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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m1009–m1010.
Published online 2010 July 24. doi:  10.1107/S1600536810028515
PMCID: PMC3007501

Poly[[bis­{μ3-2-[(3,5-dimethyl-1H-pyrazol-1-yl)(phen­yl)meth­yl]propane­dioato}tetra­sodium(I)] 7.5-hydrate]

Abstract

The asymmetric unit of the title polymer, {[Na4(C15H14N2O4)2]·7.5H2O}n, contains two 2-[(3,5-dimethyl-1H-pyrazol-1-yl)(phen­yl)meth­yl]propane­dioate (ppmp) anions, eight water mol­ecules (one located on a twofold rotation axis) and five sodium cations (one located on an inversion center and the other one located on a twofold rotation axis). The carboxyl­ate groups of the ppmp anions and the water mol­ecules bridge the Na cations, forming a two-dimensional polymeric structure. In the structure there are two types of coordination environment around the metal cations: one Na cation is coordinated by five O atoms in a distorted square-pyramidal geometry while the other four Na cations are coordinated by six O atoms in a distorted octa­hedral geometry. Extensive O—H(...)O and O—H(...)N hydrogen bonding is present in the crystal structure. The H atoms of one methyl group of the ppmp anion are disordered equally over two positions.

Related literature

For related compounds displaying biological activity, see: Dayam et al. (2007 [triangle]); Patil et al. (2007 [triangle]); Ramkumar et al. (2008 [triangle]); Sechi et al. (2009 [triangle]); Zeng et al. (2008 [triangle]). For the synthetic procedure, see: Pommier & Neamati (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1009-scheme1.jpg

Experimental

Crystal data

  • [Na4(C15H14N2O4)2]·7.5H2O
  • M r = 799.64
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1009-efi1.jpg
  • a = 31.8211 (11) Å
  • b = 14.4951 (4) Å
  • c = 16.1113 (5) Å
  • β = 102.139 (3)°
  • V = 7265.2 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.16 mm−1
  • T = 293 K
  • 0.45 × 0.38 × 0.19 mm

Data collection

  • Bruker X8 APEXII CCD area-detector diffractometer
  • 76380 measured reflections
  • 9034 independent reflections
  • 6490 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.130
  • S = 1.02
  • 9034 reflections
  • 488 parameters
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810028515/xu2795sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028515/xu2795Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by grants from Project PGR-UMP-BH-2005, the Centre National de Recherche Scientif­ique, CNRS (France), the Centre National pour la Recherche Scientifique et Technique, CNRST (Morocco) and the CURI (Morocco).

supplementary crystallographic information

Comment

The rational design of new HIV-1 Integrase (H–I) inhibitors, one validated target for chemotherapeutic intervention (Dayam et al., 2007), is fundamentally based on intermolecular coordination between H—I / chemical inhibitor / metals (Mg+2 and Mn+2, co-factors of the enzyme), leading in the formation of bimetallic complexes (Zeng et al., 2008; Sechi et al., 2009). Thereby, several bimetallic metal complexes, in many cases exploring the known-well polydentate ligands, appear in this scenario as the most promising concept to employ in either enzyme / drug interaction or electron transfer process, in the last case involving the biological oxygen transfer (Sechi et al., 2009; Ramkumar et al., 2008). Another exciting example of application for such polydentate ligand involves the synergic water activation, that occurs via the so-called -remote metallic atoms-. Such organometallic compounds are structurally deemed to promote or block the H—I activity (Zeng et al., 2008).

The asymmetric unit of the title polymer contains two (3,5-dimethyl-1H-pyrazol-1-yl)(phenyl)methylpropanedioate (ppmp) anions, eight water molecules (O41 atom located at a twofold rotation axis) and five sodium cations (Na1 located on an inversion center and Na3 located at a twofold rotation axis). The carboxyl groups of ppmp anions and water molecules bridge the Na cations to form the two-dimensional polymeric structure. In the structure there are two types of coodination environment around the metal cations. The Na2 cation is coordinated by five oxygen atoms with a distorted square-pyramidal geometry; the other four Na cations are coordinated by six oxygen atoms with the distorted octahedral geometry. The Na—O bond distances ate ranged from 2.3113 (11) to 2.6812 (15) Å (Table 1). The extensive O—H···O and O—H···N hydrogen bonding is present in the crystal structure (Table 2).

Experimental

A mixture of the sodium salt of 2-[(phenyl)-3,5-dimethyl-pyrazol-1-yl-]-malonic acid (Pommier & Neamati, 2006) (0.2 g, 0.61 mmol) and (0,13, 1.22 mmol) of sodium dicarbonate in water (5 ml) was stirred at room temperature, then (0.047 g, 0.305 mmol) of (VOSO4) was added. The mixture was allowed to stand to ambient temperature. Single crystals suitable for X-ray diffraction were obtained a few days later. Yield: 37%.

Refinement

All H atoms attached to C were fixed geometrically and treated as riding with C—H = 0.96 Å (methyl), 0.98 Å (methine) or 0.93 Å (aromatic) with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl). H atoms of water molecule were located in difference Fourier maps and included in the subsequent refinement using restraints (O—H= 0.85 (1) Å and H···H = 1.39 (2) Å) with Uiso(H) = 1.5Ueq(O). In the last stage of refinement, they were treated as riding on their parent O atoms. The H atoms of the one methyl group in the ligand are disordered equally over two positions.

Figures

Fig. 1.
Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
Partial packing view showing the chain generated by C—H···O hydrogen bonds shown as dashed lines.

Crystal data

[Na4(C15H14N2O4)2]·7.5H2OF(000) = 3352
Mr = 799.64Dx = 1.462 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2648 reflections
a = 31.8211 (11) Åθ = 1.5–26.3°
b = 14.4951 (4) ŵ = 0.16 mm1
c = 16.1113 (5) ÅT = 293 K
β = 102.139 (3)°Block, colourless
V = 7265.2 (4) Å30.45 × 0.38 × 0.19 mm
Z = 8

Data collection

Bruker X8 APEXII CCD area-detector diffractometer6490 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
graphiteθmax = 28.3°, θmin = 1.3°
[var phi] and ω scansh = −42→42
76380 measured reflectionsk = −19→19
9034 independent reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0783P)2 + 2.736P] where P = (Fo2 + 2Fc2)/3
9034 reflections(Δ/σ)max = 0.006
488 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = −0.44 e Å3

Special details

Experimental. IR (KBr, [UTF-8]I1/2 cm-1): 1592.46 (C=O), 3248 (OH).The data collection nominally covered a sphere of reciprocal space, by a combination of seven sets of exposures; each set had a different [var phi] angle for the crystal and each exposure covered 0.5° in ω and 20 s in time. The crystal-to-detector distance was 37.5 mm.
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)

xyzUiso*/UeqOcc. (<1)
C10.13673 (5)0.43818 (11)0.21255 (10)0.0157 (3)
H10.12880.50330.20360.019*
C20.09753 (5)0.38687 (10)0.23022 (10)0.0146 (3)
H20.10490.32150.23900.018*
N10.14699 (4)0.40316 (9)0.13308 (8)0.0171 (3)
N20.15635 (5)0.31192 (9)0.12560 (9)0.0217 (3)
C110.14801 (5)0.45027 (12)0.06112 (11)0.0211 (3)
C1110.17568 (5)0.43350 (12)0.28481 (10)0.0189 (3)
C1120.18973 (7)0.35192 (14)0.32677 (13)0.0351 (5)
H1120.17470.29750.31090.042*
C1130.22592 (7)0.35053 (16)0.39193 (15)0.0451 (6)
H1130.23500.29530.41930.054*
C1140.24851 (6)0.43032 (17)0.41628 (14)0.0420 (5)
H1140.27280.42920.45990.050*
C1150.23495 (7)0.51153 (16)0.37580 (16)0.0450 (6)
H1150.25010.56570.39200.054*
C1160.19862 (6)0.51313 (14)0.31076 (14)0.0328 (4)
H1160.18950.56870.28420.039*
C120.15814 (6)0.38751 (13)0.00471 (11)0.0268 (4)
H120.16100.3990−0.05060.032*
C130.16321 (6)0.30294 (12)0.04696 (12)0.0249 (4)
C140.17451 (8)0.21067 (14)0.01556 (14)0.0417 (5)
H14A0.17530.16530.05930.063*
H14B0.20220.21410.00090.063*
H14C0.15330.1935−0.03370.063*
C150.13940 (7)0.55134 (13)0.05108 (13)0.0308 (4)
H15A0.11110.56430.05980.046*
H15B0.14140.5701−0.00510.046*
H15C0.16020.58460.09200.046*
C210.08148 (5)0.42241 (11)0.30808 (10)0.0177 (3)
C220.05932 (5)0.39513 (11)0.15432 (10)0.0163 (3)
O10.09050 (4)0.50303 (8)0.33362 (8)0.0245 (3)
O20.05884 (4)0.36630 (9)0.33884 (8)0.0292 (3)
O30.04974 (4)0.47344 (8)0.12450 (8)0.0246 (3)
O40.03947 (4)0.32106 (8)0.12934 (8)0.0227 (3)
C30.12948 (5)−0.12031 (11)0.19213 (10)0.0152 (3)
H30.1257−0.18480.20730.018*
C40.08996 (5)−0.06637 (11)0.20531 (10)0.0141 (3)
H40.0968−0.00050.20540.017*
N30.16800 (4)−0.08512 (9)0.25020 (9)0.0177 (3)
N40.17591 (4)0.00742 (9)0.25847 (9)0.0203 (3)
C310.20142 (6)−0.13530 (13)0.29413 (12)0.0249 (4)
C3110.13456 (5)−0.11851 (11)0.10044 (10)0.0175 (3)
C3120.13502 (6)−0.20186 (12)0.05790 (12)0.0274 (4)
H3120.1330−0.25700.08630.033*
C3130.13850 (7)−0.20368 (14)−0.02656 (13)0.0345 (5)
H3130.1389−0.2598−0.05430.041*
C3140.14133 (6)−0.12223 (14)−0.06929 (12)0.0296 (4)
H3140.1435−0.1234−0.12600.035*
C3150.14097 (6)−0.03861 (13)−0.02781 (11)0.0255 (4)
H3150.14310.0163−0.05650.031*
C3160.13747 (5)−0.03674 (12)0.05677 (11)0.0222 (3)
H3160.13710.01950.08430.027*
C320.23146 (6)−0.07307 (13)0.33379 (13)0.0299 (4)
H320.2578−0.08620.36950.036*
C330.21456 (5)0.01393 (12)0.30977 (12)0.0243 (4)
C340.23424 (6)0.10641 (14)0.33425 (14)0.0369 (5)
H34A0.21500.15390.30780.055*0.50
H34B0.26100.11130.31590.055*0.50
H34C0.23940.11330.39480.055*0.50
H34D0.26190.09840.37120.055*0.50
H34E0.21590.14110.36310.055*0.50
H34F0.23750.13910.28420.055*0.50
C350.20217 (7)−0.23784 (14)0.29361 (15)0.0399 (5)
H35A0.1782−0.26100.31490.060*
H35B0.2285−0.25930.32900.060*
H35C0.2003−0.25940.23660.060*
C410.05116 (5)−0.08420 (11)0.13273 (10)0.0154 (3)
C420.07637 (5)−0.08894 (11)0.28921 (10)0.0156 (3)
O50.03524 (4)−0.01421 (8)0.09023 (7)0.0191 (2)
O60.03787 (4)−0.16533 (8)0.11998 (8)0.0230 (3)
O70.08345 (4)−0.16799 (8)0.32102 (8)0.0239 (3)
O80.05735 (4)−0.02532 (8)0.31923 (7)0.0229 (3)
Na10.00000.50000.00000.0202 (2)
Na20.03995 (2)0.00005 (4)0.44768 (4)0.01928 (15)
Na30.00000.28300 (6)0.25000.0230 (2)
Na40.03267 (3)−0.34679 (6)0.13857 (5)0.0347 (2)
Na50.04893 (2)0.15926 (4)0.10917 (4)0.02081 (15)
O11−0.03287 (4)0.35116 (8)0.00998 (7)0.0201 (2)
H111−0.04800.36920.04500.030*
H11B−0.00860.33650.04000.030*
O12−0.03957 (4)0.59680 (9)0.07746 (8)0.0276 (3)
H121−0.05420.56420.10430.041*
H122−0.05540.63690.04890.041*
O210.04694 (4)−0.16789 (8)0.46475 (7)0.0231 (3)
H2110.0208−0.17620.44040.035*
H2120.0611−0.17490.42630.035*
O220.02907 (4)0.15783 (8)0.42770 (8)0.0231 (3)
H2210.04350.17220.39080.035*
H2220.03680.19420.46970.035*
O310.04933 (4)0.15204 (8)0.26444 (8)0.0225 (3)
H31A0.05000.09420.27490.034*
H31B0.07500.16730.26480.034*
O410.0000−0.27849 (13)0.25000.0307 (4)
H4110.0213−0.24700.27360.046*
O420.09668 (4)−0.33909 (8)0.24137 (8)0.0279 (3)
H4210.0932−0.38700.26910.042*
H4220.0940−0.29250.27180.042*
O510.12258 (4)0.15927 (8)0.19318 (8)0.0242 (3)
H5110.14100.11690.21150.036*
H5120.13610.20270.17440.036*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0160 (7)0.0154 (7)0.0155 (8)−0.0014 (6)0.0030 (6)−0.0002 (6)
C20.0146 (7)0.0150 (7)0.0137 (7)−0.0007 (5)0.0018 (6)0.0003 (6)
N10.0197 (7)0.0161 (6)0.0162 (7)−0.0001 (5)0.0056 (5)0.0010 (5)
N20.0266 (7)0.0171 (7)0.0229 (8)0.0015 (6)0.0086 (6)−0.0003 (6)
C110.0212 (8)0.0232 (9)0.0191 (8)0.0007 (6)0.0051 (7)0.0050 (7)
C1110.0150 (7)0.0245 (8)0.0174 (8)−0.0013 (6)0.0039 (6)−0.0019 (6)
C1120.0344 (11)0.0277 (10)0.0349 (11)−0.0031 (8)−0.0113 (9)0.0033 (8)
C1130.0409 (12)0.0434 (13)0.0409 (13)0.0032 (10)−0.0145 (10)0.0094 (10)
C1140.0238 (10)0.0651 (15)0.0314 (12)−0.0069 (10)−0.0074 (8)−0.0027 (10)
C1150.0347 (11)0.0490 (14)0.0448 (14)−0.0203 (10)−0.0066 (10)−0.0067 (11)
C1160.0308 (10)0.0290 (10)0.0352 (11)−0.0083 (8)−0.0006 (8)0.0001 (8)
C120.0344 (10)0.0299 (10)0.0178 (9)0.0019 (7)0.0090 (7)0.0022 (7)
C130.0286 (9)0.0248 (9)0.0234 (9)−0.0002 (7)0.0099 (7)−0.0022 (7)
C140.0624 (15)0.0312 (11)0.0370 (12)0.0035 (10)0.0229 (11)−0.0055 (9)
C150.0402 (11)0.0237 (9)0.0294 (10)0.0042 (8)0.0093 (8)0.0096 (8)
C210.0153 (7)0.0232 (8)0.0133 (8)−0.0004 (6)0.0004 (6)−0.0002 (6)
C220.0152 (7)0.0207 (8)0.0136 (7)−0.0004 (6)0.0044 (6)−0.0012 (6)
O10.0314 (7)0.0219 (6)0.0219 (6)−0.0028 (5)0.0097 (5)−0.0056 (5)
O20.0354 (7)0.0332 (7)0.0227 (7)−0.0136 (6)0.0143 (6)−0.0036 (5)
O30.0253 (6)0.0210 (6)0.0235 (7)−0.0020 (5)−0.0040 (5)0.0064 (5)
O40.0211 (6)0.0196 (6)0.0237 (6)−0.0021 (5)−0.0035 (5)−0.0039 (5)
C30.0161 (7)0.0152 (7)0.0144 (7)0.0005 (6)0.0034 (6)−0.0009 (6)
C40.0147 (7)0.0145 (7)0.0132 (7)0.0006 (5)0.0031 (6)0.0006 (6)
N30.0169 (6)0.0181 (7)0.0174 (7)0.0021 (5)0.0020 (5)0.0003 (5)
N40.0195 (7)0.0176 (7)0.0232 (8)−0.0007 (5)0.0031 (6)−0.0005 (6)
C310.0201 (8)0.0272 (9)0.0264 (9)0.0069 (7)0.0024 (7)0.0052 (7)
C3110.0146 (7)0.0219 (8)0.0167 (8)0.0012 (6)0.0053 (6)−0.0013 (6)
C3120.0383 (10)0.0216 (9)0.0245 (9)0.0015 (7)0.0113 (8)−0.0018 (7)
C3130.0460 (12)0.0328 (11)0.0262 (10)0.0016 (9)0.0110 (9)−0.0115 (8)
C3140.0245 (9)0.0476 (12)0.0175 (9)−0.0009 (8)0.0066 (7)−0.0037 (8)
C3150.0236 (9)0.0345 (10)0.0184 (9)−0.0029 (7)0.0044 (7)0.0041 (7)
C3160.0243 (8)0.0232 (9)0.0198 (9)0.0001 (7)0.0059 (7)−0.0007 (7)
C320.0182 (8)0.0349 (11)0.0327 (11)0.0033 (7)−0.0033 (7)0.0026 (8)
C330.0180 (8)0.0295 (10)0.0251 (9)−0.0021 (7)0.0038 (7)−0.0013 (7)
C340.0271 (10)0.0353 (11)0.0457 (13)−0.0096 (8)0.0022 (9)−0.0067 (9)
C350.0343 (11)0.0265 (10)0.0536 (14)0.0121 (8)−0.0028 (10)0.0041 (9)
C410.0142 (7)0.0218 (8)0.0114 (7)0.0017 (6)0.0056 (6)−0.0003 (6)
C420.0168 (7)0.0176 (7)0.0118 (7)−0.0008 (6)0.0016 (6)−0.0007 (6)
O50.0207 (6)0.0224 (6)0.0138 (6)0.0041 (4)0.0025 (4)0.0036 (4)
O60.0229 (6)0.0218 (6)0.0219 (6)−0.0030 (5)−0.0007 (5)−0.0010 (5)
O70.0366 (7)0.0202 (6)0.0177 (6)0.0055 (5)0.0118 (5)0.0047 (5)
O80.0326 (7)0.0204 (6)0.0185 (6)0.0062 (5)0.0119 (5)0.0012 (5)
Na10.0243 (5)0.0168 (4)0.0175 (5)−0.0013 (3)−0.0003 (4)0.0014 (4)
Na20.0231 (3)0.0201 (3)0.0154 (3)0.0022 (2)0.0059 (3)−0.0001 (2)
Na30.0219 (5)0.0212 (5)0.0263 (5)0.0000.0060 (4)0.000
Na40.0301 (4)0.0529 (5)0.0206 (4)−0.0048 (3)0.0045 (3)−0.0084 (3)
Na50.0230 (3)0.0220 (3)0.0168 (3)0.0017 (3)0.0027 (3)−0.0014 (3)
O110.0199 (6)0.0241 (6)0.0160 (6)0.0008 (4)0.0033 (5)0.0002 (5)
O120.0253 (6)0.0326 (7)0.0259 (7)0.0014 (5)0.0080 (5)0.0062 (5)
O210.0230 (6)0.0302 (7)0.0165 (6)0.0021 (5)0.0049 (5)0.0016 (5)
O220.0264 (6)0.0201 (6)0.0236 (6)0.0001 (5)0.0073 (5)−0.0035 (5)
O310.0241 (6)0.0185 (6)0.0260 (7)0.0012 (5)0.0078 (5)0.0035 (5)
O410.0288 (10)0.0320 (10)0.0328 (11)0.0000.0099 (8)0.000
O420.0353 (7)0.0197 (6)0.0292 (7)−0.0003 (5)0.0080 (6)0.0001 (5)
O510.0214 (6)0.0181 (6)0.0337 (7)0.0005 (5)0.0073 (5)0.0057 (5)

Geometric parameters (Å, °)

Na1—O32.3113 (11)C13—C141.500 (3)
Na1—O3i2.3113 (11)C14—H14A0.9600
Na1—O112.4177 (11)C14—H14B0.9600
Na1—O11i2.4177 (11)C14—H14C0.9600
Na1—O122.4028 (13)C15—H15A0.9600
Na1—O12i2.4028 (13)C15—H15B0.9600
Na2—O5ii2.3507 (13)C15—H15C0.9600
Na2—O5iii2.3417 (13)C21—O11.252 (2)
Na2—O82.2818 (13)C21—O21.256 (2)
Na2—O212.4546 (13)C22—O31.245 (2)
Na2—O222.3253 (13)C22—O41.2676 (19)
Na3—O22.4259 (14)C3—N31.468 (2)
Na3—O2ii2.4259 (14)C3—C3111.520 (2)
Na3—O312.4430 (14)C3—C41.533 (2)
Na3—O31ii2.4430 (14)C3—H30.9800
Na3—O42.5862 (13)C4—C411.533 (2)
Na3—O4ii2.5862 (13)C4—C421.538 (2)
Na4—O3iv2.6812 (15)C4—H40.9800
Na4—O62.6565 (14)N3—C311.358 (2)
Na4—O11v2.3956 (14)N3—N41.3661 (19)
Na4—O12iv2.4434 (15)N4—C331.333 (2)
Na4—O412.4634 (11)C31—C321.371 (3)
Na4—O422.3423 (15)C31—C351.487 (3)
Na5—O42.3952 (13)C311—C3121.391 (2)
Na5—O52.5592 (13)C311—C3161.391 (2)
Na5—O21vi2.3176 (13)C312—C3131.389 (3)
Na5—O22ii2.4275 (14)C312—H3120.9300
Na5—O312.5011 (14)C313—C3141.379 (3)
Na5—O512.4478 (14)C313—H3130.9300
Na1—Na4vii3.1655 (8)C314—C3151.385 (3)
Na1—Na4v3.1655 (8)C314—H3140.9300
Na1—H1112.6295C315—C3161.391 (2)
Na1—H11B2.4858C315—H3150.9300
Na2—Na2viii3.3331 (13)C316—H3160.9300
Na2—Na5iii3.4453 (9)C32—C331.393 (3)
Na2—Na5ii3.6158 (9)C32—H320.9300
Na2—H2112.6231C33—C341.497 (3)
Na2—H2122.6649C34—H34A0.9600
Na2—H2212.6683C34—H34B0.9600
Na3—Na53.5036 (8)C34—H34C0.9600
Na3—Na5ii3.5036 (8)C34—H34D0.9600
Na4—Na1iv3.1655 (8)C34—H34E0.9600
Na4—H4212.6015C34—H34F0.9600
Na5—Na2vi3.4453 (9)C35—H35A0.9600
Na5—Na2ii3.6158 (9)C35—H35B0.9600
Na5—H31B2.4723C35—H35C0.9600
C1—N11.476 (2)C41—O61.252 (2)
C1—C1111.513 (2)C41—O51.2684 (19)
C1—C21.530 (2)C42—O81.2544 (19)
C1—H10.9800C42—O71.2562 (19)
C2—C221.537 (2)O11—Na4v2.3956 (14)
C2—C211.539 (2)O11—H1110.8553
C2—H20.9800O11—H11B0.8487
N1—C111.352 (2)O12—Na4vii2.4434 (15)
N1—N21.3665 (19)O12—H1210.8438
N2—C131.337 (2)O12—H1220.8399
C11—C121.371 (2)O21—Na5iii2.3176 (13)
C11—C151.493 (2)O21—H2110.8507
C111—C1161.383 (2)O21—H2120.8458
C111—C1121.389 (3)O22—Na5ii2.4275 (14)
C112—C1131.386 (3)O22—H2210.8489
C112—H1120.9300O22—H2220.8522
C113—C1141.375 (3)O31—H31A0.8540
C113—H1130.9300O31—H31B0.8440
C114—C1151.371 (3)O41—Na4ii2.4634 (11)
C114—H1140.9300O41—H4110.8398
C115—C1161.388 (3)O42—H4210.8453
C115—H1150.9300O42—H4220.8494
C116—H1160.9300O51—H5110.8572
C12—C131.395 (3)O51—H5120.8533
C12—H120.9300
N1—C1—C111110.93 (13)H111—Na1—H11B30.6
N1—C1—C2109.38 (12)O8—Na2—O2295.19 (5)
C111—C1—C2113.78 (13)O8—Na2—O5iii168.93 (5)
N1—C1—H1107.5O22—Na2—O5iii90.64 (5)
C111—C1—H1107.5O8—Na2—O5ii100.26 (5)
C2—C1—H1107.5O22—Na2—O5ii86.37 (5)
C1—C2—C22110.71 (12)O5iii—Na2—O5ii89.48 (5)
C1—C2—C21114.35 (13)O8—Na2—O2184.74 (4)
C22—C2—C21106.25 (12)O22—Na2—O21176.60 (5)
C1—C2—H2108.5O5iii—Na2—O2190.00 (4)
C22—C2—H2108.5O5ii—Na2—O2190.30 (4)
C21—C2—H2108.5O8—Na2—Na2viii144.59 (5)
C11—N1—N2111.61 (13)O22—Na2—Na2viii87.89 (4)
C11—N1—C1128.29 (14)O5iii—Na2—Na2viii44.85 (3)
N2—N1—C1120.09 (12)O5ii—Na2—Na2viii44.63 (3)
C13—N2—N1105.07 (13)O21—Na2—Na2viii90.21 (4)
N1—C11—C12106.54 (15)O8—Na2—Na5iii125.41 (4)
N1—C11—C15123.48 (15)O22—Na2—Na5iii138.59 (4)
C12—C11—C15129.98 (16)O5iii—Na2—Na5iii47.97 (3)
C116—C111—C112117.92 (17)O5ii—Na2—Na5iii93.18 (4)
C116—C111—C1119.36 (16)O21—Na2—Na5iii42.23 (3)
C112—C111—C1122.72 (15)Na2viii—Na2—Na5iii64.45 (2)
C113—C112—C111120.82 (18)O8—Na2—Na5ii101.49 (4)
C113—C112—H112119.6O22—Na2—Na5ii41.53 (3)
C111—C112—H112119.6O5iii—Na2—Na5ii89.11 (4)
C114—C113—C112120.4 (2)O5ii—Na2—Na5ii44.86 (3)
C114—C113—H113119.8O21—Na2—Na5ii135.15 (4)
C112—C113—H113119.8Na2viii—Na2—Na5ii59.28 (2)
C115—C114—C113119.57 (19)Na5iii—Na2—Na5ii123.73 (2)
C115—C114—H114120.2O8—Na2—H21184.3
C113—C114—H114120.2O22—Na2—H211157.7
C114—C115—C116120.17 (19)O5iii—Na2—H21193.8
C114—C115—H115119.9O5ii—Na2—H21171.8
C116—C115—H115119.9O21—Na2—H21118.9
C111—C116—C115121.16 (19)Na2viii—Na2—H21180.0
C111—C116—H116119.4Na5iii—Na2—H21150.4
C115—C116—H116119.4Na5ii—Na2—H211116.6
C11—C12—C13106.19 (16)O8—Na2—H21267.3
C11—C12—H12126.9O22—Na2—H212162.3
C13—C12—H12126.9O5iii—Na2—H212106.3
N2—C13—C12110.59 (15)O5ii—Na2—H21298.9
N2—C13—C14120.33 (16)O21—Na2—H21218.4
C12—C13—C14129.07 (17)Na2viii—Na2—H212107.8
C13—C14—H14A109.5Na5iii—Na2—H21258.4
C13—C14—H14B109.5Na5ii—Na2—H212141.3
H14A—C14—H14B109.5H211—Na2—H21229.6
C13—C14—H14C109.5O8—Na2—H22178.7
H14A—C14—H14C109.5O22—Na2—H22117.9
H14B—C14—H14C109.5O5iii—Na2—H221105.7
C11—C15—H15A109.5O5ii—Na2—H22196.1
C11—C15—H15B109.5O21—Na2—H221163.0
H15A—C15—H15B109.5Na2viii—Na2—H221105.4
C11—C15—H15C109.5Na5iii—Na2—H221152.0
H15A—C15—H15C109.5Na5ii—Na2—H22153.4
H15B—C15—H15C109.5H211—Na2—H221157.1
O1—C21—O2125.86 (15)H212—Na2—H221144.6
O1—C21—C2119.19 (14)O2—Na3—O2ii120.30 (8)
O2—C21—C2114.91 (14)O2—Na3—O31ii147.53 (5)
O3—C22—O4125.76 (15)O2ii—Na3—O31ii85.97 (4)
O3—C22—C2117.81 (14)O2—Na3—O3185.97 (4)
O4—C22—C2116.40 (14)O2ii—Na3—O31147.53 (5)
C21—O2—Na3121.68 (11)O31ii—Na3—O3178.02 (6)
C22—O3—Na1123.65 (10)O2—Na3—O484.31 (4)
C22—O3—Na4vii152.98 (11)O2ii—Na3—O483.51 (4)
Na1—O3—Na4vii78.32 (4)O31ii—Na3—O4119.87 (4)
C22—O4—Na5143.51 (11)O31—Na3—O480.41 (4)
C22—O4—Na3103.32 (10)O2—Na3—O4ii83.51 (4)
Na5—O4—Na389.30 (5)O2ii—Na3—O4ii84.31 (4)
N3—C3—C311111.60 (12)O31ii—Na3—O4ii80.41 (4)
N3—C3—C4109.50 (12)O31—Na3—O4ii119.87 (4)
C311—C3—C4112.58 (13)O4—Na3—O4ii155.37 (7)
N3—C3—H3107.6O2—Na3—Na5104.12 (3)
C311—C3—H3107.6O2ii—Na3—Na5105.40 (3)
C4—C3—H3107.6O31ii—Na3—Na584.53 (4)
C3—C4—C41111.15 (12)O31—Na3—Na545.55 (3)
C3—C4—C42113.80 (12)O4—Na3—Na543.13 (3)
C41—C4—C42107.72 (12)O4ii—Na3—Na5161.48 (4)
C3—C4—H4108.0O2—Na3—Na5ii105.40 (3)
C41—C4—H4108.0O2ii—Na3—Na5ii104.12 (3)
C42—C4—H4108.0O31ii—Na3—Na5ii45.55 (3)
C31—N3—N4111.53 (14)O31—Na3—Na5ii84.53 (4)
C31—N3—C3127.11 (14)O4—Na3—Na5ii161.48 (4)
N4—N3—C3121.02 (13)O4ii—Na3—Na5ii43.13 (3)
C33—N4—N3104.89 (13)Na5—Na3—Na5ii118.41 (3)
N3—C31—C32106.47 (16)O42—Na4—O11v121.53 (5)
N3—C31—C35122.97 (17)O42—Na4—O12iv154.89 (6)
C32—C31—C35130.56 (17)O11v—Na4—O12iv77.79 (5)
C312—C311—C316118.83 (16)O42—Na4—O4184.44 (4)
C312—C311—C3118.58 (15)O11v—Na4—O41145.99 (5)
C316—C311—C3122.56 (14)O12iv—Na4—O4185.57 (4)
C313—C312—C311120.71 (17)O42—Na4—O688.10 (5)
C313—C312—H312119.6O11v—Na4—O684.27 (5)
C311—C312—H312119.6O12iv—Na4—O6111.20 (5)
C314—C313—C312120.00 (18)O41—Na4—O674.34 (5)
C314—C313—H313120.0O42—Na4—O3iv86.82 (5)
C312—C313—H313120.0O11v—Na4—O3iv81.18 (4)
C313—C314—C315120.01 (17)O12iv—Na4—O3iv80.27 (5)
C313—C314—H314120.0O41—Na4—O3iv125.19 (6)
C315—C314—H314120.0O6—Na4—O3iv159.10 (5)
C314—C315—C316120.01 (17)O42—Na4—Na1iv129.79 (4)
C314—C315—H315120.0O11v—Na4—Na1iv49.18 (3)
C316—C315—H315120.0O12iv—Na4—Na1iv48.66 (3)
C315—C316—C311120.43 (16)O41—Na4—Na1iv132.04 (4)
C315—C316—H316119.8O6—Na4—Na1iv129.35 (4)
C311—C316—H316119.8O3iv—Na4—Na1iv45.64 (3)
C31—C32—C33105.99 (16)O42—Na4—H42118.8
C31—C32—H32127.0O11v—Na4—H421130.1
C33—C32—H32127.0O12iv—Na4—H421136.4
N4—C33—C32111.11 (15)O41—Na4—H42181.7
N4—C33—C34120.47 (16)O6—Na4—H421105.1
C32—C33—C34128.42 (17)O3iv—Na4—H42173.9
C33—C34—H34A109.5Na1iv—Na4—H421119.4
C33—C34—H34B109.5O21vi—Na5—O496.07 (5)
H34A—C34—H34B109.5O21vi—Na5—O22ii86.80 (5)
C33—C34—H34C109.5O4—Na5—O22ii83.71 (4)
H34A—C34—H34C109.5O21vi—Na5—O51112.08 (5)
H34B—C34—H34C109.5O4—Na5—O5193.32 (4)
C33—C34—H34D109.5O22ii—Na5—O51161.11 (5)
H34A—C34—H34D141.1O21vi—Na5—O31178.58 (5)
H34B—C34—H34D56.3O4—Na5—O3183.09 (4)
H34C—C34—H34D56.3O22ii—Na5—O3191.97 (5)
C33—C34—H34E109.5O51—Na5—O3169.14 (4)
H34A—C34—H34E56.3O21vi—Na5—O588.01 (4)
H34B—C34—H34E141.1O4—Na5—O5162.77 (5)
H34C—C34—H34E56.3O22ii—Na5—O579.79 (4)
H34D—C34—H34E109.5O51—Na5—O5100.67 (4)
C33—C34—H34F109.5O31—Na5—O592.47 (4)
H34A—C34—H34F56.3O21vi—Na5—Na2vi45.38 (3)
H34B—C34—H34F56.3O4—Na5—Na2vi139.98 (4)
H34C—C34—H34F141.1O22ii—Na5—Na2vi83.76 (4)
H34D—C34—H34F109.5O51—Na5—Na2vi109.59 (4)
H34E—C34—H34F109.5O31—Na5—Na2vi135.19 (4)
C31—C35—H35A109.5O5—Na5—Na2vi42.81 (3)
C31—C35—H35B109.5O21vi—Na5—Na3134.47 (4)
H35A—C35—H35B109.5O4—Na5—Na347.57 (4)
C31—C35—H35C109.5O22ii—Na5—Na365.93 (3)
H35A—C35—H35C109.5O51—Na5—Na398.40 (4)
H35B—C35—H35C109.5O31—Na5—Na344.21 (3)
O6—C41—O5125.44 (15)O5—Na5—Na3119.51 (4)
O6—C41—C4118.26 (13)Na2vi—Na5—Na3148.72 (2)
O5—C41—C4116.30 (14)O21vi—Na5—Na2ii85.72 (4)
O8—C42—O7124.95 (15)O4—Na5—Na2ii123.06 (4)
O8—C42—C4115.47 (13)O22ii—Na5—Na2ii39.43 (3)
O7—C42—C4119.54 (13)O51—Na5—Na2ii138.34 (4)
C41—O5—Na2vi119.93 (10)O31—Na5—Na2ii93.78 (3)
C41—O5—Na2ii118.67 (10)O5—Na5—Na2ii40.38 (3)
Na2vi—O5—Na2ii90.52 (5)Na2vi—Na5—Na2ii56.27 (2)
C41—O5—Na5133.06 (10)Na3—Na5—Na2ii93.46 (2)
Na2vi—O5—Na589.22 (4)O21vi—Na5—H31B161.5
Na2ii—O5—Na594.76 (4)O4—Na5—H31B80.8
C41—O6—Na4159.80 (11)O22ii—Na5—H31B110.8
C42—O8—Na2134.19 (11)O51—Na5—H31B50.3
O3—Na1—O3i180.00 (8)O31—Na5—H31B19.5
O3—Na1—O12i90.88 (4)O5—Na5—H31B100.4
O3i—Na1—O12i89.12 (4)Na2vi—Na5—H31B139.0
O3—Na1—O1289.12 (4)Na3—Na5—H31B54.5
O3i—Na1—O1290.88 (4)Na2ii—Na5—H31B111.4
O12i—Na1—O12180.00 (5)Na4v—O11—Na182.24 (4)
O3—Na1—O11i88.82 (4)Na4v—O11—H111141.9
O3i—Na1—O11i91.18 (4)Na1—O11—H11194.7
O12i—Na1—O11i101.84 (4)Na4v—O11—H11B111.7
O12—Na1—O11i78.16 (4)Na1—O11—H11B84.6
O3—Na1—O1191.18 (4)H111—O11—H11B105.7
O3i—Na1—O1188.82 (4)Na1—O12—Na4vii81.56 (4)
O12i—Na1—O1178.16 (4)Na1—O12—H121110.1
O12—Na1—O11101.84 (4)Na4vii—O12—H121123.7
O11i—Na1—O11180.00 (7)Na1—O12—H122116.0
O3—Na1—Na4vii56.04 (3)Na4vii—O12—H122113.2
O3i—Na1—Na4vii123.96 (3)H121—O12—H122109.7
O12i—Na1—Na4vii130.22 (3)Na5iii—O21—Na292.39 (5)
O12—Na1—Na4vii49.78 (3)Na5iii—O21—H211106.7
O11i—Na1—Na4vii48.58 (3)Na2—O21—H21191.8
O11—Na1—Na4vii131.42 (3)Na5iii—O21—H212146.6
O3—Na1—Na4v123.96 (3)Na2—O21—H21295.0
O3i—Na1—Na4v56.04 (3)H211—O21—H212105.5
O12i—Na1—Na4v49.78 (3)Na2—O22—Na5ii99.04 (5)
O12—Na1—Na4v130.22 (3)Na2—O22—H221104.5
O11i—Na1—Na4v131.42 (3)Na5ii—O22—H221120.1
O11—Na1—Na4v48.58 (3)Na2—O22—H222119.2
Na4vii—Na1—Na4v180.00 (2)Na5ii—O22—H222107.5
O3—Na1—H11188.4H221—O22—H222107.1
O3i—Na1—H11191.6Na3—O31—Na590.24 (4)
O12i—Na1—H11196.9Na3—O31—H31A140.3
O12—Na1—H11183.1Na5—O31—H31A103.5
O11i—Na1—H111161.1Na3—O31—H31B113.4
O11—Na1—H11118.9Na5—O31—H31B78.3
Na4vii—Na1—H111115.8H31A—O31—H31B105.8
Na4v—Na1—H11164.2Na4—O41—Na4ii132.60 (9)
O3—Na1—H11B73.0Na4—O41—H41197.1
O3i—Na1—H11B107.0Na4ii—O41—H411108.3
O12i—Na1—H11B71.1Na4—O42—H42198.2
O12—Na1—H11B108.9Na4—O42—H422105.5
O11i—Na1—H11B160.1H421—O42—H422107.9
O11—Na1—H11B19.9Na5—O51—H511134.1
Na4vii—Na1—H11B121.6Na5—O51—H512107.4
Na4v—Na1—H11B58.4H511—O51—H512107.0

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O11—H111···O2ii0.861.972.7404 (16)149
O11—H11B···O40.851.882.7067 (16)165
O12—H121···O1ii0.841.902.7391 (17)174
O21—H211···O6ii0.851.922.7566 (17)167
O21—H212···O70.851.972.8007 (16)165
O22—H221···O310.852.102.8381 (17)145
O22—H222···O11ii0.852.312.9707 (16)135
O22—H222···O6iii0.852.453.0532 (18)128
O31—H31A···O80.851.872.7128 (16)169
O31—H31B···O510.842.092.8085 (17)142
O41—H411···O70.842.273.1061 (16)172
O42—H421···O1iv0.851.922.7582 (17)175
O42—H422···O70.852.032.8639 (17)168
O51—H511···N40.861.992.8424 (18)171
O51—H512···N20.851.942.7799 (18)169

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2795).

References

  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dayam, R., Al-Mawsawi, L. Q. & Neamati, N. (2007). Bioorg. Med. Chem. Lett.17, 6155–6159. [PubMed]
  • Patil, S., Kamath, S., Sanchez, T., Neamati, N., Schinazi, R. F. & Buolamwini, J. K. (2007). Bioorg. Med. Chem.15, 1212–1228. [PubMed]
  • Pommier, Y. & Neamati, N. (2006). Bioorg. Med. Chem.14, 3785–3792. [PubMed]
  • Ramkumar, K., Tambov, K. V., Gundla, R., Manaev, A. V., Yarovenko, V., Traven, V. F. & Neamati, N. (2008). Bioorg. Med. Chem.16, 8988–8998. [PubMed]
  • Sechi, M., Carta, F., Sannia, L., Dallocchio, R., Dessì, A., Al-Safi, R. I. & Neamati, N. (2009). Antivir. Res.81, 267–276. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.
  • Zeng, L.-F., Zhang, H.-S., Wang, Y.-H., Sanchez, T., Zheng, Y.-T., Neamati, N. & Long, Y.-Q. (2008). Bioorg. Med. Chem. Lett.18, 4521–4524. [PubMed]

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