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In the title complex, [Ni(H2O)6](C6H10N2O6PS)2·6H2O, the asymmetric unit consists of one-half of an Ni atom (which lies on an inversion centre) with three coordinated water mol­ecules, one complete 2-carboxyl­ato-2-(isothio­uronium-S-ylmethyl)­propane-1,3-diyl phosphate anion and three non­coordinated water mol­ecules. The hexa­aqua­nickel(II) cations have distorted octa­hedral coordination and are connected via water chains to form two-dimensional supra­molecular networks parallel to the ab plane. The phosphate ester anion is linked via N—H...O and O—H...O hydrogen bonds, thus creating various ring, dimer and chain hydrogen-bonding patterns, and building up a second two-dimensional supra­molecular network parallel to the ab plane. The crystal structure is further stabilized by an intra- and inter­layer hydrogen-bond network. This work illustrates that a carboxyl­ate with a caged phosphate ester can open its ring in the presence of dichlorido­tetra­kis(thio­urea)nickel, and the re­sulting polyfunctional anion can be used for constructing a complex hydrogen-bonding scheme.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108007956/av3143sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108007956/av3143Isup2.hkl
Contains datablock I

CCDC reference: 690174

Comment top

This study was initiated as an exploration of a complex containing both a proton donor and a proton acceptor, formed via reaction of a carboxylate with a caged phosphate ester, OP(OCH2)3CCOO-, with Ni(thiourea)4Cl2, because there are currently two main strategies in crystal engineering, based on the use of either co-coordinative bonds or weaker intermolecular interactions (Burrows et al., 2000). The reaction of the coordinated thiourea with the caged phosphate ester unexpectedly produced a polyfunctional anion, 2-N-isothiouronium-S-ylmethyl-2-carboxy-1,3-propandiyl phosphate, where the structure of the bicyclic OP(OCH2)3C cage is opened. Intermolecular interactions between the N-isothiouronium cation and the carboxylate anion, between the 1,3-propandiyl phosphate and water molecules, and so on, result in a wide variety of hydrogen-bond patterns. In addition, intermolecular interactions between the hexaaquanickel(II) cation and non-coordinated water molecules also create a number of interesting water chains and hydrogen-bonded ring graph sets. We describe here the interesting structure of the title compound, (I), with rich O—H···O intra- and interlayer hydrogen-bonding and N—H···O dimer hydrogen-bond patterns, leading to a three-dimensional supramolecular network.

The asymmetric unit of (I) comprises one-half of an Ni atom with three coordinated water molecules, one complete 2-N-isothiouronium-S-ylmethyl-2-carboxy-1,3-propandiyl phosphate anion and three non-coordinated water molecules, and is shown in Fig. 1 in a symmetry-expanded view, which displays the full coordination of the hexaaquanickel(II) cation and the phosphate ester anion. Selected geometric parameters are given in Table 1.

The hexaaquanickel(II) cation of (I) has a distorted octahedral environment. The interactions of the coordinated water molecules and atoms O11 and O12 form network architectures of interesting topology. In the crystallographic b direction, atoms H3B and H2B coordinate to O11v and O11, respectively [symmetry codes: (v) x, y+1, z]. Similarly, atoms H3A and H1A connect to O12 and O12iv, respectively, in the crystallographic a direction [symmetry codes: (iv) x-1, y, z]. Each of them results in the formation of a 12-membered hydrogen-bonded R42(12) ring graph set (Bernstein et al., 1995), which links two hexaaquanickel(II) cations together. These distinct hydrogen-bonding interactions (Fig. 2) are together responsible for the formation of a 20-membered hydrogen-bonded R84(20) ring graph set with two chains of five water molecules. In this way, the hexaaquanickel(II) cations are interconnected together and a two-dimensional supramolecular network of the structure parallel to the ab plane (Fig. 2) is formed.

The 2-N-isothiouronium-S-ylmethyl-2-carboxy-1,3-propandiyl phosphate anion contains a phosphate ester anion, a carboxylate anion and a N-isothiouronium cation. The deprotonated carboxylate group O8/C4/O9 lies on the equatorial site of atom C2 of the chair six-membered ring and its two C—O bonds are equivalent. The N-isothiouronium cation N1/C6/N2 is connected with the methyl group on the axial site of atom C2 via S1 atom and its N—C—N bond is also in a conjugated system (Table 1). In the present structure, there is an intermolecular dimer hydrogen-bonded D22(8) graph set interaction between the O atoms of the carboxylate group and the N—H bonds of the N-isothiouronium cation (Fig. 3). Interactions between N2—H2D and O8iii [symmetry codes: (iii) -x+1, -y, -z] result in the connectivity of these D22(8) graph sets to form two C(6) graph sets along the crystallographic a direction. N1—H1D and the water molecules O10 and O9v are also engaged in the connectivity with the phosphate ester anion. They are responsible for the formation of a hydrogen-bonded C22(10) graph set in the crystallographic b direction. Thus, another two-dimensional layer network of the phosphate ester anion parallel to ab plane is formed.

The structure of (I) as a whole consists of these two distinct types of layers, which are stacked alternately in the [001] direction. The connectivity between the neighbouring layers is mainly completed via the hydrogen-bond interactions between the O atoms of the P—O bond and water molecules. The P1 atom has a distorted tetrahedral environment. The P1—O bonds are longer than corresponding ones in C12H9N2+.OP(OCH2)3CCOO-.OP(OCH2)3CCOOH.H2O (Wang, et al., 2007) and in O=P(OCH2)3CCH2OH (Guo & Zang, 2007), where P=O distances are in the range 1.446 (3)–1.4573 (15) Å, while P—O single bond distances cover the range 1.535 (4)–1.5667 (15) Å. This indicates that the ring stretch of the present phosphate ester anion is smaller than that of the caged phosphate ester. The O4—P1—O5 bond share a negative charge, so atoms O4 and O5 can act as efficient H-atom acceptors. Thus, for atoms O4 and O5 there are three hydrogen-bond interactions, respectively (Table 2). Interestingly, atom H11A is involved in an unexpected intermolecular O11—H11A···O7vii hydrogen bond [symmetry codes: (vii) -x+1, -y, -z+1], where the O atom of C2—O7—P1 group acts as acceptor. The water molecules (atoms O10, O11 and O12) act as both proton donor and proton acceptor to link the phosphate ester anion to the Ni atoms via coordinated water molecules. The whole three-dimensional structure is maintained and stabilized by the presence of these intra- and interlayer hydrogen bonds (Table 2).

Experimental top

Ni(thiourea)4Cl2 (0.69 g, 1.6 mmol) was added to a mixture of an aqueous solution (20 ml) of anhydrous sodium carbonate (0.16 g, 1.5 mmol) and 1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-4-carboxylic acid (0.61 g, 3.2 mmol) with stirring at room temperature for 20 min. After filtration, slow evaporation of the filtrate for three weeks at room temperature provided crystals of (I).

Refinement top

All water H atoms were found in a difference Fourier map and were fixed during refinement at O—H distances of 0.85 Å, with Uiso(H) = 1.2Ueq(O). The H atoms of the C—H and N—H groups were treated as riding, with C—H = 0.97 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. A view of the structure of (I), showing the atom-numbering scheme and the coordination environments of the Ni atom and the phosphate ester anion. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) 1 - x, 1 - y, 1 - z].
[Figure 2] Fig. 2. A packing plot for (I), showing the two-dimensional layer connectivity and the hydrogen-bonding interactions (dashed lines) of the hexaaquanickel(II) cations and water molecules O11 and O12 parallel to ab plane, viewed down the c axis.
[Figure 3] Fig. 3. A packing diagram for (I), showing the hydrogen-bonding interactions as dashed lines in the ab plane.
Hexaaquanickel(II) bis[2-carboxylato-2-(isothiouronium-S-ylmethyl)propane-1,3-diyl phosphate] hexahydrate top
Crystal data top
[Ni(H2O)6](C6H10N2O6PS)2·6H2OZ = 1
Mr = 813.28F(000) = 426
Triclinic, P1Dx = 1.710 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2701 (12) ÅCell parameters from 2700 reflections
b = 6.4816 (12) Åθ = 3.1–26.4°
c = 19.616 (4) ŵ = 0.95 mm1
α = 95.807 (3)°T = 294 K
β = 93.091 (3)°Block, green
γ = 93.760 (3)°0.28 × 0.24 × 0.22 mm
V = 789.9 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2789 independent reflections
Radiation source: fine-focus sealed tube2482 reflections with I > 2σ
Graphite monochromatorRint = 0.018
ϕ and ω scansθmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 67
Tmin = 0.765, Tmax = 0.818k = 77
4055 measured reflectionsl = 2223
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0402P)2 + 0.6065P]
where P = (Fo2 + 2Fc2)/3
2789 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
[Ni(H2O)6](C6H10N2O6PS)2·6H2Oγ = 93.760 (3)°
Mr = 813.28V = 789.9 (3) Å3
Triclinic, P1Z = 1
a = 6.2701 (12) ÅMo Kα radiation
b = 6.4816 (12) ŵ = 0.95 mm1
c = 19.616 (4) ÅT = 294 K
α = 95.807 (3)°0.28 × 0.24 × 0.22 mm
β = 93.091 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2789 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2482 reflections with I > 2σ
Tmin = 0.765, Tmax = 0.818Rint = 0.018
4055 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.084H-atom parameters constrained
S = 1.05Δρmax = 0.49 e Å3
2789 reflectionsΔρmin = 0.49 e Å3
205 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
xyzUiso*/Ueq
Ni10.50000.50000.50000.02462 (13)
P10.64559 (9)0.08749 (10)0.30461 (3)0.02290 (16)
S10.41441 (10)0.32226 (9)0.11184 (3)0.03093 (17)
C10.5881 (3)0.0897 (4)0.17245 (11)0.0215 (5)
H1E0.60040.23840.16440.026*
H1F0.64310.02630.13360.026*
C20.2682 (4)0.1298 (4)0.24308 (11)0.0273 (5)
H2E0.12100.09540.24750.033*
H2F0.27050.28010.23890.033*
C30.3530 (3)0.0470 (3)0.17813 (11)0.0214 (5)
C40.2195 (4)0.1605 (3)0.11498 (11)0.0227 (5)
C50.3200 (4)0.1877 (4)0.18258 (12)0.0279 (5)
H5A0.39260.25410.22480.033*
H5B0.16830.20580.18560.033*
C60.2075 (4)0.2744 (4)0.04664 (12)0.0251 (5)
N10.0039 (3)0.2580 (3)0.05896 (11)0.0322 (5)
H1C0.09190.24180.02540.039*
H1D0.03380.26330.10060.039*
N20.2711 (3)0.2671 (3)0.01556 (10)0.0318 (5)
H2C0.17850.25110.05000.038*
H2D0.40560.27830.02220.038*
O10.4141 (3)0.4878 (3)0.39677 (9)0.0368 (4)
H1A0.28050.47790.38600.044*
H1B0.49470.54830.37010.044*
O20.6239 (3)0.2199 (3)0.48119 (10)0.0449 (5)
H2A0.64090.16840.44030.054*
H2B0.69240.16870.51290.054*
O30.7910 (3)0.6462 (3)0.48574 (11)0.0497 (5)
H3A0.87870.60060.45770.060*
H3B0.82140.76650.50690.060*
O40.7617 (3)0.0529 (3)0.36138 (9)0.0345 (4)
O50.6648 (3)0.3155 (3)0.30392 (9)0.0366 (4)
O60.7158 (2)0.0076 (2)0.23479 (8)0.0242 (4)
O70.3974 (3)0.0411 (3)0.30427 (8)0.0274 (4)
O80.3045 (3)0.1790 (3)0.05863 (8)0.0290 (4)
O90.0299 (3)0.2200 (3)0.12484 (9)0.0335 (4)
O100.1238 (3)0.4457 (3)0.18989 (11)0.0498 (5)
H10A0.17710.47400.22830.060*
H10B0.04710.54510.17560.060*
O110.8514 (3)0.0065 (3)0.57508 (9)0.0372 (4)
H11A0.75990.00500.60540.045*
H11B0.98230.00700.58950.045*
O120.9792 (4)0.4581 (4)0.36201 (14)0.0675 (7)
H12A0.91800.53740.33570.081*
H12B0.91510.33820.36170.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0262 (2)0.0255 (2)0.0222 (2)0.00081 (17)0.00170 (17)0.00310 (17)
P10.0195 (3)0.0325 (3)0.0169 (3)0.0038 (2)0.0031 (2)0.0045 (2)
S10.0334 (3)0.0281 (3)0.0296 (3)0.0028 (3)0.0151 (3)0.0069 (3)
C10.0207 (11)0.0267 (12)0.0162 (11)0.0012 (9)0.0031 (9)0.0003 (9)
C20.0201 (11)0.0432 (14)0.0182 (11)0.0004 (10)0.0034 (9)0.0047 (10)
C30.0194 (11)0.0275 (12)0.0167 (11)0.0022 (9)0.0036 (9)0.0016 (9)
C40.0235 (12)0.0234 (11)0.0209 (12)0.0050 (9)0.0068 (9)0.0036 (9)
C50.0338 (13)0.0310 (13)0.0185 (11)0.0107 (10)0.0068 (10)0.0005 (10)
C60.0290 (13)0.0228 (12)0.0225 (12)0.0034 (9)0.0090 (10)0.0023 (9)
N10.0289 (11)0.0464 (13)0.0204 (10)0.0033 (9)0.0053 (8)0.0028 (9)
N20.0239 (11)0.0468 (13)0.0238 (11)0.0020 (9)0.0060 (8)0.0031 (9)
O10.0321 (10)0.0533 (12)0.0253 (9)0.0031 (8)0.0009 (8)0.0108 (8)
O20.0714 (14)0.0403 (11)0.0260 (10)0.0245 (10)0.0026 (9)0.0051 (8)
O30.0438 (12)0.0558 (13)0.0448 (12)0.0170 (10)0.0158 (9)0.0114 (10)
O40.0288 (9)0.0503 (11)0.0221 (9)0.0042 (8)0.0072 (7)0.0028 (8)
O50.0396 (11)0.0364 (10)0.0363 (10)0.0093 (8)0.0007 (8)0.0131 (8)
O60.0189 (8)0.0347 (9)0.0183 (8)0.0016 (7)0.0035 (6)0.0043 (7)
O70.0211 (8)0.0450 (10)0.0160 (8)0.0049 (7)0.0018 (6)0.0020 (7)
O80.0260 (9)0.0409 (10)0.0190 (8)0.0023 (7)0.0021 (7)0.0010 (7)
O90.0215 (9)0.0517 (11)0.0258 (9)0.0040 (8)0.0048 (7)0.0040 (8)
O100.0473 (12)0.0615 (14)0.0422 (12)0.0111 (10)0.0096 (10)0.0057 (10)
O110.0254 (9)0.0547 (12)0.0316 (10)0.0040 (8)0.0027 (8)0.0072 (9)
O120.0414 (13)0.0567 (14)0.106 (2)0.0055 (10)0.0184 (13)0.0355 (14)
Geometric parameters (Å, º) top
Ni1—O2i2.0286 (18)C4—O81.251 (3)
Ni1—O12.0595 (17)C4—O91.256 (3)
Ni1—O22.0286 (18)C5—H5A0.9699
Ni1—O3i2.0463 (19)C5—H5B0.9700
Ni1—O32.0463 (19)C6—N11.312 (3)
Ni1—O1i2.0595 (17)C6—N21.301 (3)
P1—O41.4896 (18)N1—H1C0.8600
P1—O51.4893 (19)N1—H1D0.8600
P1—O61.5862 (16)N2—H2C0.8600
P1—O71.6042 (17)N2—H2D0.8600
S1—C61.761 (2)O1—H1A0.8495
S1—C51.817 (3)O1—H1B0.8529
C1—O61.458 (3)O2—H2A0.8524
C1—C31.525 (3)O2—H2B0.8450
C1—H1E0.9700O3—H3A0.8440
C1—H1F0.9700O3—H3B0.8507
C2—O71.457 (3)O10—H10A0.8485
C2—C31.539 (3)O10—H10B0.8579
C2—H2E0.9700O11—H11A0.8536
C2—H2F0.9700O11—H11B0.8536
C3—C51.543 (3)O12—H12A0.8580
C3—C41.549 (3)O12—H12B0.8501
O2i—Ni1—O2180.0C2—C3—C5107.77 (19)
O2i—Ni1—O3i89.98 (9)C1—C3—C4109.43 (18)
O2—Ni1—O3i90.02 (9)C2—C3—C4108.18 (18)
O2i—Ni1—O390.02 (9)C5—C3—C4109.38 (18)
O2—Ni1—O389.98 (9)O8—C4—O9125.5 (2)
O3i—Ni1—O3180.0O8—C4—C3118.3 (2)
O2i—Ni1—O191.52 (7)O9—C4—C3116.1 (2)
O2—Ni1—O188.48 (8)C3—C5—S1115.87 (16)
O3i—Ni1—O189.11 (8)C3—C5—H5A108.3
O3—Ni1—O190.89 (8)S1—C5—H5A108.3
O2i—Ni1—O1i88.48 (8)C3—C5—H5B108.4
O2—Ni1—O1i91.52 (7)S1—C5—H5B108.3
O3i—Ni1—O1i90.89 (8)H5A—C5—H5B107.4
O3—Ni1—O1i89.11 (8)N2—C6—N1121.9 (2)
O1—Ni1—O1i180.0N2—C6—S1114.78 (18)
O5—P1—O4118.18 (11)N1—C6—S1123.27 (18)
O5—P1—O6111.08 (10)C6—N1—H1C120.0
O4—P1—O6106.96 (10)C6—N1—H1D120.0
O5—P1—O7109.23 (10)H1C—N1—H1D120.0
O4—P1—O7107.75 (10)C6—N2—H2C120.0
O6—P1—O7102.45 (9)C6—N2—H2D120.0
C6—S1—C5105.13 (12)H2C—N2—H2D120.0
O6—C1—C3111.29 (17)Ni1—O1—H1A115.9
O6—C1—H1E109.3Ni1—O1—H1B120.4
C3—C1—H1E109.4H1A—O1—H1B116.9
O6—C1—H1F109.4Ni1—O2—H2A121.0
C3—C1—H1F109.4Ni1—O2—H2B120.1
H1E—C1—H1F108.0H2A—O2—H2B116.6
O7—C2—C3111.13 (18)Ni1—O3—H3A124.8
O7—C2—H2E109.4Ni1—O3—H3B117.7
C3—C2—H2E109.5H3A—O3—H3B117.3
O7—C2—H2F109.4C1—O6—P1116.99 (13)
C3—C2—H2F109.4C2—O7—P1115.02 (14)
H2E—C2—H2F108.0H10A—O10—H10B115.5
C1—C3—C2110.17 (18)H11A—O11—H11B115.6
C1—C3—C5111.83 (19)H12A—O12—H12B114.2
O6—C1—C3—C254.0 (2)C2—C3—C5—S1178.64 (15)
O6—C1—C3—C565.8 (2)C4—C3—C5—S164.0 (2)
O6—C1—C3—C4172.86 (17)C6—S1—C5—C382.51 (19)
O7—C2—C3—C156.1 (2)C5—S1—C6—N2149.09 (19)
O7—C2—C3—C566.2 (2)C5—S1—C6—N134.3 (2)
O7—C2—C3—C4175.65 (18)C3—C1—O6—P157.0 (2)
C1—C3—C4—O833.4 (3)O5—P1—O6—C163.31 (17)
C2—C3—C4—O8153.4 (2)O4—P1—O6—C1166.40 (15)
C5—C3—C4—O889.4 (2)O7—P1—O6—C153.21 (16)
C1—C3—C4—O9149.0 (2)C3—C2—O7—P159.6 (2)
C2—C3—C4—O929.0 (3)O5—P1—O7—C263.65 (18)
C5—C3—C4—O988.1 (2)O4—P1—O7—C2166.80 (16)
C1—C3—C5—S157.4 (2)O6—P1—O7—C254.19 (17)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O8ii0.862.052.911 (3)174
N1—H1D···O100.862.142.904 (3)149
N2—H2C···O9ii0.861.902.758 (3)179
N2—H2D···O8iii0.862.102.910 (3)156
O1—H1A···O12iv0.851.912.764 (3)180
O1—H1B···O5v0.851.962.816 (3)176
O2—H2A···O40.851.872.696 (3)163
O2—H2B···O110.851.962.798 (3)170
O3—H3A···O120.842.152.944 (4)156
O3—H3B···O11v0.851.942.767 (3)164
O10—H10A···O5vi0.852.233.007 (3)152
O10—H10B···O9v0.861.952.770 (3)159
O11—H11A···O7vii0.852.082.902 (2)162
O11—H11B···O4viii0.851.912.735 (2)162
O12—H12A···O5v0.862.012.795 (3)152
O12—H12B···O40.852.032.877 (3)180
Symmetry codes: (ii) x, y, z; (iii) x+1, y, z; (iv) x1, y, z; (v) x, y+1, z; (vi) x1, y+1, z; (vii) x+1, y, z+1; (viii) x+2, y, z+1.

Experimental details

Crystal data
Chemical formula[Ni(H2O)6](C6H10N2O6PS)2·6H2O
Mr813.28
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)6.2701 (12), 6.4816 (12), 19.616 (4)
α, β, γ (°)95.807 (3), 93.091 (3), 93.760 (3)
V3)789.9 (3)
Z1
Radiation typeMo Kα
µ (mm1)0.95
Crystal size (mm)0.28 × 0.24 × 0.22
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.765, 0.818
No. of measured, independent and
observed (I > 2σ) reflections
4055, 2789, 2482
Rint0.018
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.084, 1.05
No. of reflections2789
No. of parameters205
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.49

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Bruker, 2001).

Selected geometric parameters (Å, º) top
P1—O41.4896 (18)C4—O81.251 (3)
P1—O51.4893 (19)C4—O91.256 (3)
P1—O61.5862 (16)C6—N11.312 (3)
P1—O71.6042 (17)C6—N21.301 (3)
O5—P1—O4118.18 (11)O4—P1—O7107.75 (10)
O5—P1—O6111.08 (10)O6—P1—O7102.45 (9)
O4—P1—O6106.96 (10)O8—C4—O9125.5 (2)
O5—P1—O7109.23 (10)N2—C6—N1121.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O8i0.862.052.911 (3)174.3
N1—H1D···O100.862.142.904 (3)148.6
N2—H2C···O9i0.861.902.758 (3)178.6
N2—H2D···O8ii0.862.102.910 (3)155.6
O1—H1A···O12iii0.851.912.764 (3)179.5
O1—H1B···O5iv0.851.962.816 (3)176.2
O2—H2A···O40.851.872.696 (3)162.9
O2—H2B···O110.851.962.798 (3)170.0
O3—H3A···O120.842.152.944 (4)156.3
O3—H3B···O11iv0.851.942.767 (3)164.2
O10—H10A···O5v0.852.233.007 (3)152.4
O10—H10B···O9iv0.861.952.770 (3)159.4
O11—H11A···O7vi0.852.082.902 (2)161.8
O11—H11B···O4vii0.851.912.735 (2)162.4
O12—H12A···O5iv0.862.012.795 (3)152.3
O12—H12B···O40.852.032.877 (3)179.7
Symmetry codes: (i) x, y, z; (ii) x+1, y, z; (iii) x1, y, z; (iv) x, y+1, z; (v) x1, y+1, z; (vi) x+1, y, z+1; (vii) x+2, y, z+1.
 

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