research communications
μ2-diaqua-diaqua-μ2-L-proline-κ2O:O′-strontium] dibromide]
of poly[[aCrystal Growth Laboratory, PG and Research Department of Physics, Periyar EVR College (Autonomous), Tiruchirappalli 620 023, India, bCrystal Growth and Thin Film Laboratory, Department of Physics and Nanotechnology, SRM University, Kattankulathur 603 203, India, and cBiomolecular Crystallography Laboratory, Department of Bioinformatics, School of Chemical and Biotechnology, SASTRA University, Thanjavur 613 401, India
*Correspondence e-mail: balacrystalgrowth@gmail.com, thamu@scbt.sastra.edu
In the title coordination polymer, {[Sr(C5H9NO2)(H2O)4]Br2}n, the proline molecule exists in a zwitterionic form with one of the ring C atoms disordered over two sites [site-occupancy factors = 0.57 (6):0.43 (6)]. The SrII ion is nine-coordinated by six water O atoms, two monodentate and two μ2-bridging, and three carboxylate O atoms of the proline ligands, with two bridging [Sr—O range = 2.524 (4)–2.800 (5) Å]. In the crystal, there is no direct interaction between the proline molecules. However, the proline and water molecules associate with the bromide counter-anions through a number of intermolecular O—H⋯Br and N—H⋯Br hydrogen-bonding interactions, giving a three-dimensional supramolecular structure.
Keywords: crystal structure; proline; amino acid; strontium coordination polymer; N/O—H⋯Br hydrogen bonds.
CCDC reference: 1424731
1. Chemical context
The study of coordination polymers has been an area of rapid development in recent years due to their interesting structures and their wide range of applications as functional materials (Lyhs et al., 2012). Reports of the crystal structures of alkaline earth metal ions combined with anions of amino acids are very limited. As part of our ongoing investigations of the crystal and molecular structures of a series of metal complexes generated from amino acids (Revathi et al., 2015; Sathiskumar et al., 2015a,b; Balakrishnan et al., 2013), we report here the of a polymeric strontium–proline complex, {[Sr(C5H9NO2)(H2O)4]2+ 2(Br−)}n, (I).
2. Structural commentary
The contains one Sr2+ ion, one bridging proline ligand and four water molecules, two of which are monodentate and two bridging, and two bromide counter-anions (Fig. 1). In (I), the bond lengths involving the carboxylate atoms and the protonation of the amino group suggest that the proline molecule exists in a zwitterionic form. The SrII ion is nine-coordinated by six water oxygen atoms [Sr—O = 2.582 (6)–2.707 (5)Å] and three carboxylate oxygen atoms of zwitterionic proline ligands [Sr—O = 2.524 (4)–2.800 (4) Å; Table 1]. In the strontium–glycine complex, the Sr—O (water) and Sr—O(carboxylate) distances ranges are 2.526 (4)–2.661 (2) and 2.605 (2)–2.703 (2) Å, respectively (Revathi et al., 2015). In (I), one of the carbon atoms (C4) of the pyrrolidine ring is disordered over two sites. In the major component of the pyrrolidine ring, there is a twist conformation on the C2—C5 bond with a pseudo-rotation angle Δ = 40.1 (14)° and a maximum torsion angle φm = 43.8 (10)° for the atom sequence N1–C2–C5–C4A–C3 (Rao et al., 1981). In the minor component, the pyrrolidine ring exhibits an on N1 with a pseudo-rotation angle Δ = 341.5 (19)° and a maximum torsion angle φm = 36.0 (9)° for the atom sequence N1–C2–C5–C4B–C3 (Rao et al., 1981). As shown in Fig. 2, the title complex forms a coordination polymeric chain that lies parallel to the a axis. Adjacent SrII ions are separated by 3.9387 (7) Å within a chain.
of the title complex (I)3. Supramolecular features
The , is stabilized by intermolecular N—H⋯Br and O—H⋯Br hydrogen bonds (Table 2). One of the characteristic features observed in amino acid complexes is the head-to-tail sequence in which amino acids are self-associated through their amino and carboxylate groups (Sharma et al., 2006; Selvaraj et al., 2007; Balakrishnan et al., 2013; Revathi et al., 2015). In the of the L-proline lithium bromide monohydrate complex, there is a head-to-tail sequence observed (Sathiskumar et al., 2015a). In contrast, there is no direct hydrogen-bonding interaction between the proline molecules in (I).
of (I)As shown in Fig. 3, two water molecules and two bromide anions along with Sr2+ ions generate a hydrogen-bonded sheet which lies parallel to the a axis. Within this sheet, two Sr2+ ions and two water oxygens form a cyclic motif. Water molecules (O3 and O4) interconnect the bromide anions, forming a chain. In (I), two molecules (O5 and O6) act as donors for intermolecular O—H⋯Br hydrogen bonds. These hydrogen bonds generate a cyclic dibromide motif similar to that observed in a related structure (Revathi et al., 2015). Adjacent dibromide motifs in (I), which run parallel to the b axis, are interconnected by proline ligands through intermolecular N—H⋯Br hydrogen bonds on both sides (Fig. 3). Adjacent supramolecular arrangements of cyclic dibromide⋯proline⋯cyclic dibromide motifs are interlinked further by water molecules (O3 and O4) through O—H⋯Br hydrogen bonds. This entire arrangement forms a butterfly-like structure. The overall hydrogen-bonded supramolecular structure (Fig. 4) is three-dimensional.
4. Synthesis and crystallization
Single crystals of the title complex were obtained by slow evaporation from an aqueous solution of L-proline and strontium bromide hexahydrate in a 1:1 stoichiometric molar ratio at 306 K. The prepared solution was stirred well and filtered. The resultant filtered solution was left undisturbed to allow evaporation. After 15 days, colourless prismatic crystals were harvested.
5. Refinement
Crystal data, data collection and structure . One of the carbon (C4) atoms of the pyrrolidine ring appears to be disordered over two sites. These positions were defined for this atom and of the site-occupation factors led to a value of 0.57 (6) for the major component. The positions of amino and water H atoms were located from difference Fourier maps. Further, the O—H distances in the water molecules were restrained to 0.85 (2) Å. The N—H distances of amino group were also restrained, to 0.89 (2) Å. The remaining hydrogen atoms were placed in geometrically idealized positions (C—H = 0.97 Å with Uiso(H) = 1.2Ueq(C) and were constrained to ride on their parent atom. The Flack parameter was determined to be 0.008 (8) (788 Friedel pairs; Parsons et al., 2013), indicating an S configuration for C2, consistent with that for the parent L-proline (Kayushina & Vainshtein, 1965).
details are summarized in Table 3
|
Supporting information
CCDC reference: 1424731
10.1107/S2056989015017302/zs2346sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015017302/zs2346Isup2.hkl
The study of coordination polymers has been an area of rapid development in recent years due to their interesting structures and their wide range of applications as functional materials (Lyhs et al., 2012). Reports of the crystal structures of alkaline earth metal ions combined with anions of amino acids are very limited. As part of our ongoing investigations of the crystal and molecular structures of a series of metal complexes generated from amino acids (Revathi et al.,2015; Sathiskumar et al., 2015a,b; Balakrishnan et al., 2013), we report here the
of a polymeric strontium–proline complex, {[Sr(C5H9NO2)(H2O)4]2+ 2(Br-)}n, (I).The φm = 43.8 (10)° for the atom sequence N1–C2–C5–C4A–C3 (Rao et al., 1981). In the minor component, the pyrrolidine ring exhibits an on N1 with a pseudo-rotation angle Δ = 341.5 (19)° and a maximum torsion angle φm = 36.0 (9)° for the atom sequence N1–C2–C5–C4B–C3 (Rao et al., 1981). As shown in Fig. 2, the title complex forms a coordination polymeric chain that lies parallel to the a axis. Adjacent SrII ions are separated by 3.9387 (7) Å within a chain.
of the title complex (I) contains one Sr ion, one bridging proline ligand and four water molecules, two of which are monodentate and two bridging, and two bromide counter-anions (Fig. 1). In (I), the bond lengths involving the carboxylate atoms and the protonation of the amino group suggest that the proline molecule exists in a zwitterionic form. The SrII ion is nine-coordinated by six water oxygen atoms [Sr—O = 2.582 (6)–2.707 (5)Å] and three carboxylate oxygen atoms of zwitterionic proline ligands [Sr—O = 2.524 (4)–2.800 (4) Å; Table 1]. In the strontium–glycine complex, the Sr—O (water) and Sr—O(carboxylate) distances ranges are 2.526 (4)–2.661 (2) and 2.605 (2)–2.703 (2)Å, respectively (Revathi et al., 2015). In (I), one of the carbon atoms (C4) of the pyrrolidine ring is disordered over two sites. In the major component of the pyrrolidine ring, there is a twist conformation on the C2—C5 bond with a pseudo-rotation angle Δ = 40.1 (14)° and a maximum torsion angleThe
of (I), is stabilized by intermolecular N—H···Br and O—H···Br hydrogen bonds (Table 2). One of the characteristic features observed in amino acid complexes is the head-to-tail sequence in which amino acids are self-associated through their amino and carboxylate groups (Sharma et al., 2006; Selvaraj et al., 2007; Balakrishnan et al., 2013; Revathi et al., 2015). In the of the L-proline lithium bromide monohydrate complex, there is a head-to-tail sequence observed (Sathiskumar et al., 2015a). In contrast, there is no direct hydrogen-bonding interaction between the proline molecules in (I).As shown in Fig. 3, two water molecules and two bromide anions along with Sr ions generate a hydrogen-bonded sheet which lies parallel to the a axis. Within this sheet, two Sr ions and two water oxygens form a cyclic motif. Water molecules (O3 and O4) interconnect the bromide anions, forming a chain. In (I), two molecules (O5 and O6) act as donors for intermolecular O—H···Br hydrogen bonds. These hydrogen bonds generate a cyclic dibromide motif similar to that observed in a related structure (Revathi et al., 2015). Adjacent dibromide motifs in (I), which run parallel to the b axis, are interconnected by proline ligands through intermolecular N—H···Br hydrogen bonds on both sides (Fig. 3). Adjacent supramolecular arrangements of cyclic dibromide···proline···cyclic dibromide motifs are interlinked further by water molecules (O3 and O4) through O—H···Br hydrogen bonds. This entire arrangement forms a butterfly-like structure. The overall hydrogen-bonded supramolecular structure (Fig. 4) is three-dimensional.
Single crystals of the title complex were obtained by slow evaporation from an aqueous solution of L-proline and strontium bromide hexahydrate in a 1:1 stoichiometric molar ratio at room temperature (306 K). The prepared solution was stirred well and filtered. The resultant filtered solution was left undisturbed to allow evaporation. After 15 days, colourless prismatic crystals were harvested.
Crystal data, data collection and structure
details are summarized in Table 3. One of the carbon (C4) atoms of the pyrrolidine ring appears to be disordered over two sites. These positions were defined for this atom and of the site-occupation factors led to a value of 0.57 (6) for the major component. The positions of amino and water H atoms were located from difference Fourier maps. Further, the O—H distances in the water molecules were restrained to 0.85 (2) Å. The N—H distances of amino group were also restrained, to 0.89 (2) Å. The remaining hydrogen atoms were placed in geometrically idealized positions (C—H = 0.97 Å with Uiso(H) = 1.2Ueq(C) and were constrained to ride on their parent atom. The Flack parameter was determined to be 0.008 (8) (788 Friedel pairs; Parsons et al., 2013), indicating an S configuration for C2, consistent with that for the parent L-proline (Kayushina & Vainshtein, 1965).Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).Fig. 1. The coordination sphere of Sr2+ in the crystal structure of (I). Only the major components of the proline ligands are shown. Displacement ellipsoids are drawn at the 50% probability level. For symmetry codes, see Table 1. | |
Fig. 2. The Sr–water coordination polymeric chain substructure of (I), with peripheral water O—H···Br hydrogen bonds shown as dashed lines. | |
Fig. 3. The butterfly-like supramolecular arrangements generated by intermolecular N—H···Br and O—H···Br hydrogen bonds. Only atoms involved in hydrogen-bonding interactions are labelled. | |
Fig. 4. The crystal packing of (I) viewed along the a axis, with hydrogen bonds shown as dashed lines. C-bound H atoms have been omitted for clarity. |
[Sr(C5H9NO2)(H2O)4]Br2 | Dx = 2.157 Mg m−3 |
Mr = 434.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 7063 reflections |
a = 6.7079 (4) Å | θ = 2.6–28.5° |
b = 12.9125 (9) Å | µ = 10.01 mm−1 |
c = 15.4499 (11) Å | T = 296 K |
V = 1338.20 (16) Å3 | Block, brown |
Z = 4 | 0.15 × 0.10 × 0.10 mm |
F(000) = 840 |
Bruker Kappa APEXII CCD diffractometer | 2081 reflections with I > 2σ(I) |
Radiation source: Sealed tube | Rint = 0.068 |
ω nd φ scan | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (SABABS; Bruker, 2004) | h = −7→7 |
Tmin = 0.26, Tmax = 0.44 | k = −15→15 |
14183 measured reflections | l = −18→18 |
2345 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0267P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.063 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.60 e Å−3 |
2345 reflections | Δρmin = −0.86 e Å−3 |
186 parameters | Absolute structure: Flack x determined using 788 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
26 restraints | Absolute structure parameter: 0.008 (8) |
[Sr(C5H9NO2)(H2O)4]Br2 | V = 1338.20 (16) Å3 |
Mr = 434.63 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.7079 (4) Å | µ = 10.01 mm−1 |
b = 12.9125 (9) Å | T = 296 K |
c = 15.4499 (11) Å | 0.15 × 0.10 × 0.10 mm |
Bruker Kappa APEXII CCD diffractometer | 2345 independent reflections |
Absorption correction: multi-scan (SABABS; Bruker, 2004) | 2081 reflections with I > 2σ(I) |
Tmin = 0.26, Tmax = 0.44 | Rint = 0.068 |
14183 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.063 | Δρmax = 0.60 e Å−3 |
S = 1.07 | Δρmin = −0.86 e Å−3 |
2345 reflections | Absolute structure: Flack x determined using 788 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
186 parameters | Absolute structure parameter: 0.008 (8) |
26 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sr1 | 1.34882 (8) | 0.24302 (5) | 0.43342 (4) | 0.0174 (2) | |
O1 | 1.0492 (6) | 0.2322 (4) | 0.3350 (3) | 0.0257 (16) | |
O2 | 0.7439 (6) | 0.2420 (4) | 0.3916 (3) | 0.0243 (16) | |
O3 | 1.5725 (8) | 0.3885 (5) | 0.5016 (4) | 0.0243 (19) | |
O4 | 1.5819 (8) | 0.1162 (4) | 0.5200 (4) | 0.0213 (17) | |
O5 | 1.3443 (9) | 0.0648 (4) | 0.3561 (4) | 0.035 (2) | |
O6 | 1.3860 (9) | 0.3899 (5) | 0.3212 (4) | 0.038 (2) | |
N1 | 0.9404 (8) | 0.2529 (6) | 0.1734 (4) | 0.026 (2) | |
C1 | 0.8660 (9) | 0.2426 (5) | 0.3307 (4) | 0.018 (2) | |
C2 | 0.7837 (9) | 0.2600 (6) | 0.2411 (4) | 0.021 (2) | |
C3 | 0.8370 (12) | 0.2347 (7) | 0.0890 (5) | 0.042 (3) | |
C4A | 0.623 (2) | 0.211 (3) | 0.1117 (11) | 0.034 (7) | 0.57 (6) |
C5 | 0.6277 (12) | 0.1840 (7) | 0.2082 (5) | 0.042 (3) | |
C4B | 0.660 (5) | 0.167 (3) | 0.1117 (13) | 0.035 (8) | 0.43 (6) |
Br2 | 0.18627 (12) | 0.02641 (6) | 0.15165 (6) | 0.0389 (3) | |
Br3 | 0.22307 (13) | 0.44596 (7) | 0.11973 (6) | 0.0466 (3) | |
H1A | 1.024 (9) | 0.199 (4) | 0.180 (5) | 0.02 (2)* | |
H1B | 1.033 (10) | 0.303 (5) | 0.175 (6) | 0.05 (3)* | |
H3C | 1.522 (13) | 0.429 (5) | 0.538 (4) | 0.06 (3)* | |
H3D | 1.622 (13) | 0.422 (5) | 0.460 (4) | 0.07 (4)* | |
H4E | 1.532 (12) | 0.085 (5) | 0.563 (3) | 0.05 (3)* | |
H4F | 1.640 (10) | 0.075 (4) | 0.487 (4) | 0.04 (3)* | |
H5C | 1.281 (10) | 0.060 (6) | 0.308 (3) | 0.06 (3)* | |
H5D | 1.450 (7) | 0.030 (6) | 0.353 (5) | 0.06 (3)* | |
H6C | 1.478 (8) | 0.432 (5) | 0.327 (5) | 0.03 (3)* | |
H6D | 1.319 (11) | 0.402 (7) | 0.276 (4) | 0.09 (4)* | |
H31 | 0.89720 | 0.17700 | 0.05850 | 0.0500* | 0.57 (6) |
H32 | 0.84480 | 0.29580 | 0.05270 | 0.0500* | 0.57 (6) |
H41 | 0.57440 | 0.15290 | 0.07800 | 0.0410* | 0.57 (6) |
H42 | 0.53890 | 0.27050 | 0.10120 | 0.0410* | 0.57 (6) |
H51 | 0.49920 | 0.19560 | 0.23530 | 0.0500* | 0.57 (6) |
H52 | 0.66830 | 0.11280 | 0.21770 | 0.0500* | 0.57 (6) |
H2 | 0.72630 | 0.32970 | 0.23900 | 0.0250* | |
H33 | 0.92450 | 0.19970 | 0.04850 | 0.0500* | 0.43 (6) |
H34 | 0.79360 | 0.29960 | 0.06370 | 0.0500* | 0.43 (6) |
H43 | 0.68850 | 0.09490 | 0.09960 | 0.0420* | 0.43 (6) |
H44 | 0.54310 | 0.18790 | 0.07910 | 0.0420* | 0.43 (6) |
H53 | 0.49510 | 0.21140 | 0.21840 | 0.0500* | 0.43 (6) |
H54 | 0.63970 | 0.11870 | 0.23880 | 0.0500* | 0.43 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sr1 | 0.0142 (3) | 0.0215 (4) | 0.0165 (3) | 0.0003 (3) | −0.0010 (3) | 0.0006 (3) |
O1 | 0.017 (2) | 0.041 (3) | 0.019 (3) | 0.006 (2) | −0.001 (2) | −0.003 (3) |
O2 | 0.024 (2) | 0.033 (3) | 0.016 (3) | 0.004 (3) | 0.004 (2) | 0.002 (3) |
O3 | 0.025 (3) | 0.029 (3) | 0.019 (4) | 0.000 (2) | 0.000 (3) | −0.003 (3) |
O4 | 0.024 (3) | 0.024 (3) | 0.016 (3) | 0.000 (2) | 0.003 (3) | 0.000 (3) |
O5 | 0.033 (3) | 0.044 (4) | 0.029 (4) | 0.006 (3) | −0.002 (3) | −0.010 (3) |
O6 | 0.034 (4) | 0.043 (4) | 0.037 (4) | −0.012 (3) | −0.011 (3) | 0.017 (3) |
N1 | 0.022 (3) | 0.035 (4) | 0.022 (4) | −0.005 (4) | 0.000 (3) | 0.004 (4) |
C1 | 0.025 (4) | 0.011 (3) | 0.017 (4) | −0.001 (3) | −0.003 (3) | −0.004 (3) |
C2 | 0.024 (3) | 0.026 (4) | 0.013 (4) | 0.005 (4) | 0.002 (3) | 0.000 (4) |
C3 | 0.052 (5) | 0.059 (6) | 0.015 (4) | 0.000 (5) | −0.001 (4) | −0.001 (4) |
C4A | 0.036 (10) | 0.041 (15) | 0.025 (9) | 0.001 (8) | −0.007 (7) | −0.014 (9) |
C5 | 0.035 (5) | 0.066 (6) | 0.025 (5) | −0.025 (4) | −0.006 (4) | −0.004 (5) |
C4B | 0.033 (13) | 0.042 (17) | 0.030 (11) | −0.010 (13) | 0.005 (10) | −0.023 (11) |
Br2 | 0.0357 (5) | 0.0379 (5) | 0.0432 (5) | 0.0057 (4) | −0.0102 (4) | −0.0197 (4) |
Br3 | 0.0505 (6) | 0.0484 (6) | 0.0409 (6) | −0.0239 (4) | −0.0107 (4) | 0.0197 (5) |
Sr1—O1 | 2.524 (4) | N1—H1A | 0.90 (6) |
Sr1—O3 | 2.625 (6) | N1—H1B | 0.90 (7) |
Sr1—O4 | 2.630 (6) | C1—C2 | 1.507 (9) |
Sr1—O5 | 2.593 (5) | C2—C5 | 1.522 (11) |
Sr1—O6 | 2.582 (6) | C3—C4A | 1.509 (17) |
Sr1—O2i | 2.728 (4) | C3—C4B | 1.52 (4) |
Sr1—O3ii | 2.707 (6) | C4A—C5 | 1.53 (2) |
Sr1—O4ii | 2.651 (5) | C4B—C5 | 1.52 (2) |
Sr1—O2iii | 2.800 (5) | C2—H2 | 0.9800 |
O1—C1 | 1.238 (7) | C3—H31 | 0.9700 |
O2—C1 | 1.248 (8) | C3—H32 | 0.9700 |
O3—H3C | 0.84 (7) | C3—H33 | 0.9700 |
O3—H3D | 0.84 (7) | C3—H34 | 0.9700 |
O4—H4E | 0.85 (6) | C4A—H41 | 0.9700 |
O4—H4F | 0.83 (6) | C4A—H42 | 0.9700 |
O5—H5D | 0.84 (6) | C4B—H43 | 0.9700 |
O5—H5C | 0.86 (5) | C4B—H44 | 0.9700 |
O6—H6D | 0.85 (7) | C5—H51 | 0.9700 |
O6—H6C | 0.83 (6) | C5—H54 | 0.9700 |
N1—C3 | 1.496 (10) | C5—H52 | 0.9700 |
N1—C2 | 1.486 (8) | C5—H53 | 0.9700 |
O1—Sr1—O3 | 137.44 (18) | Sr1—O6—H6D | 130 (6) |
O1—Sr1—O4 | 138.19 (17) | Sr1—O6—H6C | 119 (5) |
O1—Sr1—O5 | 70.37 (18) | H6C—O6—H6D | 111 (8) |
O1—Sr1—O6 | 73.32 (18) | C2—N1—C3 | 107.2 (5) |
O1—Sr1—O2i | 129.10 (14) | C3—N1—H1B | 117 (6) |
O1—Sr1—O3ii | 69.11 (17) | H1A—N1—H1B | 97 (5) |
O1—Sr1—O4ii | 70.35 (17) | C2—N1—H1A | 114 (5) |
O1—Sr1—O2iii | 112.66 (13) | C2—N1—H1B | 115 (5) |
O3—Sr1—O4 | 84.36 (18) | C3—N1—H1A | 105 (5) |
O3—Sr1—O5 | 145.76 (18) | O1—C1—C2 | 115.4 (5) |
O3—Sr1—O6 | 71.85 (19) | O2—C1—C2 | 117.0 (5) |
O2i—Sr1—O3 | 62.82 (16) | O1—C1—O2 | 127.6 (6) |
O3—Sr1—O3ii | 133.75 (19) | N1—C2—C5 | 102.2 (6) |
O3—Sr1—O4ii | 77.67 (17) | N1—C2—C1 | 112.2 (5) |
O2iii—Sr1—O3 | 72.95 (16) | C1—C2—C5 | 117.6 (6) |
O4—Sr1—O5 | 71.86 (18) | N1—C3—C4B | 104.6 (10) |
O4—Sr1—O6 | 137.87 (18) | N1—C3—C4A | 105.7 (8) |
O2i—Sr1—O4 | 62.60 (16) | C3—C4A—C5 | 104.7 (10) |
O3ii—Sr1—O4 | 80.08 (17) | C3—C4B—C5 | 104.8 (19) |
O4—Sr1—O4ii | 133.67 (19) | C2—C5—C4A | 101.1 (12) |
O2iii—Sr1—O4 | 72.62 (16) | C2—C5—C4B | 108.8 (15) |
O5—Sr1—O6 | 110.10 (19) | N1—C2—H2 | 108.00 |
O2i—Sr1—O5 | 84.14 (17) | C1—C2—H2 | 108.00 |
O3ii—Sr1—O5 | 66.80 (19) | C5—C2—H2 | 108.00 |
O4ii—Sr1—O5 | 136.53 (18) | N1—C3—H31 | 111.00 |
O2iii—Sr1—O5 | 120.21 (17) | N1—C3—H32 | 111.00 |
O2i—Sr1—O6 | 75.56 (17) | N1—C3—H33 | 111.00 |
O3ii—Sr1—O6 | 140.90 (18) | N1—C3—H34 | 111.00 |
O4ii—Sr1—O6 | 75.16 (19) | C4A—C3—H31 | 111.00 |
O2iii—Sr1—O6 | 128.45 (18) | C4A—C3—H32 | 111.00 |
O2i—Sr1—O3ii | 138.60 (17) | H31—C3—H32 | 109.00 |
O2i—Sr1—O4ii | 136.37 (16) | C4B—C3—H33 | 111.00 |
O2i—Sr1—O2iii | 118.24 (13) | C4B—C3—H34 | 111.00 |
O3ii—Sr1—O4ii | 82.36 (17) | H33—C3—H34 | 109.00 |
O2iii—Sr1—O3ii | 60.87 (16) | C3—C4A—H41 | 111.00 |
O2iii—Sr1—O4ii | 61.37 (16) | C3—C4A—H42 | 111.00 |
Sr1—O1—C1 | 144.8 (4) | C5—C4A—H41 | 111.00 |
Sr1iv—O2—C1 | 144.7 (4) | C5—C4A—H42 | 111.00 |
Sr1ii—O2—C1 | 124.2 (4) | H41—C4A—H42 | 109.00 |
Sr1iv—O2—Sr1ii | 90.87 (13) | H43—C4B—H44 | 109.00 |
Sr1—O3—Sr1iii | 95.2 (2) | C3—C4B—H44 | 111.00 |
Sr1—O4—Sr1iii | 96.47 (17) | C5—C4B—H43 | 111.00 |
H3C—O3—H3D | 111 (6) | C3—C4B—H43 | 111.00 |
Sr1iii—O3—H3C | 115 (5) | C5—C4B—H44 | 111.00 |
Sr1iii—O3—H3D | 110 (5) | C2—C5—H52 | 112.00 |
Sr1—O3—H3C | 119 (6) | C2—C5—H53 | 110.00 |
Sr1—O3—H3D | 107 (5) | C2—C5—H51 | 112.00 |
H4E—O4—H4F | 111 (6) | C4B—C5—H54 | 110.00 |
Sr1—O4—H4E | 117 (5) | H53—C5—H54 | 108.00 |
Sr1—O4—H4F | 111 (4) | C2—C5—H54 | 110.00 |
Sr1iii—O4—H4F | 107 (4) | C4A—C5—H51 | 112.00 |
Sr1iii—O4—H4E | 112 (5) | C4A—C5—H52 | 112.00 |
Sr1—O5—H5D | 119 (5) | H51—C5—H52 | 109.00 |
Sr1—O5—H5C | 118 (5) | C4B—C5—H53 | 110.00 |
H5C—O5—H5D | 109 (7) | ||
O3—Sr1—O1—C1 | −76.6 (8) | O5iii—Sr1iii—O3—Sr1 | −158.1 (2) |
O4—Sr1—O1—C1 | 101.4 (8) | O6iii—Sr1iii—O3—Sr1 | −64.4 (3) |
O5—Sr1—O1—C1 | 128.0 (8) | O1—Sr1—O4—Sr1iii | 171.61 (16) |
O6—Sr1—O1—C1 | −112.8 (8) | O3—Sr1—O4—Sr1iii | −9.71 (18) |
O2i—Sr1—O1—C1 | −167.5 (7) | O5—Sr1—O4—Sr1iii | 145.3 (2) |
O3ii—Sr1—O1—C1 | 56.1 (8) | O6—Sr1—O4—Sr1iii | 45.1 (3) |
O4ii—Sr1—O1—C1 | −33.0 (8) | O2i—Sr1—O4—Sr1iii | 52.53 (16) |
O2iii—Sr1—O1—C1 | 12.5 (8) | O3ii—Sr1—O4—Sr1iii | −146.0 (2) |
O1iv—Sr1iv—O2—C1 | 5.3 (8) | O4ii—Sr1—O4—Sr1iii | −76.7 (3) |
O3iv—Sr1iv—O2—C1 | −125.2 (8) | O2iii—Sr1—O4—Sr1iii | −83.58 (18) |
O4iv—Sr1iv—O2—C1 | 136.7 (8) | O3—Sr1iii—O4—Sr1 | 9.45 (18) |
O5iv—Sr1iv—O2—C1 | 64.1 (8) | O2i—Sr1iii—O4—Sr1 | −51.45 (16) |
O6iv—Sr1iv—O2—C1 | −48.4 (8) | O1iii—Sr1iii—O4—Sr1 | 79.93 (18) |
O2ii—Sr1iv—O2—C1 | −174.6 (7) | O3iii—Sr1iii—O4—Sr1 | −128.6 (2) |
O3iv—Sr1ii—O2—C1 | 127.5 (6) | O4iii—Sr1iii—O4—Sr1 | −58.9 (3) |
O4iv—Sr1ii—O2—C1 | −135.0 (6) | O5iii—Sr1iii—O4—Sr1 | 53.5 (3) |
O1ii—Sr1ii—O2—C1 | 175.1 (5) | O6iii—Sr1iii—O4—Sr1 | 157.2 (2) |
O3ii—Sr1ii—O2—C1 | −50.0 (5) | Sr1—O1—C1—O2 | −19.8 (13) |
O4ii—Sr1ii—O2—C1 | 39.4 (5) | Sr1—O1—C1—C2 | 158.9 (6) |
O5ii—Sr1ii—O2—C1 | 95.3 (5) | Sr1iv—O2—C1—O1 | −172.8 (5) |
O6ii—Sr1ii—O2—C1 | −98.7 (5) | Sr1ii—O2—C1—O1 | 13.2 (10) |
O2iii—Sr1ii—O2—C1 | −5.0 (6) | Sr1iv—O2—C1—C2 | 8.5 (11) |
O1—Sr1—O3—Sr1iii | −171.81 (15) | Sr1ii—O2—C1—C2 | −165.5 (4) |
O4—Sr1—O3—Sr1iii | 9.48 (18) | C2—N1—C3—C4A | −10.6 (17) |
O5—Sr1—O3—Sr1iii | −36.0 (4) | C3—N1—C2—C5 | 34.0 (8) |
O6—Sr1—O3—Sr1iii | −135.3 (2) | C3—N1—C2—C1 | 160.9 (6) |
O2i—Sr1—O3—Sr1iii | −52.54 (16) | O1—C1—C2—N1 | 4.6 (9) |
O3ii—Sr1—O3—Sr1iii | 80.0 (3) | O2—C1—C2—C5 | −58.5 (9) |
O4ii—Sr1—O3—Sr1iii | 146.5 (2) | O2—C1—C2—N1 | −176.6 (6) |
O2iii—Sr1—O3—Sr1iii | 83.01 (17) | O1—C1—C2—C5 | 122.7 (7) |
O4—Sr1iii—O3—Sr1 | −9.45 (18) | N1—C2—C5—C4A | −43.4 (12) |
O2i—Sr1iii—O3—Sr1 | 51.95 (16) | C1—C2—C5—C4A | −166.7 (12) |
O1iii—Sr1iii—O3—Sr1 | −81.27 (18) | N1—C3—C4A—C5 | −17 (2) |
O3iii—Sr1iii—O3—Sr1 | 55.3 (3) | C3—C4A—C5—C2 | 37 (2) |
O4iii—Sr1iii—O3—Sr1 | 127.5 (2) |
Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+1/2, −z+1; (iv) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Br2i | 0.90 (6) | 2.52 (5) | 3.374 (7) | 159 (6) |
N1—H1B···Br3i | 0.90 (7) | 2.40 (7) | 3.240 (7) | 156 (8) |
O3—H3C···Br3v | 0.84 (7) | 2.63 (7) | 3.440 (6) | 163 (7) |
O3—H3D···Br2vi | 0.84 (7) | 2.54 (7) | 3.376 (6) | 172 (5) |
O4—H4E···Br2vii | 0.85 (6) | 2.47 (7) | 3.281 (6) | 162 (7) |
O4—H4F···Br3viii | 0.83 (6) | 2.52 (6) | 3.347 (6) | 174 (6) |
O5—H5C···Br2i | 0.86 (5) | 2.54 (5) | 3.369 (6) | 164 (6) |
O5—H5D···Br3viii | 0.84 (6) | 2.48 (6) | 3.304 (6) | 166 (6) |
O6—H6C···Br2vi | 0.83 (6) | 2.58 (6) | 3.393 (6) | 167 (5) |
O6—H6D···Br3i | 0.85 (7) | 2.56 (6) | 3.378 (6) | 162 (7) |
Symmetry codes: (i) x+1, y, z; (v) −x+3/2, −y+1, z+1/2; (vi) −x+2, y+1/2, −z+1/2; (vii) −x+3/2, −y, z+1/2; (viii) −x+2, y−1/2, −z+1/2. |
Sr1—O1 | 2.524 (4) | Sr1—O2i | 2.728 (4) |
Sr1—O3 | 2.625 (6) | Sr1—O3ii | 2.707 (6) |
Sr1—O4 | 2.630 (6) | Sr1—O4ii | 2.651 (5) |
Sr1—O5 | 2.593 (5) | Sr1—O2iii | 2.800 (5) |
Sr1—O6 | 2.582 (6) |
Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Br2i | 0.90 (6) | 2.52 (5) | 3.374 (7) | 159 (6) |
N1—H1B···Br3i | 0.90 (7) | 2.40 (7) | 3.240 (7) | 156 (8) |
O3—H3C···Br3iv | 0.84 (7) | 2.63 (7) | 3.440 (6) | 163 (7) |
O3—H3D···Br2v | 0.84 (7) | 2.54 (7) | 3.376 (6) | 172 (5) |
O4—H4E···Br2vi | 0.85 (6) | 2.47 (7) | 3.281 (6) | 162 (7) |
O4—H4F···Br3vii | 0.83 (6) | 2.52 (6) | 3.347 (6) | 174 (6) |
O5—H5C···Br2i | 0.86 (5) | 2.54 (5) | 3.369 (6) | 164 (6) |
O5—H5D···Br3vii | 0.84 (6) | 2.48 (6) | 3.304 (6) | 166 (6) |
O6—H6C···Br2v | 0.83 (6) | 2.58 (6) | 3.393 (6) | 167 (5) |
O6—H6D···Br3i | 0.85 (7) | 2.56 (6) | 3.378 (6) | 162 (7) |
Symmetry codes: (i) x+1, y, z; (iv) −x+3/2, −y+1, z+1/2; (v) −x+2, y+1/2, −z+1/2; (vi) −x+3/2, −y, z+1/2; (vii) −x+2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Sr(C5H9NO2)(H2O)4]Br2 |
Mr | 434.63 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 6.7079 (4), 12.9125 (9), 15.4499 (11) |
V (Å3) | 1338.20 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 10.01 |
Crystal size (mm) | 0.15 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SABABS; Bruker, 2004) |
Tmin, Tmax | 0.26, 0.44 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14183, 2345, 2081 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.063, 1.07 |
No. of reflections | 2345 |
No. of parameters | 186 |
No. of restraints | 26 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.60, −0.86 |
Absolute structure | Flack x determined using 788 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Absolute structure parameter | 0.008 (8) |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008).
Acknowledgements
TB and SS would like to acknowledge the University Grants Commission (UGC), India for providing financial support [Project No. 41-956/2012(SR)]. ST is very grateful to the management of SASTRA University for infrastructural and financial support (Professor TRR grant).
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