Aqua­(2,2′-bipyridine)(2-formyl-4,6-di­nitro­phenolato)nickel(II) perchlorate

Zhong, F.; Luo, Q.-Y.; Duan, D.-P.; Wang, Q.; Ying, S.-M.

doi:10.1107/S1600536807033442

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Aqua(2,2′-bipyridine)(2-formyl-4,6-dinitrophenolato)nickel(II) perchlorate

F. Zhong, Q.-Y. Luo, D.-P. Duan, Q. Wang and S.-M. Ying

In the title complex, [Ni(C₇H₃N₂O₆)(C₁₀H₈N₂)(H₂O)]ClO₄, the Ni^II ion adopts a distorted square-pyramidal coordination geometry, with the coordinated water molecule occupying the apical position. The Ni^II complex cation is linked to the ClO₄⁻ anion by O—H

O hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033442/xu2289sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033442/xu2289Isup2.hkl Contains datablock I

CCDC reference: 657571

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.052
wR factor = 0.161
Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O10     ..       6.01 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N2      ..       5.52 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ni1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       2.07

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Synthesis of transition metal complexes with aldehyde groups has been a subject of considerable importance (Huang & Gladysz, 1998). A series complexes of this type has been report (Li & Chen, 2006; Das et al., 1997; Wang et al., 2001). Recent years, research effort has been devoted to the study of substituted bis(salicylaldehydato)nickel(II) complexes because of their catalytic activity in the dimerization of propylene and in olefin oligomerization when used together with an aluminium co-catalyst and/or phosphine ligand (Wu & Lu, 2003). In order to study the structure of bis(salicylaldehydato)nickel(II) complexes, We reported here the synthesis and crystal structure of a new nickle(II) complex.

As shown in Fig. 1, the title compound contains one Ni(II) ion, one 2-formyl-4,6-dinitrophenolate (L) ligand, one 2,2'-bipyridine, one coordinated water molecules and one ClO₄^- anion. This compound exhibits a mononuclear structure. The Ni atom is five coordinated by two O atoms from the L ligand, two N atoms from the bidentate ligand (bipy) and one O atom from the coordinated water molecule, forming a slightly distorted square pyramidal geometry, with N1, N2, O10, O1 in the basal plane and O1W in the axial position. The bond lengths of Ni—O or Ni—N are similar to those reported for other Ni complexes (Das et al., 1997). The [Ni(2,2'-bipy)(L)(H₂O)]⁺ cations and the ClO₄^- anions are interlinked into a supramolecular structure by the O···O hydrogen bond which exists between the oxygen atoms of the water molecule and the oxygen atoms of the perchlorate (Fig. 2).

Related literature top

For general background, see Huang & Gladysz (1988); Li & Chen (2006); Wang et al. (2001); Wu & Lu (2003). For a related structure, see Das et al. (1997).

Experimental top

An aqueous solution (10 ml) nickel perchloride (0.46 g, 1 mmol) was added dropwise inyo an ethanol-water solution of 2-hydroxy-3,5-dinitrobenzaldehyde (0.21 g, 1 mmol). Then an ethanol solution (3 ml) of 2,2'-bipy (0.16 g, 1 mmol) was mixed with the above solution. The mixture was stirred for 1 h at room temperature. The green crystal was separated by slow evaporation of the solvent at room temperature over a period of about two weeks.

Structure description top

For general background, see Huang & Gladysz (1988); Li & Chen (2006); Wang et al. (2001); Wu & Lu (2003). For a related structure, see Das et al. (1997).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.
	Fig. 2. Projection of the title compound viewed down the c axis.

Aqua(2,2'-bipyridine)(2-formyl-4,6-dinitrophenolato)nickel(II) perchlorate top

Crystal data top

[Ni(C₇H₃N₂O₆)(C₁₀H₈N₂)(H₂O)]ClO₄	F(000) = 1104
M_r = 543.47	D_x = 1.734 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3862 reflections
a = 7.4481 (3) Å	θ = 2.0–25.5°
b = 24.1832 (9) Å	µ = 1.13 mm⁻¹
c = 11.6691 (4) Å	T = 293 K
β = 98.021 (2)°	Block, green
V = 2081.26 (13) Å³	0.28 × 0.22 × 0.16 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	3862 independent reflections
Radiation source: fine-focus sealed tube	2976 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→9
T_min = 0.742, T_max = 0.840	k = −25→29
11140 measured reflections	l = −13→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0899P)² + 1.1617P] where P = (F_o² + 2F_c²)/3
3862 reflections	(Δ/σ)_max = 0.002
307 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Ni(C₇H₃N₂O₆)(C₁₀H₈N₂)(H₂O)]ClO₄	V = 2081.26 (13) Å³
M_r = 543.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4481 (3) Å	µ = 1.13 mm⁻¹
b = 24.1832 (9) Å	T = 293 K
c = 11.6691 (4) Å	0.28 × 0.22 × 0.16 mm
β = 98.021 (2)°

Data collection top

Bruker APEX area-detector diffractometer	3862 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	2976 reflections with I > 2σ(I)
T_min = 0.742, T_max = 0.840	R_int = 0.036
11140 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.05	Δρ_max = 0.53 e Å⁻³
3862 reflections	Δρ_min = −0.42 e Å⁻³
307 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
Ni1	0.38844 (6)	0.12807 (2)	0.36590 (4)	0.0515 (2)
Cl1	0.72075 (18)	0.29702 (6)	0.25988 (10)	0.0786 (4)
N1	0.5932 (4)	0.10590 (14)	0.2851 (3)	0.0552 (8)
N2	0.3009 (5)	0.16174 (13)	0.2129 (3)	0.0602 (8)
N3	0.6769 (5)	0.02080 (16)	0.6778 (3)	0.0671 (9)
N4	0.2015 (7)	0.05604 (18)	0.9129 (4)	0.0847 (12)
O1	0.4707 (4)	0.08100 (12)	0.4955 (2)	0.0634 (7)
O2	0.7174 (5)	−0.02028 (15)	0.7391 (3)	0.0905 (10)
O3	0.7727 (5)	0.03745 (18)	0.6097 (3)	0.1009 (13)
O4	0.2983 (7)	0.03533 (18)	0.9933 (3)	0.1120 (14)
O5	0.0433 (7)	0.0705 (2)	0.9158 (4)	0.1288 (17)
O6	0.8095 (11)	0.3113 (3)	0.1710 (6)	0.206 (3)
O7	0.7424 (13)	0.3400 (3)	0.3349 (6)	0.223 (4)
O8	0.5391 (9)	0.2903 (3)	0.2204 (7)	0.212 (4)
O9	0.7850 (8)	0.2486 (3)	0.3140 (7)	0.181 (3)
O10	0.1627 (4)	0.14491 (14)	0.4282 (3)	0.0718 (8)
O1W	0.5206 (5)	0.20274 (14)	0.4487 (3)	0.0907 (11)
H1W	0.5704	0.2073	0.5167	0.136*
H2W	0.5965	0.2181	0.4059	0.136*
C1	0.4103 (5)	0.07758 (15)	0.5925 (3)	0.0510 (8)
C2	0.5053 (5)	0.04762 (16)	0.6876 (3)	0.0548 (9)
C3	0.4404 (6)	0.04219 (16)	0.7917 (3)	0.0601 (10)
H3	0.5072	0.0230	0.8524	0.072*
C4	0.2758 (6)	0.06537 (16)	0.8056 (3)	0.0603 (10)
C5	0.1757 (6)	0.09459 (16)	0.7184 (4)	0.0611 (10)
H5	0.0649	0.1099	0.7297	0.073*
C6	0.2406 (5)	0.10143 (16)	0.6121 (3)	0.0541 (9)
C7	0.1301 (6)	0.13249 (18)	0.5261 (4)	0.0667 (11)
H7	0.0203	0.1450	0.5457	0.080*
C8	0.7379 (6)	0.07741 (19)	0.3332 (4)	0.0669 (11)
H8	0.7462	0.0670	0.4105	0.080*
C9	0.8763 (6)	0.0629 (2)	0.2709 (5)	0.0772 (13)
H9	0.9765	0.0432	0.3055	0.093*
C10	0.8616 (7)	0.0785 (2)	0.1571 (5)	0.0804 (14)
H10	0.9532	0.0693	0.1138	0.096*
C11	0.7148 (7)	0.1070 (2)	0.1069 (4)	0.0756 (13)
H11	0.7039	0.1167	0.0291	0.091*
C12	0.5786 (6)	0.12171 (16)	0.1738 (4)	0.0616 (11)
C13	0.4126 (6)	0.15312 (17)	0.1330 (3)	0.0618 (10)
C14	0.3683 (8)	0.1739 (2)	0.0216 (4)	0.0780 (13)
H14	0.4454	0.1680	−0.0335	0.094*
C15	0.2122 (10)	0.2028 (2)	−0.0067 (4)	0.0951 (18)
H15	0.1825	0.2171	−0.0810	0.114*
C16	0.0993 (8)	0.2109 (2)	0.0742 (5)	0.0856 (15)
H16	−0.0089	0.2302	0.0556	0.103*
C17	0.1483 (6)	0.18994 (18)	0.1844 (4)	0.0693 (11)
H17	0.0722	0.1957	0.2401	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0540 (3)	0.0636 (3)	0.0395 (3)	0.0065 (2)	0.0162 (2)	0.0060 (2)
Cl1	0.0865 (8)	0.0984 (9)	0.0533 (6)	−0.0131 (7)	0.0182 (5)	−0.0012 (6)
N1	0.061 (2)	0.0607 (17)	0.0473 (18)	−0.0045 (16)	0.0191 (15)	−0.0026 (14)
N2	0.074 (2)	0.0582 (19)	0.0496 (18)	−0.0063 (17)	0.0124 (16)	0.0028 (15)
N3	0.060 (2)	0.082 (2)	0.060 (2)	0.0082 (18)	0.0111 (17)	0.0163 (18)
N4	0.115 (4)	0.085 (3)	0.059 (2)	0.011 (3)	0.031 (2)	0.002 (2)
O1	0.0602 (16)	0.0836 (19)	0.0509 (15)	0.0152 (14)	0.0231 (13)	0.0131 (14)
O2	0.084 (2)	0.099 (2)	0.091 (2)	0.0278 (19)	0.0200 (18)	0.034 (2)
O3	0.068 (2)	0.143 (3)	0.099 (3)	0.027 (2)	0.036 (2)	0.050 (2)
O4	0.164 (4)	0.118 (3)	0.059 (2)	0.019 (3)	0.032 (2)	0.018 (2)
O5	0.138 (4)	0.169 (4)	0.095 (3)	0.036 (3)	0.073 (3)	0.026 (3)
O6	0.253 (8)	0.236 (7)	0.159 (5)	−0.084 (6)	0.134 (6)	−0.007 (5)
O7	0.321 (10)	0.208 (7)	0.140 (5)	0.025 (7)	0.034 (6)	−0.081 (5)
O8	0.131 (5)	0.253 (8)	0.234 (8)	−0.073 (5)	−0.039 (5)	0.082 (7)
O9	0.146 (5)	0.164 (5)	0.243 (7)	0.041 (4)	0.070 (5)	0.066 (5)
O10	0.0678 (19)	0.096 (2)	0.0543 (17)	0.0221 (16)	0.0180 (14)	0.0176 (15)
O1W	0.129 (3)	0.085 (2)	0.0584 (19)	−0.018 (2)	0.0141 (19)	−0.0086 (16)
C1	0.057 (2)	0.054 (2)	0.045 (2)	−0.0015 (16)	0.0182 (16)	0.0034 (16)
C2	0.053 (2)	0.059 (2)	0.054 (2)	0.0031 (17)	0.0145 (17)	0.0046 (17)
C3	0.074 (3)	0.061 (2)	0.046 (2)	0.001 (2)	0.0104 (18)	0.0061 (17)
C4	0.081 (3)	0.059 (2)	0.045 (2)	0.000 (2)	0.025 (2)	−0.0009 (17)
C5	0.066 (3)	0.063 (2)	0.060 (2)	0.0050 (19)	0.027 (2)	−0.0043 (19)
C6	0.057 (2)	0.063 (2)	0.045 (2)	0.0048 (18)	0.0161 (16)	0.0024 (16)
C7	0.062 (3)	0.083 (3)	0.060 (3)	0.016 (2)	0.025 (2)	0.005 (2)
C8	0.065 (3)	0.080 (3)	0.059 (2)	0.001 (2)	0.021 (2)	−0.002 (2)
C9	0.064 (3)	0.086 (3)	0.088 (3)	0.002 (2)	0.035 (2)	−0.011 (3)
C10	0.076 (3)	0.088 (3)	0.087 (3)	−0.009 (3)	0.048 (3)	−0.019 (3)
C11	0.093 (4)	0.084 (3)	0.058 (3)	−0.018 (3)	0.040 (3)	−0.011 (2)
C12	0.077 (3)	0.060 (2)	0.051 (2)	−0.017 (2)	0.023 (2)	−0.0082 (18)
C13	0.083 (3)	0.055 (2)	0.050 (2)	−0.018 (2)	0.018 (2)	−0.0012 (18)
C14	0.113 (4)	0.076 (3)	0.048 (2)	−0.012 (3)	0.021 (2)	0.009 (2)
C15	0.140 (5)	0.090 (4)	0.052 (3)	−0.014 (4)	0.002 (3)	0.019 (3)
C16	0.096 (4)	0.077 (3)	0.080 (3)	0.003 (3)	−0.006 (3)	0.022 (3)
C17	0.078 (3)	0.069 (3)	0.060 (3)	0.004 (2)	0.006 (2)	0.007 (2)

Geometric parameters (Å, º) top

Ni1—O1	1.924 (3)	C2—C3	1.375 (5)
Ni1—O10	1.965 (3)	C3—C4	1.378 (6)
Ni1—N1	1.975 (3)	C3—H3	0.9300
Ni1—N2	1.988 (3)	C4—C5	1.371 (6)
Ni1—O1W	2.213 (3)	C5—C6	1.402 (5)
Cl1—O6	1.351 (5)	C5—H5	0.9300
Cl1—O7	1.355 (6)	C6—C7	1.421 (6)
Cl1—O9	1.384 (6)	C7—H7	0.9300
Cl1—O8	1.377 (6)	C8—C9	1.386 (6)
N1—C8	1.335 (5)	C8—H8	0.9300
N1—C12	1.344 (5)	C9—C10	1.370 (7)
N2—C17	1.328 (5)	C9—H9	0.9300
N2—C13	1.349 (5)	C10—C11	1.355 (8)
N3—O3	1.209 (5)	C10—H10	0.9300
N3—O2	1.237 (5)	C11—C12	1.410 (6)
N3—C2	1.452 (5)	C11—H11	0.9300
N4—O4	1.209 (6)	C12—C13	1.472 (7)
N4—O5	1.235 (6)	C13—C14	1.390 (6)
N4—C4	1.455 (5)	C14—C15	1.358 (8)
O1—C1	1.278 (4)	C14—H14	0.9300
O10—C7	1.238 (5)	C15—C16	1.364 (8)
O1W—H1W	0.8354	C15—H15	0.9300
O1W—H2W	0.8863	C16—C17	1.383 (7)
C1—C2	1.427 (5)	C16—H16	0.9300
C1—C6	1.437 (5)	C17—H17	0.9300

O1—Ni1—O10	91.56 (11)	C5—C4—C3	121.5 (4)
O1—Ni1—N1	91.83 (12)	C5—C4—N4	119.1 (4)
O10—Ni1—N1	171.87 (14)	C3—C4—N4	119.3 (4)
O1—Ni1—N2	167.74 (13)	C4—C5—C6	119.9 (4)
O10—Ni1—N2	93.27 (13)	C4—C5—H5	120.0
N1—Ni1—N2	82.00 (14)	C6—C5—H5	120.0
O1—Ni1—O1W	93.80 (13)	C5—C6—C7	116.8 (4)
O10—Ni1—O1W	91.19 (14)	C5—C6—C1	120.9 (4)
N1—Ni1—O1W	95.96 (14)	C7—C6—C1	122.4 (3)
N2—Ni1—O1W	97.36 (13)	O10—C7—C6	127.7 (4)
O6—Cl1—O7	105.8 (5)	O10—C7—H7	116.1
O6—Cl1—O9	113.1 (5)	C6—C7—H7	116.1
O7—Cl1—O9	110.6 (5)	N1—C8—C9	121.7 (4)
O6—Cl1—O8	109.7 (5)	N1—C8—H8	119.1
O7—Cl1—O8	109.3 (6)	C9—C8—H8	119.1
O9—Cl1—O8	108.3 (4)	C10—C9—C8	118.3 (5)
C8—N1—C12	120.3 (4)	C10—C9—H9	120.8
C8—N1—Ni1	124.9 (3)	C8—C9—H9	120.8
C12—N1—Ni1	114.8 (3)	C11—C10—C9	120.6 (4)
C17—N2—C13	119.7 (4)	C11—C10—H10	119.7
C17—N2—Ni1	126.7 (3)	C9—C10—H10	119.7
C13—N2—Ni1	113.6 (3)	C10—C11—C12	119.3 (4)
O3—N3—O2	122.0 (4)	C10—C11—H11	120.4
O3—N3—C2	120.6 (4)	C12—C11—H11	120.4
O2—N3—C2	117.4 (3)	N1—C12—C11	119.7 (4)
O4—N4—O5	124.4 (5)	N1—C12—C13	114.2 (4)
O4—N4—C4	118.3 (5)	C11—C12—C13	126.0 (4)
O5—N4—C4	117.3 (5)	N2—C13—C14	120.1 (4)
C1—O1—Ni1	128.5 (2)	N2—C13—C12	115.3 (4)
C7—O10—Ni1	125.4 (3)	C14—C13—C12	124.6 (4)
Ni1—O1W—H1W	129.3	C15—C14—C13	119.8 (5)
Ni1—O1W—H2W	112.1	C15—C14—H14	120.1
H1W—O1W—H2W	104.2	C13—C14—H14	120.1
O1—C1—C2	121.6 (3)	C16—C15—C14	119.7 (5)
O1—C1—C6	122.8 (3)	C16—C15—H15	120.1
C2—C1—C6	115.6 (3)	C14—C15—H15	120.1
C3—C2—C1	122.6 (4)	C15—C16—C17	118.9 (5)
C3—C2—N3	116.6 (4)	C15—C16—H16	120.6
C1—C2—N3	120.8 (3)	C17—C16—H16	120.6
C2—C3—C4	119.5 (4)	N2—C17—C16	121.8 (5)
C2—C3—H3	120.2	N2—C17—H17	119.1
C4—C3—H3	120.2	C16—C17—H17	119.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O6ⁱ	0.84	2.39	3.149 (8)	151
O1W—H1W···O8ⁱ	0.84	2.42	3.159 (9)	148
O1W—H2W···O9	0.89	2.02	2.906 (8)	175

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₃N₂O₆)(C₁₀H₈N₂)(H₂O)]ClO₄
M_r	543.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.4481 (3), 24.1832 (9), 11.6691 (4)
β (°)	98.021 (2)
V (Å³)	2081.26 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.28 × 0.22 × 0.16

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.742, 0.840
No. of measured, independent and observed [I > 2σ(I)] reflections	11140, 3862, 2976
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.161, 1.05
No. of reflections	3862
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.42

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O6ⁱ	0.84	2.39	3.149 (8)	151
O1W—H1W···O8ⁱ	0.84	2.42	3.159 (9)	148
O1W—H2W···O9	0.89	2.02	2.906 (8)	175

Symmetry code: (i) x, −y+1/2, z+1/2.

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