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Acta Cryst. (2007). E63, m3089-m3090    [ doi:10.1107/S1600536807058722 ]

4,4'-Bipyridinediium triaquabis(pyridine-2,6-dicarboxylato)strontium(II) trihydrate

J. Soleimannejad, H. Aghabozorg, S. Hooshmand and H. Adams

Abstract top

The reaction of strontium(II) nitrate with pyridine-2,6-dicarboxylic acid, (pydcH2) and 4,4'-bipyridine (bipy) in a 1:2:4 molar ratio leads to the formation of the title compound, (C10H10N2)[Sr(C7H3NO4)2(H2O)3]·3H2O, or (bipyH2)[Sr(pydc)2(H2O)3]·3H2O, in aqueous solution. This compound is composed of an anionic complex, [Sr(pydc)2(H2O)3]2-, a protonated 4,4'-bipyridine as a counter-ion, (bipyH2)2+ (site symmetry \overline 1), and three uncoordinated water molecules. The anion is a nine-coordinate complex, with a distorted tricapped trigonal-prismatic geometry around the SrII atom. The coordination environment consists of two tridentate pyridine-2,6-dicarboxylate, (pydc)2-, groups and three O atoms of the coordinated water molecules. In the crystal structure, intermolecular O-H...O, N-H...O and C-H...O hydrogen bonds, [pi]-[pi] stacking between two aromatic rings [with distances of 3.5723 (7)-3.7494 (7) Å] and C-O...[pi] stacking [distance of 3.5228 (12) Å] connect the various components into a supramolecular structure.

Comment top

Intermolecular intractions, such as hydrogen bonding, π-π stacking, ion pairing and donor-acceptor intractions, are famous for making aggregates of molecules. One or more of these interactions may result in the formation of specific and spontaneous self-associations or self-associated compounds. Research has shown that hydrogen bonding plays a key role in the preparation of self-assembled compounds. There is a very close relationship between hydrogen bonding and the formation of proton transfer compounds (Aghabozorg, Attar, Ghadermazi et al., 2007; Aghabozorg, Attar, Ghasemikhah et al., 2007; Aghabozorg, Daneshvar et al., 2007).

Here, we report on the synthesis and crystal structure of the title compound, (I). Selected bond lengths and angles are given in Table 1. Compound (I) is composed of an anionic complex, [Sr(pydc)2(H2O)3]2–, a protonated 4,4'-bipyridine as a counter ion, (bipyH2)2+, and three uncoordinated water molecules (Fig. 1).

The SrII atom is nine-coordinated by two pyridine-2,6-dicarboxylate, (pydc)2–, groups, which act as a tridentate ligand through two O atom and one N atom, and three O atoms of coordinated waters molecules. The dihedral angle between the two (pydc)2– planes is 37.30 (6)°.

The sum of bond angles, N2—Sr1—O4, O4—Sr1—O1 and O1—Sr1—N2 is equal to 358.04° and indicates that SrII is located in the center of the O1O4N2 plane. The three O atoms, O8, O10 and O11, form a triangle and atoms, O5, O9 and N1, form another triangle around the SrII atom. Considering the angles between the atoms (Table 1), it is found that they are almost eclipsed. So a prism consisting of the five O atoms and one N atom and three caps on its faces is proposed. The coordination polyhedron can be descibed as a highly distorted tricapped trigonal prism.

An important feature of compound (I) is the presence of π-π and C—O···π stacking interactions. The π-π stacking between aromatic rings Cg1 [Cg1: N1/C2—C6] and Cg3 [Cg3: N3/C17—C19] with distances of 3.5723 (7) Å (x, y, z), Cg2 [Cg2: N2/C9—C13] and Cg4 [Cg4: N4/C21—C25] with distances of 3.5941 (8)Å (1 − x, 1 − y, −z), Cg1 and Cg1 with distances of 3.6836 (7)Å (1 − x, −y, 1 − z) and Cg3 and Cg3 with distances of 3.7494 (7) Å (2 − x, 1 − y, 1 − z) are observed (Fig. 2). The C—O···π distances are 3.5228 (12) Å (−x, −y, −z) (Fig. 3). Intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds with D···A distances ranging from 2.5500 (15) Å to 3.4867 (19) Å (Table 2) seem to be effective in the stabilization of the crystal structure. This results in the formation of an interesting supramolecular structure (Fig. 4).

Related literature top

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermaz et al. (2007);Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007); Aghabozorg, Daneshvar et al. (2007).

Experimental top

A solution of Sr(NO3)2 (106 mg, 0.5 mmol) in water (5 ml) was added to an aqueous solution of pyridine-2,6-dicarboxylic acid (167 mg, 1 mmol) and 4,4'-bipyridine (312 mg, 2 mmol) in water (10 ml) in a 1:2:4 molar ratio and refluxed for an hour. Colorless crystals of (I) were obtained after allowing the mixture to stand for two weeks at room temperature.

Refinement top

(type here to add refinement details)

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (I), with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. π-π Stacking interactions between Cg1 [N1/C2—C6] and Cg3 [N3/C17—C19], Cg2 [N2/C9—C13] and Cg4 [N4/C21—C25] and two Cg1 [N1/C2—C6] of (I). The average distances between the planes are 3.5723 (7) Å (x, y, z), 3.5941 (8) Å (1 − x, 1 − y, −z) and 3.6836 (7) Å (1 − x, −y, 1 − z), respectively.
[Figure 3] Fig. 3. The C—O···π stacking interactions of the carbonyl groups of the (pydc)2– fragments. The C—O···π distances [measured to the centre of the ring (N2/C9—C13)] are 3.5228 (12) Å (−x, −y, −z).
[Figure 4] Fig. 4. The crystal packing of compound (I). Hydrogen bonds are shown as dashed lines.
4,4'-Bipyridindiium triaquabis(pyridine-2,6-dicarboxylato)strontium(II) trihydrate top
Crystal data top
(C10H10N2)[Sr(C7H3NO4)2(H2O)3]·3H2OZ = 2
Mr = 684.12F000 = 700
Triclinic, P1Dx = 1.643 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 6.9994 (1) ÅCell parameters from 19317 reflections
b = 11.6876 (2) Åθ = 2.4–30.6º
c = 17.9748 (3) ŵ = 2.03 mm−1
α = 104.120 (1)ºT = 296 (2) K
β = 100.975 (1)ºBlock, colourless
γ = 95.901 (1)º0.49 × 0.26 × 0.16 mm
V = 1382.63 (4) Å3
Data collection top
Bruker SMART 1000
diffractometer		11270 independent reflections
Radiation source: fine-focus sealed tube10117 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
Detector resolution: 100 pixels mm-1θmax = 36.0º
T = 296(2) Kθmin = 1.2º
ω scansh = −10→11
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		k = −19→16
Tmin = 0.436, Tmax = 0.737l = −27→27
32412 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.074  w = 1/[σ2(Fo2) + (0.0371P)2 + 0.5264P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
11270 reflectionsΔρmax = 0.55 e Å−3
388 parametersΔρmin = −0.45 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
(C10H10N2)[Sr(C7H3NO4)2(H2O)3]·3H2Oγ = 95.901 (1)º
Mr = 684.12V = 1382.63 (4) Å3
Triclinic, P1Z = 2
a = 6.9994 (1) ÅMo Kα
b = 11.6876 (2) ŵ = 2.03 mm−1
c = 17.9748 (3) ÅT = 296 (2) K
α = 104.120 (1)º0.49 × 0.26 × 0.16 mm
β = 100.975 (1)º
Data collection top
Bruker SMART 1000
diffractometer		11270 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		10117 reflections with I > 2σ(I)
Tmin = 0.436, Tmax = 0.737Rint = 0.018
32412 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.027388 parameters
wR(F2) = 0.074H-atom parameters constrained
S = 1.07Δρmax = 0.55 e Å−3
11270 reflectionsΔρmin = −0.45 e Å−3
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 > 2sigma(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
Sr10.307652 (15)0.128882 (9)0.237424 (6)0.01445 (3)
O10.60785 (14)0.00307 (8)0.24267 (5)0.02076 (16)
O1S0.32246 (19)0.72765 (10)0.27767 (8)0.0391 (3)
H1A0.45690.72230.29610.047*
H1B0.24970.65070.26220.047*
O20.82991 (15)−0.08672 (9)0.30428 (6)0.02578 (19)
O2S−0.26586 (17)0.49429 (9)0.23393 (7)0.0313 (2)
H2B−0.12920.50070.23440.038*
H2A−0.26760.56770.27070.038*
O30.22149 (14)0.25616 (9)0.50121 (5)0.02306 (18)
O3S0.71963 (18)−0.29136 (9)0.34024 (6)0.0293 (2)
H3A0.7463−0.26630.39610.035*
H3B0.7656−0.22120.32700.035*
O40.18013 (14)0.20685 (10)0.37060 (5)0.02483 (19)
O50.26973 (16)0.35859 (9)0.26076 (6)0.0273 (2)
O60.11805 (17)0.50023 (9)0.22108 (8)0.0351 (3)
O70.24198 (16)−0.03028 (9)−0.03564 (5)0.02638 (19)
O80.31399 (14)0.00750 (8)0.09486 (5)0.01968 (16)
O90.63918 (15)0.25817 (9)0.23992 (7)0.0274 (2)
H9A0.75110.22400.22840.033*
H9B0.66710.33850.23780.033*
O100.14922 (15)−0.08710 (9)0.23239 (7)0.0273 (2)
H10B0.2128−0.15010.24500.033*
H10A0.0341−0.08850.25310.033*
O11−0.08144 (13)0.10537 (9)0.19017 (5)0.02129 (17)
H11B−0.12490.07850.13450.026*
H11A−0.15890.05810.21310.026*
N10.50015 (14)0.09789 (9)0.37780 (6)0.01496 (16)
N20.20743 (15)0.22243 (8)0.11289 (6)0.01635 (17)
N30.91685 (15)0.35890 (9)0.49464 (6)0.01948 (18)
H3C1.02540.31630.49640.023*
N40.41975 (17)0.79713 (9)0.05747 (7)0.0220 (2)
H4C0.39480.87690.07300.026*
C10.70090 (17)−0.01926 (10)0.30273 (7)0.01692 (19)
C20.65680 (16)0.04143 (10)0.38089 (7)0.01547 (18)
C30.77792 (18)0.03998 (12)0.45150 (7)0.0205 (2)
H30.8856−0.00050.45160.025*
C40.73572 (18)0.09976 (12)0.52175 (7)0.0212 (2)
H40.81650.10200.56980.025*
C50.57031 (18)0.15618 (11)0.51890 (7)0.0178 (2)
H50.53690.19600.56500.021*
C60.45556 (16)0.15184 (10)0.44566 (7)0.01495 (18)
C70.27066 (17)0.20877 (10)0.43679 (7)0.01640 (19)
C80.18459 (19)0.40237 (11)0.20962 (8)0.0221 (2)
C90.15631 (17)0.33162 (10)0.12402 (8)0.0192 (2)
C100.0827 (2)0.37711 (12)0.06158 (9)0.0253 (2)
H100.04960.45360.07090.030*
C110.0593 (2)0.30680 (13)−0.01467 (9)0.0258 (3)
H110.00970.3354−0.05720.031*
C120.11055 (19)0.19322 (12)−0.02696 (8)0.0215 (2)
H120.09520.1439−0.07750.026*
C130.18595 (17)0.15537 (10)0.03903 (7)0.01627 (19)
C140.25074 (17)0.03444 (10)0.03112 (7)0.01667 (19)
C150.58895 (16)0.47071 (10)0.49884 (7)0.01624 (19)
C160.71839 (18)0.47043 (11)0.56843 (7)0.0204 (2)
H160.69590.50880.61700.024*
C170.87996 (18)0.41260 (12)0.56417 (8)0.0211 (2)
H170.96470.41090.61040.025*
C190.79738 (18)0.35895 (11)0.42720 (7)0.0195 (2)
H190.82600.32130.37960.023*
C200.63196 (17)0.41406 (11)0.42711 (7)0.0186 (2)
H200.54980.41360.37980.022*
C210.4775 (3)0.74127 (12)0.11225 (9)0.0314 (3)
H210.49660.78180.16510.038*
C220.5096 (3)0.62398 (12)0.09167 (8)0.0312 (3)
H220.54890.58580.13050.037*
C230.48263 (19)0.56312 (10)0.01228 (8)0.0202 (2)
C240.42385 (19)0.62453 (11)−0.04326 (8)0.0210 (2)
H240.40500.5869−0.09660.025*
C250.39352 (19)0.74164 (11)−0.01906 (8)0.0219 (2)
H250.35440.7823−0.05640.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sr10.01633 (5)0.01467 (5)0.01249 (5)0.00548 (3)0.00343 (3)0.00248 (3)
O10.0245 (4)0.0243 (4)0.0169 (4)0.0106 (3)0.0082 (3)0.0063 (3)
O1S0.0376 (6)0.0235 (5)0.0527 (7)0.0066 (4)−0.0001 (5)0.0107 (5)
O20.0284 (5)0.0283 (5)0.0301 (5)0.0189 (4)0.0160 (4)0.0121 (4)
O2S0.0322 (5)0.0231 (4)0.0361 (6)0.0056 (4)0.0094 (4)0.0017 (4)
O30.0228 (4)0.0325 (5)0.0173 (4)0.0163 (4)0.0084 (3)0.0051 (3)
O3S0.0422 (6)0.0250 (4)0.0216 (4)0.0089 (4)0.0092 (4)0.0047 (4)
O40.0241 (4)0.0359 (5)0.0166 (4)0.0170 (4)0.0044 (3)0.0064 (4)
O50.0348 (5)0.0209 (4)0.0234 (4)0.0091 (4)0.0067 (4)−0.0013 (3)
O60.0335 (5)0.0170 (4)0.0525 (7)0.0115 (4)0.0117 (5)0.0005 (4)
O70.0374 (5)0.0247 (4)0.0145 (4)0.0094 (4)0.0032 (4)0.0007 (3)
O80.0299 (4)0.0158 (3)0.0140 (4)0.0086 (3)0.0045 (3)0.0034 (3)
O90.0231 (4)0.0208 (4)0.0391 (6)0.0056 (3)0.0104 (4)0.0061 (4)
O100.0259 (5)0.0239 (4)0.0394 (6)0.0081 (4)0.0151 (4)0.0142 (4)
O110.0192 (4)0.0287 (4)0.0166 (4)0.0045 (3)0.0044 (3)0.0068 (3)
N10.0154 (4)0.0165 (4)0.0146 (4)0.0063 (3)0.0052 (3)0.0041 (3)
N20.0165 (4)0.0139 (4)0.0190 (4)0.0037 (3)0.0046 (3)0.0042 (3)
N30.0164 (4)0.0190 (4)0.0237 (5)0.0078 (3)0.0060 (4)0.0037 (4)
N40.0271 (5)0.0142 (4)0.0248 (5)0.0060 (4)0.0094 (4)0.0015 (4)
C10.0178 (5)0.0163 (4)0.0199 (5)0.0060 (4)0.0092 (4)0.0057 (4)
C20.0150 (4)0.0165 (4)0.0169 (5)0.0057 (4)0.0056 (4)0.0052 (4)
C30.0174 (5)0.0254 (5)0.0199 (5)0.0109 (4)0.0033 (4)0.0060 (4)
C40.0193 (5)0.0277 (6)0.0164 (5)0.0087 (4)0.0015 (4)0.0054 (4)
C50.0200 (5)0.0211 (5)0.0132 (4)0.0068 (4)0.0047 (4)0.0039 (4)
C60.0150 (4)0.0157 (4)0.0153 (4)0.0057 (3)0.0049 (4)0.0036 (3)
C70.0166 (4)0.0180 (4)0.0164 (5)0.0076 (4)0.0063 (4)0.0041 (4)
C80.0211 (5)0.0146 (5)0.0298 (6)0.0039 (4)0.0087 (5)0.0014 (4)
C90.0168 (5)0.0152 (4)0.0268 (6)0.0042 (4)0.0058 (4)0.0065 (4)
C100.0225 (6)0.0202 (5)0.0371 (7)0.0072 (4)0.0058 (5)0.0139 (5)
C110.0229 (6)0.0283 (6)0.0305 (6)0.0059 (5)0.0023 (5)0.0181 (5)
C120.0200 (5)0.0251 (5)0.0199 (5)0.0026 (4)0.0012 (4)0.0101 (4)
C130.0156 (4)0.0164 (4)0.0171 (5)0.0023 (4)0.0030 (4)0.0059 (4)
C140.0185 (5)0.0159 (4)0.0155 (5)0.0025 (4)0.0042 (4)0.0039 (4)
C150.0148 (4)0.0139 (4)0.0187 (5)0.0046 (3)0.0039 (4)0.0009 (4)
C160.0189 (5)0.0228 (5)0.0186 (5)0.0092 (4)0.0040 (4)0.0015 (4)
C170.0190 (5)0.0244 (5)0.0197 (5)0.0093 (4)0.0033 (4)0.0036 (4)
C190.0182 (5)0.0196 (5)0.0208 (5)0.0069 (4)0.0072 (4)0.0018 (4)
C200.0163 (5)0.0194 (5)0.0181 (5)0.0061 (4)0.0035 (4)0.0003 (4)
C210.0548 (9)0.0175 (5)0.0239 (6)0.0117 (6)0.0153 (6)0.0021 (5)
C220.0587 (10)0.0180 (5)0.0205 (6)0.0130 (6)0.0145 (6)0.0045 (4)
C230.0253 (5)0.0131 (4)0.0227 (5)0.0045 (4)0.0098 (4)0.0018 (4)
C240.0220 (5)0.0163 (5)0.0227 (5)0.0053 (4)0.0048 (4)0.0008 (4)
C250.0228 (5)0.0166 (5)0.0256 (6)0.0064 (4)0.0055 (4)0.0030 (4)
Geometric parameters (Å, °) top
Sr1—O82.6199 (9)N4—H4C0.9500
Sr1—O92.6223 (10)C1—C21.5153 (16)
Sr1—O102.6239 (10)C2—C31.3907 (16)
Sr1—O112.6580 (9)C3—C41.3870 (17)
Sr1—O52.6633 (10)C3—H30.9300
Sr1—O12.6858 (9)C4—C51.3888 (17)
Sr1—O42.6970 (9)C4—H40.9300
Sr1—N22.7299 (10)C5—C61.3920 (16)
Sr1—N12.7504 (10)C5—H50.9300
O1—C11.2499 (15)C6—C71.5143 (15)
O1S—H1A0.9500C8—C91.5230 (18)
O1S—H1B0.9352C9—C101.3911 (18)
O2—C11.2591 (14)C10—C111.385 (2)
O2S—H2B0.9500C10—H100.9300
O2S—H2A0.9499C11—C121.3874 (19)
O3—C71.2821 (14)C11—H110.9300
O3S—H3A0.9501C12—C131.3952 (16)
O3S—H3B0.9500C12—H120.9300
O4—C71.2307 (15)C13—C141.5105 (16)
O5—C81.2433 (17)C15—C161.3988 (17)
O6—C81.2643 (15)C15—C201.4012 (16)
O7—C141.2391 (14)C15—C15i1.484 (2)
O8—C141.2725 (14)C16—C171.3807 (16)
O9—H9A0.9500C16—H160.9300
O9—H9B0.9501C17—H170.9300
O10—H10B0.9500C19—C201.3816 (16)
O10—H10A0.9501C19—H190.9300
O11—H11B0.9501C20—H200.9300
O11—H11A0.9500C21—C221.3835 (19)
N1—C21.3358 (14)C21—H210.9300
N1—C61.3390 (14)C22—C231.3973 (18)
N2—C131.3386 (15)C22—H220.9300
N2—C91.3391 (15)C23—C241.3910 (18)
N3—C191.3353 (16)C23—C23ii1.493 (2)
N3—C171.3401 (16)C24—C251.3827 (17)
N3—H3C0.9500C24—H240.9300
N4—C211.3327 (19)C25—H250.9300
N4—C251.3382 (17)
O8—Sr1—O987.77 (3)N1—C2—C1116.49 (10)
O8—Sr1—O1077.70 (3)C3—C2—C1120.87 (10)
O9—Sr1—O10143.16 (3)C4—C3—C2119.01 (10)
O8—Sr1—O1187.84 (3)C4—C3—H3120.5
O9—Sr1—O11143.04 (3)C2—C3—H3120.5
O10—Sr1—O1170.77 (3)C3—C4—C5118.61 (11)
O8—Sr1—O5117.81 (3)C3—C4—H4120.7
O9—Sr1—O569.08 (3)C5—C4—H4120.7
O10—Sr1—O5147.32 (3)C4—C5—C6118.60 (10)
O11—Sr1—O580.80 (3)C4—C5—H5120.7
O8—Sr1—O170.16 (3)C6—C5—H5120.7
O9—Sr1—O168.30 (3)N1—C6—C5122.84 (10)
O10—Sr1—O174.93 (3)N1—C6—C7114.85 (10)
O11—Sr1—O1142.46 (3)C5—C6—C7122.31 (10)
O5—Sr1—O1136.17 (3)O4—C7—O3125.13 (11)
O8—Sr1—O4160.45 (3)O4—C7—C6119.40 (10)
O9—Sr1—O4111.64 (3)O3—C7—C6115.48 (10)
O10—Sr1—O487.33 (3)O5—C8—O6126.75 (13)
O11—Sr1—O475.27 (3)O5—C8—C9117.22 (10)
O5—Sr1—O469.72 (3)O6—C8—C9116.02 (12)
O1—Sr1—O4118.22 (3)N2—C9—C10122.18 (12)
O8—Sr1—N259.48 (3)N2—C9—C8115.40 (11)
O9—Sr1—N277.25 (3)C10—C9—C8122.43 (11)
O10—Sr1—N2120.88 (3)C11—C10—C9119.02 (12)
O11—Sr1—N269.00 (3)C11—C10—H10120.5
O5—Sr1—N259.38 (3)C9—C10—H10120.5
O1—Sr1—N2119.01 (3)C10—C11—C12119.34 (12)
O4—Sr1—N2120.81 (3)C10—C11—H11120.3
O8—Sr1—N1127.75 (3)C12—C11—H11120.3
O9—Sr1—N185.89 (3)C11—C12—C13117.86 (12)
O10—Sr1—N177.18 (3)C11—C12—H12121.1
O11—Sr1—N1124.65 (3)C13—C12—H12121.1
O5—Sr1—N1107.88 (3)N2—C13—C12123.13 (11)
O1—Sr1—N159.37 (3)N2—C13—C14115.44 (10)
O4—Sr1—N159.06 (3)C12—C13—C14121.43 (11)
N2—Sr1—N1161.65 (3)O7—C14—O8124.69 (11)
C1—O1—Sr1125.70 (7)O7—C14—C13118.75 (10)
H1A—O1S—H1B108.4O8—C14—C13116.55 (10)
H2B—O2S—H2A100.3C16—C15—C20118.14 (10)
H3A—O3S—H3B102.8C16—C15—C15i120.77 (13)
C7—O4—Sr1124.53 (8)C20—C15—C15i121.09 (13)
C8—O5—Sr1124.51 (8)C17—C16—C15119.27 (11)
C14—O8—Sr1126.81 (7)C17—C16—H16120.4
Sr1—O9—H9A122.7C15—C16—H16120.4
Sr1—O9—H9B131.0N3—C17—C16121.18 (11)
H9A—O9—H9B104.4N3—C17—H17119.4
Sr1—O10—H10B128.6C16—C17—H17119.4
Sr1—O10—H10A113.2N3—C19—C20120.96 (11)
H10B—O10—H10A106.2N3—C19—H19119.5
Sr1—O11—H11B112.5C20—C19—H19119.5
Sr1—O11—H11A117.0C19—C20—C15119.50 (11)
H11B—O11—H11A108.8C19—C20—H20120.2
C2—N1—C6118.24 (10)C15—C20—H20120.2
C2—N1—Sr1120.39 (7)N4—C21—C22121.02 (13)
C6—N1—Sr1120.81 (7)N4—C21—H21119.5
C13—N2—C9118.47 (10)C22—C21—H21119.5
C13—N2—Sr1120.70 (7)C21—C22—C23119.67 (13)
C9—N2—Sr1120.37 (8)C21—C22—H22120.2
C19—N3—C17120.93 (10)C23—C22—H22120.2
C19—N3—H3C122.7C24—C23—C22117.74 (11)
C17—N3—H3C116.2C24—C23—C23ii121.00 (14)
C21—N4—C25120.82 (11)C22—C23—C23ii121.26 (15)
C21—N4—H4C119.5C25—C24—C23119.94 (12)
C25—N4—H4C119.6C25—C24—H24120.0
O1—C1—O2125.84 (11)C23—C24—H24120.0
O1—C1—C2117.22 (10)N4—C25—C24120.81 (12)
O2—C1—C2116.93 (11)N4—C25—H25119.6
N1—C2—C3122.62 (10)C24—C25—H25119.6
O8—Sr1—O1—C1−163.64 (10)C6—N1—C2—C3−2.12 (17)
O9—Sr1—O1—C1100.68 (10)Sr1—N1—C2—C3169.43 (9)
O10—Sr1—O1—C1−81.53 (10)C6—N1—C2—C1179.50 (10)
O11—Sr1—O1—C1−106.00 (10)Sr1—N1—C2—C1−8.94 (13)
O5—Sr1—O1—C186.46 (10)O1—C1—C2—N110.68 (16)
O4—Sr1—O1—C1−3.02 (11)O2—C1—C2—N1−170.11 (11)
N2—Sr1—O1—C1161.19 (9)O1—C1—C2—C3−167.72 (11)
N1—Sr1—O1—C12.29 (9)O2—C1—C2—C311.49 (17)
O8—Sr1—O4—C7125.26 (11)N1—C2—C3—C4−0.27 (19)
O9—Sr1—O4—C7−62.04 (11)C1—C2—C3—C4178.03 (11)
O10—Sr1—O4—C785.47 (11)C2—C3—C4—C51.79 (19)
O11—Sr1—O4—C7156.28 (11)C3—C4—C5—C6−0.94 (19)
O5—Sr1—O4—C7−118.26 (11)C2—N1—C6—C53.04 (17)
O1—Sr1—O4—C714.16 (12)Sr1—N1—C6—C5−168.47 (9)
N2—Sr1—O4—C7−149.76 (10)C2—N1—C6—C7−177.30 (10)
N1—Sr1—O4—C78.83 (10)Sr1—N1—C6—C711.18 (13)
O8—Sr1—O5—C828.13 (12)C4—C5—C6—N1−1.53 (18)
O9—Sr1—O5—C8103.72 (11)C4—C5—C6—C7178.85 (11)
O10—Sr1—O5—C8−83.98 (12)Sr1—O4—C7—O3172.81 (9)
O11—Sr1—O5—C8−54.48 (11)Sr1—O4—C7—C6−7.15 (16)
O1—Sr1—O5—C8117.86 (10)N1—C6—C7—O4−2.99 (16)
O4—Sr1—O5—C8−132.08 (11)C5—C6—C7—O4176.66 (12)
N2—Sr1—O5—C816.49 (10)N1—C6—C7—O3177.05 (10)
N1—Sr1—O5—C8−178.05 (10)C5—C6—C7—O3−3.29 (17)
O9—Sr1—O8—C14−84.81 (10)Sr1—O5—C8—O6160.40 (11)
O10—Sr1—O8—C14129.27 (10)Sr1—O5—C8—C9−19.52 (16)
O11—Sr1—O8—C1458.49 (10)C13—N2—C9—C10−0.18 (18)
O5—Sr1—O8—C14−19.93 (11)Sr1—N2—C9—C10−172.45 (9)
O1—Sr1—O8—C14−152.51 (10)C13—N2—C9—C8179.89 (10)
O4—Sr1—O8—C1488.40 (13)Sr1—N2—C9—C87.62 (13)
N2—Sr1—O8—C14−8.31 (9)O5—C8—C9—N27.03 (17)
N1—Sr1—O8—C14−167.86 (9)O6—C8—C9—N2−172.89 (11)
O8—Sr1—N1—C220.85 (10)O5—C8—C9—C10−172.90 (12)
O9—Sr1—N1—C2−63.12 (9)O6—C8—C9—C107.17 (18)
O10—Sr1—N1—C283.95 (9)N2—C9—C10—C110.7 (2)
O11—Sr1—N1—C2139.34 (8)C8—C9—C10—C11−179.34 (12)
O5—Sr1—N1—C2−129.58 (8)C9—C10—C11—C12−0.3 (2)
O1—Sr1—N1—C24.04 (8)C10—C11—C12—C13−0.60 (19)
O4—Sr1—N1—C2178.58 (10)C9—N2—C13—C12−0.81 (17)
N2—Sr1—N1—C2−86.25 (12)Sr1—N2—C13—C12171.43 (9)
O8—Sr1—N1—C6−167.81 (8)C9—N2—C13—C14178.74 (10)
O9—Sr1—N1—C6108.22 (9)Sr1—N2—C13—C14−9.02 (13)
O10—Sr1—N1—C6−104.72 (9)C11—C12—C13—N21.20 (18)
O11—Sr1—N1—C6−49.32 (9)C11—C12—C13—C14−178.32 (11)
O5—Sr1—N1—C641.75 (9)Sr1—O8—C14—O7−173.87 (9)
O1—Sr1—N1—C6175.37 (10)Sr1—O8—C14—C137.26 (15)
O4—Sr1—N1—C6−10.08 (8)N2—C13—C14—O7−177.24 (11)
N2—Sr1—N1—C685.09 (12)C12—C13—C14—O72.32 (18)
O8—Sr1—N2—C138.61 (8)N2—C13—C14—O81.70 (16)
O9—Sr1—N2—C13103.60 (9)C12—C13—C14—O8−178.75 (11)
O10—Sr1—N2—C13−41.56 (9)C20—C15—C16—C17−1.47 (18)
O11—Sr1—N2—C13−91.73 (9)C15i—C15—C16—C17178.44 (14)
O5—Sr1—N2—C13176.66 (10)C19—N3—C17—C16−0.5 (2)
O1—Sr1—N2—C1347.58 (9)C15—C16—C17—N31.3 (2)
O4—Sr1—N2—C13−148.63 (8)C17—N3—C19—C20−0.18 (19)
N1—Sr1—N2—C13127.28 (10)N3—C19—C20—C15−0.01 (19)
O8—Sr1—N2—C9−179.30 (10)C16—C15—C20—C190.83 (18)
O9—Sr1—N2—C9−84.30 (9)C15i—C15—C20—C19−179.07 (13)
O10—Sr1—N2—C9130.54 (8)C25—N4—C21—C22−0.8 (2)
O11—Sr1—N2—C980.37 (9)N4—C21—C22—C230.5 (3)
O5—Sr1—N2—C9−11.25 (8)C21—C22—C23—C240.0 (2)
O1—Sr1—N2—C9−140.32 (8)C21—C22—C23—C23ii179.49 (17)
O4—Sr1—N2—C923.47 (10)C22—C23—C24—C25−0.2 (2)
N1—Sr1—N2—C9−60.62 (14)C23ii—C23—C24—C25−179.68 (14)
Sr1—O1—C1—O2173.40 (9)C21—N4—C25—C240.6 (2)
Sr1—O1—C1—C2−7.47 (15)C23—C24—C25—N4−0.1 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1S—H1A···O3Siii0.951.902.8462 (17)175
O1S—H1B···O60.941.812.7370 (16)173
O2S—H2B···O60.951.792.7358 (16)172
O2S—H2A···O3Siv0.951.832.7800 (15)178
O3S—H3A···O3v0.951.792.7216 (14)166
O3S—H3B···O20.951.752.7016 (15)175
O9—H9B···O2Svi0.951.852.8043 (15)177
O10—H10B···O1Svii0.951.852.8008 (15)174
O10—H10A···O2viii0.951.842.7864 (14)174
O11—H11B···O7ix0.951.742.6773 (13)171
O11—H11A···O1viii0.951.912.8013 (13)156
O11—H11A···O2viii0.952.633.4752 (14)148
N3—H3C···O3vi0.951.602.5500 (13)175
N4—H4C···O8iii0.951.672.6081 (13)171
N4—H4C···O7iii0.952.573.1285 (15)118
C16—H16···O5i0.932.313.2097 (16)162
C19—H19···O90.932.493.2130 (17)135
C20—H20···O50.932.513.4087 (16)162
C21—H21···O1iii0.932.583.2867 (18)133
C22—H22···O2Svi0.932.573.4867 (19)167
C24—H24···O2Sx0.932.393.2888 (18)164
C25—H25···O7iii0.932.373.0280 (17)127
Symmetry codes: (iii) x, y+1, z; (iv) x−1, y+1, z; (v) −x+1, −y, −z+1; (vi) x+1, y, z; (vii) x, y−1, z; (viii) x−1, y, z; (ix) −x, −y, −z; (i) −x+1, −y+1, −z+1; (x) −x, −y+1, −z.
Selected geometric parameters (Å, °) top
Sr1—O82.6199 (9)Sr1—O12.6858 (9)
Sr1—O92.6223 (10)Sr1—O42.6970 (9)
Sr1—O102.6239 (10)Sr1—N22.7299 (10)
Sr1—O112.6580 (9)Sr1—N12.7504 (10)
Sr1—O52.6633 (10)
O8—Sr1—O1077.70 (3)O1—Sr1—N2119.01 (3)
O8—Sr1—O1187.84 (3)O4—Sr1—N2120.81 (3)
O10—Sr1—O1170.77 (3)O9—Sr1—N185.89 (3)
O9—Sr1—O569.08 (3)O5—Sr1—N1107.88 (3)
O1—Sr1—O4118.22 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1S—H1A···O3Si0.951.902.8462 (17)175
O1S—H1B···O60.941.812.7370 (16)173
O2S—H2B···O60.951.792.7358 (16)172
O2S—H2A···O3Sii0.951.832.7800 (15)178
O3S—H3A···O3iii0.951.792.7216 (14)166
O3S—H3B···O20.951.752.7016 (15)175
O9—H9B···O2Siv0.951.852.8043 (15)177
O10—H10B···O1Sv0.951.852.8008 (15)174
O10—H10A···O2vi0.951.842.7864 (14)174
O11—H11B···O7vii0.951.742.6773 (13)171
O11—H11A···O1vi0.951.912.8013 (13)156
O11—H11A···O2vi0.952.633.4752 (14)148
N3—H3C···O3iv0.951.602.5500 (13)175
N4—H4C···O8i0.951.672.6081 (13)171
N4—H4C···O7i0.952.573.1285 (15)118
C16—H16···O5viii0.932.313.2097 (16)162
C19—H19···O90.932.493.2130 (17)135
C20—H20···O50.932.513.4087 (16)162
C21—H21···O1i0.932.583.2867 (18)133
C22—H22···O2Siv0.932.573.4867 (19)167
C24—H24···O2Six0.932.393.2888 (18)164
C25—H25···O7i0.932.373.0280 (17)127
Symmetry codes: (i) x, y+1, z; (ii) x−1, y+1, z; (iii) −x+1, −y, −z+1; (iv) x+1, y, z; (v) x, y−1, z; (vi) x−1, y, z; (vii) −x, −y, −z; (viii) −x+1, −y+1, −z+1; (ix) −x, −y+1, −z.
Acknowledgements top

Financial support from Ilam University and the Teacher Training University is gratefully acknowledged.

references
References top

Aghabozorg, H., Attar Gharamaleki, J., Ghadermazi, M., Ghasemikhah, P. & Soleimannejad, J. (2007). Acta Cryst. E63, m1803–m1804.

Aghabozorg, H., Attar Gharamaleki, J., Ghasemikhah, P., Ghadermazi, M. & Soleimannejad, J. (2007). Acta Cryst. E63, m1710–m1711.

Aghabozorg, H., Daneshvar, S., Motyeian, E., Ghadermazi, M. & Attar Gharamaleki, J. (2007). Acta Cryst. E63, m2468–m2469.

Bruker (1998). SMART (Version 5.0), SAINT (Version 4.0) and SADABS (Version 2.0). Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2005). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Gottingen, Germany.