catena-Poly­[[[{N-(6-amino-3,4-di­hydro-3-methyl-5-nitro­so-4-oxopyrimidin-2-yl)­glycinato-O}pentaaquastrontium]-μ-N-(6-amino-3,4-di­hydro-3-methyl-5-nitro­so-4-oxopyrimidin-2-yl)­glycinato-O:O′] mono­hydrate]: coordination polymer chains linked by hydrogen bonds into a three-dimensional framework

In the title compound, [Sr(C₇H₈N₅O₄)₂(H₂O)₅]·H₂O, one of the anionic (C₇H₈N₅O₄)⁻ ligands acts as a simple monodentate ligand coordinated via a carboxyl O atom, while the other acts as a bridging ligand between pairs of Sr atoms, utilizing one carboxyl O and the nitroso O atom, so generating a one-dimensional coordination polymer. Five water mol­ecules are coordinated to Sr, resulting in eight-coordination in the form of a distorted square antiprism, while the sixth water mol­ecule is hydrogen bonded to a coordinated water. The coordination polymer chains are reinforced by O—H...N and O—H...O hydrogen bonds and are linked into a three-dimensional framework by an extensive series of N—H...O and O—H...O hydrogen bonds.

S1. Comment

We have recently described and discussed the structures of a number of hydrated metal salts of the anions N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)glycinate, (L¹)^- and N-(6-amino-3,4-dihydro-3-methyl- 5-nitroso-4-oxopyrimidin-2-yl)glycylglycinate, (L²)^- (Arranz Mascarós et al., 1999, 2000; Low, Arranz et al., 2001a,b; Low, Moreno Sánchez et al., 2001). The simpler ligand (L¹)^- can form simple hydrated salts [M(H₂O)₆](L¹)₂, with no coordination of (L¹)^- to the metal cation, as when M²⁺ = Mg²⁺ or Zn²⁺ (Arranz Mascarós et al., 1999, 2000); finite molecular aggregates [Li(L¹)(H₂O)₃] and [Mn(L¹)₂(H₂O)₄]·6H₂O are formed with Li⁺ and Mn²⁺, where the molecular aggregates are linked into three-dimensional frameworks by extensive hydrogen bonding (Low, Moreno Sánchez et al., 2001); and with Na⁺ and K⁺, organic-inorganic hybrid sheets are formed, consisting of cations and anions only, which are then linked into three-dimensional frameworks by hydrogen bonds (Low, Moreno Sánchez et al., 2001). The hydrated K⁺ salt of (L²)^- takes the form of a three-dimensional coordination polymer, in whose construction the water molecules play no direct role (Low, Arranz et al., 2001b), while in [Ca(L²)₂(H₂O)₃], there are one-dimensional coordination polymer chains built from cations and anions only, linked by hydrogen bonds into a continuous framework (Low, Arranz et al., 2001a). Continuing with our structural study of the metal salts formed by (L¹)^-, we have now studied the hydrated Sr²⁺ salt.

Although the composition of the Sr²⁺ derivative (I) is identical to that of the Mg²⁺ analogue, M(L¹)₂·6H₂O, the constitution is entirely different. In particular, both anions in (I) are directly coordinated in monodentate fashion to the Sr via a carboxylate O, [Sr(L¹)₂(H₂O)₅]·H₂O, whereas in the Mg salt there is no coordination of the anions to the cation, thus [Mg(H₂O)₆](L¹)₂; one of the anions in (I) is also coordinated, via nitroso O25, to another Sr at the symmetry position (1 - x, 0.5 + y, 0.5 - z); the Sr coordination number is eight, as opposed to six in the Mg salt, but only five of the water molecules are directly bonded to Sr, while the sixth is hydrogen bonded to one of the coordinated water molecules (Fig. 1).

The range of Sr—O distances, 2.501 (2) - 2.751 (2) Å, has an overall mean value of 2.618 (2) Å. However, within this range it is possible to distinguish three types of Sr—O interaction: the bonds to carboxylate O have mean value 2.555 (2) Å, those to water O have mean value 2.616 (2) Å, while the unique bond to nitrosyl O has length 2.751 (2) Å. This ordering of the different types is consistent with the variations observed in the hydrated Na⁺ and K⁺ salts of (L¹)^- (Low, Moreno Sánchez et al., 2001). In [Ca(L²)₂(H₂O)₃], the mean Ca—O distance is 2.420 (4) Å, if all seven ligating O are included, or 2.377 (4) Å if the outlier value for one weakly bound O is omitted. The difference between the mean Sr—O distance in (I) and the mean Ca—O distances in [Ca(L²)₂(H₂O)₃] are ca 0.20 Å if Ca is regarded as seven-coordinate and ca 0.24 Å if Ca is regarded as six coordinate: these differences precisely reflect the differences between the corresponding ionic radii as tabulated by Shannon & Prewitt (1970): Ca²⁺ (seven coordinate) 1.07 Å, Ca²⁺ (six coordinate) 1.00 Å, and Sr²⁺ (eight coordinate) 1.25 Å. The geometry of the SrO₈ polyhedron takes the form of a distorted square antiprism, typical of this coordination number.

The effect of the bridging action of one of the anions in (I) is the generation of a coordination polymer chain running parallel to the [010] direction, and generated by the 2₁ screw axis along (1/2, y, 1/4) (Fig. 2): a second, antiparallel chain is generated by the 2₁ axis along (1/2, -y, 3/4). It is striking that the formation of the coordination polymer involves only one of the two independent anionic ligands: in the one dimensional coordination polymer formed by Ca²⁺ and the related anion (L²)^- (Low, Arranz et al., 2001a), the polymer chains lie across twofold rotation axes so that both anionic ligands participate in the chain formation. The formation of the one-dimensional chain polymers [Sr(L¹)₂]_n and [Ca(L²)₂]_n may be contrasted with the formation of organic-inorganic hybrid sheets in the hydrated Na and K salts of (L¹)^-, in which the nitroso groups act as η¹ and η² ligands to Na and K respectively (Low, Moreno Sánchez et al., 2001).

As in [Ca(L²)₂]_n, the coordination polymer chains in [Sr(L¹)₂]_n are linked into a single three-dimensional framework by an extensive series of hydrogen bonds. In addition to the intramolecular N—H···O hydrogen bonds as normally found in the anion (Low, Moreno Sánchez et al., 2001). and the O5—H51C···O6 hydrogen bond to the sixth water molecule within the asymmetric unit, there are a total of sixteen independent hydrogen bonds linking the neutral molecular aggregates; some of these reinforce the polymer chains and some link adjacent chains. There are two strictly planar three-centre O—H····O/N systems in which a water O—H moiety acts as the hydrogen bond donor and the ortho-substituent atoms On4 and Nn5 (n = 1 or 2) act as the pair of acceptors (Table 2). In addition there are twelve two-centre hydrogen bonds linking the molecular units, nine of O—H···O type and three of N—H···O type.

Water O1 acts as hydrogen-bond donor, via H11C, to O222^iv [symmetry operators are as defined in Table 2], and water O3 acts as donor, via H31C and H31D to O221^iv and O4^iv respectively: these three translational hydrogen bonds all reinforce the coordination polymer chain along [010]. Similarly water O2 acts as donor, via H21C, to both O24^v and N25^v in a three-centre hydrogen bond, which again reinforces the [010] chain by following the 2₁ axis along (1/2, y, 1/4).

To analyse the linking of the coordination polymer chains it is not, in fact, necessary to consider all of the inter-aggregate hydrogen bonds. Just three of the remaining hydrogen bonds, two of N—H···O type and one of the O—H···O hydrogen bonds suffice to demonstrate the three-dimensional framework structure. Amino N16 in the type 1 anion (linked to Sr via O121) acts as hydrogen bond donor, via H16A, to amido O14ⁱ, so producing a C(6) zigzag chain running parallel to [001] and generated by the glide plane at y = 0.25: in an entirely similar manner, N26 in the type 2 anion (linked to Sr via O221)acts as hydrogen-bond donor, via H26A, to O24ⁱⁱⁱ, so producing a second C(6) chain parallel to [001], this time generated by the glide plane at y = -0.25. The combination and propagation, of these two simple chain motifs generates a deeply puckered sheet parallel to (100) in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of R⁴₄(48) ring (Fig. 3). Two sheets of this type run through each unit cell and they are linked by the coordination polymer chain into bilayers comprising cations and anions. There are, of course, water molecules present which add considerable complexity to the overall hydrogen bonding: nonetheless it is possible to identify both one- and two-dimensional sub-structures (Figs. 2 and 3) built from the ionic components only.

The linking of the (100) bilayers into a continuous framework is most simply envisaged in terms of the formation of a [100] chain motif involving the ionic components together with just one of the water molecules, that containing O4. The cation-anion aggregates at (x, y, z) and (1 - x, -y, 1 - z) are linked by that at (x, 0.5 - y, 0.5 + z): N16 at (x, y, z) acts as hydrogen-bond donor to O14 at (x, 0.5 - y, 0.5 + z) (cf. Fig. 3), while O25 at (1 - x, -y, 1 - z) is coordinated to the Sr at (x, 0.5 - y, 0.5 + z) (cf. Fig. 3). At the same time the aggregates at (1 - x, -y, 1 - z) and (1 + x, y, z) are linked by the O4 water molecule (Table 2): O4 at (1 + x, y, z), which is coordinated to the Sr at (1 + x, y, z) acts as hydrogen-bond donor, via H41C, to O15 at (1 - x, -y, 1 - z), and O4 at (1 - x, -y, 1 - z) similarly acts as donor to O15 at (1 + x, y, z), so generating a centrosymmetric R²₂(26) ring. In this way the ionic aggregates at (x, y, z) and (1 + x, y, z) are linked via a C²₂(28)[R²₂(26)] chain of rings, and hence all of the (100) bilayers are linked into a continuous framework.

Not only do the two anionic ligands in (I) exhibit different modes of coordination to the Sr, but they adopt significantly different conformations (Table 1). In the type 1 anion, the torsional angles along the sequence of bonds from Sr1 to N11 can be classified as ac, ap, ap, sp (where ap denotes antiperiplanar and so on), while the corresponding sequence of torsional angles in the type 2 anions is sp, ap, ac, sp (cf. Fig. 1).

Within the anionic ligands, the pattern of bond distances reproduces the pattern observed earlier, both in salts of (L¹)^- (Low, Moreno Sánchez et al., 2001) and in the neutral HL¹ (Low et al., 2000), and point to the delocalized form (B) as more important than the classically localized form (A). We note in particular that the values of Δ [Δ ={d(C—N)-d(N—O)}] for the nitroso groups in the two independent anions are 0.060 (4) Å and 0.053 (4) Å, comfortably within the range previously observed in other metal salts of (L¹)^-, consistent with (B). In this connection it is of interest to note that the O4—H41C···O15ⁱ [i = (-x, -y, 1 - z)] hydrogen bond having the uncoordinated nitroso O as acceptor has very short H···O and O···O distances (Table 2), characteristic of O—H···O hydrogen bonds having anionic rather than neutral O as acceptor and thus entirely consistent with the dominance of the polarized form (B). In the other anion, nitroso O25 does not act as an acceptor of intermolecular hydrogen bonds as it is coordinated to the Sr.

S2. Experimental

Equimolar quantities of strontium chloride hexahydrate and of (NH₄)(L¹) were separately dissolved in water. When the solutions were mixed a pink crystalline precipitate of (I) was produced. Analysis, found C 26.0, H 4.3, N 21.6%; C₁₄H₂₈N₁₀O₁₄Sr requires C 25.9, H 4.4, N 21.6%. Crystals suitable for single-crystal X-ray diffraction were selected directly from the analytical sample.

S3. Refinement

H atoms were treated as riding atoms with C—H 0.98 Å (CH₃) or 0.99 Å (CH₂), and N—H 0.88 Å; water molecules were handled via DFIX followed by AFIX. The barium analogue appears to be isomorphous, with a = 24.8881 (8), b = 6.8332 (2), c = 14.6302 (3) Å, β = 93.5292 (9)°, V = 2483.27 (12) ų.

Computing details

Data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. The asymmetric unit of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I) showing formation of a coordination polymer chain along [010]. For the sake of clarity, the water molecules and the H atoms bonded to C are omitted. The atoms marked with a star (*), hash (#) or dollar sign ($) are at the symmetry positions (1 - x, 0.5 + y, 0.5 - z), (x, 1 + y, z) and (1 - x, 1.5 + y, 0.5 - z) respectively.
	Fig. 3. Stereoview of part of the crystal structure of (I) showing formation of a hydrogen-bonded (100) sheet of R^44(48) rings built from the ionic components only. For the sake of clarity, the water molecules and the H atoms bonded to C are omitted.

catena-Poly[penta-aquabis{N-(6-amino-3,4-dihydro-3-methyl-5-nitroso- 4-oxopyrimidin-2-yl)glycinate}strontium monohydrate]

Crystal data

C14H26N10O13Sr·H2O	F(000) = 1328
Mr = 648.08	Dx = 1.779 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.0078 (8) Å	Cell parameters from 5162 reflections
b = 6.7416 (1) Å	θ = 3.0–27.5°
c = 14.3677 (4) Å	µ = 2.32 mm^−1
β = 92.495 (1)°	T = 120 K
V = 2419.99 (11) Å^3	Block, pink
Z = 4	0.46 × 0.28 × 0.20 mm

Data collection

Kappa-CCD diffractometer	5162 independent reflections
Radiation source: fine-focus sealed X-ray tube	4318 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ϕ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −32→32
Tmin = 0.415, Tmax = 0.654	k = −8→5
10993 measured reflections	l = −11→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 1.798P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
5162 reflections	Δρmax = 0.62 e Å^−3
355 parameters	Δρmin = −0.69 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0151 (7)

Special details

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sr1	0.278327 (10)	0.14831 (4)	0.407412 (18)	0.01843 (11)
N11	0.01874 (9)	0.2683 (4)	0.53178 (17)	0.0208 (5)
C12	0.05038 (11)	0.2338 (4)	0.4614 (2)	0.0205 (6)
N12	0.10277 (9)	0.2441 (4)	0.47859 (17)	0.0220 (5)
C121	0.12639 (11)	0.3021 (4)	0.5692 (2)	0.0218 (6)
C122	0.18571 (11)	0.3467 (4)	0.5615 (2)	0.0210 (6)
O121	0.20475 (8)	0.3312 (3)	0.48286 (15)	0.0266 (5)
O122	0.21081 (8)	0.3955 (3)	0.63527 (15)	0.0262 (5)
C13	0.06986 (12)	0.1649 (5)	0.2968 (2)	0.0264 (7)
N13	0.03225 (9)	0.1908 (4)	0.37172 (17)	0.0214 (5)
C14	−0.02214 (11)	0.1642 (4)	0.3499 (2)	0.0213 (6)
O14	−0.03737 (8)	0.1097 (3)	0.27222 (15)	0.0289 (5)
C15	−0.05790 (11)	0.2048 (4)	0.4251 (2)	0.0194 (6)
N15	−0.11010 (10)	0.1790 (4)	0.40233 (18)	0.0234 (5)
O15	−0.14334 (8)	0.2143 (3)	0.46589 (15)	0.0264 (5)
C16	−0.03460 (11)	0.2595 (4)	0.5153 (2)	0.0210 (6)
N16	−0.06507 (10)	0.3018 (4)	0.58490 (18)	0.0240 (5)
N21	0.45799 (10)	−0.1293 (3)	0.17412 (17)	0.0204 (5)
C22	0.42906 (11)	−0.1471 (4)	0.0951 (2)	0.0193 (6)
N22	0.37728 (9)	−0.1013 (4)	0.09359 (17)	0.0202 (5)
C221	0.35075 (11)	−0.0345 (4)	0.17601 (19)	0.0208 (6)
C222	0.32671 (11)	−0.2006 (4)	0.2331 (2)	0.0198 (6)
O221	0.31165 (8)	−0.1533 (3)	0.31213 (14)	0.0227 (4)
O222	0.32238 (9)	−0.3706 (3)	0.19718 (15)	0.0276 (5)
C23	0.41327 (11)	−0.2412 (5)	−0.0713 (2)	0.0233 (6)
N23	0.44894 (9)	−0.2118 (4)	0.01147 (16)	0.0196 (5)
C24	0.50256 (11)	−0.2608 (4)	0.0059 (2)	0.0206 (6)
O24	0.51986 (8)	−0.3288 (3)	−0.06648 (14)	0.0259 (5)
C25	0.53598 (11)	−0.2266 (4)	0.0896 (2)	0.0197 (6)
N25	0.58752 (9)	−0.2685 (4)	0.07911 (17)	0.0223 (5)
O25	0.62163 (8)	−0.2452 (3)	0.14750 (14)	0.0243 (4)
C26	0.51094 (11)	−0.1593 (4)	0.1726 (2)	0.0205 (6)
N26	0.54082 (10)	−0.1304 (4)	0.24855 (17)	0.0250 (6)
O1	0.25470 (8)	0.3568 (3)	0.26200 (14)	0.0247 (5)
O2	0.34375 (8)	0.1136 (3)	0.55056 (15)	0.0255 (5)
O3	0.29895 (8)	0.5366 (3)	0.44185 (14)	0.0227 (4)
O4	0.24605 (8)	−0.1119 (3)	0.52799 (15)	0.0299 (5)
O5	0.19435 (8)	−0.0023 (3)	0.32021 (15)	0.0260 (5)
O6	0.15973 (9)	−0.3963 (3)	0.29473 (16)	0.0298 (5)
H12	0.1242	0.2149	0.4336	0.026*
H12A	0.1218	0.1936	0.6146	0.026*
H12B	0.1079	0.4212	0.5921	0.026*
H13A	0.0914	0.0454	0.3088	0.040*
H13B	0.0935	0.2807	0.2948	0.040*
H13C	0.0498	0.1513	0.2371	0.040*
H16A	−0.0504	0.3343	0.6396	0.029*
H16B	−0.1001	0.2977	0.5768	0.029*
H22	0.3584	−0.1119	0.0407	0.024*
H22A	0.3219	0.0590	0.1565	0.025*
H22B	0.3769	0.0393	0.2164	0.025*
H23A	0.3842	−0.3314	−0.0561	0.035*
H23B	0.4336	−0.2987	−0.1215	0.035*
H23C	0.3982	−0.1133	−0.0916	0.035*
H26A	0.5261	−0.0916	0.3000	0.030*
H26B	0.5756	−0.1498	0.2481	0.030*
H11C	0.2817	0.4222	0.2405	0.030*
H12D	0.2337	0.2858	0.2165	0.030*
H21C	0.3793	0.1390	0.5398	0.031*
H22D	0.3489	0.0223	0.5938	0.031*
H31C	0.3052	0.6360	0.4020	0.027*
H32D	0.2696	0.5802	0.4805	0.027*
H41C	0.2111	−0.1501	0.5350	0.036*
H42D	0.2670	−0.1227	0.5810	0.036*
H51C	0.1875	−0.1460	0.3263	0.031*
H51D	0.1976	0.0242	0.2603	0.031*
H61C	0.1412	−0.3777	0.2341	0.036*
H62D	0.1916	−0.4864	0.2983	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sr1	0.01743 (15)	0.02178 (16)	0.01626 (15)	0.00020 (10)	0.00287 (10)	0.00017 (10)
N11	0.0192 (12)	0.0236 (12)	0.0197 (12)	−0.0001 (9)	0.0027 (10)	0.0017 (10)
C12	0.0194 (13)	0.0204 (14)	0.0217 (15)	−0.0006 (11)	0.0018 (11)	0.0020 (11)
N12	0.0201 (12)	0.0271 (14)	0.0190 (13)	−0.0012 (10)	0.0030 (10)	−0.0008 (10)
C121	0.0205 (14)	0.0264 (15)	0.0186 (14)	0.0001 (11)	0.0031 (11)	0.0000 (12)
C122	0.0199 (13)	0.0206 (14)	0.0223 (15)	0.0032 (11)	0.0000 (11)	0.0016 (11)
O121	0.0208 (10)	0.0371 (12)	0.0221 (11)	−0.0003 (9)	0.0041 (9)	−0.0047 (9)
O122	0.0247 (10)	0.0308 (11)	0.0227 (11)	0.0022 (9)	−0.0027 (9)	−0.0031 (9)
C13	0.0216 (14)	0.0361 (17)	0.0217 (15)	−0.0011 (12)	0.0052 (12)	0.0001 (13)
N13	0.0180 (11)	0.0290 (13)	0.0173 (12)	−0.0003 (10)	0.0029 (10)	0.0006 (10)
C14	0.0199 (13)	0.0235 (15)	0.0204 (15)	−0.0012 (11)	0.0000 (11)	0.0025 (11)
O14	0.0251 (11)	0.0422 (13)	0.0195 (11)	−0.0041 (9)	0.0011 (9)	−0.0011 (9)
C15	0.0161 (12)	0.0231 (14)	0.0191 (14)	0.0021 (10)	0.0018 (11)	0.0015 (11)
N15	0.0217 (12)	0.0234 (13)	0.0251 (14)	−0.0002 (9)	0.0019 (10)	0.0046 (10)
O15	0.0184 (10)	0.0325 (11)	0.0288 (12)	−0.0006 (9)	0.0053 (9)	0.0001 (9)
C16	0.0209 (14)	0.0205 (14)	0.0217 (15)	0.0004 (11)	0.0028 (11)	0.0039 (11)
N16	0.0185 (12)	0.0322 (14)	0.0215 (13)	−0.0001 (10)	0.0022 (10)	−0.0006 (11)
N21	0.0210 (12)	0.0236 (13)	0.0166 (12)	0.0008 (9)	0.0020 (10)	−0.0001 (9)
C22	0.0218 (13)	0.0188 (13)	0.0176 (14)	−0.0001 (11)	0.0040 (11)	0.0006 (11)
N22	0.0201 (11)	0.0242 (12)	0.0165 (12)	0.0013 (9)	0.0038 (9)	−0.0008 (10)
C221	0.0214 (14)	0.0227 (14)	0.0187 (14)	0.0010 (11)	0.0068 (11)	−0.0018 (11)
C222	0.0162 (13)	0.0261 (14)	0.0172 (14)	0.0001 (11)	0.0021 (11)	0.0007 (11)
O221	0.0239 (10)	0.0263 (11)	0.0183 (10)	0.0010 (8)	0.0048 (8)	−0.0015 (8)
O222	0.0365 (12)	0.0241 (11)	0.0229 (11)	−0.0053 (9)	0.0102 (9)	−0.0045 (9)
C23	0.0212 (14)	0.0300 (16)	0.0187 (14)	−0.0011 (12)	0.0009 (11)	−0.0010 (12)
N23	0.0210 (12)	0.0225 (12)	0.0156 (12)	0.0017 (9)	0.0038 (10)	0.0003 (9)
C24	0.0227 (14)	0.0206 (14)	0.0187 (14)	−0.0006 (11)	0.0038 (11)	0.0024 (11)
O24	0.0272 (11)	0.0330 (12)	0.0181 (11)	0.0043 (9)	0.0073 (9)	−0.0033 (9)
C25	0.0195 (13)	0.0229 (14)	0.0170 (14)	0.0003 (11)	0.0037 (11)	0.0005 (11)
N25	0.0224 (12)	0.0237 (13)	0.0210 (13)	0.0012 (10)	0.0027 (10)	0.0032 (10)
O25	0.0211 (10)	0.0295 (12)	0.0223 (11)	0.0025 (8)	0.0011 (8)	0.0030 (9)
C26	0.0221 (14)	0.0207 (14)	0.0189 (14)	0.0013 (11)	0.0045 (11)	0.0010 (11)
N26	0.0221 (12)	0.0374 (15)	0.0157 (12)	0.0033 (10)	0.0025 (10)	−0.0010 (10)
O1	0.0245 (10)	0.0290 (11)	0.0204 (11)	−0.0069 (8)	0.0013 (9)	0.0024 (8)
O2	0.0214 (10)	0.0331 (12)	0.0222 (11)	−0.0022 (8)	0.0028 (8)	0.0053 (9)
O3	0.0216 (10)	0.0236 (11)	0.0233 (11)	−0.0002 (8)	0.0070 (9)	0.0012 (8)
O4	0.0206 (10)	0.0436 (14)	0.0255 (12)	−0.0060 (9)	0.0009 (9)	0.0074 (10)
O5	0.0252 (11)	0.0303 (11)	0.0224 (11)	−0.0026 (9)	0.0012 (9)	0.0004 (9)
O6	0.0284 (11)	0.0329 (12)	0.0279 (12)	0.0019 (9)	−0.0009 (9)	−0.0010 (10)

Geometric parameters (Å, º)

Sr1—O121	2.501 (2)	N23—C24	1.387 (4)
Sr1—O1	2.566 (2)	C24—C25	1.453 (4)
Sr1—O2	2.582 (2)	C25—C26	1.445 (4)
Sr1—O5	2.604 (2)	C26—N21	1.341 (4)
N11—C12	1.331 (4)	C22—N22	1.330 (4)
C12—N13	1.379 (4)	C23—N23	1.469 (4)
N13—C14	1.394 (3)	C24—O24	1.232 (3)
C14—C15	1.458 (4)	C25—N25	1.334 (4)
C15—C16	1.446 (4)	N25—O25	1.282 (3)
C16—N11	1.346 (4)	C26—N26	1.310 (4)
C12—N12	1.325 (4)	N22—C221	1.454 (3)
C13—N13	1.470 (4)	N22—H22	0.8800
C14—O14	1.220 (4)	C221—C222	1.526 (4)
C15—N15	1.343 (4)	C221—H22A	0.9900
N15—O15	1.284 (3)	C221—H22B	0.9900
C16—N16	1.314 (4)	C222—O221	1.253 (3)
Sr1—O221	2.608 (2)	C222—O222	1.260 (3)
Sr1—O4	2.617 (2)	C23—H23A	0.9800
Sr1—O3	2.710 (2)	C23—H23B	0.9800
Sr1—O25^i	2.751 (2)	C23—H23C	0.9800
N12—C121	1.460 (4)	N26—H26A	0.8800
N12—H12	0.8800	N26—H26B	0.8800
C121—C122	1.522 (4)	O1—H11C	0.8742
C121—H12A	0.9900	O1—H12D	0.9498
C121—H12B	0.9900	O2—H21C	0.9239
C122—O121	1.250 (4)	O2—H22D	0.8795
C122—O122	1.252 (4)	O3—H31C	0.8996
C13—H13A	0.9800	O3—H32D	0.9842
C13—H13B	0.9800	O4—H41C	0.9209
C13—H13C	0.9800	O4—H42D	0.9082
N16—H16A	0.8800	O5—H51C	0.9884
N16—H16B	0.8800	O5—H51D	0.8868
N21—C22	1.325 (4)	O6—H61C	0.9770
C22—N23	1.390 (4)	O6—H62D	1.0008
O121—Sr1—O1	86.28 (7)	N16—C16—C15	120.9 (3)
O121—Sr1—O2	98.75 (7)	N11—C16—C15	121.7 (3)
O1—Sr1—O2	144.45 (7)	C16—N16—H16A	120.0
O121—Sr1—O5	78.91 (7)	C16—N16—H16B	120.0
O1—Sr1—O5	70.70 (7)	H16A—N16—H16B	120.0
O2—Sr1—O5	144.84 (7)	C22—N21—C26	118.4 (3)
O121—Sr1—O221	150.43 (7)	N21—C22—N22	119.2 (3)
O1—Sr1—O221	93.85 (6)	N21—C22—N23	124.5 (3)
O2—Sr1—O221	98.14 (7)	N22—C22—N23	116.3 (3)
O5—Sr1—O221	73.31 (6)	C22—N22—C221	122.5 (2)
O121—Sr1—O4	77.85 (7)	C22—N22—H22	118.8
O1—Sr1—O4	147.08 (7)	C221—N22—H22	118.8
O2—Sr1—O4	67.36 (7)	N22—C221—C222	114.5 (2)
O5—Sr1—O4	77.98 (7)	N22—C221—H22A	108.6
O221—Sr1—O4	86.55 (7)	C222—C221—H22A	108.6
O121—Sr1—O3	65.31 (6)	N22—C221—H22B	108.6
O1—Sr1—O3	69.79 (6)	C222—C221—H22B	108.6
O2—Sr1—O3	80.40 (6)	H22A—C221—H22B	107.6
O5—Sr1—O3	127.41 (6)	O221—C222—O222	125.3 (3)
O221—Sr1—O3	141.86 (6)	O221—C222—C221	116.2 (2)
O4—Sr1—O3	126.04 (7)	O222—C222—C221	118.5 (2)
O121—Sr1—O25^i	133.72 (6)	C222—O221—Sr1	142.12 (19)
O1—Sr1—O25^i	78.68 (6)	N23—C23—H23A	109.5
O2—Sr1—O25^i	72.51 (6)	N23—C23—H23B	109.5
O5—Sr1—O25^i	133.48 (6)	H23A—C23—H23B	109.5
O221—Sr1—O25^i	74.79 (6)	N23—C23—H23C	109.5
O4—Sr1—O25^i	132.46 (6)	H23A—C23—H23C	109.5
O3—Sr1—O25^i	68.41 (6)	H23B—C23—H23C	109.5
C12—N11—C16	118.5 (3)	C24—N23—C22	120.5 (2)
N12—C12—N11	117.7 (3)	C24—N23—C23	118.4 (2)
N12—C12—N13	117.9 (3)	C22—N23—C23	121.0 (2)
N11—C12—N13	124.4 (3)	O24—C24—N23	120.9 (3)
C12—N12—C121	122.6 (2)	O24—C24—C25	123.2 (3)
C12—N12—H12	118.7	N23—C24—C25	115.9 (3)
C121—N12—H12	118.7	N25—C25—C26	127.9 (3)
N12—C121—C122	110.2 (2)	N25—C25—C24	113.4 (3)
N12—C121—H12A	109.6	C26—C25—C24	118.6 (3)
C122—C121—H12A	109.6	O25—N25—C25	120.1 (2)
N12—C121—H12B	109.6	N25—O25—Sr1^ii	109.34 (16)
C122—C121—H12B	109.6	N26—C26—N21	119.5 (3)
H12A—C121—H12B	108.1	N26—C26—C25	118.9 (3)
O121—C122—O122	126.2 (3)	N21—C26—C25	121.6 (3)
O121—C122—C121	117.4 (3)	C26—N26—H26A	120.0
O122—C122—C121	116.4 (3)	C26—N26—H26B	120.0
C122—O121—Sr1	138.56 (19)	H26A—N26—H26B	120.0
N13—C13—H13A	109.5	Sr1—O1—H11C	114.3
N13—C13—H13B	109.5	Sr1—O1—H12D	112.6
H13A—C13—H13B	109.5	H11C—O1—H12D	115.1
N13—C13—H13C	109.5	Sr1—O2—H21C	115.5
H13A—C13—H13C	109.5	Sr1—O2—H22D	133.9
H13B—C13—H13C	109.5	H21C—O2—H22D	97.9
C12—N13—C14	121.0 (2)	Sr1—O3—H31C	129.8
C12—N13—C13	121.0 (2)	Sr1—O3—H32D	104.5
C14—N13—C13	118.0 (2)	H31C—O3—H32D	106.9
O14—C14—N13	120.4 (3)	Sr1—O4—H41C	125.5
O14—C14—C15	123.9 (3)	Sr1—O4—H42D	115.2
N13—C14—C15	115.7 (3)	H41C—O4—H42D	113.7
N15—C15—C16	126.9 (3)	Sr1—O5—H51C	118.6
N15—C15—C14	114.6 (3)	Sr1—O5—H51D	106.5
C16—C15—C14	118.4 (2)	H51C—O5—H51D	107.8
O15—N15—C15	117.1 (2)	H61C—O6—H62D	118.0
N16—C16—N11	117.4 (3)
C16—N11—C12—N12	179.6 (3)	C26—N21—C22—N23	5.8 (4)
C16—N11—C12—N13	0.5 (4)	N21—C22—N22—C221	−0.9 (4)
N11—C12—N12—C121	−3.5 (4)	N23—C22—N22—C221	179.1 (2)
N13—C12—N12—C121	175.6 (2)	C22—N22—C221—C222	−90.3 (3)
C12—N12—C121—C122	−166.9 (2)	N22—C221—C222—O221	168.3 (2)
N12—C121—C122—O121	1.0 (4)	N22—C221—C222—O222	−13.2 (4)
N12—C121—C122—O122	−179.0 (2)	O222—C222—O221—Sr1	−152.5 (2)
O122—C122—O121—Sr1	56.2 (4)	C221—C222—O221—Sr1	25.8 (4)
C121—C122—O121—Sr1	−123.8 (3)	O121—Sr1—O221—C222	106.8 (3)
O1—Sr1—O121—C122	−173.3 (3)	O1—Sr1—O221—C222	17.5 (3)
O2—Sr1—O121—C122	−28.8 (3)	O2—Sr1—O221—C222	−128.9 (3)
O5—Sr1—O121—C122	115.6 (3)	O5—Sr1—O221—C222	86.0 (3)
O221—Sr1—O121—C122	95.4 (3)	O4—Sr1—O221—C222	164.5 (3)
O4—Sr1—O121—C122	35.7 (3)	O3—Sr1—O221—C222	−44.2 (3)
O3—Sr1—O121—C122	−103.9 (3)	O25^i—Sr1—O221—C222	−59.7 (3)
O25^i—Sr1—O121—C122	−102.9 (3)	N21—C22—N23—C24	−0.8 (4)
N12—C12—N13—C14	175.6 (3)	N22—C22—N23—C24	179.3 (2)
N11—C12—N13—C14	−5.4 (4)	N21—C22—N23—C23	175.5 (3)
N12—C12—N13—C13	−2.3 (4)	N22—C22—N23—C23	−4.4 (4)
N11—C12—N13—C13	176.8 (3)	C22—N23—C24—O24	175.9 (3)
C12—N13—C14—O14	−173.8 (3)	C23—N23—C24—O24	−0.6 (4)
C13—N13—C14—O14	4.2 (4)	C22—N23—C24—C25	−4.2 (4)
C12—N13—C14—C15	6.1 (4)	C23—N23—C24—C25	179.4 (2)
C13—N13—C14—C15	−176.0 (2)	O24—C24—C25—N25	2.6 (4)
O14—C14—C15—N15	−0.4 (4)	N23—C24—C25—N25	−177.4 (2)
N13—C14—C15—N15	179.7 (2)	O24—C24—C25—C26	−175.8 (3)
O14—C14—C15—C16	177.1 (3)	N23—C24—C25—C26	4.3 (4)
N13—C14—C15—C16	−2.7 (4)	C26—C25—N25—O25	−1.8 (4)
C16—C15—N15—O15	3.2 (4)	C24—C25—N25—O25	−180.0 (2)
C14—C15—N15—O15	−179.5 (2)	C25—N25—O25—Sr1^ii	179.7 (2)
C12—N11—C16—N16	−177.4 (3)	C22—N21—C26—N26	175.8 (3)
C12—N11—C16—C15	3.0 (4)	C22—N21—C26—C25	−5.5 (4)
N15—C15—C16—N16	−4.2 (5)	N25—C25—C26—N26	1.2 (5)
C14—C15—C16—N16	178.5 (3)	C24—C25—C26—N26	179.2 (3)
N15—C15—C16—N11	175.4 (3)	N25—C25—C26—N21	−177.6 (3)
C14—C15—C16—N11	−1.8 (4)	C24—C25—C26—N21	0.4 (4)
C26—N21—C22—N22	−174.3 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N16—H16A···O14^iii	0.88	1.96	2.814 (3)	164
N16—H16B···O15	0.88	1.97	2.610 (3)	129
N22—H22···O3^iv	0.88	2.07	2.900 (3)	156
N26—H26A···O24^v	0.88	2.00	2.745 (3)	141
N26—H26B···O25	0.88	1.99	2.654 (3)	131
O1—H11C···O222^vi	0.87	1.85	2.692 (3)	161
O1—H12D···O122^iv	0.95	1.77	2.691 (3)	163
O2—H21C···O24^i	0.93	2.54	3.431 (3)	161
O2—H21C···N25^i	0.93	2.03	2.708 (3)	129
O2—H22D···O222^v	0.88	1.94	2.740 (3)	150
O3—H31C···O221^vi	0.90	1.93	2.828 (3)	175
O3—H32D···O4^vi	0.98	2.27	3.007 (3)	131
O4—H41C···O15^vii	0.92	1.75	2.665 (3)	173
O4—H42D···O222^v	0.91	2.12	3.027 (3)	174
O5—H51C···O6	0.99	1.87	2.813 (3)	158
O5—H51D···O122^iv	0.89	1.92	2.801 (3)	173
O6—H61C···O14^viii	0.98	2.60	3.168 (3)	118
O6—H61C···N15^viii	0.98	2.11	3.084 (3)	173
O6—H62D···O1^ix	1.00	1.99	2.955 (3)	161

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