Magnesium, calcium and strontium salts of phenyl­acetic acid

Three alkaline earth metal salts of phenyl­acetic acid were examined and all were found to have similar structural types to analogous salts of benzoic and halobenzoic acids. Thus, a synchrotron study shows that the cations in catena-poly[[[tetra­aqua­magnesium(II)]-μ-phenyl­acetato-κ²O:O′] phenyl­acetate], {[Mg(C₈H₇O₂)(H₂O)₄](C₈H₇O₂)}_n, form a one-dimensional coordination polymer that propagates through Mg—O—C—O—Mg inter­actions involving both crystallographically independent Mg centres (Z′ = 2) and through translation along the a axis. The polymeric chains pack to give alternate inorganic layers and organic bilayers. The Ca and Sr species catena-poly[[[diaqua­(phenyl­acetato-κ²O,O′)calcium(II)]-μ₃-phenylacetato-1′:1:1′′κ⁴O:O,O′:O′] monohydrate], {[Ca(C₈H₇O₂)₂(H₂O)₂]·H₂O}_n, and catena-poly[[[diaqua­(phenyl­acetato-κ²O,O′)strontium(II)]-μ₃-phenyl­acet­ato-1′:1:1′′κ⁴O:O,O′:O′] monohydrate], {[Sr(C₈H₇O₂)₂(H₂O)₂]·H₂O}_n, are essentially isostructural. Both form one-dimensional coordination polymers through a carboxyl­ate group that forms four M—O bonds. The polymeric chains propagate via 2₁ screw axes parallel to the b axis and are further linked in the bc plane by hydrogen bonding involving the non-metal-bound water mol­ecule. Similarly to the Mg salt, both have inorganic layers that alternate with organic bilayers.

S1. Comment

Often, the simplest way to alter the physicochemical properties of an active pharmaceutical ingredient (API) is to make different salt forms of it. As many of the performance-critical properties of an API (such as solubility, melting point and hygroscopicity) are dependant upon the solid-state structure, a true understanding of structure–property relationships should allow the most appropriate counterion to be chosen for any such desired property. However, such structure–property relationships are poorly understood, and thus salt selection of API forms is currently undertaken using time-consuming trial and error methods (Stahl & Wermuth, 2002). One reason for the lack of understanding is a general dearth of large groups of systematically related crystal structures with associated phase-specific physicochemical data. Such studies do exist (for example Collier et al., 2006; Black et al., 2007; Kennedy et al., 2011) but are relatively uncommon. As a contribution to this field, Arlin et al. (2011) showed that Mg, Ca and Sr (but not Ba) salt forms of a set of simple benzoate-derived anions could be systematically structurally classified and that these structural features help rationalize the comparative aqueous solubility data gathered. A major aim of this earlier work was to use the lessons learned from simple model compounds to predict behaviour in larger commercial APIs with similar functionality. Many APIs have aryl carboxylate groups (e.g. aspirin and fluoroquinolones), as do the reported model benzoate structures (Arlin et al., 2011). However, several important drug classes (e.g. profens and naproxens) have a Csp³ atom inserted between the aromatic ring and the carboxylate group, and this structural feature was not included in the model data set. To help fill this gap, the Mg, Ca and Sr complexes of phenylacetate (PAA) have been investigated in order to show what effect the extra `spacer' Csp³ atom has on crystal stucture, and thus to determine if the model benzoate data set could be a useful comparative tool for use with salts of ibuprofen and naproxen. Structural studies of both co-crystals and organic salts of PAA have recently been published (Brittain, 2010; Smith & Wermuth, 2010a,b), but the only s-block metal salt of PAA to be structurally characterized is the K salt, which is found to exist as the co-crystal K(PAA)(HPAA) (Bacon et al., 1977).

Crystals of catena-poly[[[tetraaquamagnesium(II)]-µ-phenylacetato-κ²O:O'] phenylacetate], MgPAA, form as very thin plates which required the use of synchrotron radiation to characterize them as [Mg(PAA)(H₂O)₄](PAA), with two crystallographically independent fragments per asymmetric unit (Z' = 2). Each Mg centre is approximately octahedral and bonds to four terminal water ligands and to single O atoms of two PAA anions. These last are in mutually cis positions (see Table 1 for geometric details and Fig. 1 for an illustration). Although the shortest Mg—O lengths involve the PAA anions, some of the Mg—OH₂ bonds are shorter than the other Mg—PAA bonds. Thus, bonding to the PAA anion does not appear to be systematically stronger than Mg bonding to water. Two of the PAA anions each bridge across two Mg centres using both O atoms of their carboxylate groups to make single O—Mg contacts. This results in a one-dimensional coordination chain based on Mg—O—C—O—Mg units, which propagates by translation along the crystallographic a direction (Fig. 2). The remaining two PAA anions form no Mg—O bonds. Fig. 3 shows that the structure packs to give alternate hydrophobic and hydrophilic layers along the c direction. The organic bilayer thus formed means that, although all the water molecules utilize both of their H atoms to form hydrogen bonds, these only connect the structure in two dimensions, e.g. there is a hydrogen-bonding network in the ab plane. This packing motif with alternating layers, an organic bilayer and a one-dimensional coordination chain based on bridging carboxylates is that found previously for Mg salts of benzoate and halobenzoates. It is conspicously different from the structures found for other benzoate ions with hydroxy, amino or nitro substituents (Arlin et al., 2011).

The structures of the calcium(II) and strontium(II) compounds catena-poly[[[diaqua(phenylacetato-κ²O,O')calcium(II)]-µ₃-phenylacetato-1':1:1''κ⁴O:O,O':O'] monohydrate] and catena-poly[[[diaqua(phenylacetato-κ²O,O')strontium(II)]-µ₃-phenylacetato-1':1:1''κ⁴O:O,O':O'] monohydrate], CaPAA and SrPAA, respectively, were found to be essentially isostructural, with the composition [M(PAA)₂(H₂O)₂].H₂O (Figs. 4 and 5). This again reflects the structures of the benzoate derivatives, where the Ca and Sr structures were found to have similar structural types and even, for salicylate, p-aminosalicylate and p-aminobenzoate, to form isostructural pairs. In each structure herein, the metal centre is formally eight-coordinate, although, as Cotton & Bergman (1964) classically showed, if each chelated group is assigned to one coordination site rather than two, then the structures can be described as distorted octahedral. The water ligands are both trans to chelated carboxylate groups. As with MgPAA, the M—OH₂ distances are not systematically longer or shorter than the M—O(PAA) distances. One PAA anion is a terminal ligand and uses both its O atoms to bond to a single metal centre, whilst the second PPA anion chelates to one metal centre and bridges to a further two. As both water ligands are terminal, it is this second PAA anion type that leads to the propagation of a one-dimensional coordination chain along the 2₁ screw axis parallel to the b direction (Fig. 6). These coordination chains are interlinked by hydrogen bonding through atom O3W, the non-metal-bound water molecule. This gives a hydrophilic layer in the bc plane with alternating hydrophilic and hydrophobic layers along the crystallographic a direction. Again, organic bilayers are formed. This alternating layer motif with organic bilayers is identical to that observed in the Ca salt of benzoate and the Ca and Sr salts of p-fluoro- and p-chlorobenzoate (Senkovska & Thewalt, 2005; Karipides et al., 1988; Arlin et al., 2011). The bonding of the coordination polymer is also somewhat similar to these species, in that the bridging –COO^- group plays an identical role. However, in the benzoate derivatives there is no terminal carboxylate ligand. Instead, the third water molecule forms an extra bridge between the metal centres and the benzoate anion plays the role of linker group, hydrogen-bonding between the one-dimensional coordination chains. As with MgPAA, both the packing mode and the bonding within the coordination chains are extremely different from those typically observed for benzoates with hydroxy, amino or nitro substituents (Arlin et al., 2011).

In summary, despite the additional Csp³ atom between the aryl and –COO^- groups, all three PAA structures presented here have structural types closely related to those found for analogous benzoate and halobenzoate salts. This is shown by similarities in hydration state and in packing and layering behaviour, and by the formation of one-dimensional coordination polymers via –COO^- bridges. There is some variation from the benzoate structures in the detail of the metal bonding, but this is on a similar scale to the variation already found within the group of benzoate structures themselves. As the PAA salt structures are markedly different from those found for benzoate ions with active hydrogen-bonding substituents, it is concluded that the addition of CH₂ has less overall effect on structure than the addition of hydroxy, amino or nitro groups to the aryl ring.

Related literature

For related literature, see: Arlin et al. (2011); Bacon et al. (1977); Black et al. (2007); Brittain (2010); Collier et al. (2006); Cotton & Bergman (1964); Karipides et al. (1988); Kennedy et al. (2011); Senkovska & Thewalt (2005); Smith & Wermuth (2010a, 2010b); Stahl & Wermuth (2002).

S2. Experimental

All samples were prepared by slowly adding a slight excess of an aqueous solution of the appropriate metal carbonate to a stirred aqueous slurry of phenylacetic acid. The volumes of the resulting clear solutions were reduced until white precipitates were deposited, and these were collected by filtration. Colourless crystals suitable for single-crystal diffraction studies were obtained by recrystallization of the samples from warm water.

S3. Refinement

The H atoms of water molecules were positioned as found by difference syntheses and were refined with restraints such that the O—H and H···H distances approximated 0.88 and 1.33 Å, respectively; U_iso(H) values were set at 1.5U_eq(O). This introduced 24, nine and nine restraints for MgPAA, CaPAA and SrPAA, respectively. H atoms bonded to C atoms were positioned geometrically and refined in riding mode, with C—H = 0.95 and 0.99 Å for CH and CH₂ groups, respectively, and with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: APEX2 (Bruker, 2007) for MgPAA; DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998) for CaPAA; CrysAlis CCD (Oxford Diffraction, 2009) for SrPAA. Cell refinement: SAINT (Bruker, 2007) for MgPAA; DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998) for CaPAA; CrysAlis CCD (Oxford Diffraction, 2009) for SrPAA. Data reduction: SAINT (Bruker, 2007) for MgPAA; DENZO (Otwinowski & Minor, 1997) for CaPAA; CrysAlis RED (Oxford Diffraction, 2009) for SrPAA. For all compounds, program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: ORTEP-3 (Farrugia, 1997) and X-SEED (Barbour, 2001) for MgPAA, CaPAA; ORTEP-3 (Farrugia, 1997) for SrPAA. For all compounds, software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The contents of the asymmetric unit of MgPPA, showing the atom-numbering scheme (for clarity, only essential atom labels are shown). Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. Part of the one-dimensional coordination polymer found in MgPAA. The polymer chain is parallel to the crystallographic a direction. The noncoordinating PAA anions are not shown.
	Fig. 3. The packing mode of MgPAA, viewed down a to show the alternating inorganic layers and organic bilayers along the c direction.
	Fig. 4. The contents of the asymmetric unit of CaPPA, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 5. The contents of the asymmetric unit of SrPPA, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 6. Part of the one-dimensional coordination polymer found in CaPAA. The polymer propagates in the crystallographic b direction. Non-metal-bound water and all H atoms have been omitted for clarity

(MgPAA) catena-poly[[[tetraaquamagnesium(II)]-µ-phenylacetato- κ²O:O'] phenylacetate]

Crystal data

[Mg(C8H7O2)(H2O)4](C8H7O2)	F(000) = 1552
Mr = 366.65	Dx = 1.373 Mg m^−3
Orthorhombic, P212121	Synchrotron radiation, λ = 0.68840 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5842 reflections
a = 9.7979 (7) Å	θ = 2.3–26.9°
b = 10.0424 (8) Å	µ = 0.14 mm^−1
c = 36.052 (3) Å	T = 120 K
V = 3547.3 (5) Å^3	Plate, colourless
Z = 8	0.12 × 0.08 × 0.001 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	6253 independent reflections
Radiation source: Daresbury SRS Station 9.8	5231 reflections with I > 2σ(I)
Silicon 111 monochromator	Rint = 0.050
fine–slice ω scans	θmax = 24.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.844, Tmax = 1.000	k = −11→11
26335 measured reflections	l = −42→42

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.2732P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.096	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.29 e Å^−3
6253 reflections	Δρmin = −0.25 e Å^−3
500 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
24 restraints	Extinction coefficient: 0.0078 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with how many Friedel pairs?
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.5 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Mg1	0.87409 (8)	−0.01782 (8)	0.20171 (2)	0.0165 (2)
Mg2	0.37300 (9)	0.12071 (8)	0.20086 (2)	0.0171 (2)
O1	0.55301 (18)	0.05611 (17)	0.17986 (5)	0.0197 (4)
O2	0.76058 (18)	0.03754 (18)	0.15584 (5)	0.0207 (4)
O1W	0.3453 (2)	−0.06871 (17)	0.22289 (5)	0.0220 (4)
H1W	0.303 (3)	−0.137 (2)	0.2137 (7)	0.033*
H2W	0.341 (3)	−0.087 (3)	0.2466 (3)	0.033*
O3	0.05435 (18)	0.04603 (17)	0.18056 (5)	0.0198 (4)
O2W	0.19056 (19)	0.19528 (18)	0.22621 (5)	0.0204 (4)
H3W	0.184 (3)	0.160 (3)	0.2483 (4)	0.031*
H4W	0.131 (2)	0.149 (2)	0.2136 (6)	0.031*
O4	0.25838 (18)	0.06915 (18)	0.15450 (5)	0.0209 (4)
O3W	0.42737 (19)	0.30700 (18)	0.18460 (5)	0.0210 (4)
H5W	0.384 (2)	0.3796 (18)	0.1897 (8)	0.031*
H6W	0.5137 (11)	0.327 (3)	0.1872 (8)	0.031*
O5	0.19124 (18)	0.71901 (17)	0.19916 (5)	0.0216 (4)
O4W	0.45625 (19)	0.16285 (18)	0.25402 (5)	0.0218 (4)
H7W	0.5303 (19)	0.138 (3)	0.2658 (7)	0.033*
H8W	0.438 (3)	0.2358 (18)	0.2664 (7)	0.033*
O6	0.33485 (18)	0.54884 (16)	0.20485 (5)	0.0218 (4)
O5W	0.69033 (19)	−0.09172 (18)	0.22636 (5)	0.0199 (4)
H9W	0.631 (2)	−0.046 (2)	0.2135 (6)	0.030*
H10W	0.683 (3)	−0.054 (2)	0.2481 (4)	0.030*
O7	0.68888 (18)	0.38352 (17)	0.19966 (5)	0.0218 (4)
O6W	0.95600 (19)	−0.05905 (18)	0.25519 (5)	0.0218 (4)
H11W	1.027 (2)	−0.033 (3)	0.2676 (7)	0.033*
H12W	0.939 (3)	−0.1390 (15)	0.2638 (7)	0.033*
O8	0.83275 (18)	0.55423 (17)	0.20467 (5)	0.0218 (4)
O7W	0.92905 (19)	−0.20417 (17)	0.18503 (5)	0.0209 (4)
H13W	1.0144 (12)	−0.229 (3)	0.1872 (8)	0.031*
H14W	0.885 (2)	−0.2765 (18)	0.1906 (8)	0.031*
O8W	0.8467 (2)	0.17253 (17)	0.22385 (5)	0.0217 (4)
H15W	0.834 (3)	0.189 (3)	0.2477 (3)	0.032*
H16W	0.795 (3)	0.234 (2)	0.2140 (6)	0.032*
C1	0.6397 (3)	0.0758 (2)	0.15402 (7)	0.0178 (5)
C2	0.5917 (3)	0.1517 (3)	0.12002 (7)	0.0222 (6)
H2A	0.4907	0.1539	0.1201	0.027*
H2B	0.6243	0.2447	0.1219	0.027*
C3	0.6388 (3)	0.0951 (3)	0.08337 (7)	0.0208 (6)
C4	0.5480 (3)	0.0228 (3)	0.06230 (8)	0.0360 (7)
H4	0.4570	0.0109	0.0708	0.043*
C5	0.5880 (4)	−0.0329 (4)	0.02879 (9)	0.0484 (9)
H5	0.5244	−0.0837	0.0148	0.058*
C6	0.7191 (3)	−0.0153 (3)	0.01546 (8)	0.0327 (7)
H6	0.7461	−0.0537	−0.0075	0.039*
C7	0.8102 (3)	0.0589 (3)	0.03608 (8)	0.0309 (7)
H7	0.9002	0.0732	0.0271	0.037*
C8	0.7705 (3)	0.1127 (3)	0.06995 (7)	0.0276 (6)
H8	0.8344	0.1623	0.0841	0.033*
C9	0.1362 (3)	0.0321 (2)	0.15337 (7)	0.0191 (6)
C10	0.0807 (3)	−0.0359 (3)	0.11900 (7)	0.0227 (6)
H10A	0.0968	−0.1328	0.1216	0.027*
H10B	−0.0193	−0.0222	0.1184	0.027*
C11	0.1377 (3)	0.0077 (3)	0.08230 (7)	0.0226 (6)
C12	0.1770 (3)	−0.0852 (3)	0.05540 (7)	0.0277 (6)
H12	0.1758	−0.1775	0.0612	0.033*
C13	0.2179 (3)	−0.0438 (3)	0.02033 (8)	0.0333 (7)
H13	0.2421	−0.1081	0.0022	0.040*
C14	0.2236 (3)	0.0899 (4)	0.01165 (8)	0.0383 (8)
H14	0.2530	0.1178	−0.0122	0.046*
C15	0.1863 (3)	0.1822 (3)	0.03789 (8)	0.0369 (7)
H15	0.1900	0.2743	0.0320	0.044*
C16	0.1435 (3)	0.1423 (3)	0.07278 (8)	0.0288 (6)
H16	0.1176	0.2076	0.0905	0.035*
C17	0.2396 (3)	0.6088 (3)	0.18818 (7)	0.0183 (6)
C18	0.1828 (3)	0.5460 (3)	0.15308 (7)	0.0240 (6)
H18A	0.1005	0.5953	0.1451	0.029*
H18B	0.1558	0.4528	0.1583	0.029*
C19	0.2880 (3)	0.5479 (3)	0.12208 (7)	0.0239 (6)
C20	0.3281 (3)	0.4308 (3)	0.10452 (8)	0.0308 (7)
H20	0.2903	0.3483	0.1123	0.037*
C21	0.4222 (3)	0.4328 (4)	0.07594 (8)	0.0382 (8)
H21	0.4481	0.3522	0.0641	0.046*
C22	0.4787 (3)	0.5524 (4)	0.06459 (8)	0.0400 (8)
H22	0.5426	0.5542	0.0448	0.048*
C23	0.4421 (3)	0.6680 (3)	0.08205 (8)	0.0378 (8)
H23	0.4819	0.7499	0.0745	0.045*
C24	0.3474 (3)	0.6668 (3)	0.11065 (8)	0.0304 (7)
H24	0.3230	0.7478	0.1225	0.036*
C25	0.7344 (3)	0.4951 (3)	0.18898 (7)	0.0187 (5)
C26	0.6691 (3)	0.5612 (3)	0.15537 (8)	0.0258 (6)
H26A	0.5910	0.5065	0.1469	0.031*
H26B	0.6335	0.6497	0.1626	0.031*
C27	0.7693 (3)	0.5778 (3)	0.12370 (7)	0.0225 (6)
C28	0.8426 (3)	0.4702 (3)	0.11062 (8)	0.0294 (7)
H28	0.8305	0.3854	0.1219	0.035*
C29	0.9332 (4)	0.4836 (4)	0.08143 (9)	0.0398 (8)
H29	0.9821	0.4085	0.0725	0.048*
C30	0.9520 (4)	0.6064 (4)	0.06540 (8)	0.0409 (8)
H30	1.0157	0.6163	0.0457	0.049*
C31	0.8795 (4)	0.7148 (3)	0.07753 (8)	0.0369 (8)
H31	0.8912	0.7989	0.0659	0.044*
C32	0.7889 (3)	0.7008 (3)	0.10690 (7)	0.0291 (7)
H32	0.7398	0.7761	0.1156	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mg1	0.0159 (4)	0.0175 (4)	0.0161 (4)	0.0003 (3)	0.0000 (4)	−0.0002 (3)
Mg2	0.0158 (4)	0.0177 (4)	0.0178 (4)	−0.0003 (3)	0.0001 (4)	−0.0006 (3)
O1	0.0196 (9)	0.0203 (10)	0.0191 (9)	0.0026 (8)	0.0020 (8)	0.0025 (7)
O2	0.0184 (10)	0.0273 (10)	0.0165 (9)	0.0036 (8)	0.0012 (8)	0.0010 (8)
O1W	0.0266 (11)	0.0197 (10)	0.0196 (9)	−0.0041 (8)	−0.0013 (9)	−0.0003 (8)
O3	0.0185 (9)	0.0240 (10)	0.0169 (9)	−0.0019 (8)	0.0013 (7)	−0.0031 (7)
O2W	0.0210 (10)	0.0226 (10)	0.0176 (9)	0.0009 (8)	−0.0023 (8)	−0.0018 (8)
O4	0.0152 (10)	0.0276 (10)	0.0197 (9)	−0.0022 (8)	0.0007 (8)	−0.0008 (8)
O3W	0.0169 (9)	0.0199 (9)	0.0263 (10)	−0.0007 (8)	−0.0003 (8)	−0.0006 (8)
O5	0.0222 (10)	0.0186 (9)	0.0240 (9)	0.0020 (8)	−0.0020 (8)	−0.0017 (8)
O4W	0.0224 (10)	0.0202 (10)	0.0228 (10)	0.0021 (8)	−0.0052 (8)	−0.0028 (8)
O6	0.0221 (10)	0.0216 (10)	0.0216 (9)	0.0034 (8)	−0.0017 (8)	0.0005 (8)
O5W	0.0198 (10)	0.0227 (10)	0.0170 (9)	0.0024 (8)	−0.0005 (8)	0.0029 (8)
O7	0.0221 (10)	0.0186 (9)	0.0248 (9)	−0.0020 (8)	−0.0008 (8)	0.0021 (8)
O6W	0.0252 (11)	0.0209 (10)	0.0194 (10)	−0.0027 (9)	−0.0053 (8)	0.0032 (8)
O8	0.0201 (10)	0.0226 (10)	0.0225 (10)	−0.0030 (8)	−0.0031 (8)	0.0014 (8)
O7W	0.0180 (9)	0.0187 (9)	0.0259 (10)	0.0004 (8)	−0.0006 (8)	−0.0014 (8)
O8W	0.0288 (11)	0.0189 (10)	0.0173 (9)	0.0039 (8)	0.0001 (8)	0.0010 (8)
C1	0.0164 (13)	0.0181 (13)	0.0188 (13)	−0.0006 (11)	−0.0004 (11)	−0.0030 (10)
C2	0.0198 (14)	0.0262 (15)	0.0208 (14)	0.0033 (12)	0.0002 (11)	0.0030 (11)
C3	0.0240 (15)	0.0201 (13)	0.0183 (13)	0.0030 (12)	−0.0046 (12)	0.0052 (11)
C4	0.0270 (16)	0.056 (2)	0.0253 (15)	−0.0104 (15)	0.0035 (13)	−0.0047 (14)
C5	0.044 (2)	0.074 (3)	0.0273 (17)	−0.0217 (19)	−0.0016 (15)	−0.0110 (17)
C6	0.0375 (18)	0.0436 (18)	0.0171 (14)	−0.0041 (15)	0.0036 (13)	−0.0047 (13)
C7	0.0271 (16)	0.0369 (16)	0.0285 (15)	0.0029 (14)	0.0036 (13)	0.0039 (13)
C8	0.0283 (16)	0.0314 (15)	0.0230 (14)	0.0008 (13)	−0.0006 (12)	0.0012 (12)
C9	0.0228 (14)	0.0171 (13)	0.0175 (13)	0.0011 (11)	−0.0011 (12)	0.0027 (10)
C10	0.0208 (14)	0.0272 (14)	0.0201 (13)	−0.0045 (12)	−0.0004 (11)	−0.0032 (11)
C11	0.0194 (14)	0.0312 (15)	0.0172 (13)	−0.0035 (12)	−0.0017 (12)	−0.0033 (11)
C12	0.0214 (14)	0.0396 (17)	0.0220 (14)	−0.0012 (13)	−0.0005 (11)	−0.0045 (12)
C13	0.0278 (16)	0.052 (2)	0.0205 (15)	−0.0010 (15)	0.0009 (12)	−0.0064 (13)
C14	0.0342 (18)	0.057 (2)	0.0236 (15)	−0.0098 (16)	0.0022 (13)	0.0067 (15)
C15	0.0372 (18)	0.0411 (18)	0.0324 (16)	−0.0078 (15)	−0.0071 (14)	0.0075 (14)
C16	0.0320 (16)	0.0290 (16)	0.0256 (14)	−0.0034 (13)	−0.0004 (13)	−0.0004 (12)
C17	0.0176 (13)	0.0211 (14)	0.0164 (13)	−0.0012 (11)	0.0042 (11)	0.0007 (10)
C18	0.0192 (14)	0.0287 (15)	0.0241 (14)	−0.0004 (12)	−0.0020 (11)	−0.0042 (11)
C19	0.0246 (15)	0.0286 (15)	0.0185 (14)	0.0038 (12)	−0.0046 (11)	−0.0025 (11)
C20	0.0356 (18)	0.0354 (17)	0.0214 (14)	0.0065 (15)	−0.0064 (13)	−0.0051 (12)
C21	0.0383 (19)	0.051 (2)	0.0255 (16)	0.0144 (17)	−0.0026 (14)	−0.0090 (14)
C22	0.0320 (17)	0.067 (2)	0.0209 (15)	0.0100 (17)	0.0015 (13)	0.0037 (15)
C23	0.0355 (18)	0.0468 (19)	0.0310 (16)	0.0002 (16)	0.0019 (14)	0.0139 (14)
C24	0.0262 (16)	0.0329 (16)	0.0321 (16)	0.0037 (13)	−0.0005 (13)	0.0050 (12)
C25	0.0177 (13)	0.0197 (13)	0.0187 (13)	0.0051 (11)	0.0002 (11)	0.0003 (11)
C26	0.0253 (15)	0.0278 (15)	0.0244 (14)	0.0003 (13)	−0.0026 (12)	0.0044 (12)
C27	0.0224 (14)	0.0301 (15)	0.0151 (13)	−0.0029 (12)	−0.0054 (11)	0.0008 (11)
C28	0.0315 (17)	0.0314 (16)	0.0254 (15)	−0.0036 (14)	−0.0026 (13)	−0.0014 (12)
C29	0.0396 (19)	0.048 (2)	0.0320 (17)	0.0005 (17)	0.0022 (15)	−0.0128 (16)
C30	0.0397 (19)	0.064 (2)	0.0189 (15)	−0.0146 (18)	0.0045 (14)	−0.0033 (15)
C31	0.047 (2)	0.0428 (18)	0.0211 (14)	−0.0196 (16)	−0.0059 (14)	0.0095 (13)
C32	0.0383 (18)	0.0295 (16)	0.0194 (14)	−0.0052 (14)	−0.0056 (13)	0.0025 (12)

Geometric parameters (Å, º)

Mg1—O3^i	2.0278 (19)	C7—C8	1.391 (4)
Mg1—O7W	2.0381 (19)	C7—H7	0.9500
Mg1—O2	2.0691 (19)	C8—H8	0.9500
Mg1—O8W	2.0888 (19)	C9—C10	1.515 (4)
Mg1—O6W	2.1291 (19)	C10—C11	1.501 (4)
Mg1—O5W	2.141 (2)	C10—H10A	0.9900
Mg2—O1	2.026 (2)	C10—H10B	0.9900
Mg2—O3W	2.032 (2)	C11—C16	1.396 (4)
Mg2—O1W	2.0790 (19)	C11—C12	1.399 (4)
Mg2—O4	2.079 (2)	C12—C13	1.390 (4)
Mg2—O4W	2.1252 (19)	C12—H12	0.9500
Mg2—O2W	2.143 (2)	C13—C14	1.379 (5)
O1—C1	1.276 (3)	C13—H13	0.9500
O2—C1	1.247 (3)	C14—C15	1.374 (5)
O1W—H1W	0.866 (10)	C14—H14	0.9500
O1W—H2W	0.875 (10)	C15—C16	1.386 (4)
O3—C9	1.274 (3)	C15—H15	0.9500
O3—Mg1^ii	2.0278 (19)	C16—H16	0.9500
O2W—H3W	0.874 (10)	C17—C18	1.519 (4)
O2W—H4W	0.875 (10)	C18—C19	1.520 (4)
O4—C9	1.255 (3)	C18—H18A	0.9900
O3W—H5W	0.865 (10)	C18—H18B	0.9900
O3W—H6W	0.873 (10)	C19—C24	1.391 (4)
O5—C17	1.267 (3)	C19—C20	1.393 (4)
O4W—H7W	0.877 (10)	C20—C21	1.383 (5)
O4W—H8W	0.878 (10)	C20—H20	0.9500
O6—C17	1.263 (3)	C21—C22	1.384 (5)
O5W—H9W	0.875 (10)	C21—H21	0.9500
O5W—H10W	0.875 (10)	C22—C23	1.369 (4)
O7—C25	1.266 (3)	C22—H22	0.9500
O6W—H11W	0.869 (10)	C23—C24	1.387 (4)
O6W—H12W	0.877 (10)	C23—H23	0.9500
O8—C25	1.265 (3)	C24—H24	0.9500
O7W—H13W	0.876 (10)	C25—C26	1.523 (4)
O7W—H14W	0.868 (10)	C26—C27	1.515 (4)
O8W—H15W	0.886 (10)	C26—H26A	0.9900
O8W—H16W	0.874 (10)	C26—H26B	0.9900
C1—C2	1.518 (3)	C27—C28	1.380 (4)
C2—C3	1.510 (4)	C27—C32	1.389 (4)
C2—H2A	0.9900	C28—C29	1.384 (4)
C2—H2B	0.9900	C28—H28	0.9500
C3—C4	1.377 (4)	C29—C30	1.374 (5)
C3—C8	1.389 (4)	C29—H29	0.9500
C4—C5	1.388 (4)	C30—C31	1.371 (5)
C4—H4	0.9500	C30—H30	0.9500
C5—C6	1.383 (5)	C31—C32	1.389 (4)
C5—H5	0.9500	C31—H31	0.9500
C6—C7	1.380 (4)	C32—H32	0.9500
C6—H6	0.9500
O3^i—Mg1—O7W	87.09 (8)	C3—C8—H8	119.5
O3^i—Mg1—O2	94.74 (8)	C7—C8—H8	119.5
O7W—Mg1—O2	98.79 (8)	O4—C9—O3	122.9 (2)
O3^i—Mg1—O8W	88.06 (8)	O4—C9—C10	120.2 (2)
O7W—Mg1—O8W	170.75 (9)	O3—C9—C10	116.9 (2)
O2—Mg1—O8W	89.45 (8)	C11—C10—C9	117.1 (2)
O3^i—Mg1—O6W	94.23 (8)	C11—C10—H10A	108.0
O7W—Mg1—O6W	89.38 (8)	C9—C10—H10A	108.0
O2—Mg1—O6W	168.15 (8)	C11—C10—H10B	108.0
O8W—Mg1—O6W	83.13 (7)	C9—C10—H10B	108.0
O3^i—Mg1—O5W	176.69 (8)	H10A—C10—H10B	107.3
O7W—Mg1—O5W	91.51 (8)	C16—C11—C12	117.6 (3)
O2—Mg1—O5W	88.44 (7)	C16—C11—C10	120.9 (2)
O8W—Mg1—O5W	92.90 (8)	C12—C11—C10	121.3 (3)
O6W—Mg1—O5W	82.74 (8)	C13—C12—C11	120.7 (3)
O1—Mg2—O3W	87.63 (8)	C13—C12—H12	119.7
O1—Mg2—O1W	87.90 (8)	C11—C12—H12	119.7
O3W—Mg2—O1W	170.73 (9)	C14—C13—C12	120.6 (3)
O1—Mg2—O4	95.16 (8)	C14—C13—H13	119.7
O3W—Mg2—O4	97.99 (8)	C12—C13—H13	119.7
O1W—Mg2—O4	90.50 (8)	C15—C14—C13	119.3 (3)
O1—Mg2—O4W	93.83 (8)	C15—C14—H14	120.3
O3W—Mg2—O4W	88.63 (8)	C13—C14—H14	120.3
O1W—Mg2—O4W	83.56 (8)	C14—C15—C16	120.7 (3)
O4—Mg2—O4W	169.04 (8)	C14—C15—H15	119.6
O1—Mg2—O2W	175.97 (8)	C16—C15—H15	119.6
O3W—Mg2—O2W	91.14 (8)	C15—C16—C11	121.0 (3)
O1W—Mg2—O2W	92.76 (8)	C15—C16—H16	119.5
O4—Mg2—O2W	88.81 (7)	C11—C16—H16	119.5
O4W—Mg2—O2W	82.31 (8)	O6—C17—O5	122.9 (2)
C1—O1—Mg2	143.39 (17)	O6—C17—C18	118.0 (2)
C1—O2—Mg1	129.46 (17)	O5—C17—C18	119.1 (2)
Mg2—O1W—H1W	129.8 (18)	C17—C18—C19	111.1 (2)
Mg2—O1W—H2W	124.5 (18)	C17—C18—H18A	109.4
H1W—O1W—H2W	101.1 (18)	C19—C18—H18A	109.4
C9—O3—Mg1^ii	143.38 (16)	C17—C18—H18B	109.4
Mg2—O2W—H3W	108 (2)	C19—C18—H18B	109.4
Mg2—O2W—H4W	98.4 (19)	H18A—C18—H18B	108.0
H3W—O2W—H4W	101.7 (18)	C24—C19—C20	118.2 (3)
C9—O4—Mg2	128.00 (17)	C24—C19—C18	120.8 (2)
Mg2—O3W—H5W	125.8 (19)	C20—C19—C18	121.0 (3)
Mg2—O3W—H6W	115.6 (18)	C21—C20—C19	121.0 (3)
H5W—O3W—H6W	105.4 (19)	C21—C20—H20	119.5
Mg2—O4W—H7W	134.0 (18)	C19—C20—H20	119.5
Mg2—O4W—H8W	123.1 (18)	C20—C21—C22	120.0 (3)
H7W—O4W—H8W	99.6 (18)	C20—C21—H21	120.0
Mg1—O5W—H9W	99 (2)	C22—C21—H21	120.0
Mg1—O5W—H10W	107 (2)	C23—C22—C21	119.7 (3)
H9W—O5W—H10W	101.2 (18)	C23—C22—H22	120.2
Mg1—O6W—H11W	135.5 (18)	C21—C22—H22	120.2
Mg1—O6W—H12W	115.3 (18)	C22—C23—C24	120.6 (3)
H11W—O6W—H12W	104.0 (19)	C22—C23—H23	119.7
Mg1—O7W—H13W	119.2 (18)	C24—C23—H23	119.7
Mg1—O7W—H14W	124.7 (19)	C23—C24—C19	120.5 (3)
H13W—O7W—H14W	102.3 (19)	C23—C24—H24	119.7
Mg1—O8W—H15W	124.2 (18)	C19—C24—H24	119.7
Mg1—O8W—H16W	124.5 (18)	O8—C25—O7	123.2 (2)
H15W—O8W—H16W	100.4 (18)	O8—C25—C26	118.1 (2)
O2—C1—O1	123.1 (2)	O7—C25—C26	118.7 (2)
O2—C1—C2	119.4 (2)	C27—C26—C25	112.0 (2)
O1—C1—C2	117.5 (2)	C27—C26—H26A	109.2
C3—C2—C1	115.0 (2)	C25—C26—H26A	109.2
C3—C2—H2A	108.5	C27—C26—H26B	109.2
C1—C2—H2A	108.5	C25—C26—H26B	109.2
C3—C2—H2B	108.5	H26A—C26—H26B	107.9
C1—C2—H2B	108.5	C28—C27—C32	118.4 (3)
H2A—C2—H2B	107.5	C28—C27—C26	120.5 (2)
C4—C3—C8	118.4 (3)	C32—C27—C26	121.1 (3)
C4—C3—C2	118.9 (3)	C27—C28—C29	121.1 (3)
C8—C3—C2	122.7 (2)	C27—C28—H28	119.4
C3—C4—C5	120.7 (3)	C29—C28—H28	119.4
C3—C4—H4	119.7	C30—C29—C28	119.6 (3)
C5—C4—H4	119.7	C30—C29—H29	120.2
C6—C5—C4	120.9 (3)	C28—C29—H29	120.2
C6—C5—H5	119.5	C31—C30—C29	120.6 (3)
C4—C5—H5	119.5	C31—C30—H30	119.7
C7—C6—C5	118.8 (3)	C29—C30—H30	119.7
C7—C6—H6	120.6	C30—C31—C32	119.6 (3)
C5—C6—H6	120.6	C30—C31—H31	120.2
C6—C7—C8	120.1 (3)	C32—C31—H31	120.2
C6—C7—H7	119.9	C31—C32—C27	120.7 (3)
C8—C7—H7	119.9	C31—C32—H32	119.6
C3—C8—C7	121.1 (3)	C27—C32—H32	119.6
O3W—Mg2—O1—C1	−33.9 (3)	O3—C9—C10—C11	148.1 (2)
O1W—Mg2—O1—C1	154.2 (3)	C9—C10—C11—C16	−50.7 (4)
O4—Mg2—O1—C1	63.9 (3)	C9—C10—C11—C12	134.3 (3)
O4W—Mg2—O1—C1	−122.4 (3)	C16—C11—C12—C13	−1.1 (4)
O3^i—Mg1—O2—C1	−148.7 (2)	C10—C11—C12—C13	174.1 (3)
O7W—Mg1—O2—C1	123.5 (2)	C11—C12—C13—C14	1.6 (4)
O8W—Mg1—O2—C1	−60.7 (2)	C12—C13—C14—C15	−1.0 (5)
O6W—Mg1—O2—C1	−9.6 (5)	C13—C14—C15—C16	0.1 (5)
O5W—Mg1—O2—C1	32.2 (2)	C14—C15—C16—C11	0.4 (5)
O1—Mg2—O4—C9	148.4 (2)	C12—C11—C16—C15	0.1 (4)
O3W—Mg2—O4—C9	−123.3 (2)	C10—C11—C16—C15	−175.1 (3)
O1W—Mg2—O4—C9	60.4 (2)	O6—C17—C18—C19	−67.6 (3)
O4W—Mg2—O4—C9	3.4 (6)	O5—C17—C18—C19	111.3 (3)
O2W—Mg2—O4—C9	−32.3 (2)	C17—C18—C19—C24	−56.1 (3)
Mg1—O2—C1—O1	−18.2 (4)	C17—C18—C19—C20	123.5 (3)
Mg1—O2—C1—C2	160.66 (17)	C24—C19—C20—C21	−1.4 (4)
Mg2—O1—C1—O2	159.3 (2)	C18—C19—C20—C21	179.0 (3)
Mg2—O1—C1—C2	−19.6 (4)	C19—C20—C21—C22	0.5 (5)
O2—C1—C2—C3	44.0 (3)	C20—C21—C22—C23	0.7 (5)
O1—C1—C2—C3	−137.1 (2)	C21—C22—C23—C24	−0.9 (5)
C1—C2—C3—C4	102.9 (3)	C22—C23—C24—C19	0.0 (4)
C1—C2—C3—C8	−77.0 (3)	C20—C19—C24—C23	1.2 (4)
C8—C3—C4—C5	1.1 (5)	C18—C19—C24—C23	−179.2 (3)
C2—C3—C4—C5	−178.8 (3)	O8—C25—C26—C27	61.9 (3)
C3—C4—C5—C6	−1.1 (6)	O7—C25—C26—C27	−117.4 (3)
C4—C5—C6—C7	0.0 (5)	C25—C26—C27—C28	53.2 (3)
C5—C6—C7—C8	1.1 (5)	C25—C26—C27—C32	−127.5 (3)
C4—C3—C8—C7	0.0 (4)	C32—C27—C28—C29	−0.2 (4)
C2—C3—C8—C7	179.9 (3)	C26—C27—C28—C29	179.2 (3)
C6—C7—C8—C3	−1.1 (4)	C27—C28—C29—C30	0.7 (5)
Mg2—O4—C9—O3	14.7 (4)	C28—C29—C30—C31	−1.5 (5)
Mg2—O4—C9—C10	−163.65 (17)	C29—C30—C31—C32	1.6 (5)
Mg1^ii—O3—C9—O4	−162.3 (2)	C30—C31—C32—C27	−1.1 (4)
Mg1^ii—O3—C9—C10	16.1 (4)	C28—C27—C32—C31	0.3 (4)
O4—C9—C10—C11	−33.5 (4)	C26—C27—C32—C31	−179.0 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O5^iii	0.87 (1)	1.89 (1)	2.749 (3)	171 (3)
O1W—H2W···O7^iv	0.88 (1)	1.98 (1)	2.853 (3)	173 (3)
O2W—H3W···O8^iv	0.87 (1)	2.01 (1)	2.875 (2)	172 (3)
O2W—H4W···O3	0.88 (1)	1.75 (1)	2.595 (2)	163 (3)
O3W—H5W···O6	0.87 (1)	1.85 (1)	2.693 (2)	165 (3)
O3W—H6W···O7	0.87 (1)	1.86 (1)	2.729 (3)	171 (3)
O4W—H7W···O6^iv	0.88 (1)	1.91 (1)	2.775 (3)	166 (3)
O4W—H8W···O5W^v	0.88 (1)	2.15 (2)	2.939 (3)	149 (2)
O5W—H9W···O1	0.88 (1)	1.76 (1)	2.613 (2)	164 (3)
O5W—H10W···O6^iv	0.88 (1)	1.99 (1)	2.864 (2)	175 (2)
O6W—H11W···O8^vi	0.87 (1)	1.91 (1)	2.770 (3)	169 (3)
O6W—H12W···O2W^iv	0.88 (1)	2.12 (1)	2.932 (3)	153 (3)
O7W—H13W···O5^vii	0.88 (1)	1.86 (1)	2.730 (3)	172 (3)
O7W—H14W···O8^iii	0.87 (1)	1.85 (1)	2.698 (2)	166 (2)
O8W—H15W···O5^iv	0.89 (1)	1.95 (1)	2.839 (2)	178 (2)
O8W—H16W···O7	0.87 (1)	1.90 (1)	2.764 (2)	171 (3)

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

(CaPAA) catena-poly[[[diaqua(phenylacetato-κ²O,O')calcium(II)]- µ₃-phenylacetato-1':1:1''κ⁴O:O,O':O'] monohydrate]

Crystal data

[Ca(C8H7O2)2(H2O)2]·H2O	F(000) = 1536
Mr = 364.40	Dx = 1.391 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4276 reflections
a = 29.2249 (10) Å	θ = 1.0–27.5°
b = 6.6941 (3) Å	µ = 0.39 mm^−1
c = 17.8109 (5) Å	T = 150 K
β = 92.520 (2)°	Rod, colourless
V = 3481.1 (2) Å^3	0.36 × 0.08 × 0.07 mm
Z = 8

Data collection

Enraf–Nonius KappaCCD area-detector diffractometer	2429 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
Graphite monochromator	θmax = 27.0°, θmin = 3.1°
ω and ϕ scans	h = −37→37
7271 measured reflections	k = −8→8
3814 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0414P)^2 + 1.822P] where P = (Fo^2 + 2Fc^2)/3
3814 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.39 e Å^−3
9 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ca1	0.246964 (14)	0.04803 (7)	0.69169 (2)	0.02085 (14)
O1	0.27663 (5)	−0.1143 (2)	0.81164 (8)	0.0252 (4)
O2	0.27710 (5)	0.2128 (2)	0.81443 (8)	0.0268 (4)
O1W	0.17465 (5)	0.0444 (3)	0.74864 (8)	0.0274 (4)
H1W	0.1702 (8)	0.144 (2)	0.7786 (11)	0.041*
H2W	0.1698 (9)	−0.058 (2)	0.7775 (11)	0.041*
O3	0.31944 (5)	−0.1207 (3)	0.65373 (10)	0.0375 (4)
O2W	0.23614 (6)	0.0638 (3)	0.55625 (9)	0.0389 (4)
H3W	0.2177 (7)	0.017 (4)	0.5205 (12)	0.058*
H4W	0.2616 (5)	0.007 (4)	0.5461 (15)	0.058*
O4	0.32184 (5)	0.2059 (2)	0.65610 (9)	0.0311 (4)
O3W	0.32264 (8)	0.5501 (3)	0.55370 (10)	0.0526 (5)
H5W	0.3223 (11)	0.652 (3)	0.5846 (13)	0.079*
H6W	0.3270 (11)	0.452 (3)	0.5854 (13)	0.079*
C1	0.28835 (6)	0.0469 (4)	0.84278 (11)	0.0185 (4)
C2	0.31925 (7)	0.0405 (4)	0.91398 (12)	0.0257 (5)
H2A	0.3149	0.1633	0.9438	0.031*
H2B	0.3110	−0.0756	0.9450	0.031*
C3	0.36885 (7)	0.0239 (4)	0.89374 (11)	0.0233 (5)
C4	0.39824 (8)	0.1862 (4)	0.90139 (13)	0.0346 (6)
H4	0.3871	0.3103	0.9189	0.041*
C5	0.44388 (8)	0.1682 (4)	0.88358 (15)	0.0421 (7)
H5	0.4638	0.2798	0.8893	0.051*
C6	0.46032 (9)	−0.0102 (4)	0.85766 (14)	0.0391 (7)
H6	0.4915	−0.0217	0.8454	0.047*
C7	0.43140 (8)	−0.1728 (4)	0.84956 (12)	0.0329 (6)
H7	0.4427	−0.2962	0.8317	0.040*
C8	0.38605 (7)	−0.1561 (4)	0.86741 (12)	0.0278 (5)
H8	0.3663	−0.2685	0.8617	0.033*
C9	0.34169 (8)	0.0410 (4)	0.65413 (12)	0.0247 (5)
C10	0.39353 (8)	0.0287 (4)	0.65570 (15)	0.0360 (6)
H10A	0.4047	−0.0053	0.7074	0.043*
H10B	0.4025	−0.0816	0.6223	0.043*
C11	0.41691 (7)	0.2164 (4)	0.63188 (12)	0.0255 (5)
C12	0.42567 (7)	0.2474 (4)	0.55726 (13)	0.0307 (6)
H12	0.4180	0.1460	0.5216	0.037*
C13	0.44526 (8)	0.4220 (4)	0.53343 (13)	0.0345 (6)
H13	0.4505	0.4408	0.4816	0.041*
C14	0.45720 (8)	0.5688 (4)	0.58418 (13)	0.0325 (6)
H14	0.4703	0.6900	0.5675	0.039*
C15	0.45026 (8)	0.5408 (4)	0.65951 (13)	0.0352 (6)
H15	0.4592	0.6408	0.6950	0.042*
C16	0.42997 (8)	0.3644 (4)	0.68319 (13)	0.0349 (6)
H16	0.4250	0.3452	0.7351	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ca1	0.0211 (2)	0.0130 (2)	0.0283 (2)	0.0003 (2)	0.00002 (17)	−0.0001 (2)
O1	0.0292 (9)	0.0133 (9)	0.0325 (9)	−0.0012 (7)	−0.0051 (6)	−0.0009 (7)
O2	0.0301 (9)	0.0145 (9)	0.0353 (9)	0.0013 (7)	−0.0026 (7)	0.0026 (7)
O1W	0.0268 (8)	0.0150 (8)	0.0407 (10)	−0.0001 (8)	0.0059 (7)	0.0020 (8)
O3	0.0311 (9)	0.0161 (9)	0.0665 (12)	−0.0017 (8)	0.0160 (8)	0.0025 (9)
O2W	0.0425 (10)	0.0404 (12)	0.0336 (10)	−0.0035 (10)	0.0006 (8)	−0.0038 (9)
O4	0.0243 (8)	0.0164 (9)	0.0529 (10)	0.0029 (7)	0.0065 (7)	−0.0040 (8)
O3W	0.0840 (15)	0.0313 (11)	0.0405 (11)	0.0045 (12)	−0.0205 (10)	0.0014 (9)
C1	0.0156 (10)	0.0146 (11)	0.0259 (11)	0.0022 (11)	0.0059 (8)	0.0010 (11)
C2	0.0280 (12)	0.0248 (13)	0.0243 (11)	0.0009 (11)	0.0018 (9)	−0.0008 (11)
C3	0.0254 (12)	0.0229 (14)	0.0209 (11)	0.0001 (11)	−0.0073 (9)	0.0023 (10)
C4	0.0360 (14)	0.0243 (15)	0.0426 (15)	0.0001 (12)	−0.0074 (11)	0.0003 (12)
C5	0.0313 (14)	0.0332 (18)	0.0608 (17)	−0.0108 (14)	−0.0077 (12)	0.0050 (15)
C6	0.0246 (13)	0.052 (2)	0.0399 (14)	0.0010 (13)	−0.0036 (11)	0.0058 (13)
C7	0.0298 (13)	0.0391 (17)	0.0295 (13)	0.0088 (13)	−0.0025 (10)	−0.0036 (12)
C8	0.0292 (12)	0.0258 (15)	0.0278 (12)	−0.0006 (12)	−0.0049 (9)	−0.0011 (11)
C9	0.0265 (12)	0.0218 (13)	0.0262 (12)	0.0028 (13)	0.0064 (9)	0.0038 (11)
C10	0.0263 (13)	0.0294 (15)	0.0526 (16)	0.0059 (12)	0.0053 (11)	0.0107 (13)
C11	0.0155 (11)	0.0249 (14)	0.0362 (13)	0.0045 (10)	0.0036 (9)	0.0061 (11)
C12	0.0276 (13)	0.0302 (15)	0.0340 (14)	−0.0025 (11)	−0.0008 (10)	−0.0005 (11)
C13	0.0346 (13)	0.0387 (18)	0.0304 (13)	−0.0009 (13)	0.0048 (10)	0.0044 (12)
C14	0.0268 (12)	0.0282 (15)	0.0427 (15)	−0.0035 (12)	0.0038 (10)	0.0020 (13)
C15	0.0372 (14)	0.0318 (15)	0.0366 (14)	0.0003 (14)	0.0012 (11)	−0.0086 (13)
C16	0.0348 (14)	0.0417 (17)	0.0286 (13)	0.0073 (13)	0.0067 (10)	0.0003 (13)

Geometric parameters (Å, º)

Ca1—O2^i	2.3527 (16)	C3—C4	1.388 (3)
Ca1—O1^ii	2.3632 (16)	C3—C8	1.395 (3)
Ca1—O1W	2.3843 (15)	C4—C5	1.390 (3)
Ca1—O2W	2.4214 (16)	C4—H4	0.9500
Ca1—O1	2.5167 (14)	C5—C6	1.375 (4)
Ca1—O3	2.5188 (16)	C5—H5	0.9500
Ca1—O4	2.5355 (15)	C6—C7	1.381 (4)
Ca1—O2	2.5695 (15)	C6—H6	0.9500
Ca1—C9	2.877 (2)	C7—C8	1.381 (3)
Ca1—C1	2.901 (2)	C7—H7	0.9500
O1—C1	1.254 (3)	C8—H8	0.9500
O1—Ca1^i	2.3632 (16)	C9—C10	1.516 (3)
O2—C1	1.258 (3)	C10—C11	1.501 (3)
O2—Ca1^ii	2.3527 (16)	C10—H10A	0.9900
O1W—H1W	0.867 (9)	C10—H10B	0.9900
O1W—H2W	0.875 (9)	C11—C12	1.380 (3)
O3—C9	1.263 (3)	C11—C16	1.390 (3)
O2W—H3W	0.872 (10)	C12—C13	1.377 (3)
O2W—H4W	0.862 (10)	C12—H12	0.9500
O4—C9	1.248 (3)	C13—C14	1.370 (3)
O3W—H5W	0.875 (10)	C13—H13	0.9500
O3W—H6W	0.873 (10)	C14—C15	1.379 (3)
C1—C2	1.525 (3)	C14—H14	0.9500
C2—C3	1.513 (3)	C15—C16	1.395 (4)
C2—H2A	0.9900	C15—H15	0.9500
C2—H2B	0.9900	C16—H16	0.9500
O2^i—Ca1—O1^ii	145.58 (5)	Ca1^i—Ca1—H4W	114.9 (5)
O2^i—Ca1—O1W	75.01 (6)	C1—O1—Ca1^i	155.21 (13)
O1^ii—Ca1—O1W	75.95 (6)	C1—O1—Ca1	94.65 (12)
O2^i—Ca1—O2W	88.26 (6)	Ca1^i—O1—Ca1	107.61 (6)
O1^ii—Ca1—O2W	84.73 (6)	C1—O2—Ca1^ii	158.93 (14)
O1W—Ca1—O2W	110.18 (6)	C1—O2—Ca1	92.08 (12)
O2^i—Ca1—O1	73.66 (5)	Ca1^ii—O2—Ca1	106.23 (5)
O1^ii—Ca1—O1	121.57 (4)	Ca1—O1W—H1W	114.4 (16)
O1W—Ca1—O1	85.02 (5)	Ca1—O1W—H2W	115.4 (16)
O2W—Ca1—O1	152.82 (6)	H1W—O1W—H2W	102.1 (17)
O2^i—Ca1—O3	79.22 (5)	C9—O3—Ca1	93.04 (13)
O1^ii—Ca1—O3	132.07 (6)	Ca1—O2W—H3W	139.5 (19)
O1W—Ca1—O3	151.78 (6)	Ca1—O2W—H4W	96.5 (18)
O2W—Ca1—O3	80.02 (6)	H3W—O2W—H4W	101.5 (18)
O1—Ca1—O3	76.82 (5)	C9—O4—Ca1	92.62 (13)
O2^i—Ca1—O4	130.20 (6)	H5W—O3W—H6W	100.6 (18)
O1^ii—Ca1—O4	81.32 (5)	O1—C1—O2	121.38 (18)
O1W—Ca1—O4	154.35 (6)	O1—C1—C2	118.9 (2)
O2W—Ca1—O4	79.00 (6)	O2—C1—C2	119.6 (2)
O1—Ca1—O4	97.08 (5)	O1—C1—Ca1	59.83 (10)
O3—Ca1—O4	51.29 (5)	O2—C1—Ca1	62.25 (10)
O2^i—Ca1—O2	122.64 (4)	C2—C1—Ca1	168.22 (14)
O1^ii—Ca1—O2	72.51 (5)	C3—C2—C1	110.03 (17)
O1W—Ca1—O2	85.38 (5)	C3—C2—H2A	109.7
O2W—Ca1—O2	148.63 (6)	C1—C2—H2A	109.7
O1—Ca1—O2	51.00 (5)	C3—C2—H2B	109.7
O3—Ca1—O2	99.21 (5)	C1—C2—H2B	109.7
O4—Ca1—O2	76.50 (5)	H2A—C2—H2B	108.2
O2^i—Ca1—C9	105.21 (7)	C4—C3—C8	118.6 (2)
O1^ii—Ca1—C9	107.01 (7)	C4—C3—C2	121.0 (2)
O1W—Ca1—C9	168.18 (6)	C8—C3—C2	120.4 (2)
O2W—Ca1—C9	81.60 (6)	C3—C4—C5	120.4 (2)
O1—Ca1—C9	83.76 (6)	C3—C4—H4	119.8
O3—Ca1—C9	25.99 (6)	C5—C4—H4	119.8
O4—Ca1—C9	25.69 (6)	C6—C5—C4	120.3 (2)
O2—Ca1—C9	84.70 (6)	C6—C5—H5	119.8
O2^i—Ca1—C1	98.75 (6)	C4—C5—H5	119.8
O1^ii—Ca1—C1	97.76 (6)	C5—C6—C7	119.9 (2)
O1W—Ca1—C1	86.93 (5)	C5—C6—H6	120.1
O2W—Ca1—C1	162.74 (6)	C7—C6—H6	120.1
O1—Ca1—C1	25.52 (5)	C8—C7—C6	120.1 (2)
O3—Ca1—C1	85.79 (6)	C8—C7—H7	120.0
O4—Ca1—C1	84.48 (5)	C6—C7—H7	120.0
O2—Ca1—C1	25.67 (5)	C7—C8—C3	120.7 (2)
C9—Ca1—C1	81.34 (6)	C7—C8—H8	119.6
O2^i—Ca1—Ca1^ii	147.28 (4)	C3—C8—H8	119.6
O1^ii—Ca1—Ca1^ii	37.52 (3)	O4—C9—O3	121.2 (2)
O1W—Ca1—Ca1^ii	78.73 (4)	O4—C9—C10	120.9 (2)
O2W—Ca1—Ca1^ii	119.29 (5)	O3—C9—C10	117.9 (2)
O1—Ca1—Ca1^ii	85.03 (4)	O4—C9—Ca1	61.69 (11)
O3—Ca1—Ca1^ii	120.24 (4)	O3—C9—Ca1	60.96 (11)
O4—Ca1—Ca1^ii	76.01 (4)	C10—C9—Ca1	165.35 (15)
O2—Ca1—Ca1^ii	34.99 (4)	C11—C10—C9	114.6 (2)
C9—Ca1—Ca1^ii	96.60 (5)	C11—C10—H10A	108.6
C1—Ca1—Ca1^ii	60.39 (5)	C9—C10—H10A	108.6
O2^i—Ca1—Ca1^i	38.78 (3)	C11—C10—H10B	108.6
O1^ii—Ca1—Ca1^i	146.34 (4)	C9—C10—H10B	108.6
O1W—Ca1—Ca1^i	77.72 (4)	H10A—C10—H10B	107.6
O2W—Ca1—Ca1^i	124.28 (5)	C12—C11—C16	118.0 (2)
O1—Ca1—Ca1^i	34.88 (4)	C12—C11—C10	120.3 (2)
O3—Ca1—Ca1^i	75.03 (4)	C16—C11—C10	121.7 (2)
O4—Ca1—Ca1^i	117.82 (4)	C13—C12—C11	121.4 (2)
O2—Ca1—Ca1^i	84.85 (4)	C13—C12—H12	119.3
C9—Ca1—Ca1^i	95.00 (5)	C11—C12—H12	119.3
C1—Ca1—Ca1^i	60.09 (5)	C14—C13—C12	120.2 (2)
Ca1^ii—Ca1—Ca1^i	116.36 (2)	C14—C13—H13	119.9
O2^i—Ca1—H4W	85.2 (6)	C12—C13—H13	119.9
O1^ii—Ca1—H4W	97.7 (5)	C13—C14—C15	120.0 (2)
O1W—Ca1—H4W	126.7 (4)	C13—C14—H14	120.0
O2W—Ca1—H4W	18.8 (3)	C15—C14—H14	120.0
O1—Ca1—H4W	135.9 (4)	C14—C15—C16	119.5 (2)
O3—Ca1—H4W	61.2 (3)	C14—C15—H15	120.3
O4—Ca1—H4W	67.8 (5)	C16—C15—H15	120.3
O2—Ca1—H4W	144.1 (5)	C11—C16—C15	120.8 (2)
C9—Ca1—H4W	64.8 (3)	C11—C16—H16	119.6
C1—Ca1—H4W	145.6 (3)	C15—C16—H16	119.6
Ca1^ii—Ca1—H4W	126.6 (6)
O2^i—Ca1—O1—C1	−169.14 (12)	O1^ii—Ca1—C1—O2	−10.34 (12)
O1^ii—Ca1—O1—C1	−23.17 (10)	O1W—Ca1—C1—O2	−85.71 (12)
O1W—Ca1—O1—C1	−93.32 (12)	O2W—Ca1—C1—O2	86.9 (3)
O2W—Ca1—O1—C1	140.66 (14)	O1—Ca1—C1—O2	−170.56 (19)
O3—Ca1—O1—C1	108.41 (12)	O3—Ca1—C1—O2	121.58 (12)
O4—Ca1—O1—C1	60.97 (12)	O4—Ca1—C1—O2	70.10 (12)
O2—Ca1—O1—C1	−5.24 (11)	C9—Ca1—C1—O2	95.79 (13)
C9—Ca1—O1—C1	82.98 (12)	Ca1^ii—Ca1—C1—O2	−6.94 (10)
Ca1^ii—Ca1—O1—C1	−14.24 (11)	Ca1^i—Ca1—C1—O2	−163.29 (13)
Ca1^i—Ca1—O1—C1	−168.94 (15)	O2^i—Ca1—C1—C2	97.9 (8)
O2^i—Ca1—O1—Ca1^i	−0.20 (6)	O1^ii—Ca1—C1—C2	−112.5 (8)
O1^ii—Ca1—O1—Ca1^i	145.77 (8)	O1W—Ca1—C1—C2	172.2 (8)
O1W—Ca1—O1—Ca1^i	75.62 (7)	O2W—Ca1—C1—C2	−15.2 (10)
O2W—Ca1—O1—Ca1^i	−50.40 (14)	O1—Ca1—C1—C2	87.3 (8)
O3—Ca1—O1—Ca1^i	−82.65 (6)	O3—Ca1—C1—C2	19.5 (8)
O4—Ca1—O1—Ca1^i	−130.09 (6)	O4—Ca1—C1—C2	−32.0 (8)
O2—Ca1—O1—Ca1^i	163.69 (9)	O2—Ca1—C1—C2	−102.1 (9)
C9—Ca1—O1—Ca1^i	−108.08 (7)	C9—Ca1—C1—C2	−6.3 (8)
C1—Ca1—O1—Ca1^i	168.94 (15)	Ca1^ii—Ca1—C1—C2	−109.0 (8)
Ca1^ii—Ca1—O1—Ca1^i	154.70 (5)	Ca1^i—Ca1—C1—C2	94.6 (8)
O2^i—Ca1—O2—C1	23.64 (10)	O1—C1—C2—C3	83.8 (2)
O1^ii—Ca1—O2—C1	169.26 (13)	O2—C1—C2—C3	−92.5 (2)
O1W—Ca1—O2—C1	92.54 (12)	Ca1—C1—C2—C3	3.2 (9)
O2W—Ca1—O2—C1	−145.32 (13)	C1—C2—C3—C4	106.2 (2)
O1—Ca1—O2—C1	5.22 (11)	C1—C2—C3—C8	−74.3 (3)
O3—Ca1—O2—C1	−59.40 (12)	C8—C3—C4—C5	−0.4 (3)
O4—Ca1—O2—C1	−105.74 (12)	C2—C3—C4—C5	179.1 (2)
C9—Ca1—O2—C1	−81.04 (12)	C3—C4—C5—C6	0.5 (4)
Ca1^ii—Ca1—O2—C1	169.45 (15)	C4—C5—C6—C7	−0.3 (4)
Ca1^i—Ca1—O2—C1	14.49 (11)	C5—C6—C7—C8	0.0 (4)
O2^i—Ca1—O2—Ca1^ii	−145.81 (8)	C6—C7—C8—C3	0.0 (3)
O1^ii—Ca1—O2—Ca1^ii	−0.20 (5)	C4—C3—C8—C7	0.2 (3)
O1W—Ca1—O2—Ca1^ii	−76.91 (7)	C2—C3—C8—C7	−179.34 (19)
O2W—Ca1—O2—Ca1^ii	45.23 (13)	Ca1—O4—C9—O3	13.8 (2)
O1—Ca1—O2—Ca1^ii	−164.24 (9)	Ca1—O4—C9—C10	−163.40 (18)
O3—Ca1—O2—Ca1^ii	131.15 (6)	Ca1—O3—C9—O4	−13.9 (2)
O4—Ca1—O2—Ca1^ii	84.81 (6)	Ca1—O3—C9—C10	163.38 (17)
C9—Ca1—O2—Ca1^ii	109.51 (7)	O2^i—Ca1—C9—O4	167.94 (12)
C1—Ca1—O2—Ca1^ii	−169.45 (15)	O1^ii—Ca1—C9—O4	0.24 (14)
Ca1^i—Ca1—O2—Ca1^ii	−154.96 (5)	O1W—Ca1—C9—O4	−102.6 (3)
O2^i—Ca1—O3—C9	−178.59 (14)	O2W—Ca1—C9—O4	82.06 (13)
O1^ii—Ca1—O3—C9	17.82 (16)	O1—Ca1—C9—O4	−120.91 (13)
O1W—Ca1—O3—C9	−154.33 (13)	O3—Ca1—C9—O4	166.5 (2)
O2W—Ca1—O3—C9	91.29 (14)	O2—Ca1—C9—O4	−69.64 (13)
O1—Ca1—O3—C9	−103.04 (13)	C1—Ca1—C9—O4	−95.28 (13)
O4—Ca1—O3—C9	7.45 (12)	Ca1^ii—Ca1—C9—O4	−36.67 (12)
O2—Ca1—O3—C9	−56.89 (13)	Ca1^i—Ca1—C9—O4	−153.98 (12)
C1—Ca1—O3—C9	−78.84 (14)	O2^i—Ca1—C9—O3	1.44 (14)
Ca1^ii—Ca1—O3—C9	−26.90 (14)	O1^ii—Ca1—C9—O3	−166.26 (12)
Ca1^i—Ca1—O3—C9	−138.99 (13)	O1W—Ca1—C9—O3	90.9 (4)
O2^i—Ca1—O4—C9	−15.31 (15)	O2W—Ca1—C9—O3	−84.44 (13)
O1^ii—Ca1—O4—C9	−179.77 (13)	O1—Ca1—C9—O3	72.59 (13)
O1W—Ca1—O4—C9	152.50 (14)	O4—Ca1—C9—O3	−166.5 (2)
O2W—Ca1—O4—C9	−93.50 (13)	O2—Ca1—C9—O3	123.86 (13)
O1—Ca1—O4—C9	59.25 (13)	C1—Ca1—C9—O3	98.22 (14)
O3—Ca1—O4—C9	−7.53 (12)	Ca1^ii—Ca1—C9—O3	156.83 (12)
O2—Ca1—O4—C9	106.25 (13)	Ca1^i—Ca1—C9—O3	39.52 (13)
C1—Ca1—O4—C9	81.49 (13)	O2^i—Ca1—C9—C10	−88.0 (7)
Ca1^ii—Ca1—O4—C9	142.31 (13)	O1^ii—Ca1—C9—C10	104.3 (7)
Ca1^i—Ca1—O4—C9	29.61 (14)	O1W—Ca1—C9—C10	1.4 (10)
Ca1^i—O1—C1—O2	−144.4 (2)	O2W—Ca1—C9—C10	−173.9 (7)
Ca1—O1—C1—O2	9.8 (2)	O1—Ca1—C9—C10	−16.9 (7)
Ca1^i—O1—C1—C2	39.3 (4)	O3—Ca1—C9—C10	−89.5 (7)
Ca1—O1—C1—C2	−166.53 (16)	O4—Ca1—C9—C10	104.1 (8)
Ca1^i—O1—C1—Ca1	−154.1 (3)	O2—Ca1—C9—C10	34.4 (7)
Ca1^ii—O2—C1—O1	141.2 (3)	C1—Ca1—C9—C10	8.8 (7)
Ca1—O2—C1—O1	−9.56 (19)	Ca1^ii—Ca1—C9—C10	67.4 (7)
Ca1^ii—O2—C1—C2	−42.5 (5)	Ca1^i—Ca1—C9—C10	−49.9 (7)
Ca1—O2—C1—C2	166.74 (16)	O4—C9—C10—C11	−21.1 (3)
Ca1^ii—O2—C1—Ca1	150.7 (4)	O3—C9—C10—C11	161.6 (2)
O2^i—Ca1—C1—O1	10.54 (12)	Ca1—C9—C10—C11	−116.9 (7)
O1^ii—Ca1—C1—O1	160.22 (9)	C9—C10—C11—C12	−89.4 (3)
O1W—Ca1—C1—O1	84.86 (12)	C9—C10—C11—C16	90.0 (3)
O2W—Ca1—C1—O1	−102.5 (2)	C16—C11—C12—C13	−2.2 (3)
O3—Ca1—C1—O1	−67.86 (12)	C10—C11—C12—C13	177.1 (2)
O4—Ca1—C1—O1	−119.34 (12)	C11—C12—C13—C14	1.0 (4)
O2—Ca1—C1—O1	170.56 (19)	C12—C13—C14—C15	1.0 (4)
C9—Ca1—C1—O1	−93.64 (12)	C13—C14—C15—C16	−1.6 (4)
Ca1^ii—Ca1—C1—O1	163.63 (13)	C12—C11—C16—C15	1.6 (3)
Ca1^i—Ca1—C1—O1	7.27 (10)	C10—C11—C16—C15	−177.8 (2)
O2^i—Ca1—C1—O2	−160.02 (9)	C14—C15—C16—C11	0.4 (4)

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O3^ii	0.87 (1)	2.00 (1)	2.838 (2)	163 (2)
O1W—H2W···O4^i	0.88 (1)	1.98 (1)	2.830 (2)	164 (2)
O2W—H3W···O3W^iii	0.87 (1)	1.79 (1)	2.659 (2)	174 (3)
O2W—H4W···O3	0.86 (1)	2.64 (2)	3.177 (2)	121 (2)
O3W—H5W···O3^iv	0.88 (1)	1.96 (1)	2.838 (3)	178 (3)
O3W—H6W···O4	0.87 (1)	2.08 (1)	2.939 (3)	167 (3)

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1/2, −y+1/2, −z+1; (iv) x, y+1, z.

(SrPAA) catena-poly[[[diaqua(phenylacetato- κ²O,O')strontium(II)]- µ₃-phenylacetato-1':1:1''κ⁴O:O,O':O'] monohydrate]

Crystal data

[Sr(C8H7O2)2(H2O)2]·H2O	F(000) = 1680
Mr = 411.94	Dx = 1.529 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4111 reflections
a = 29.5111 (15) Å	θ = 2.5–29.0°
b = 6.8560 (5) Å	µ = 3.05 mm^−1
c = 17.7229 (11) Å	T = 123 K
β = 93.453 (3)°	Fragment, colourless
V = 3579.3 (4) Å^3	0.30 × 0.15 × 0.10 mm
Z = 8

Data collection

Oxford Gemini diffractometer	4034 independent reflections
Radiation source: fine-focus sealed tube	3175 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −37→36
Tmin = 0.564, Tmax = 0.767	k = −8→8
20190 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0366P)^2] where P = (Fo^2 + 2Fc^2)/3
4034 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.57 e Å^−3
9 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Sr1	0.247337 (6)	0.05325 (3)	0.186735 (11)	0.01670 (7)
O1	0.32379 (5)	−0.1130 (2)	0.14975 (9)	0.0297 (4)
O2	0.32591 (5)	0.2074 (2)	0.15518 (9)	0.0277 (4)
O1W	0.17258 (5)	0.0481 (2)	0.25205 (9)	0.0246 (3)
H1W	0.1678 (9)	−0.048 (2)	0.2820 (11)	0.037*
H2W	0.1712 (8)	0.148 (2)	0.2807 (11)	0.037*
O3	0.27964 (5)	0.2129 (2)	0.31907 (8)	0.0242 (3)
O2W	0.23636 (7)	0.0698 (3)	0.04151 (10)	0.0465 (5)
H3W	0.2178 (8)	0.023 (4)	0.0071 (14)	0.070*
H4W	0.2615 (6)	0.013 (4)	0.0401 (19)	0.070*
O4	0.28020 (5)	−0.1067 (2)	0.31504 (8)	0.0223 (3)
O3W	0.32987 (7)	0.5609 (3)	0.05315 (10)	0.0446 (5)
H5W	0.3278 (10)	0.664 (2)	0.0804 (13)	0.067*
H6W	0.3323 (11)	0.468 (3)	0.0855 (12)	0.067*
C1	0.34546 (7)	0.0462 (3)	0.15234 (12)	0.0204 (4)
C2	0.39673 (8)	0.0364 (4)	0.15408 (14)	0.0306 (5)
H2A	0.4084	0.0036	0.2061	0.037*
H2B	0.4056	−0.0707	0.1205	0.037*
C3	0.41915 (6)	0.2212 (3)	0.13017 (12)	0.0224 (5)
C4	0.43087 (8)	0.3682 (4)	0.18172 (13)	0.0296 (5)
H4	0.4258	0.3502	0.2337	0.035*
C5	0.44990 (8)	0.5406 (4)	0.15812 (14)	0.0321 (6)
H5	0.4580	0.6394	0.1940	0.039*
C6	0.45718 (7)	0.5700 (3)	0.08325 (13)	0.0288 (5)
H6	0.4696	0.6896	0.0670	0.035*
C7	0.44626 (7)	0.4245 (3)	0.03191 (13)	0.0273 (5)
H7	0.4515	0.4434	−0.0199	0.033*
C8	0.42770 (7)	0.2505 (4)	0.05516 (12)	0.0263 (5)
H8	0.4208	0.1505	0.0192	0.032*
C9	0.29210 (7)	0.0515 (3)	0.34608 (11)	0.0162 (4)
C10	0.32477 (7)	0.0459 (3)	0.41529 (12)	0.0226 (5)
H10A	0.3217	0.1673	0.4448	0.027*
H10B	0.3171	−0.0654	0.4477	0.027*
C11	0.37316 (7)	0.0256 (3)	0.39319 (11)	0.0211 (5)
C12	0.38891 (7)	−0.1507 (4)	0.36606 (11)	0.0252 (5)
H12	0.3688	−0.2588	0.3605	0.030*
C13	0.43334 (8)	−0.1705 (4)	0.34709 (12)	0.0309 (6)
H13	0.4437	−0.2918	0.3288	0.037*
C14	0.46272 (9)	−0.0144 (4)	0.35471 (15)	0.0373 (6)
H14	0.4934	−0.0283	0.3420	0.045*
C15	0.44756 (8)	0.1619 (4)	0.38083 (14)	0.0400 (6)
H15	0.4677	0.2698	0.3857	0.048*
C16	0.40290 (8)	0.1820 (4)	0.39999 (13)	0.0324 (6)
H16	0.3926	0.3039	0.4179	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sr1	0.01780 (10)	0.00786 (9)	0.02426 (12)	−0.00023 (8)	−0.00010 (7)	0.00034 (9)
O1	0.0283 (9)	0.0126 (8)	0.0496 (10)	0.0005 (6)	0.0133 (8)	0.0013 (7)
O2	0.0218 (8)	0.0153 (8)	0.0465 (10)	0.0002 (6)	0.0053 (7)	−0.0043 (7)
O1W	0.0287 (8)	0.0134 (8)	0.0325 (9)	−0.0003 (7)	0.0077 (7)	0.0008 (7)
O3	0.0286 (8)	0.0110 (8)	0.0322 (8)	0.0016 (6)	−0.0058 (7)	−0.0003 (6)
O2W	0.0548 (12)	0.0583 (15)	0.0263 (9)	−0.0231 (11)	0.0013 (9)	−0.0042 (9)
O4	0.0268 (8)	0.0113 (8)	0.0281 (8)	−0.0007 (6)	−0.0037 (7)	−0.0010 (6)
O3W	0.0667 (13)	0.0316 (11)	0.0337 (10)	0.0113 (10)	−0.0113 (10)	−0.0031 (8)
C1	0.0229 (11)	0.0187 (11)	0.0200 (11)	0.0017 (9)	0.0053 (9)	0.0029 (10)
C2	0.0245 (12)	0.0265 (13)	0.0411 (14)	0.0056 (10)	0.0056 (11)	0.0067 (11)
C3	0.0131 (10)	0.0232 (12)	0.0310 (13)	0.0047 (9)	0.0029 (9)	0.0036 (10)
C4	0.0275 (12)	0.0374 (14)	0.0245 (12)	0.0042 (11)	0.0072 (10)	0.0025 (11)
C5	0.0318 (13)	0.0290 (13)	0.0352 (14)	−0.0007 (11)	0.0002 (11)	−0.0090 (12)
C6	0.0239 (12)	0.0237 (13)	0.0393 (14)	−0.0008 (10)	0.0051 (10)	0.0026 (11)
C7	0.0247 (12)	0.0322 (14)	0.0254 (12)	0.0000 (10)	0.0062 (10)	0.0016 (10)
C8	0.0251 (12)	0.0260 (12)	0.0279 (13)	−0.0027 (10)	0.0014 (10)	−0.0017 (10)
C9	0.0172 (10)	0.0117 (10)	0.0204 (10)	0.0012 (9)	0.0058 (8)	0.0002 (9)
C10	0.0257 (11)	0.0210 (11)	0.0210 (11)	−0.0001 (10)	0.0003 (9)	−0.0023 (10)
C11	0.0236 (11)	0.0214 (12)	0.0175 (11)	0.0002 (9)	−0.0058 (9)	0.0025 (9)
C12	0.0271 (12)	0.0245 (12)	0.0229 (11)	−0.0001 (10)	−0.0068 (9)	−0.0022 (10)
C13	0.0318 (13)	0.0342 (14)	0.0260 (12)	0.0078 (11)	−0.0043 (10)	−0.0058 (11)
C14	0.0242 (13)	0.0506 (18)	0.0366 (14)	0.0015 (12)	−0.0019 (11)	0.0055 (13)
C15	0.0267 (13)	0.0381 (16)	0.0542 (16)	−0.0103 (12)	−0.0069 (12)	0.0043 (14)
C16	0.0329 (13)	0.0216 (12)	0.0415 (14)	−0.0011 (10)	−0.0073 (11)	−0.0020 (11)

Geometric parameters (Å, º)

Sr1—O3^i	2.4655 (14)	C3—C8	1.383 (3)
Sr1—O4^ii	2.4688 (14)	C3—C4	1.390 (3)
Sr1—O1W	2.5528 (15)	C4—C5	1.384 (3)
Sr1—O2W	2.5772 (18)	C4—H4	0.9500
Sr1—O2	2.6386 (14)	C5—C6	1.372 (3)
Sr1—O1	2.6453 (15)	C5—H5	0.9500
Sr1—O4	2.6548 (14)	C6—C7	1.375 (3)
Sr1—O3	2.7089 (14)	C6—H6	0.9500
Sr1—C1	2.995 (2)	C7—C8	1.385 (3)
Sr1—C9	3.045 (2)	C7—H7	0.9500
O1—C1	1.265 (3)	C8—H8	0.9500
O2—C1	1.249 (2)	C9—C10	1.514 (3)
O1W—H1W	0.865 (9)	C10—C11	1.510 (3)
O1W—H2W	0.853 (9)	C10—H10A	0.9900
O3—C9	1.252 (2)	C10—H10B	0.9900
O3—Sr1^ii	2.4655 (14)	C11—C16	1.386 (3)
O2W—H3W	0.859 (10)	C11—C12	1.391 (3)
O2W—H4W	0.841 (10)	C12—C13	1.380 (3)
O4—C9	1.256 (2)	C12—H12	0.9500
O4—Sr1^i	2.4688 (14)	C13—C14	1.379 (4)
O3W—H5W	0.862 (10)	C13—H13	0.9500
O3W—H6W	0.857 (10)	C14—C15	1.379 (4)
C1—C2	1.513 (3)	C14—H14	0.9500
C2—C3	1.502 (3)	C15—C16	1.388 (3)
C2—H2A	0.9900	C15—H15	0.9500
C2—H2B	0.9900	C16—H16	0.9500
O3^i—Sr1—O4^ii	142.00 (5)	O1—Sr1—H4W	61.8 (3)
O3^i—Sr1—O1W	73.74 (5)	O4—Sr1—H4W	136.0 (4)
O4^ii—Sr1—O1W	74.10 (5)	O3—Sr1—H4W	144.8 (6)
O3^i—Sr1—O2W	88.80 (6)	C1—Sr1—H4W	65.8 (4)
O4^ii—Sr1—O2W	85.66 (6)	C9—Sr1—H4W	144.8 (3)
O1W—Sr1—O2W	113.17 (6)	Sr1^ii—Sr1—H4W	128.1 (7)
O3^i—Sr1—O2	130.98 (5)	Sr1^i—Sr1—H4W	116.3 (6)
O4^ii—Sr1—O2	84.95 (5)	H2W—Sr1—H4W	137.9 (5)
O1W—Sr1—O2	153.67 (5)	C1—O1—Sr1	93.22 (13)
O2W—Sr1—O2	80.21 (5)	C1—O2—Sr1	93.92 (12)
O3^i—Sr1—O1	81.94 (5)	Sr1—O1W—H1W	117.8 (16)
O4^ii—Sr1—O1	133.54 (5)	Sr1—O1W—H2W	109.3 (15)
O1W—Sr1—O1	151.60 (5)	H1W—O1W—H2W	103.4 (17)
O2W—Sr1—O1	80.17 (6)	C9—O3—Sr1^ii	159.89 (14)
O2—Sr1—O1	49.19 (5)	C9—O3—Sr1	93.08 (12)
O3^i—Sr1—O4	75.24 (4)	Sr1^ii—O3—Sr1	104.50 (5)
O4^ii—Sr1—O4	120.26 (4)	Sr1—O2W—H3W	137 (2)
O1W—Sr1—O4	83.51 (5)	Sr1—O2W—H4W	87 (2)
O2W—Sr1—O4	153.00 (6)	H3W—O2W—H4W	109 (2)
O2—Sr1—O4	93.81 (5)	C9—O4—Sr1^i	154.67 (14)
O1—Sr1—O4	76.19 (5)	C9—O4—Sr1	95.55 (12)
O3^i—Sr1—O3	120.96 (4)	Sr1^i—O4—Sr1	106.03 (5)
O4^ii—Sr1—O3	74.20 (4)	H5W—O3W—H6W	104.1 (19)
O1W—Sr1—O3	83.21 (5)	O2—C1—O1	122.08 (19)
O2W—Sr1—O3	149.70 (5)	O2—C1—C2	120.2 (2)
O2—Sr1—O3	75.75 (5)	O1—C1—C2	117.73 (19)
O1—Sr1—O3	97.34 (5)	O2—C1—Sr1	61.50 (11)
O4—Sr1—O3	48.24 (4)	O1—C1—Sr1	61.85 (11)
O3^i—Sr1—C1	106.85 (6)	C2—C1—Sr1	167.01 (15)
O4^ii—Sr1—C1	109.52 (5)	C3—C2—C1	114.43 (19)
O1W—Sr1—C1	164.71 (5)	C3—C2—H2A	108.7
O2W—Sr1—C1	82.09 (6)	C1—C2—H2A	108.7
O2—Sr1—C1	24.58 (5)	C3—C2—H2B	108.7
O1—Sr1—C1	24.93 (5)	C1—C2—H2B	108.7
O4—Sr1—C1	81.94 (5)	H2A—C2—H2B	107.6
O3—Sr1—C1	83.61 (5)	C8—C3—C4	118.3 (2)
O3^i—Sr1—C9	98.97 (5)	C8—C3—C2	120.2 (2)
O4^ii—Sr1—C9	98.03 (5)	C4—C3—C2	121.5 (2)
O1W—Sr1—C9	85.29 (5)	C5—C4—C3	120.7 (2)
O2W—Sr1—C9	161.41 (6)	C5—C4—H4	119.7
O2—Sr1—C9	81.98 (5)	C3—C4—H4	119.7
O1—Sr1—C9	84.22 (5)	C6—C5—C4	120.5 (2)
O4—Sr1—C9	24.25 (5)	C6—C5—H5	119.7
O3—Sr1—C9	24.25 (5)	C4—C5—H5	119.7
C1—Sr1—C9	79.51 (5)	C5—C6—C7	119.3 (2)
O3^i—Sr1—Sr1^ii	144.77 (3)	C5—C6—H6	120.3
O4^ii—Sr1—Sr1^ii	38.55 (3)	C7—C6—H6	120.3
O1W—Sr1—Sr1^ii	76.64 (4)	C6—C7—C8	120.6 (2)
O2W—Sr1—Sr1^ii	120.57 (5)	C6—C7—H7	119.7
O2—Sr1—Sr1^ii	77.03 (3)	C8—C7—H7	119.7
O1—Sr1—Sr1^ii	119.43 (4)	C3—C8—C7	120.6 (2)
O4—Sr1—Sr1^ii	82.91 (3)	C3—C8—H8	119.7
O3—Sr1—Sr1^ii	35.66 (3)	C7—C8—H8	119.7
C1—Sr1—Sr1^ii	96.85 (4)	O3—C9—O4	121.84 (18)
C9—Sr1—Sr1^ii	59.68 (4)	O3—C9—C10	119.34 (19)
O3^i—Sr1—Sr1^i	39.83 (3)	O4—C9—C10	118.71 (18)
O4^ii—Sr1—Sr1^i	143.08 (3)	O3—C9—Sr1	62.67 (10)
O1W—Sr1—Sr1^i	75.27 (4)	O4—C9—Sr1	60.21 (10)
O2W—Sr1—Sr1^i	125.60 (5)	C10—C9—Sr1	166.14 (14)
O2—Sr1—Sr1^i	116.50 (3)	C11—C10—C9	110.99 (17)
O1—Sr1—Sr1^i	76.69 (3)	C11—C10—H10A	109.4
O4—Sr1—Sr1^i	35.42 (3)	C9—C10—H10A	109.4
O3—Sr1—Sr1^i	82.20 (3)	C11—C10—H10B	109.4
C1—Sr1—Sr1^i	95.29 (4)	C9—C10—H10B	109.4
C9—Sr1—Sr1^i	59.24 (4)	H10A—C10—H10B	108.0
Sr1^ii—Sr1—Sr1^i	113.710 (10)	C16—C11—C12	118.6 (2)
O3^i—Sr1—H2W	88.6 (3)	C16—C11—C10	120.7 (2)
O4^ii—Sr1—H2W	62.5 (3)	C12—C11—C10	120.7 (2)
O1W—Sr1—H2W	15.9 (3)	C13—C12—C11	120.8 (2)
O2W—Sr1—H2W	120.0 (4)	C13—C12—H12	119.6
O2—Sr1—H2W	137.8 (3)	C11—C12—H12	119.6
O1—Sr1—H2W	157.7 (4)	C14—C13—C12	120.1 (2)
O4—Sr1—H2W	81.8 (4)	C14—C13—H13	120.0
O3—Sr1—H2W	70.3 (4)	C12—C13—H13	120.0
C1—Sr1—H2W	153.8 (4)	C15—C14—C13	119.9 (2)
C9—Sr1—H2W	77.3 (4)	C15—C14—H14	120.0
Sr1^ii—Sr1—H2W	60.8 (3)	C13—C14—H14	120.0
Sr1^i—Sr1—H2W	83.1 (4)	C14—C15—C16	120.1 (2)
O3^i—Sr1—H4W	86.0 (7)	C14—C15—H15	119.9
O4^ii—Sr1—H4W	99.0 (6)	C16—C15—H15	119.9
O1W—Sr1—H4W	129.0 (4)	C11—C16—C15	120.5 (2)
O2W—Sr1—H4W	18.3 (3)	C11—C16—H16	119.8
O2—Sr1—H4W	69.2 (6)	C15—C16—H16	119.8
O3^i—Sr1—O1—C1	−177.45 (13)	C9—Sr1—C1—O1	98.93 (13)
O4^ii—Sr1—O1—C1	18.08 (15)	Sr1^ii—Sr1—C1—O1	156.28 (12)
O1W—Sr1—O1—C1	−146.36 (13)	Sr1^i—Sr1—C1—O1	41.58 (12)
O2W—Sr1—O1—C1	92.37 (13)	O3^i—Sr1—C1—C2	−89.0 (7)
O2—Sr1—O1—C1	6.87 (12)	O4^ii—Sr1—C1—C2	102.2 (7)
O4—Sr1—O1—C1	−100.75 (13)	O1W—Sr1—C1—C2	0.9 (8)
O3—Sr1—O1—C1	−57.08 (13)	O2W—Sr1—C1—C2	−175.3 (7)
C9—Sr1—O1—C1	−77.51 (13)	O2—Sr1—C1—C2	100.9 (7)
Sr1^ii—Sr1—O1—C1	−27.29 (13)	O1—Sr1—C1—C2	−91.6 (7)
Sr1^i—Sr1—O1—C1	−137.22 (13)	O4—Sr1—C1—C2	−17.2 (7)
O3^i—Sr1—O2—C1	−12.63 (15)	O3—Sr1—C1—C2	31.5 (7)
O4^ii—Sr1—O2—C1	−178.83 (13)	C9—Sr1—C1—C2	7.3 (7)
O1W—Sr1—O2—C1	144.16 (13)	Sr1^ii—Sr1—C1—C2	64.6 (7)
O2W—Sr1—O2—C1	−92.38 (13)	Sr1^i—Sr1—C1—C2	−50.1 (7)
O1—Sr1—O2—C1	−6.96 (12)	O2—C1—C2—C3	−21.9 (3)
O4—Sr1—O2—C1	61.09 (13)	O1—C1—C2—C3	159.7 (2)
O3—Sr1—O2—C1	106.21 (13)	Sr1—C1—C2—C3	−115.6 (6)
C9—Sr1—O2—C1	82.31 (13)	C1—C2—C3—C8	−90.4 (3)
Sr1^ii—Sr1—O2—C1	142.92 (13)	C1—C2—C3—C4	88.1 (3)
Sr1^i—Sr1—O2—C1	32.66 (13)	C8—C3—C4—C5	1.1 (3)
O3^i—Sr1—O3—C9	27.22 (10)	C2—C3—C4—C5	−177.5 (2)
O4^ii—Sr1—O3—C9	168.97 (13)	C3—C4—C5—C6	0.5 (4)
O1W—Sr1—O3—C9	93.62 (12)	C4—C5—C6—C7	−1.4 (3)
O2W—Sr1—O3—C9	−140.82 (14)	C5—C6—C7—C8	0.6 (3)
O2—Sr1—O3—C9	−102.32 (12)	C4—C3—C8—C7	−1.8 (3)
O1—Sr1—O3—C9	−57.76 (12)	C2—C3—C8—C7	176.74 (19)
O4—Sr1—O3—C9	6.27 (11)	C6—C7—C8—C3	1.0 (3)
C1—Sr1—O3—C9	−78.62 (12)	Sr1^ii—O3—C9—O4	139.5 (3)
Sr1^ii—Sr1—O3—C9	170.15 (14)	Sr1—O3—C9—O4	−11.7 (2)
Sr1^i—Sr1—O3—C9	17.64 (11)	Sr1^ii—O3—C9—C10	−44.4 (5)
O3^i—Sr1—O3—Sr1^ii	−142.93 (7)	Sr1—O3—C9—C10	164.41 (16)
O4^ii—Sr1—O3—Sr1^ii	−1.18 (5)	Sr1^ii—O3—C9—Sr1	151.2 (4)
O1W—Sr1—O3—Sr1^ii	−76.53 (5)	Sr1^i—O4—C9—O3	−136.6 (2)
O2W—Sr1—O3—Sr1^ii	49.03 (13)	Sr1—O4—C9—O3	12.0 (2)
O2—Sr1—O3—Sr1^ii	87.53 (5)	Sr1^i—O4—C9—C10	47.3 (4)
O1—Sr1—O3—Sr1^ii	132.09 (5)	Sr1—O4—C9—C10	−164.15 (16)
O4—Sr1—O3—Sr1^ii	−163.88 (8)	Sr1^i—O4—C9—Sr1	−148.6 (3)
C1—Sr1—O3—Sr1^ii	111.23 (6)	O3^i—Sr1—C9—O3	−156.60 (9)
C9—Sr1—O3—Sr1^ii	−170.15 (14)	O4^ii—Sr1—C9—O3	−10.71 (12)
Sr1^i—Sr1—O3—Sr1^ii	−152.51 (5)	O1W—Sr1—C9—O3	−83.90 (12)
O3^i—Sr1—O4—C9	−167.79 (12)	O2W—Sr1—C9—O3	89.6 (2)
O4^ii—Sr1—O4—C9	−25.62 (10)	O2—Sr1—C9—O3	72.99 (12)
O1W—Sr1—O4—C9	−92.95 (12)	O1—Sr1—C9—O3	122.52 (12)
O2W—Sr1—O4—C9	136.59 (14)	O4—Sr1—C9—O3	−168.6 (2)
O2—Sr1—O4—C9	60.75 (12)	C1—Sr1—C9—O3	97.78 (12)
O1—Sr1—O4—C9	107.05 (12)	Sr1^ii—Sr1—C9—O3	−6.63 (10)
O3—Sr1—O4—C9	−6.27 (11)	Sr1^i—Sr1—C9—O3	−159.55 (13)
C1—Sr1—O4—C9	82.33 (12)	O3^i—Sr1—C9—O4	11.95 (12)
Sr1^ii—Sr1—O4—C9	−15.66 (11)	O4^ii—Sr1—C9—O4	157.84 (9)
Sr1^i—Sr1—O4—C9	−166.58 (14)	O1W—Sr1—C9—O4	84.65 (12)
O3^i—Sr1—O4—Sr1^i	−1.21 (5)	O2W—Sr1—C9—O4	−101.8 (2)
O4^ii—Sr1—O4—Sr1^i	140.96 (7)	O2—Sr1—C9—O4	−118.46 (12)
O1W—Sr1—O4—Sr1^i	73.64 (6)	O1—Sr1—C9—O4	−68.93 (11)
O2W—Sr1—O4—Sr1^i	−56.83 (13)	O3—Sr1—C9—O4	168.6 (2)
O2—Sr1—O4—Sr1^i	−132.67 (5)	C1—Sr1—C9—O4	−93.67 (12)
O1—Sr1—O4—Sr1^i	−86.36 (6)	Sr1^ii—Sr1—C9—O4	161.92 (13)
O3—Sr1—O4—Sr1^i	160.31 (8)	Sr1^i—Sr1—C9—O4	9.00 (10)
C1—Sr1—O4—Sr1^i	−111.09 (6)	O3^i—Sr1—C9—C10	101.4 (6)
C9—Sr1—O4—Sr1^i	166.58 (14)	O4^ii—Sr1—C9—C10	−112.7 (6)
Sr1^ii—Sr1—O4—Sr1^i	150.92 (5)	O1W—Sr1—C9—C10	174.1 (6)
Sr1—O2—C1—O1	13.1 (2)	O2W—Sr1—C9—C10	−12.4 (7)
Sr1—O2—C1—C2	−165.21 (18)	O2—Sr1—C9—C10	−29.0 (6)
Sr1—O1—C1—O2	−13.0 (2)	O1—Sr1—C9—C10	20.5 (6)
Sr1—O1—C1—C2	165.30 (17)	O4—Sr1—C9—C10	89.4 (6)
O3^i—Sr1—C1—O2	170.07 (12)	O3—Sr1—C9—C10	−102.0 (6)
O4^ii—Sr1—C1—O2	1.24 (14)	C1—Sr1—C9—C10	−4.2 (6)
O1W—Sr1—C1—O2	−100.0 (2)	Sr1^ii—Sr1—C9—C10	−108.6 (6)
O2W—Sr1—C1—O2	83.74 (13)	Sr1^i—Sr1—C9—C10	98.5 (6)
O1—Sr1—C1—O2	167.4 (2)	O3—C9—C10—C11	−94.8 (2)
O4—Sr1—C1—O2	−118.09 (13)	O4—C9—C10—C11	81.5 (2)
O3—Sr1—C1—O2	−69.47 (12)	Sr1—C9—C10—C11	−0.2 (7)
C9—Sr1—C1—O2	−93.64 (13)	C9—C10—C11—C16	107.2 (2)
Sr1^ii—Sr1—C1—O2	−36.29 (12)	C9—C10—C11—C12	−73.3 (2)
Sr1^i—Sr1—C1—O2	−150.99 (12)	C16—C11—C12—C13	0.7 (3)
O3^i—Sr1—C1—O1	2.64 (13)	C10—C11—C12—C13	−178.85 (19)
O4^ii—Sr1—C1—O1	−166.19 (12)	C11—C12—C13—C14	−0.2 (3)
O1W—Sr1—C1—O1	92.6 (2)	C12—C13—C14—C15	−0.4 (4)
O2W—Sr1—C1—O1	−83.68 (13)	C13—C14—C15—C16	0.5 (4)
O2—Sr1—C1—O1	−167.4 (2)	C12—C11—C16—C15	−0.7 (3)
O4—Sr1—C1—O1	74.48 (12)	C10—C11—C16—C15	178.9 (2)
O3—Sr1—C1—O1	123.10 (13)	C14—C15—C16—C11	0.1 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2^i	0.87 (1)	2.01 (1)	2.855 (2)	164 (2)
O1W—H2W···O1^ii	0.85 (1)	2.05 (1)	2.901 (2)	173 (2)
O2W—H3W···O3W^iii	0.86 (1)	1.81 (1)	2.654 (3)	169 (3)
O3W—H5W···O1^iv	0.86 (1)	1.97 (1)	2.828 (3)	175 (3)
O3W—H6W···O2	0.86 (1)	2.19 (1)	3.031 (3)	168 (3)

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