Polymeric strontium ranelate nona­hydrate

Stahl, K.; Frankaer, C.G.; Raffalt, A.C.; Sørensen, S.R.; Andersen, J.E.T.

doi:10.1107/S1600536811010099

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m471-m472

doi:10.1107/S1600536811010099

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Polymeric strontium ranelate nonahydrate

Kenny Stahl,^a ^* Christian G. Frankaer,^a Anders C. Raffalt,^a Søren R. Sørensen ^a and Jens E. T. Andersen ^a

^aDepartment of Chemistry, Technical University of Denmark, DK-2800 Lyngby, Denmark
^*Correspondence e-mail: kenny@kemi.dtu.dk

(Received 9 March 2011; accepted 17 March 2011; online 23 March 2011)

The title compound, poly[[μ-aqua-tetraaqua{μ-5-[bis(carboxylatomethyl)amino]-3-carboxylatomethyl-4-cyanothiophene-2-carboxylato}distrontium(II)] tetrahydrate], [Sr₂(C₁₂H₆N₂O₈S)(H₂O)₅]·3.79H₂O, crystallizes with nine- and eight-coordinated Sr²⁺ cations. They are bound to seven of the eight ranelate O atoms and five of the water molecules. The SrO₈ and SrO₉ polyhedra are interconnected by edge-sharing, forming hollow layers parallel to (011). The layers are, in turn, interconnected by ranelate anions, forming a metal–organic framework (MOF) structure with channels along the a axis. The four water molecules not coordinated to strontium are located in these channels and hydrogen bonded to each other and to the ranelates. Part of the water H atoms are disordered. The compound dehydrates very easily and 0.210 (4) water molecules out of nine were lost during crystal mounting causing additional disorder in the water structure.

Related literature

For the effect of strontium on osteroporosis, see Schrooten et al. (2003). For a patent describing the synthesis and powder diffraction pattern of the title compound, see Horvath et al. (2008 ). For related strontium carboxylate structures, see, for example: Stahl et al. (2006 ).

Experimental

Crystal data

[Sr₂(C₁₂H₆N₂O₈S)(H₂O)₅]·3.79H₂O
M_r = 671.84
Triclinic, $[P \overline 1]$
a = 8.3585 (3) Å
b = 12.3865 (5) Å
c = 12.6474 (5) Å
α = 109.880 (1)°
β = 97.148 (1)°
γ = 105.321 (1)°
V = 1154.00 (8) Å³
Z = 2
Mo Kα radiation
μ = 4.80 mm⁻¹
T = 120 K
0.15 × 0.10 × 0.07 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.574, T_max = 0.710
17404 measured reflections
6617 independent reflections
5375 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.075
S = 1.02
6617 reflections
375 parameters
21 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.48 e Å⁻³
Δρ_min = −1.23 e Å⁻³

Table 1
Selected bond lengths (Å)

Sr1—O8	2.4557 (18)
Sr1—O3ⁱ	2.4782 (19)
Sr1—O5	2.5234 (16)
Sr1—O7ⁱⁱ	2.6149 (19)
Sr1—O25	2.652 (2)
Sr1—O22	2.6560 (19)
Sr1—O27	2.657 (2)
Sr1—O8ⁱⁱ	2.7834 (17)
Sr2—O6ⁱⁱⁱ	2.5452 (16)
Sr2—O23	2.5921 (18)
Sr2—O2ⁱ	2.6222 (17)
Sr2—O21	2.6445 (17)
Sr2—O6	2.6628 (16)
Sr2—O2^iv	2.6848 (16)
Sr2—O1^iv	2.6944 (17)
Sr2—O22	2.7108 (18)
Sr2—O5	2.7228 (16)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) -x, -y, -z+1; (iv) x, y-1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O21—H21A⋯O25	0.81 (2)	1.98 (2)	2.781 (3)	169 (3)
O21—H21B⋯O24ⁱⁱⁱ	0.85 (2)	1.93 (2)	2.765 (3)	169 (3)
O22—H22A⋯O2ⁱ	0.81 (2)	2.16 (3)	2.761 (2)	131 (3)
O22—H22B⋯O26^iv	0.82 (2)	1.94 (2)	2.755 (3)	173 (3)
O23—H23A⋯O21ⁱⁱⁱ	0.81 (2)	1.96 (2)	2.766 (3)	174 (4)
O23—H23B⋯O26ⁱ	0.80 (2)	2.11 (2)	2.867 (3)	159 (3)
O24—H24A⋯O1^v	0.82 (2)	2.03 (2)	2.760 (3)	148 (3)
O24—H24B⋯O4	0.84 (2)	1.93 (2)	2.756 (3)	172 (3)
O25—H25A⋯N1ⁱⁱ	0.82 (2)	2.15 (2)	2.898 (3)	152 (3)
O25—H25B⋯O27ⁱⁱ	0.80 (2)	1.93 (2)	2.648 (3)	150 (4)
O26—H26A⋯O28^vi	0.85 (2)	1.90 (2)	2.731 (3)	164 (5)
O26—H26C⋯N1	0.85 (2)	2.37 (4)	3.108 (3)	146 (5)
O27—H27A⋯O4ⁱ	0.83 (2)	1.79 (2)	2.615 (3)	172 (4)
O27—H27B⋯O29^vii	0.82 (2)	1.94 (2)	2.727 (4)	160 (4)
O28—H28A⋯O24^v	0.80 (2)	1.97 (2)	2.756 (3)	167 (4)
O28—H28B⋯O28^viii	0.82 (2)	2.02 (2)	2.835 (4)	174 (8)
O28—H28C⋯O29	0.82 (2)	2.04 (3)	2.836 (4)	164 (7)
O29—H29A⋯O7	0.83 (2)	1.78 (2)	2.595 (3)	168 (7)
O29—H29B⋯O28	0.83 (2)	2.03 (3)	2.836 (4)	164 (7)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) -x, -y, -z+1; (iv) x, y-1, z; (v) -x, -y+1, -z+1; (vi) -x+1, -y+2, -z+2; (vii) x+1, y, z; (viii) -x, -y+2, -z+2.

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and ATOMS (Dowty, 2000 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010099/si2343sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010099/si2343Isup2.hkl

checkCIF report

Comment top

In recent years it has been found that Sr has a significant influence on the development and growth of bone and the effect of dose on bone structure has been investigated in great detail (Schrooten et al. 2003). Strontium ranelate (5-[bis(carboxymethyl) amino]-3-carboxymetyl- 4-cyano-2-thiophenecarboxylate) is one promising pharmaceutical compound for treating osteoporosis marketed as Protelos^R by Servier (Horvath et al., 2008). Strontium ranelate is known to form several hydrates with totally nine, eight, seven or four waters (Horvath et al., 2008). The initial dehydration observed here results from an expulsion of O27 or O29 and migration of the remaining water to site O30. As a consequence Sr1 is partially seven-coordinated (c.f. Table 1). The water hydrogen sites connected to O26, O28 and O29 are disordered. In essence, the alternating hydrogen bonding scheme between O28 and O29 is transmitted to a partial O26 - O28 hydrogen bond, and leaves H26B and H29C without hydrogen bond acceptors (c.f. Table 2).

Related literature top

For the effect of strontium on osteroporosis, see Schrooten et al. (2003). For a patent describing the synthesis and powder diffraction pattern, see Horvath et al. (2008). For related strontium carboxylate structures, see, for example: Stahl et al. (2006).

Experimental top

Strontium ranelate nona hydrate of 97% purity (Clauson-Kaas A/S) was recrystallized at different temperatures. Recrystallization at temperatures above 353 K appeared to produce the crystals of better quality. Upon cooling to room temperature large crystals of millimeter dimensions were obtained in the saturated solution. However, when the crystals were removed from the solution they rapidly degraded into smaller units of micron dimension. The smaller crystals showed out to contain less crystal water, as compared to the large crystals, presumably seven or five water molecules per formula unit. Thus, wet crystals were quickly transferred to the goniometer for X-ray data collection at 120 K. Several crystal were tried before an acceptable structure refinement was achieved. For all cases of lower quality data the SOF of O30 was about 0.3, confirming its role in the initial dehydration of strontium ranelate and the deterioration of the crystals.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and ATOMS (Dowty, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I) showing 50% probability displacement ellipsoids and the atomic numbering. Hydrogen atoms are represented by circles of arbitrary size and shows one consistent set of water H atoms.
	Fig. 2. The crystal packing of (I) viewed down the a-axis. Hydrogen atoms are omitted for clarity.
	Fig. 3. The polyhedral layer of (I) viewed down the (011) direction.

Poly[[µ-aqua-tetraaqua{µ-5-[bis(carboxylatomethyl)amino]-3- carboxylatomethyl-4-cyanothiophene-2-carboxylato}distrontium(II)] tetrahydrate] top

Crystal data top

[Sr₂(C₁₂H₆N₂O₈S)(H₂O)₅]·3.79H₂O	Z = 2
M_r = 671.84	F(000) = 671.8
Triclinic, P1	D_x = 1.933 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3585 (3) Å	Cell parameters from 6752 reflections
b = 12.3865 (5) Å	θ = 2.6–30.6°
c = 12.6474 (5) Å	µ = 4.80 mm⁻¹
α = 109.880 (1)°	T = 120 K
β = 97.148 (1)°	Tabular, colorless
γ = 105.321 (1)°	0.15 × 0.10 × 0.07 mm
V = 1154.00 (8) Å³

Data collection top

Bruker SMART APEX diffractometer	6617 independent reflections
Radiation source: fine-focus sealed tube	5375 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scan, frame data integration	θ_max = 30.9°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −12→12
T_min = 0.574, T_max = 0.710	k = −17→17
17404 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0383P)²] where P = (F_o² + 2F_c²)/3
6617 reflections	(Δ/σ)_max = 0.002
375 parameters	Δρ_max = 1.48 e Å⁻³
21 restraints	Δρ_min = −1.23 e Å⁻³

Crystal data top

[Sr₂(C₁₂H₆N₂O₈S)(H₂O)₅]·3.79H₂O	γ = 105.321 (1)°
M_r = 671.84	V = 1154.00 (8) Å³
Triclinic, P1	Z = 2
a = 8.3585 (3) Å	Mo Kα radiation
b = 12.3865 (5) Å	µ = 4.80 mm⁻¹
c = 12.6474 (5) Å	T = 120 K
α = 109.880 (1)°	0.15 × 0.10 × 0.07 mm
β = 97.148 (1)°

Data collection top

Bruker SMART APEX diffractometer	6617 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	5375 reflections with I > 2σ(I)
T_min = 0.574, T_max = 0.710	R_int = 0.032
17404 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	21 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 1.48 e Å⁻³
6617 reflections	Δρ_min = −1.23 e Å⁻³
375 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 > 2σ(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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sr1	0.52281 (3)	0.38668 (2)	0.836097 (18)	0.01665 (6)
Sr2	0.26745 (3)	0.029136 (18)	0.557006 (17)	0.01072 (6)
S1	0.13839 (8)	0.40229 (5)	0.50122 (5)	0.01584 (12)
C1	0.1878 (3)	0.4919 (2)	0.6477 (2)	0.0160 (5)
C2	0.3059 (3)	0.6056 (2)	0.6709 (2)	0.0183 (5)
C3	0.3561 (3)	0.6182 (2)	0.5698 (2)	0.0168 (5)
C4	0.2738 (3)	0.5158 (2)	0.4721 (2)	0.0169 (5)
C5	0.3781 (4)	0.7012 (2)	0.7831 (2)	0.0237 (6)
N1	0.4382 (4)	0.7807 (2)	0.8712 (2)	0.0373 (7)
C6	0.4862 (3)	0.7305 (2)	0.5736 (2)	0.0187 (5)
H6A	0.5431	0.7077	0.5091	0.022*
H6B	0.5745	0.7663	0.6470	0.022*
C7	0.4063 (3)	0.8258 (2)	0.5642 (2)	0.0140 (4)
O1	0.3026 (2)	0.85078 (16)	0.62454 (15)	0.0218 (4)
O2	0.4503 (2)	0.87870 (15)	0.49792 (15)	0.0168 (3)
C8	0.2835 (3)	0.4871 (2)	0.3498 (2)	0.0208 (5)
O3	0.3592 (3)	0.57144 (17)	0.32159 (17)	0.0293 (4)
O4	0.2095 (3)	0.37659 (16)	0.28052 (16)	0.0253 (4)
N2	0.1127 (3)	0.44571 (17)	0.71912 (16)	0.0138 (4)
C9	0.0097 (3)	0.3176 (2)	0.6705 (2)	0.0147 (4)
H9A	−0.0850	0.3036	0.6067	0.018*
H9B	−0.0415	0.2978	0.7309	0.018*
C10	0.1092 (3)	0.2303 (2)	0.62385 (19)	0.0125 (4)
O5	0.2644 (2)	0.25859 (14)	0.67064 (14)	0.0150 (3)
O6	0.0259 (2)	0.13041 (14)	0.54187 (13)	0.0141 (3)
C11	0.0937 (3)	0.5241 (2)	0.82968 (19)	0.0167 (5)
H11A	−0.0207	0.4870	0.8398	0.020*
H11B	0.0977	0.6033	0.8259	0.020*
C12	0.2261 (3)	0.5475 (2)	0.9357 (2)	0.0177 (5)
O7	0.2069 (3)	0.60995 (17)	1.03249 (15)	0.0266 (4)
O8	0.3467 (2)	0.50536 (16)	0.92535 (15)	0.0213 (4)
O21	0.1336 (2)	0.04188 (16)	0.73788 (14)	0.0177 (4)
H21A	0.195 (3)	0.096 (2)	0.7968 (19)	0.027*
H21B	0.111 (4)	−0.021 (2)	0.753 (3)	0.027*
O22	0.5486 (2)	0.16837 (18)	0.73157 (15)	0.0218 (4)
H22A	0.608 (4)	0.162 (3)	0.686 (2)	0.033*
H22B	0.572 (4)	0.129 (3)	0.768 (3)	0.033*
O23	0.2011 (2)	−0.02488 (19)	0.33592 (16)	0.0246 (4)
H23A	0.102 (3)	−0.035 (3)	0.311 (3)	0.037*
H23B	0.249 (4)	−0.006 (3)	0.291 (2)	0.037*
O24	−0.0724 (3)	0.17943 (17)	0.24069 (16)	0.0233 (4)
H24A	−0.138 (4)	0.198 (3)	0.282 (3)	0.035*
H24B	0.015 (3)	0.240 (2)	0.260 (3)	0.035*
O25	0.3787 (3)	0.23012 (19)	0.92443 (16)	0.0299 (5)
H25A	0.430 (4)	0.204 (3)	0.965 (3)	0.045*
H25B	0.316 (4)	0.259 (3)	0.958 (3)	0.045*
O26	0.6112 (3)	1.0182 (2)	0.83803 (19)	0.0321 (5)
H26A	0.686 (5)	1.030 (5)	0.897 (3)	0.048*	0.67
H26B	0.549 (6)	1.037 (5)	0.885 (4)	0.048*	0.67
H26C	0.532 (5)	0.952 (3)	0.823 (5)	0.048*	0.67
O27	0.7186 (3)	0.6180 (2)	0.91336 (19)	0.0194 (6)	0.790 (4)
H27A	0.740 (5)	0.626 (4)	0.854 (2)	0.029*	0.79
H27B	0.811 (4)	0.640 (4)	0.959 (3)	0.029*	0.79
O28	0.1058 (3)	0.92663 (19)	0.99457 (17)	0.0302 (5)
H28A	0.111 (5)	0.896 (3)	0.9290 (18)	0.045*
H28B	0.041 (8)	0.966 (6)	1.000 (7)	0.045*	0.50
H28C	0.059 (8)	0.873 (5)	1.015 (6)	0.045*	0.50
O29	0.0120 (4)	0.7429 (3)	1.0829 (2)	0.0287 (7)	0.790 (4)
H29A	0.073 (7)	0.701 (5)	1.058 (6)	0.043*	0.53
H29B	0.045 (9)	0.806 (4)	1.071 (6)	0.043*	0.53
H29C	−0.024 (10)	0.732 (8)	1.016 (3)	0.043*	0.53
O30	−0.0951 (12)	0.6963 (8)	0.9739 (8)	0.023 (2)*	0.210 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sr1	0.01489 (12)	0.02075 (12)	0.00915 (10)	0.00204 (9)	0.00133 (8)	0.00307 (9)
Sr2	0.01086 (11)	0.01068 (10)	0.00940 (10)	0.00340 (8)	0.00144 (7)	0.00290 (8)
S1	0.0195 (3)	0.0115 (3)	0.0149 (3)	0.0032 (2)	0.0029 (2)	0.0051 (2)
C1	0.0158 (12)	0.0144 (11)	0.0177 (11)	0.0064 (9)	−0.0008 (9)	0.0067 (9)
C2	0.0197 (12)	0.0133 (11)	0.0215 (12)	0.0061 (10)	−0.0004 (10)	0.0078 (10)
C3	0.0133 (11)	0.0122 (11)	0.0255 (12)	0.0049 (9)	0.0006 (9)	0.0087 (10)
C4	0.0164 (12)	0.0138 (11)	0.0241 (12)	0.0060 (9)	0.0057 (10)	0.0105 (10)
C5	0.0287 (15)	0.0139 (12)	0.0256 (13)	0.0010 (11)	−0.0027 (11)	0.0120 (11)
N1	0.0485 (17)	0.0204 (12)	0.0261 (13)	−0.0078 (11)	−0.0058 (12)	0.0083 (10)
C6	0.0129 (11)	0.0152 (12)	0.0301 (13)	0.0046 (9)	0.0032 (10)	0.0122 (10)
C7	0.0120 (11)	0.0104 (10)	0.0167 (11)	0.0015 (8)	0.0008 (9)	0.0042 (9)
O1	0.0269 (10)	0.0231 (9)	0.0262 (9)	0.0140 (8)	0.0147 (8)	0.0152 (8)
O2	0.0174 (9)	0.0160 (8)	0.0201 (8)	0.0055 (7)	0.0065 (7)	0.0101 (7)
C8	0.0220 (13)	0.0200 (13)	0.0260 (13)	0.0100 (11)	0.0119 (11)	0.0111 (11)
O3	0.0386 (12)	0.0209 (10)	0.0317 (11)	0.0058 (9)	0.0167 (9)	0.0141 (9)
O4	0.0348 (11)	0.0179 (9)	0.0252 (10)	0.0072 (8)	0.0152 (8)	0.0092 (8)
N2	0.0185 (10)	0.0084 (9)	0.0109 (9)	0.0030 (8)	0.0002 (7)	0.0016 (7)
C9	0.0142 (11)	0.0121 (11)	0.0150 (11)	0.0029 (9)	0.0014 (9)	0.0038 (9)
C10	0.0157 (11)	0.0109 (10)	0.0106 (10)	0.0022 (9)	0.0027 (8)	0.0056 (8)
O5	0.0125 (8)	0.0144 (8)	0.0140 (8)	0.0033 (6)	−0.0023 (6)	0.0032 (6)
O6	0.0140 (8)	0.0104 (8)	0.0127 (8)	0.0016 (6)	−0.0014 (6)	0.0016 (6)
C11	0.0195 (12)	0.0164 (11)	0.0125 (11)	0.0096 (10)	0.0008 (9)	0.0017 (9)
C12	0.0235 (13)	0.0113 (11)	0.0151 (11)	0.0023 (9)	0.0003 (9)	0.0055 (9)
O7	0.0378 (12)	0.0255 (10)	0.0124 (8)	0.0109 (9)	0.0040 (8)	0.0028 (7)
O8	0.0213 (9)	0.0194 (9)	0.0199 (9)	0.0077 (7)	−0.0036 (7)	0.0056 (7)
O21	0.0200 (9)	0.0184 (9)	0.0120 (8)	0.0043 (7)	0.0025 (7)	0.0046 (7)
O22	0.0186 (9)	0.0305 (10)	0.0139 (9)	0.0109 (8)	0.0024 (7)	0.0043 (8)
O23	0.0172 (9)	0.0421 (12)	0.0195 (9)	0.0106 (9)	0.0070 (8)	0.0164 (9)
O24	0.0270 (11)	0.0201 (9)	0.0198 (9)	0.0028 (8)	0.0098 (8)	0.0066 (8)
O25	0.0413 (13)	0.0248 (11)	0.0151 (9)	0.0009 (9)	0.0046 (9)	0.0060 (8)
O26	0.0299 (12)	0.0322 (12)	0.0283 (11)	0.0011 (10)	0.0029 (9)	0.0131 (10)
O27	0.0243 (13)	0.0161 (11)	0.0129 (11)	0.0003 (9)	0.0054 (9)	0.0042 (9)
O28	0.0422 (14)	0.0295 (12)	0.0163 (9)	0.0133 (10)	0.0022 (9)	0.0060 (9)
O29	0.0313 (15)	0.0330 (15)	0.0249 (14)	0.0161 (12)	0.0070 (11)	0.0107 (12)

Geometric parameters (Å, º) top

Sr1—O8	2.4557 (18)	N2—C11	1.462 (3)
Sr1—O3ⁱ	2.4782 (19)	C9—C10	1.540 (3)
Sr1—O5	2.5234 (16)	C9—H9A	0.9900
Sr1—O7ⁱⁱ	2.6149 (19)	C9—H9B	0.9900
Sr1—O25	2.652 (2)	C10—O5	1.258 (3)
Sr1—O22	2.6560 (19)	C10—O6	1.258 (3)
Sr1—O27	2.657 (2)	C11—C12	1.517 (3)
Sr1—O8ⁱⁱ	2.7834 (17)	C11—H11A	0.9900
Sr2—O6ⁱⁱⁱ	2.5452 (16)	C11—H11B	0.9900
Sr2—O23	2.5921 (18)	C12—O8	1.253 (3)
Sr2—O2ⁱ	2.6222 (17)	C12—O7	1.262 (3)
Sr2—O21	2.6445 (17)	O21—H21A	0.809 (18)
Sr2—O6	2.6628 (16)	O21—H21B	0.845 (17)
Sr2—O2^iv	2.6848 (16)	O22—H22A	0.808 (18)
Sr2—O1^iv	2.6944 (17)	O22—H22B	0.819 (17)
Sr2—O22	2.7108 (18)	O23—H23A	0.807 (18)
Sr2—O5	2.7228 (16)	O23—H23B	0.798 (18)
S1—C1	1.733 (2)	O24—H24A	0.823 (18)
S1—C4	1.735 (2)	O24—H24B	0.837 (18)
C1—N2	1.358 (3)	O25—H25A	0.819 (18)
C1—C2	1.398 (3)	O25—H25B	0.796 (18)
C2—C5	1.431 (4)	O26—H26A	0.850 (19)
C2—C3	1.439 (4)	O26—H26B	0.849 (19)
C3—C4	1.368 (3)	O26—H26C	0.85 (2)
C3—C6	1.504 (3)	O27—H27A	0.827 (19)
C4—C8	1.482 (4)	O27—H27B	0.823 (19)
C5—N1	1.148 (3)	O28—H28A	0.799 (18)
C6—C7	1.532 (3)	O28—H28B	0.82 (2)
C6—H6A	0.9900	O28—H28C	0.82 (2)
C6—H6B	0.9900	O29—H29A	0.83 (2)
C7—O1	1.256 (3)	O29—H29B	0.83 (2)
C7—O2	1.261 (3)	O29—H29C	0.82 (2)
C8—O3	1.257 (3)	O27—O30^v	1.534 (10)
C8—O4	1.275 (3)	O29—O30	1.383 (10)
N2—C9	1.456 (3)

O8—Sr1—O3ⁱ	117.69 (6)	O22—Sr2—O5	67.10 (5)
O8—Sr1—O5	87.39 (5)	C1—S1—C4	92.44 (12)
O3ⁱ—Sr1—O5	81.32 (6)	N2—C1—C2	130.8 (2)
O8—Sr1—O7ⁱⁱ	118.97 (6)	N2—C1—S1	119.08 (17)
O3ⁱ—Sr1—O7ⁱⁱ	101.51 (7)	C2—C1—S1	110.09 (19)
O5—Sr1—O7ⁱⁱ	146.34 (5)	C1—C2—C5	125.2 (2)
O8—Sr1—O25	85.98 (7)	C1—C2—C3	113.4 (2)
O3ⁱ—Sr1—O25	150.13 (6)	C5—C2—C3	121.3 (2)
O5—Sr1—O25	81.94 (6)	C4—C3—C2	111.8 (2)
O7ⁱⁱ—Sr1—O25	79.69 (7)	C4—C3—C6	124.9 (2)
O8—Sr1—O22	147.38 (6)	C2—C3—C6	123.3 (2)
O3ⁱ—Sr1—O22	83.58 (6)	C3—C4—C8	131.1 (2)
O5—Sr1—O22	70.82 (5)	C3—C4—S1	112.22 (19)
O7ⁱⁱ—Sr1—O22	76.14 (6)	C8—C4—S1	116.67 (18)
O25—Sr1—O22	67.59 (6)	N1—C5—C2	177.5 (3)
O8—Sr1—O27	74.49 (7)	C3—C6—C7	112.26 (19)
O3ⁱ—Sr1—O27	70.14 (7)	C3—C6—H6A	109.2
O5—Sr1—O27	132.72 (6)	C7—C6—H6A	109.2
O7ⁱⁱ—Sr1—O27	77.82 (7)	C3—C6—H6B	109.2
O25—Sr1—O27	137.67 (6)	C7—C6—H6B	109.2
O22—Sr1—O27	138.07 (7)	H6A—C6—H6B	107.9
O8—Sr1—O8ⁱⁱ	70.87 (6)	O1—C7—O2	122.2 (2)
O3ⁱ—Sr1—O8ⁱⁱ	130.40 (6)	O1—C7—C6	119.1 (2)
O5—Sr1—O8ⁱⁱ	147.09 (6)	O2—C7—C6	118.7 (2)
O7ⁱⁱ—Sr1—O8ⁱⁱ	48.19 (5)	O3—C8—O4	125.2 (2)
O25—Sr1—O8ⁱⁱ	72.41 (6)	O3—C8—C4	118.9 (2)
O22—Sr1—O8ⁱⁱ	115.58 (5)	O4—C8—C4	115.9 (2)
O27—Sr1—O8ⁱⁱ	65.82 (6)	C1—N2—C9	117.63 (19)
O6ⁱⁱⁱ—Sr2—O23	69.11 (6)	C1—N2—C11	121.82 (19)
O6ⁱⁱⁱ—Sr2—O2ⁱ	138.88 (5)	C9—N2—C11	118.5 (2)
O23—Sr2—O2ⁱ	71.52 (6)	N2—C9—C10	114.24 (19)
O6ⁱⁱⁱ—Sr2—O21	79.58 (5)	N2—C9—H9A	108.7
O23—Sr2—O21	145.03 (6)	C10—C9—H9A	108.7
O2ⁱ—Sr2—O21	141.51 (5)	N2—C9—H9B	108.7
O6ⁱⁱⁱ—Sr2—O6	68.34 (6)	C10—C9—H9B	108.7
O23—Sr2—O6	81.03 (5)	H9A—C9—H9B	107.6
O2ⁱ—Sr2—O6	116.53 (5)	O5—C10—O6	123.3 (2)
O21—Sr2—O6	73.03 (5)	O5—C10—C9	119.92 (19)
O6ⁱⁱⁱ—Sr2—O2^iv	96.94 (5)	O6—C10—C9	116.7 (2)
O23—Sr2—O2^iv	81.54 (6)	N2—C11—C12	115.7 (2)
O2ⁱ—Sr2—O2^iv	65.68 (6)	N2—C11—H11A	108.3
O21—Sr2—O2^iv	118.40 (5)	C12—C11—H11A	108.3
O6—Sr2—O2^iv	160.37 (5)	N2—C11—H11B	108.3
O6ⁱⁱⁱ—Sr2—O1^iv	79.58 (5)	C12—C11—H11B	108.3
O23—Sr2—O1^iv	116.26 (6)	H11A—C11—H11B	107.4
O2ⁱ—Sr2—O1^iv	108.25 (5)	O8—C12—O7	122.9 (2)
O21—Sr2—O1^iv	71.00 (5)	O8—C12—C11	120.5 (2)
O6—Sr2—O1^iv	135.19 (5)	O7—C12—C11	116.7 (2)
O2^iv—Sr2—O1^iv	48.34 (5)	H21A—O21—H21B	106 (3)
O6ⁱⁱⁱ—Sr2—O22	156.57 (6)	H22A—O22—H22B	104 (3)
O23—Sr2—O22	133.65 (6)	H23A—O23—H23B	104 (3)
O2ⁱ—Sr2—O22	62.33 (5)	H24A—O24—H24B	108 (3)
O21—Sr2—O22	79.68 (6)	H25A—O25—H25B	109 (4)
O6—Sr2—O22	115.27 (5)	H26A—O26—H26B	87 (5)
O2^iv—Sr2—O22	83.49 (5)	H26A—O26—H26C	108 (5)
O1^iv—Sr2—O22	83.47 (6)	H26B—O26—H26C	75 (5)
O6ⁱⁱⁱ—Sr2—O5	114.87 (5)	H27A—O27—H27B	107 (4)
O23—Sr2—O5	109.66 (6)	H28A—O28—H28B	111 (6)
O2ⁱ—Sr2—O5	89.11 (5)	H28A—O28—H28C	109 (6)
O21—Sr2—O5	69.47 (5)	H28B—O28—H28C	103 (7)
O6—Sr2—O5	48.56 (5)	H29A—O29—H29B	107 (7)
O2^iv—Sr2—O5	148.19 (5)	H29A—O29—H29C	87 (6)
O1^iv—Sr2—O5	133.93 (5)	H29B—O29—H29C	68 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21A···O25	0.81 (2)	1.98 (2)	2.781 (3)	169 (3)
O21—H21B···O24ⁱⁱⁱ	0.85 (2)	1.93 (2)	2.765 (3)	169 (3)
O22—H22A···O2ⁱ	0.81 (2)	2.16 (3)	2.761 (2)	131 (3)
O22—H22B···O26^iv	0.82 (2)	1.94 (2)	2.755 (3)	173 (3)
O23—H23A···O21ⁱⁱⁱ	0.81 (2)	1.96 (2)	2.766 (3)	174 (4)
O23—H23B···O26ⁱ	0.80 (2)	2.11 (2)	2.867 (3)	159 (3)
O24—H24A···O1^vi	0.82 (2)	2.03 (2)	2.760 (3)	148 (3)
O24—H24B···O4	0.84 (2)	1.93 (2)	2.756 (3)	172 (3)
O25—H25A···N1ⁱⁱ	0.82 (2)	2.15 (2)	2.898 (3)	152 (3)
O25—H25B···O27ⁱⁱ	0.80 (2)	1.93 (2)	2.648 (3)	150 (4)
O26—H26A···O28^vii	0.85 (2)	1.90 (2)	2.731 (3)	164 (5)
O26—H26C···N1	0.85 (2)	2.37 (4)	3.108 (3)	146 (5)
O27—H27A···O4ⁱ	0.83 (2)	1.79 (2)	2.615 (3)	172 (4)
O27—H27B···O29^v	0.82 (2)	1.94 (2)	2.727 (4)	160 (4)
O28—H28A···O24^vi	0.80 (2)	1.97 (2)	2.756 (3)	167 (4)
O28—H28B···O28^viii	0.82 (2)	2.02 (2)	2.835 (4)	174 (8)
O28—H28C···O29	0.82 (2)	2.04 (3)	2.836 (4)	164 (7)
O29—H29A···O7	0.83 (2)	1.78 (2)	2.595 (3)	168 (7)
O29—H29B···O28	0.83 (2)	2.03 (3)	2.836 (4)	164 (7)

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

Experimental details

Crystal data
Chemical formula	[Sr₂(C₁₂H₆N₂O₈S)(H₂O)₅]·3.79H₂O
M_r	671.84
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.3585 (3), 12.3865 (5), 12.6474 (5)
α, β, γ (°)	109.880 (1), 97.148 (1), 105.321 (1)
V (Å³)	1154.00 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.80
Crystal size (mm)	0.15 × 0.10 × 0.07

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.574, 0.710
No. of measured, independent and observed [I > 2σ(I)] reflections	17404, 6617, 5375
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.722

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.075, 1.02
No. of reflections	6617
No. of parameters	375
No. of restraints	21
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.48, −1.23

Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and ATOMS (Dowty, 2000).

Selected bond lengths (Å) top

Sr1—O8	2.4557 (18)	Sr2—O23	2.5921 (18)
Sr1—O3ⁱ	2.4782 (19)	Sr2—O2ⁱ	2.6222 (17)
Sr1—O5	2.5234 (16)	Sr2—O21	2.6445 (17)
Sr1—O7ⁱⁱ	2.6149 (19)	Sr2—O6	2.6628 (16)
Sr1—O25	2.652 (2)	Sr2—O2^iv	2.6848 (16)
Sr1—O22	2.6560 (19)	Sr2—O1^iv	2.6944 (17)
Sr1—O27	2.657 (2)	Sr2—O22	2.7108 (18)
Sr1—O8ⁱⁱ	2.7834 (17)	Sr2—O5	2.7228 (16)
Sr2—O6ⁱⁱⁱ	2.5452 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21A···O25	0.809 (18)	1.982 (18)	2.781 (3)	169 (3)
O21—H21B···O24ⁱⁱⁱ	0.845 (17)	1.931 (18)	2.765 (3)	169 (3)
O22—H22A···O2ⁱ	0.808 (18)	2.16 (3)	2.761 (2)	131 (3)
O22—H22B···O26^iv	0.819 (17)	1.940 (18)	2.755 (3)	173 (3)
O23—H23A···O21ⁱⁱⁱ	0.807 (18)	1.962 (18)	2.766 (3)	174 (4)
O23—H23B···O26ⁱ	0.798 (18)	2.11 (2)	2.867 (3)	159 (3)
O24—H24A···O1^v	0.823 (18)	2.03 (2)	2.760 (3)	148 (3)
O24—H24B···O4	0.837 (18)	1.925 (18)	2.756 (3)	172 (3)
O25—H25A···N1ⁱⁱ	0.819 (18)	2.15 (2)	2.898 (3)	152 (3)
O25—H25B···O27ⁱⁱ	0.796 (18)	1.93 (2)	2.648 (3)	150 (4)
O26—H26A···O28^vi	0.850 (19)	1.90 (2)	2.731 (3)	164 (5)
O26—H26C···N1	0.85 (2)	2.37 (4)	3.108 (3)	146 (5)
O27—H27A···O4ⁱ	0.827 (19)	1.79 (2)	2.615 (3)	172 (4)
O27—H27B···O29^vii	0.823 (19)	1.94 (2)	2.727 (4)	160 (4)
O28—H28A···O24^v	0.799 (18)	1.97 (2)	2.756 (3)	167 (4)
O28—H28B···O28^viii	0.82 (2)	2.02 (2)	2.835 (4)	174 (8)
O28—H28C···O29	0.82 (2)	2.04 (3)	2.836 (4)	164 (7)
O29—H29A···O7	0.83 (2)	1.78 (2)	2.595 (3)	168 (7)
O29—H29B···O28	0.83 (2)	2.03 (3)	2.836 (4)	164 (7)

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

Acknowledgements

Ms L. Berring and Ms A. Schøneberg are gratefully acknowledged for the data collection and Dr Stephan Christgau for supplying the strontium ranelate.

References

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