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Acta Cryst. (2007). E63, m2251-m2252    [ doi:10.1107/S1600536807036872 ]

Heptaaqua(4-nitrobenzoato-[kappa]2O,O')strontium(II) 4-nitrobenzoate dihydrate

B. R. Srinivasan, P. Raghavaiah and J. V. Sawant

Abstract top

The title compound, [Sr(C7H4NO4)(H2O)7](C7H4NO4)·2H2O, was synthesized from the aqueous reaction of strontium carbonate with 4-nitrobenzoic acid. The structure consists of a nine-coordinate heptaaqua(4-nitrobenzoato-[kappa]2O,O')strontium(II) complex cation, an uncoordinated 4-nitrobenzoate anion and two solvent water molecules. The cations, anions and solvent water molecules are linked with the aid of several O-H...O and C-H...O interactions, resulting in a three-dimensional hydrogen-bonding network. The hydrogen bonding between a solvent water molecule and a symmetry-related solvent water molecule results in the formation of a water dimer.

Comment top

The design of supramolecular architectures employing carboxylic acids as ambidentate and templating ligands with metals providing interesting connectivity, is an area of current research (Rao et al., 2004). As part of our metal carboxylate research programme, we are curently investigating the synthesis, structure and thermal characterization of 4-nitrobenzoate (4-nba) complexes of alkali earth metals (Srinivasan, Sawant & Ragahavaiah, 2007). Recently we reported on the structures of [Mg(H2O)6](4-nba)2·2H2O (Srinivasan, Sawant et al., 2007) and [Ca(H2O)4(4-nba-κ2O,O')(4-nba-κ1O] (Srinivasan et al., 2006). In continuation of this work, we describe the structure of a nine coordinated Sr(II) complex, heptaaquo(4-nitrobenzoato-κ2O,O')strontium(II) 4-nitrobenzoate dihydrate (I).

(I) crystallizes in the monoclinic space group P 21/c with all atoms located in general positions (Fig. 1). The structure consists of a nine coordinated heptaaquo(4-nitrobenzoato-κ2O,O')strontium(II) complex cation, an uncoordinated 4-nitrobenzoate and two lattice water molecules. It is interesting to note that the Sr compound contains coordinated and crystal water molecules, a bidentate 4-nba ligand as well as an uncoordinated 4-nba anion unlike the related [Mg(H2O)6](4-nba)2·2H2O compound where both the nitrobenzoates function as anions. The calcium 4-nitrobenzoate compound [Ca(H2O)4(4-nba-κ2O,O')(4-nba-κ1O] exhibits both monodentate and bidentate 4-nba ligation and contains only coordinated water molecules. The geometric parameters of the coordinated and free 4-nba anions are comparable with the observed values in the aforementioned Mg and Ca complexes. The Sr—O bond lengths vary from 2.5702 (16) to 2.7893 (15) Å while the O—Sr—O angles scatter in a wide range between 47.56 (4) to 144.55 (6) °.

An analysis of the structure reveals that the title compound is involved in several hydrogen bonding interactions through all possible sites and the resulting hydrogen bonded network is displayed in Fig. 2. Each molecule of (I) is linked to ten others with the aid of O—H···O and and C—H···O bonds, with the O atoms of the coordinated and lattice water molecules, the nitro and carboxylate functionalities functioning as hydrogen bond acceptors. All the H atoms attached to the water molecules excepting H16A and H17A and three H atoms on the aromatic rings function function as singly shared H donors. A total of twenty O—H···O interactions ranging from 1.85 to 2.61 Å and three weak C—H···O contacts between 2.53 to 2.60 Å are observed (Table 1). All these O···H contacts are less than the sum of their van der Waals radii (Bondi, 1964). As a result of hydogen bonding, the cations and anions are organized into alternating layers in the crystallographic ac plane with the crystal waters situated in the space between them. The short O17—H17B···O16iv contact at 1.98 Å acccompanied by a O···O distance of 2.761 (4) Å between O17 and a symmetry related crystal water O16iv (for symmetry codes see Table 1) constitutes a water dimer (Infantes & Motherwell, 2002; Supriya & Das, 2003). The water dimer thus formed is further hydrogen bonded to four different complex cations and an uncoordinated 4-nba anion with the aid of eight O—H···O bonds (Fig. 3). The bifurcated acceptor nature of O16 and O17 results in a tetrahedral coordination around the O atoms of the crystal water molecules. In summary, we have described the synthesis and structural characterization of a nine coordinated strontium 4-nitrobenzoate complex, which functions as a molecular container for encapsulating a water dimer.

Related literature top

For a recent review of the chemistry of metal carboxylates, see: Rao et al. (2004). The structures of the 4-nitrobenzoate (4-nba) complexes of the lighter alkali earths [Mg(H2O)6](4-nba)2·2H2O and [Ca(H2O)4(4-nba-κ2O,O')(4-nba-κ1O] have been reported recently (Srinivasan et al., 2006; Srinivasan, Sawant et al., 2007). For related literature, see: Srinivasan, Sawant & Ragahavaiah (2007); Bondi (1964). For reviews of hydrogen-bonded water clusters in crystalline hydrates, see: Infantes & Motherwell (2002); Supriya & Das (2003).

Experimental top

A mixture of strontium carbonate (1.476 g, 10 mmol) and 4-nitrobenzoic acid (4-nbaH) (3.34 g, 20 mmol) was taken in water (50 ml) and heated on a steam bath. The insoluble starting materials slowly started dissolving accompanied with brisk effervescence of CO2. The heating of the reaction mixture was stopped when there was no more evolution of CO2. At this stage, the reaction mixture was almost clear and the pH was close to neutral. The hot solution was filtered and the filtrate was left undisturbed for 3–4 days. The colorless crystalline blocks that separated were filtered, washed thoroughly with ether and dried in air. Yield: 75%. The crystalline blocks thus obtained were suitable for X-ray diffraction studies.

Refinement top

H atoms bonded to the O atoms were located in a difference map and refined with distance restraints of O—H = 0.82 (2) Å. The H atoms on the aromatic ring were positioned geometrically and refined using a riding model, C—H = 0.93 Å and Uiso(H) = 1.2Uiso(C). The largest peak in the residual electron density map of 0.32 e Å−3 is located at a distance of 1.01 Å from Sr1 and the deepest hole of −0.33 e Å−3 is located at a distance of 1.26 Å from C5.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg 1999); software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. A view of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing diagram for (I) viewed along the b axis. O—H···O and C—H···O bonds are shown as dashed and dotted lines respectively. For symmetry codes see Table 2.
[Figure 3] Fig. 3. A view of the surroundings of the water dimer showing it linking to four complex cations and an anion with the aid of O—H···O bonds (dashed lines). For symmetry codes see Table 2.
Heptaaqua(4-nitrobenzoato-κ2O,O')strontium(II) 4-nitrobenzoate dihydrate top
Crystal data top
[Sr(C7H4NO4)(H2O)7](C7H4NO4)·2H2OF000 = 1192
Mr = 581.99Dx = 1.626 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6400 reflections
a = 6.7364 (7) Åθ = 2.2–25.9º
b = 11.1705 (12) ŵ = 2.35 mm−1
c = 31.738 (3) ÅT = 293 (2) K
β = 95.568 (2)ºBlock, colourless
V = 2377.0 (4) Å30.42 × 0.36 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4604 independent reflections
Radiation source: fine-focus sealed tube3777 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 293(2) Kθmax = 25.9º
φ and ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −7→8
Tmin = 0.375, Tmax = 0.761k = −13→13
11962 measured reflectionsl = −39→30
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)] = 0.029H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.067  w = 1/[σ2(Fo2) + (0.0364P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.004
4604 reflectionsΔρmax = 0.32 e Å−3
370 parametersΔρmin = −0.33 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Sr(C7H4NO4)(H2O)7](C7H4NO4)·2H2OV = 2377.0 (4) Å3
Mr = 581.99Z = 4
Monoclinic, P21/cMo Kα
a = 6.7364 (7) ŵ = 2.35 mm−1
b = 11.1705 (12) ÅT = 293 (2) K
c = 31.738 (3) Å0.42 × 0.36 × 0.12 mm
β = 95.568 (2)º
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4604 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		3777 reflections with I > 2σ(I)
Tmin = 0.375, Tmax = 0.761Rint = 0.026
11962 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0292 restraints
wR(F2) = 0.067H atoms treated by a mixture of
independent and constrained refinement
S = 1.02Δρmax = 0.32 e Å−3
4604 reflectionsΔρmin = −0.33 e Å−3
370 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
xyzUiso*/Ueq
C10.0025 (3)0.65965 (18)0.18550 (7)0.0300 (4)
C2−0.0562 (3)0.66764 (18)0.13846 (6)0.0301 (5)
C3−0.0877 (3)0.77767 (18)0.11883 (7)0.0327 (5)
H3−0.07420.84740.13490.039*
C4−0.1389 (3)0.7850 (2)0.07570 (7)0.0362 (5)
H4−0.16140.85880.06250.043*
C5−0.1557 (3)0.6806 (2)0.05288 (7)0.0362 (5)
C6−0.1257 (4)0.5696 (2)0.07123 (7)0.0441 (6)
H6−0.13910.50030.05500.053*
C7−0.0754 (3)0.56418 (19)0.11419 (7)0.0388 (5)
H7−0.05380.49010.12720.047*
C80.4166 (3)0.8073 (2)0.14200 (7)0.0339 (5)
C90.3714 (3)0.80910 (18)0.09441 (7)0.0324 (5)
C100.3370 (4)0.9169 (2)0.07315 (7)0.0459 (6)
H100.34250.98820.08830.055*
C110.2950 (4)0.9193 (2)0.02994 (8)0.0517 (7)
H110.27270.99150.01570.062*
C120.2867 (4)0.8128 (2)0.00817 (7)0.0431 (6)
C130.3197 (3)0.7048 (2)0.02820 (7)0.0420 (6)
H130.31320.63390.01280.050*
C140.3625 (3)0.7033 (2)0.07153 (7)0.0365 (5)
H140.38560.63070.08550.044*
N10.2398 (4)0.8156 (2)−0.03805 (7)0.0609 (6)
N2−0.2068 (3)0.6866 (2)0.00693 (6)0.0498 (5)
O50.4273 (2)0.90757 (14)0.16036 (5)0.0431 (4)
O60.4421 (2)0.70920 (15)0.15994 (5)0.0461 (4)
O70.2177 (4)0.9120 (2)−0.05542 (6)0.0964 (8)
O80.2234 (4)0.7223 (2)−0.05699 (6)0.0997 (9)
O10.0180 (2)0.75470 (13)0.20659 (4)0.0392 (4)
O20.0360 (2)0.55860 (12)0.20171 (5)0.0402 (4)
O3−0.2349 (4)0.5945 (2)−0.01283 (6)0.0863 (7)
O4−0.2209 (3)0.78452 (18)−0.01001 (6)0.0704 (6)
O9−0.2271 (2)0.51563 (14)0.27570 (6)0.0403 (4)
H9B−0.21540.46310.25810.060*
O10−0.2163 (3)0.80181 (16)0.28840 (6)0.0459 (4)
H10A−0.22050.85220.26960.069*
O110.2215 (3)0.87224 (15)0.30012 (6)0.0435 (4)
O120.4433 (3)0.67180 (18)0.24718 (6)0.0427 (4)
O130.2293 (3)0.43788 (14)0.28746 (5)0.0403 (4)
O140.4076 (3)0.63574 (16)0.34331 (6)0.0612 (5)
H14A0.44700.56620.34450.092*
O15−0.0202 (4)0.6336 (3)0.35732 (7)0.0664 (6)
O160.4203 (3)0.4644 (2)0.15802 (7)0.0553 (5)
O170.6857 (4)0.7745 (2)0.39513 (8)0.0719 (6)
Sr10.10618 (3)0.655680 (16)0.282763 (6)0.02839 (7)
H9A−0.269 (5)0.483 (3)0.2954 (9)0.082 (11)*
H11A0.142 (4)0.922 (3)0.3055 (9)0.067 (10)*
H11B0.326 (4)0.895 (2)0.3127 (9)0.061 (9)*
H15B0.072 (6)0.626 (3)0.3754 (13)0.102 (15)*
H15A−0.085 (6)0.679 (3)0.3650 (13)0.108 (18)*
H17B0.654 (7)0.841 (4)0.3855 (15)0.13 (2)*
H17A0.688 (6)0.781 (4)0.4196 (14)0.125 (18)*
H14B0.467 (4)0.677 (2)0.3609 (8)0.079 (11)*
H13A0.159 (5)0.382 (3)0.2930 (9)0.075 (10)*
H13B0.338 (4)0.421 (2)0.2993 (8)0.055 (9)*
H12B0.519 (4)0.624 (3)0.2511 (9)0.059 (10)*
H12A0.445 (4)0.687 (2)0.2224 (9)0.059 (9)*
H16B0.423 (5)0.538 (3)0.1557 (10)0.082 (12)*
H16A0.336 (6)0.451 (3)0.1718 (13)0.113 (17)*
H10B−0.321 (3)0.767 (3)0.2836 (9)0.086 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0265 (10)0.0321 (11)0.0310 (11)−0.0017 (9)0.0018 (8)0.0019 (10)
C20.0284 (11)0.0337 (12)0.0285 (11)−0.0005 (9)0.0039 (9)0.0015 (9)
C30.0364 (12)0.0293 (11)0.0325 (12)0.0022 (9)0.0047 (9)0.0006 (9)
C40.0380 (12)0.0368 (12)0.0337 (12)0.0034 (10)0.0037 (10)0.0091 (10)
C50.0369 (12)0.0455 (14)0.0262 (12)−0.0009 (10)0.0027 (9)0.0004 (9)
C60.0593 (16)0.0380 (13)0.0348 (13)−0.0038 (11)0.0034 (11)−0.0054 (10)
C70.0521 (14)0.0296 (12)0.0343 (13)−0.0019 (10)0.0026 (11)0.0014 (9)
C80.0271 (11)0.0411 (13)0.0337 (12)−0.0045 (9)0.0032 (9)−0.0011 (10)
C90.0297 (11)0.0365 (12)0.0313 (12)−0.0042 (9)0.0039 (9)−0.0004 (9)
C100.0643 (17)0.0350 (13)0.0372 (14)−0.0051 (11)−0.0009 (12)−0.0025 (10)
C110.0748 (19)0.0381 (14)0.0403 (15)−0.0098 (13)−0.0032 (13)0.0074 (11)
C120.0509 (15)0.0492 (15)0.0288 (12)−0.0097 (11)0.0015 (11)0.0016 (10)
C130.0495 (15)0.0411 (13)0.0356 (13)−0.0047 (11)0.0058 (11)−0.0069 (10)
C140.0382 (13)0.0357 (12)0.0356 (13)−0.0017 (10)0.0045 (10)0.0029 (10)
N10.0832 (18)0.0640 (16)0.0341 (12)−0.0151 (13)−0.0012 (12)0.0012 (11)
N20.0570 (14)0.0632 (15)0.0283 (11)0.0036 (11)−0.0002 (9)0.0029 (10)
O50.0516 (10)0.0400 (9)0.0370 (9)−0.0074 (8)0.0007 (7)−0.0082 (7)
O60.0618 (11)0.0411 (9)0.0351 (9)0.0020 (8)0.0028 (8)0.0046 (7)
O70.177 (3)0.0686 (15)0.0390 (12)−0.0140 (15)−0.0123 (13)0.0131 (11)
O80.185 (3)0.0688 (15)0.0414 (12)−0.0109 (16)−0.0064 (14)−0.0147 (11)
O10.0497 (9)0.0342 (8)0.0325 (8)0.0096 (7)−0.0020 (7)−0.0043 (7)
O20.0540 (10)0.0303 (8)0.0348 (9)−0.0070 (7)−0.0042 (7)0.0078 (7)
O30.147 (2)0.0734 (14)0.0348 (11)−0.0045 (15)−0.0093 (12)−0.0123 (10)
O40.1043 (16)0.0692 (13)0.0357 (10)0.0078 (12)−0.0026 (10)0.0147 (10)
O90.0466 (10)0.0359 (9)0.0395 (10)−0.0014 (7)0.0098 (8)−0.0003 (7)
O100.0447 (11)0.0459 (10)0.0472 (11)−0.0064 (8)0.0047 (8)0.0012 (8)
O110.0421 (11)0.0333 (9)0.0537 (11)0.0034 (8)−0.0023 (9)−0.0089 (8)
O120.0402 (10)0.0512 (11)0.0367 (10)0.0046 (8)0.0040 (8)0.0055 (8)
O130.0430 (11)0.0288 (9)0.0465 (10)−0.0039 (8)−0.0091 (8)0.0071 (7)
O140.0736 (13)0.0458 (11)0.0575 (12)0.0136 (10)−0.0279 (10)−0.0138 (9)
O150.0657 (15)0.0956 (18)0.0375 (11)0.0094 (13)0.0033 (11)0.0013 (11)
O160.0553 (13)0.0501 (13)0.0602 (13)0.0011 (10)0.0048 (10)0.0121 (10)
O170.0935 (17)0.0756 (17)0.0451 (14)0.0017 (13)−0.0016 (12)−0.0117 (12)
Sr10.03358 (12)0.02477 (11)0.02640 (11)−0.00023 (8)0.00075 (8)0.00064 (8)
Geometric parameters (Å, °) top
C1—O21.252 (2)N1—O71.212 (3)
C1—O11.254 (2)N2—O31.210 (3)
C1—C21.509 (3)N2—O41.219 (2)
C1—Sr13.098 (2)O1—Sr12.6723 (14)
C2—C31.385 (3)O2—Sr12.7893 (15)
C2—C71.388 (3)O9—Sr12.7277 (16)
C3—C41.381 (3)O9—H9B0.8200
C3—H30.9300O9—H9A0.80 (3)
C4—C51.372 (3)O10—Sr12.7367 (17)
C4—H40.9300O10—H10A0.8200
C5—C61.376 (3)O10—H10B0.806 (18)
C5—N21.467 (3)O11—Sr12.5838 (17)
C6—C71.374 (3)O11—H11A0.80 (3)
C6—H60.9300O11—H11B0.82 (3)
C7—H70.9300O12—Sr12.6387 (18)
C8—O61.240 (3)O12—H12B0.74 (3)
C8—O51.261 (3)O12—H12A0.81 (3)
C8—C91.512 (3)O13—Sr12.5702 (16)
C9—C141.385 (3)O13—H13A0.82 (3)
C9—C101.389 (3)O13—H13B0.81 (3)
C10—C111.373 (3)O14—Sr12.6662 (18)
C10—H100.9300O14—H14A0.8200
C11—C121.374 (3)O14—H14B0.801 (17)
C11—H110.9300O15—Sr12.603 (2)
C12—C131.371 (3)O15—H15B0.81 (4)
C12—N11.470 (3)O15—H15A0.73 (4)
C13—C141.377 (3)O16—H16B0.82 (3)
C13—H130.9300O16—H16A0.76 (4)
C14—H140.9300O17—H17B0.82 (4)
N1—O81.203 (3)O17—H17A0.78 (4)
O2—C1—O1122.79 (19)H11A—O11—H11B104 (3)
O2—C1—C2118.64 (18)Sr1—O12—H12B119 (2)
O1—C1—C2118.57 (18)Sr1—O12—H12A122 (2)
O2—C1—Sr164.11 (11)H12B—O12—H12A104 (3)
O1—C1—Sr158.75 (10)Sr1—O13—H13A124 (2)
C2—C1—Sr1176.64 (14)Sr1—O13—H13B121.3 (19)
C3—C2—C7119.17 (19)H13A—O13—H13B103 (3)
C3—C2—C1120.75 (18)Sr1—O14—H14A109.5
C7—C2—C1120.07 (18)Sr1—O14—H14B138 (2)
C4—C3—C2120.8 (2)H14A—O14—H14B112.1
C4—C3—H3119.6Sr1—O15—H15B111 (3)
C2—C3—H3119.6Sr1—O15—H15A120 (3)
C5—C4—C3118.2 (2)H15B—O15—H15A106 (4)
C5—C4—H4120.9H16B—O16—H16A106 (3)
C3—C4—H4120.9H17B—O17—H17A106 (4)
C4—C5—C6122.8 (2)O13—Sr1—O11141.74 (6)
C4—C5—N2119.1 (2)O13—Sr1—O1589.42 (8)
C6—C5—N2118.1 (2)O11—Sr1—O1590.74 (7)
C7—C6—C5118.1 (2)O13—Sr1—O1278.64 (6)
C7—C6—H6120.9O11—Sr1—O1276.93 (6)
C5—C6—H6120.9O15—Sr1—O12140.05 (8)
C6—C7—C2121.0 (2)O13—Sr1—O1470.13 (6)
C6—C7—H7119.5O11—Sr1—O1474.47 (6)
C2—C7—H7119.5O15—Sr1—O1468.30 (8)
O6—C8—O5125.0 (2)O12—Sr1—O1471.78 (7)
O6—C8—C9118.42 (19)O13—Sr1—O1119.10 (5)
O5—C8—C9116.56 (19)O11—Sr1—O180.86 (5)
C14—C9—C10119.2 (2)O15—Sr1—O1142.93 (7)
C14—C9—C8120.46 (19)O12—Sr1—O173.11 (6)
C10—C9—C8120.31 (19)O14—Sr1—O1140.66 (6)
C11—C10—C9120.7 (2)O13—Sr1—O973.76 (6)
C11—C10—H10119.6O11—Sr1—O9141.49 (6)
C9—C10—H10119.6O15—Sr1—O971.40 (7)
C10—C11—C12118.6 (2)O12—Sr1—O9137.70 (5)
C10—C11—H11120.7O14—Sr1—O9125.06 (6)
C12—C11—H11120.7O1—Sr1—O993.11 (5)
C13—C12—C11122.1 (2)O13—Sr1—O10144.55 (6)
C13—C12—N1119.4 (2)O11—Sr1—O1069.62 (6)
C11—C12—N1118.5 (2)O15—Sr1—O1070.45 (8)
C12—C13—C14118.9 (2)O12—Sr1—O10135.13 (6)
C12—C13—H13120.6O14—Sr1—O10123.81 (6)
C14—C13—H13120.6O1—Sr1—O1072.79 (5)
C13—C14—C9120.5 (2)O9—Sr1—O1072.26 (5)
C13—C14—H14119.8O13—Sr1—O273.16 (5)
C9—C14—H14119.8O11—Sr1—O2125.53 (5)
O8—N1—O7122.7 (2)O15—Sr1—O2139.50 (7)
O8—N1—C12118.7 (2)O12—Sr1—O273.00 (5)
O7—N1—C12118.5 (2)O14—Sr1—O2132.94 (5)
O3—N2—O4122.2 (2)O1—Sr1—O247.45 (4)
O3—N2—C5119.2 (2)O9—Sr1—O268.71 (5)
O4—N2—C5118.7 (2)O10—Sr1—O2103.16 (5)
C1—O1—Sr197.60 (12)O13—Sr1—C196.41 (5)
C1—O2—Sr192.07 (12)O11—Sr1—C1103.48 (6)
Sr1—O9—H9B109.5O15—Sr1—C1147.67 (7)
Sr1—O9—H9A123 (2)O12—Sr1—C172.11 (6)
H9B—O9—H9A105.9O14—Sr1—C1143.28 (6)
Sr1—O10—H10A109.5O1—Sr1—C123.65 (4)
Sr1—O10—H10B113 (2)O9—Sr1—C179.76 (5)
H10A—O10—H10B103.0O10—Sr1—C187.30 (5)
Sr1—O11—H11A120 (2)O2—Sr1—C123.82 (4)
Sr1—O11—H11B129 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O9—H9B···O11i0.822.102.894 (2)162
O10—H10A···O13ii0.822.042.841 (2)165
O14—H14A···O5iii0.821.982.788 (2)170
O9—H9A···O5i0.80 (3)2.03 (3)2.815 (2)169 (3)
O11—H11A···O2ii0.80 (3)1.95 (3)2.707 (2)160 (3)
O11—H11B···O16iv0.82 (3)2.02 (3)2.833 (3)176 (3)
O15—H15B···O7v0.81 (4)2.35 (4)3.104 (3)154 (4)
O15—H15A···O17vi0.73 (4)2.17 (4)2.881 (4)165 (4)
O17—H17B···O16iv0.82 (4)1.98 (4)2.761 (4)158 (4)
O17—H17A···O4vii0.78 (4)2.37 (4)3.087 (3)153 (4)
O17—H17A···O3vii0.78 (4)2.57 (4)3.264 (3)150 (4)
O14—H14B···O170.801 (17)2.06 (2)2.831 (3)163 (3)
O13—H13A···O1i0.82 (3)1.85 (3)2.657 (2)168 (3)
O13—H13B···O5iii0.81 (3)1.94 (3)2.732 (2)164 (3)
O12—H12B···O9viii0.74 (3)2.18 (3)2.899 (3)165 (3)
O12—H12A···O60.81 (3)2.00 (3)2.799 (2)175 (3)
O16—H16B···O60.82 (3)1.93 (3)2.739 (3)171 (3)
O16—H16A···O10i0.76 (4)2.28 (4)2.921 (3)141 (4)
O16—H16A···O20.76 (4)2.61 (4)3.229 (3)140 (4)
O10—H10B···O12vi0.806 (18)2.15 (2)2.915 (3)158 (3)
C4—H4···O7ix0.932.603.476 (3)158
C11—H11···O4ix0.932.533.396 (3)155
C6—H6···O8x0.932.553.349 (3)144
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x, −y+3/2, z+1/2; (vi) x−1, y, z; (vii) x+1, −y+3/2, z+1/2; (viii) x+1, y, z; (ix) −x, −y+2, −z; (x) −x, −y+1, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O9—H9B···O11i0.822.102.894 (2)162
O10—H10A···O13ii0.822.042.841 (2)165
O14—H14A···O5iii0.821.982.788 (2)170
O9—H9A···O5i0.80 (3)2.03 (3)2.815 (2)169 (3)
O11—H11A···O2ii0.80 (3)1.95 (3)2.707 (2)160 (3)
O11—H11B···O16iv0.82 (3)2.02 (3)2.833 (3)176 (3)
O15—H15B···O7v0.81 (4)2.35 (4)3.104 (3)154 (4)
O15—H15A···O17vi0.73 (4)2.17 (4)2.881 (4)165 (4)
O17—H17B···O16iv0.82 (4)1.98 (4)2.761 (4)158 (4)
O17—H17A···O4vii0.78 (4)2.37 (4)3.087 (3)153 (4)
O17—H17A···O3vii0.78 (4)2.57 (4)3.264 (3)150 (4)
O14—H14B···O170.801 (17)2.06 (2)2.831 (3)163 (3)
O13—H13A···O1i0.82 (3)1.85 (3)2.657 (2)168 (3)
O13—H13B···O5iii0.81 (3)1.94 (3)2.732 (2)164 (3)
O12—H12B···O9viii0.74 (3)2.18 (3)2.899 (3)165 (3)
O12—H12A···O60.81 (3)2.00 (3)2.799 (2)175 (3)
O16—H16B···O60.82 (3)1.93 (3)2.739 (3)171 (3)
O16—H16A···O10i0.76 (4)2.28 (4)2.921 (3)141 (4)
O16—H16A···O20.76 (4)2.61 (4)3.229 (3)140 (4)
O10—H10B···O12vi0.806 (18)2.15 (2)2.915 (3)158 (3)
C4—H4···O7ix0.932.603.476 (3)158
C11—H11···O4ix0.932.533.396 (3)155
C6—H6···O8x0.932.553.349 (3)144
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x, −y+3/2, z+1/2; (vi) x−1, y, z; (vii) x+1, −y+3/2, z+1/2; (viii) x+1, y, z; (ix) −x, −y+2, −z; (x) −x, −y+1, −z.
Acknowledgements top

BRS thanks Dr Samar K. Das, School of Chemistry, University of Hyderabad, for the X-ray intensity data collection. This work was supported by the Department of Science and Technology (DST), New Delhi, under grant No. SR/S1/IC-41/2003.

references
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