	0.08634 (6)	0.22875 (13)	0.0349 (3)
H2WA	1.016 (4)	0.0515 (7)	0.2020 (19)	0.042*
H2WB	1.223 (3)	0.0930 (9)	0.2031 (19)	0.042*
O3	0.2033 (3)	0.01801 (6)	0.84321 (11)	0.0344 (3)
O3W	0.6083 (3)	0.25579 (6)	0.26185 (11)	0.0338 (3)
H3WA	0.541 (4)	0.2760 (8)	0.1977 (11)	0.041*
H3WB	0.695 (4)	0.2819 (7)	0.3121 (13)	0.041*
O4W	1.1443 (3)	0.21688 (8)	0.36280 (12)	0.0450 (4)
H4WA	1.298 (2)	0.2228 (12)	0.3515 (18)	0.054*
H4WB	1.130 (4)	0.2130 (12)	0.4374 (11)	0.054*
O4	0.6810 (3)	0.12960 (7)	0.39922 (10)	0.0380 (3)
O5	0.8922 (3)	0.18553 (7)	0.55471 (11)	0.0458 (4)
N1	0.5354 (3)	0.08088 (7)	0.80195 (11)	0.0235 (3)
C1	0.6287 (4)	0.08637 (9)	0.93507 (14)	0.0259 (4)
H1A	0.8038	0.1044	0.9478	0.031*
H1B	0.6408	0.0445	0.9712	0.031*
C2	0.4524 (3)	0.12667 (8)	1.00127 (14)	0.0234 (4)
C3	0.3169 (4)	0.04332 (8)	0.76408 (15)	0.0255 (4)
C4	0.2408 (4)	0.03795 (9)	0.63301 (16)	0.0329 (4)
H4A	0.0989	0.0124	0.6020	0.039*
C5	0.3701 (4)	0.06907 (9)	0.55330 (15)	0.0306 (4)
H5A	0.3164	0.0644	0.4688	0.037*
C6	0.5855 (3)	0.10852 (8)	0.59683 (14)	0.0247 (4)
C7	0.6617 (3)	0.11259 (8)	0.72141 (14)	0.0246 (4)
H7A	0.8047	0.1379	0.7521	0.029*
C8	0.7325 (4)	0.14390 (8)	0.51148 (14)	0.0258 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.02227 (17)	0.03188 (17)	0.01840 (14)	−0.00270 (11)	0.00482 (10)	−0.00096 (10)
O1W	0.0419 (9)	0.0354 (7)	0.0353 (7)	−0.0012 (6)	0.0186 (6)	0.0025 (6)
O1	0.0263 (7)	0.0522 (8)	0.0173 (5)	−0.0076 (6)	0.0043 (5)	−0.0044 (5)
O2	0.0372 (8)	0.0405 (8)	0.0242 (6)	0.0071 (6)	0.0057 (5)	0.0040 (5)
O2W	0.0281 (7)	0.0323 (7)	0.0465 (8)	−0.0056 (6)	0.0126 (6)	−0.0034 (6)
O3	0.0410 (8)	0.0357 (7)	0.0280 (6)	−0.0135 (6)	0.0101 (6)	0.0031 (5)
O3W	0.0362 (8)	0.0342 (7)	0.0290 (6)	0.0054 (6)	−0.0006 (6)	−0.0050 (5)
O4W	0.0301 (8)	0.0731 (11)	0.0328 (7)	−0.0181 (8)	0.0082 (6)	−0.0135 (7)
O4	0.0428 (9)	0.0544 (9)	0.0186 (6)	−0.0152 (7)	0.0104 (5)	−0.0008 (6)
O5	0.0661 (11)	0.0483 (9)	0.0249 (6)	−0.0263 (8)	0.0134 (7)	−0.0039 (6)
N1	0.0253 (8)	0.0301 (8)	0.0154 (6)	−0.0033 (6)	0.0045 (5)	0.0001 (5)
C1	0.0252 (9)	0.0365 (10)	0.0157 (7)	−0.0036 (7)	0.0025 (6)	0.0026 (6)
C2	0.0234 (9)	0.0283 (9)	0.0188 (7)	−0.0087 (7)	0.0040 (6)	−0.0001 (6)
C3	0.0284 (10)	0.0255 (9)	0.0233 (8)	−0.0018 (7)	0.0059 (7)	0.0002 (6)
C4	0.0357 (11)	0.0380 (11)	0.0245 (8)	−0.0119 (9)	0.0037 (7)	−0.0043 (7)
C5	0.0340 (11)	0.0392 (10)	0.0183 (7)	−0.0023 (8)	0.0031 (7)	−0.0028 (7)
C6	0.0279 (10)	0.0274 (9)	0.0198 (7)	0.0021 (7)	0.0073 (7)	0.0009 (6)
C7	0.0242 (9)	0.0288 (9)	0.0218 (7)	−0.0032 (7)	0.0071 (7)	0.0004 (7)
C8	0.0304 (10)	0.0289 (9)	0.0194 (7)	0.0041 (8)	0.0072 (7)	0.0028 (7)

Geometric parameters (Å, º) top

Mn1—O4	2.1265 (12)	O4W—H4WB	0.837 (9)
Mn1—O1ⁱ	2.1435 (12)	O4—C8	1.255 (2)
Mn1—O2W	2.1676 (14)	O5—C8	1.248 (2)
Mn1—O4W	2.1833 (14)	N1—C7	1.357 (2)
Mn1—O1W	2.2136 (12)	N1—C3	1.387 (2)
Mn1—O3W	2.2258 (13)	N1—C1	1.468 (2)
O1W—H1WA	0.862 (9)	C1—C2	1.515 (2)
O1W—H1WB	0.838 (9)	C1—H1A	0.9700
O1—C2	1.2734 (18)	C1—H1B	0.9700
O1—Mn1ⁱⁱ	2.1435 (12)	C3—C4	1.434 (2)
O2—C2	1.240 (2)	C4—C5	1.353 (2)
O2W—H2WA	0.844 (9)	C4—H4A	0.9300
O2W—H2WB	0.837 (9)	C5—C6	1.411 (3)
O3—C3	1.2438 (19)	C5—H5A	0.9300
O3W—H3WA	0.849 (9)	C6—C7	1.363 (2)
O3W—H3WB	0.854 (9)	C6—C8	1.497 (2)
O4W—H4WA	0.830 (9)	C7—H7A	0.9300

O4—Mn1—O1ⁱ	91.77 (5)	C7—N1—C1	119.59 (14)
O4—Mn1—O2W	93.71 (5)	C3—N1—C1	117.71 (13)
O1ⁱ—Mn1—O2W	92.51 (5)	N1—C1—C2	113.31 (14)
O4—Mn1—O4W	91.85 (5)	N1—C1—H1A	108.9
O1ⁱ—Mn1—O4W	174.12 (6)	C2—C1—H1A	108.9
O2W—Mn1—O4W	91.88 (6)	N1—C1—H1B	108.9
O4—Mn1—O1W	174.26 (5)	C2—C1—H1B	108.9
O1ⁱ—Mn1—O1W	90.54 (5)	H1A—C1—H1B	107.7
O2W—Mn1—O1W	91.44 (5)	O2—C2—O1	124.35 (16)
O4W—Mn1—O1W	85.44 (5)	O2—C2—C1	120.54 (14)
O4—Mn1—O3W	89.48 (5)	O1—C2—C1	115.09 (15)
O1ⁱ—Mn1—O3W	92.25 (5)	O3—C3—N1	119.24 (15)
O2W—Mn1—O3W	174.18 (5)	O3—C3—C4	125.59 (17)
O4W—Mn1—O3W	83.15 (6)	N1—C3—C4	115.16 (14)
O1W—Mn1—O3W	85.18 (5)	C5—C4—C3	121.71 (17)
Mn1—O1W—H1WA	121.2 (14)	C5—C4—H4A	119.1
Mn1—O1W—H1WB	111.9 (14)	C3—C4—H4A	119.1
H1WA—O1W—H1WB	108.4 (14)	C4—C5—C6	120.82 (16)
C2—O1—Mn1ⁱⁱ	133.39 (11)	C4—C5—H5A	119.6
Mn1—O2W—H2WA	120.7 (14)	C6—C5—H5A	119.6
Mn1—O2W—H2WB	117.2 (14)	C7—C6—C5	117.54 (15)
H2WA—O2W—H2WB	110.4 (14)	C7—C6—C8	120.12 (16)
Mn1—O3W—H3WA	120.1 (13)	C5—C6—C8	122.32 (14)
Mn1—O3W—H3WB	112.5 (14)	N1—C7—C6	122.01 (16)
H3WA—O3W—H3WB	108.1 (13)	N1—C7—H7A	119.0
Mn1—O4W—H4WA	128.3 (15)	C6—C7—H7A	119.0
Mn1—O4W—H4WB	111.3 (15)	O5—C8—O4	124.56 (15)
H4WA—O4W—H4WB	113.2 (15)	O5—C8—C6	119.06 (14)
C8—O4—Mn1	130.38 (12)	O4—C8—C6	116.37 (16)
C7—N1—C3	122.70 (14)

O1ⁱ—Mn1—O4—C8	−162.88 (17)	O3—C3—C4—C5	177.48 (19)
O2W—Mn1—O4—C8	104.49 (17)	N1—C3—C4—C5	−1.9 (3)
O4W—Mn1—O4—C8	12.48 (17)	C3—C4—C5—C6	−0.3 (3)
O1W—Mn1—O4—C8	−49.3 (6)	C4—C5—C6—C7	1.7 (3)
O3W—Mn1—O4—C8	−70.65 (17)	C4—C5—C6—C8	−179.72 (17)
C7—N1—C1—C2	106.33 (17)	C3—N1—C7—C6	−1.5 (3)
C3—N1—C1—C2	−73.06 (19)	C1—N1—C7—C6	179.13 (16)
Mn1ⁱⁱ—O1—C2—O2	−110.55 (19)	C5—C6—C7—N1	−0.8 (3)
Mn1ⁱⁱ—O1—C2—C1	70.8 (2)	C8—C6—C7—N1	−179.43 (15)
N1—C1—C2—O2	−5.9 (2)	Mn1—O4—C8—O5	−0.2 (3)
N1—C1—C2—O1	172.80 (14)	Mn1—O4—C8—C6	178.69 (12)
C7—N1—C3—O3	−176.60 (16)	C7—C6—C8—O5	−12.9 (3)
C1—N1—C3—O3	2.8 (2)	C5—C6—C8—O5	168.55 (18)
C7—N1—C3—C4	2.8 (2)	C7—C6—C8—O4	168.11 (17)
C1—N1—C3—C4	−177.83 (16)	C5—C6—C8—O4	−10.4 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2ⁱⁱⁱ	0.86 (1)	1.83 (1)	2.6833 (18)	171 (2)
O1W—H1WA···O1ⁱⁱⁱ	0.86 (1)	2.67 (2)	3.307 (2)	132 (2)
O1W—H1WB···O5^iv	0.84 (1)	2.43 (2)	3.071 (2)	134 (2)
O2W—H2WA···O3^v	0.84 (1)	1.88 (1)	2.7006 (19)	165 (2)
O2W—H2WB···O1ⁱⁱⁱ	0.84 (1)	2.01 (1)	2.8249 (18)	165 (2)
O3W—H3WA···O5^vi	0.85 (1)	1.83 (1)	2.6733 (18)	176 (2)
O3W—H3WB···O2^iv	0.85 (1)	1.94 (1)	2.7550 (18)	159 (2)
O4W—H4WA···O3W^vii	0.83 (1)	2.13 (1)	2.911 (2)	158 (2)
O4W—H4WB···O5	0.84 (1)	2.00 (1)	2.7270 (18)	145 (2)

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

Experimental details

Crystal data
Chemical formula	[Mn(C₈H₅NO₅)(H₂O)₄]
M_r	322.13
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.1537 (2), 21.2008 (9), 10.9727 (4)
β (°)	99.182 (2)
V (Å³)	1183.54 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.21 × 0.18 × 0.13

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.787, 0.858
No. of measured, independent and observed [I > 2σ(I)] reflections	11341, 2680, 2217
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.075, 1.03
No. of reflections	2680
No. of parameters	196
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)	0.35, −0.32

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2ⁱ	0.862 (9)	1.828 (9)	2.6833 (18)	171 (2)
O1W—H1WA···O1ⁱ	0.862 (9)	2.669 (18)	3.307 (2)	131.8 (18)
O1W—H1WB···O5ⁱⁱ	0.838 (9)	2.430 (16)	3.071 (2)	134.0 (16)
O2W—H2WA···O3ⁱⁱⁱ	0.844 (9)	1.875 (9)	2.7006 (19)	165.4 (19)
O2W—H2WB···O1ⁱ	0.837 (9)	2.007 (10)	2.8249 (18)	165 (2)
O3W—H3WA···O5^iv	0.849 (9)	1.826 (9)	2.6733 (18)	176.2 (18)
O3W—H3WB···O2ⁱⁱ	0.854 (9)	1.941 (12)	2.7550 (18)	159 (2)
O4W—H4WA···O3W^v	0.830 (9)	2.125 (11)	2.911 (2)	158 (2)
O4W—H4WB···O5	0.837 (9)	2.001 (13)	2.7270 (18)	145 (2)

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

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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