In situ synthesis, crystal structures, topology and photoluminescent properties of poly[di-μ-aqua-di­aqua­[μ3-4-(1H-tetra­zol-1-id-5-yl)benzoato-κ4O:O,O′:O′′]barium(II)] and poly[μ-aqua-di­aqua­[μ3-4-(1H-tetra­zol-1-id-5-yl)benzoato-κ4O:O,O′:O′]strontium(II)]

Bensegueni, M.A.; Cherouana, A.; Merazig, H.

doi:10.1107/S2056989020006386

research communications

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ISSN: 2056-9890

Volume 76| Part 6| June 2020| Pages 877-883

https://doi.org/10.1107/S2056989020006386

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In situ synthesis, crystal structures, topology and photoluminescent properties of poly[di-μ-aqua-diaqua[μ₃-4-(1H-tetrazol-1-id-5-yl)benzoato-κ⁴O:O,O′:O′′]barium(II)] and poly[μ-aqua-diaqua[μ₃-4-(1H-tetrazol-1-id-5-yl)benzoato-κ⁴O:O,O′:O′]strontium(II)]

Mohamed Abdellatif Bensegueni,^a ^* Aouatef Cherouana ^a and Hocine Merazig ^a

^aEnvironmental, Molecular and Structural Chemistry Research Unit, University of Constantine-1, 25000, Constantine, Algeria
^*Correspondence e-mail: bensegueni.abdellatif@gmail.com

Edited by B. Therrien, University of Neuchâtel, Switzerland (Received 16 April 2020; accepted 12 May 2020; online 19 May 2020)

Two alkaline-earth coordination compounds, [Ba(C₈H₄N₄O₂)(H₂O)₄]_n, (I), and [Sr(C₈H₄N₄O₂)(H₂O)₃]_n, (II), from the one-pot hydrolysis transformation of benzoyl chloride and the in situ self-assembled [2 + 3] cycloaddition of nitrile are presented. These coordination compounds are prepared by reacting 4-cyanobenzoyl chloride with divalent alkaline-earth salts (BaCl₂ and SrCl₂) in aqueous solution under hydrothermal conditions. The mononuclear coordination compounds (I) and (II) show the same mode of coordination of the organic ligands. The cohesion of the crystalline structures is provided by hydrogen bonds and π-stacking interactions, thus forming three-dimensional supramolecular networks. The two compounds have a three-dimensional (3,6)-connected topology, and the structural differences between them is in the number of water molecules around the alkaline earth metals. Having the same emission frequencies, the compounds exhibit photoluminescence properties with a downward absorption value from (I) to (II).

Keywords: alkaline earth complexes; tetrazol-carboxylate coordination compounds; in situ synthesis; photoluminescence; TGA; FT–IR; topology; crystal structure.

CCDC references: 2003538; 2003537

1. Chemical context

In recent years, studies on a wide variety of tetrazolyl-5-substituted coordination compounds have proliferated (Klapötke & Stierstorfer, 2009 ; Fischer et al., 2011 ). The extension from the synthetic approach developed by Demko and Sharpless (2001 ) to that of Zhao and colleagues (Zhao et al., 2008 ) is the main reason for this new interest. Chemists have focused on transition-metal compounds, while studies with alkaline-earth metal–tetrazol coordination compounds remain scarce. This led us to further explore this type of compound, and to study their topological and physical properties.

The choice of ligand is essential in the design of new coordination compounds. In our study we selected a (tetrazol-carboxylate) bifunctional ligand, which is able to adopt several coordination modes, resulting in a variety of crystal structures (Ouellette et al., 2012 ; Sun et al., 2013 ; Wei et al., 2012 ).

The complexation and formation of both the tetrazole and carboxylate groups occurred in situ under hydrothermal conditions from a 4-cyano-benzoyl chloride and the alkaline earth salts BaCl₂·2H₂O and SrCl₂·6H₂O, giving the title compounds poly[di-μ-aqua-diaqua[μ₃-5-(4-carboxylatophenyl)-1H-1,2,3,4-tetrazol-1-ido-κ⁴O:O,O′:O′′]barium(II)] (I) and poly[μ-aqua-diaqua[μ₃-4-(1H-tetrazol-1-id-5-yl)benzoato-κ⁴O:O,O′:O′]strontium(II)] (II). The two compounds form one-dimensional crystalline chains, in which the coordination is ensured by chelating carboxylate groups. The two compounds were characterized by FT–IR, TGA and single-crystal X-ray diffraction analysis. A topological study was performed and the photoluminescent properties were also studied.

2. Structural commentary

Compound (I) crystallizes in the orthorhombic space group Imma while compound (II) crystallizes in Pmna. In these two coordination compounds, the asymmetric unit comprises half of a crystallographically independent alkaline-earth metal ion, half of a deprotonated 4-(tetrrazol-5-yl)benzoate anion (ttzbenz), and two halves of water molecules in compound (I) and three halves of water molecules in compound (II) (Fig. 1). The bond distances and angles of the ligands are comparable to those found in the literature for similar systems (Zheng et al., 2009 ; Jiang et al., 2007 ; Yu et al., 2009 ).

Figure 1
The coordination environment of the Ae²⁺ ion in compounds (I)

and (II)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes for (I)

: (i) 2 − x, $[{1\over 2}]$ − y, z; (ii) $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ − z; (iii) x − $[{1\over 2}]$ , $[{1\over 2}]$ − y, $[{1\over 2}]$ − z; (iv) 2 − x, y, z; (v) $[{1\over 2}]$ + x, y, $[{1\over 2}]$ − z; (vi) x − $[{1\over 2}]$ , −y, z; (vii) −x − $[{1\over 2}]$ , y, $[{1\over 2}]$ − z; and for (II)

: (i) 2 − x, y, z; (ii) $[{3\over 2}]$ − x, y, $[{1\over 2}]$ − z; (iii) x + $[{1\over 2}]$ , y, $[{1\over 2}]$ − z.]

The crystal structures of compounds (I) and (II) show similar topologies, the main difference being the coordination polyhedron around the metal center. In compound (I), a slightly distorted BaO₁₀ sphenocorona coordination geometry (Casanova et al., 2005 ) is observed (Fig. 2). The geometry deviates by 4.424 compared to the theoretical model as proposed by SHAPE 2.1 software (Casanova et al., 2005; see Table S1 in the supporting information). In (I), the barium cation is decacoordinated by four oxygen atoms from three ttzbenz ligands, two independent oxygen atoms from two terminal water molecules (O2 and O3) and four additional oxygens from bridging water molecules. In compound (II), the Sr²⁺ ion is eightfold coordinated, being surrounded by four bridging water molecules and by four oxygen atoms from three symmetry-related ttzbenz ligands (Fig. 2), thus generating a triangular dodecahedral SrO₈ coordination geometry; this geometry deviates by 3.426 compared to the theoretical model proposed by SHAPE 2.1 software (Casanova et al., 2005; see Table S1 in the supporting information).

Figure 2
Coordinating polyhedra of compounds (I)

and (II)

, the colored polyhedra with open front faces represent the ideal polyhedral shape as calculated by SHAPE 2.1 [Symmetry codes for (I)

: (i) 1 − x, $[{1\over 2}]$ − y, z; (ii) 1 − x, y, z; (iii) − $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ − z; (iv) $[{3\over 2}]$ − x, y, $[{1\over 2}]$ − z; (v) x, $[{1\over 2}]$ − y, z; and for (II)

: (i) 2 − x, y, z; (ii) $[{5\over 2}]$ − x, y, $[{1\over 2}]$ − z; (iii) − $[{1\over 2}]$ + x, y, $[{1\over 2}]$ − z.]

The bond angles (Tables 1 and 2) around the Ae²⁺ ion (Ae²⁺ = Ba²⁺ and Sr²⁺) range between 42.49 (6) and 142.50 (2)° in compound (I), and between 48.93 (6) and 148.91 (4)° in compound (II). The Ba—O bond lengths are 2.821 (2) and 2.875 (1) Å for the coordinated water molecule, and 2.660 (2) and 3.016 (2) Å for the ttzbenz oxygen atom (Table 2), and these distances are slightly longer than that in an analogous compound (Fu et al., 2010 ). The Sr—O bond lengths are 2.501 (2) and 2.660 (1) Å for the ttzbenz oxygen atom, and 2.549 (2) and 2.676 (2) Å for the coordinated water molecule (Table 2). The Ba—O bonds are longer than Sr—O bonds; this is due not only to the nature of the metal, but also, in part, to the measurement temperature [room temperature for compound (I), but 150K for compound (II). These bond-length values are close to those observed in similar compounds based on Ae²⁺ one-dimensional coordination polymers: Ba—O = 2.647–3.179 Å, Sr—O = 2.486–2.843 Å in [C₂₄H₂₈N₂O₁₃Cl₂CuSr]_n and [C₂₄H₂₈N₂O₁₃Cl₂CuBa]_n (Hari, et al., 2017 ), and in the compounds [C₈H₁₆N₁₆O₁₉Sr₄]_n and [C₈H₂₀N₁₆O₁₈Sr₄]_n where the Sr—O distances range from 2.570–2.700 Å and 2.541–2.633 Å, respectively. In the two-dimensional coordination compound [C₂H₆BaN₄O₅]_n, the Ba—O distances are 2.790 and 2.902 Å (Hartdegen et al., 2009 ), while in the three-dimensional polymers [Ba₂M(HCOO)₆(H₂O)₄]_n, Ba—O = 2.801 (2)–3.6143 (2) Å for M = Ni, Ba—O = 2.797 (2)–2.999 (2) Å for M = Zn, and Ba—O = 2.801 (2)–3.004 (2) Å for M = Co (Baggio et al., 2004 ), and in the strontium complex C₆H₁₂SrN₆O₁₀, Sr—O = 2.506–2.724 Å (Divya et al., 2017 ).

Table 1
Selected geometric parameters (Å, °) for (I)

Ba1—O1	2.6598 (17)	Ba1—O2	2.8750 (12)
Ba1—O1ⁱ	2.6598 (17)	Ba1—O2ⁱⁱⁱ	2.8750 (12)
Ba1—O3ⁱ	2.821 (2)	Ba1—O2ⁱ	2.8750 (12)
Ba1—O3	2.821 (2)	Ba1—O1ⁱⁱ	3.0157 (17)
Ba1—O2ⁱⁱ	2.8750 (12)	Ba1—O1ⁱⁱⁱ	3.0157 (17)

O1—Ba1—O1ⁱ	137.57 (7)	O2ⁱⁱ—Ba1—O2ⁱⁱⁱ	142.501 (17)
O1—Ba1—O3ⁱ	75.09 (3)	O2—Ba1—O2ⁱⁱⁱ	91.23 (5)
O3ⁱ—Ba1—O3	89.36 (11)	O1—Ba1—O1ⁱⁱ	132.46 (5)
O1—Ba1—O2ⁱⁱ	134.06 (2)	O3ⁱ—Ba1—O1ⁱⁱ	131.51 (5)
O1ⁱ—Ba1—O2ⁱⁱ	62.43 (2)	O2ⁱⁱ—Ba1—O1ⁱⁱ	58.35 (2)
O3ⁱ—Ba1—O2ⁱⁱ	74.10 (4)	O2—Ba1—O1ⁱⁱ	85.73 (2)
O3—Ba1—O2ⁱⁱ	136.98 (2)	O1ⁱⁱ—Ba1—O1ⁱⁱⁱ	42.49 (6)
O2ⁱⁱ—Ba1—O2	76.81 (4)
Symmetry codes: (i) $[-x+1, -y+{\script{3\over 2}}, z]$ ; (ii) $[x, y+{\script{1\over 2}}, -z+1]$ ; (iii) -x+1, -y+1, -z+1.

Table 2
Selected geometric parameters (Å, °) for (II)

Sr—O1	2.501 (2)	Sr—O1ⁱ	2.6602 (14)
Sr—O3	2.522 (2)	Sr—O4	2.6757 (18)
Sr—O2	2.549 (3)

O1—Sr—O1ⁱⁱ	140.67 (7)	O3—Sr—O1ⁱⁱⁱ	148.91 (4)
O1—Sr—O3	85.19 (4)	O1—Sr—O4	68.20 (5)
O1—Sr—O2	72.67 (4)	O1ⁱⁱ—Sr—O4	147.71 (5)
O3—Sr—O2	103.31 (9)	O3—Sr—O4	83.72 (5)
O1—Sr—O1ⁱ	124.21 (4)	O2—Sr—O4	139.50 (4)
O1ⁱⁱ—Sr—O1ⁱ	77.42 (5)	O1ⁱ—Sr—O4	97.37 (4)
O3—Sr—O1ⁱ	148.91 (4)	O1ⁱⁱⁱ—Sr—O4	66.00 (5)
O2—Sr—O1ⁱ	95.91 (7)	O1ⁱⁱⁱ—Sr—O4ⁱ	97.37 (4)
O1ⁱⁱ—Sr—O1ⁱⁱⁱ	124.21 (5)	O4—Sr—O4ⁱ	80.48 (7)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) -x+1, y, z; (iii) $[-x+{\script{3\over 2}}, y, -z+{\script{1\over 2}}]$ .

The ttzbenz ligand can adopt several coordination modes by involving the tetrazole ring (Yao et al., 2013 ), or the carboxylate group as in our case, where the two compounds use the ttzbenz anion to coordinate two adjacent Ae²⁺ cations in a bidentate chelate manner, thus forming a polyatomic bridge and binding neighboring Ae²⁺ ions in a zigzag manner, resulting in the formation of binuclear units [Ae–O1–Ae–O1] with a Ba⋯Ba distance of 4.0089 (4) Å for compound (I) and an Sr⋯Sr distance of 3.866 (2) Å for compound (II) (Fig. 3).

Figure 3
Coordinating polymers along the b axis.

3. Supramolecular features

In compound (I), hydrogen bonds between two coordinated water molecules and two nitrogen atoms of the tetrazole ring of the ttzbenz ligand are observed (Table 3), ensuring cohesion between the tetrazole rings and the inorganic [Ba₂O₂]_n chains. In addition to hydrogen bonds, π-stacking interactions between phenyl rings are observed (Fig. 4) with a centroid–centroid distance of 4.035 (1) Å, which enhance the cohesion of the crystal structure.

Table 3
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2^iv	0.79 (2)	2.14 (2)	2.927 (2)	175 (3)
O3—H3⋯N1^v	0.79 (3)	2.29 (3)	3.069 (2)	169 (3)
Symmetry codes: (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 4
Hydrogen bonds (blue dashed lines) and π-stacking interactions (green dashed lines) in the crystal packing of compounds (I)

and (II)

In compound (II), as well as the strong O—H⋯N hydrogen bonds (Table 4), weak intramolecular π-stacking interactions are observed, reinforcing the cohesion in the crystal structure between the tetrazole rings (centroid Cg1) and the phenyl rings (centroid Cg2) with centroid–centroid distances Cg1⋯Cg2 = 3.622 (3) Å and Cg2⋯Cg2 = 3.897 (3) Å (Fig. 4).

Table 4
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1^iv	0.85 (2)	1.96 (2)	2.800 (2)	171 (3)
O3—H3⋯N2^iv	0.85 (2)	2.62 (2)	3.314 (3)	141 (2)
O2—H2⋯N2^v	0.77 (3)	2.53 (3)	3.270 (3)	160 (3)
O4—H4⋯N2^vi	0.87 (2)	1.93 (2)	2.784 (2)	166 (2)
Symmetry codes: (iv) -x+2, -y+1, -z+1; (v) -x+2, -y, -z+1; (vi) $[x-{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

4. Topological study

To simplify the crystalline structure of the title compounds, we used the standard representation of valence-bound CPs (CP = coordination polymer) to obtain the underlying network. In such models, only metal centers and the centroids of organic ligands are considered as structural units (Alexandrov et al., 2011 ). The simplification of the crystal structure of the two compounds by this procedure and the topological classification of the two studied compounds led to the same topological network, identified as a 3.6-c net with stoichiometry (3-C)₂(6-C), which can be represented by the point symbol {4³}₂{4⁶.6⁶.8³}. Thus the two structures consist of planar layers running parallel to (100) (Fig. 5).

Figure 5
Simplification of the coordination framework in the two compounds using standard representation for valence-bonded CPs.

5. Database survey

A search for 4-(tetrazol-5-yl) benzoate in the Cambridge Structural Database (CSD Version 5.40; Groom et al., 2016 ) gave 81 hits for the ligand, alone or with co-ligands. The ttzbenz ligand has proved to be an excellent component for the assembly of new coordination complexes and polymers, whether through a bridging and/or chelating coordination mode, mono or polydentate, and as an acceptor of hydrogen bonds through the two carboxylate and tetrazolate groups. This has led to structural diversity with interesting physicochemical properties, as seen in the structures with metal ions: copper (Ouellette et al., 2009 ), cobalt (Ouellette et al., 2012), zinc (Wei et al., 2012; Jiang et al., 2007; Zheng et al., 2009), lead (Sun et al., 2013), manganese and cadmium (Cheng et al., 2016 ; Yu et al., 2009), europium, terbium (Wang et al., 2011 ). Finally, with bipyridine co-ligands (Yang et al., 2017 ; Gao et al., 2016 ), (terpyridinyl)benzoate (Zhang et al., 2016 ), phenanthroline (Werrett et al., 2015 ), 3,5-dimethyl-1,2,4-triazolato (Sheng et al., 2016 ), and N,N-dimethylacetamide (Wang et al., 2015 ).

6. Synthesis and crystallization

Colorless crystals suitable for X-ray diffraction were obtained by hydrothermal synthesis in an aqueous solution according to a literature procedure (Demko & Sharpless, 2001; Zhao et al., 2008), where an aqueous solution (10 ml) of sodium azide (0.065 g, 1 mmol) and 4-cyanobenzoyl chloride (0.165 g, 1 mmol) was added dropwise to an aqueous solution (5 ml) of BaCl₂·2H₂O (0.244 g, 1mmol) for (I) and SrCl₂·6H₂O (0.266g, 1 mmol) for (II) under constant stirring for a few minutes. The resulting solution was sealed in a 25ml teflon-lined stainless steel autoclave and heated at 453 K for 3 d.

The FT–IR spectra for compounds (I) and (II) were recorded in the frequency range 4000–400 cm⁻¹ on a Perkin Elmer FT–IR spectrophotometer Spectrum 1000. The ν, γ and δ modes are: stretching, out-of-plane bending, and in-plane bending, respectively. The absence of bands in the two regions: 2200–2280 cm⁻¹ and 2100–2270 cm⁻¹ corresponding to the functions –CN and N₃⁻, respectively, confirms that the [2 + 3] cycloaddition reaction between the cyano group and the azide anions occurred and the tetrazolate ligand was formed (Hammerl et al., 2002 , 2003 ; Damavarapu et al., 2010 ; Zhang et al., 2013 )

FT–IR of (I) (ATR, cm⁻¹): 3300 ν(O—H)_water, 3100 ν(C—H)_Ph, 1435 ν_sym (C—C), 1523 ν(N—N)_ring, 1603 ν(C—N)_ring, 628–1050 γ,δ (tetrazole).

FT–IR of (II) (ATR, cm⁻¹): 3600 ν(O—H)_water, 3200 ν(C—H)_Ph, 1408 ν_sym (C—C), 1530 ν(N—N)_ring, 1585 ν(C—N)_ring, 654–1009 γ, δ (tetrazole) (see Fig. S1 in the supporting information).

The thermogravimetric analysis (TGA) was performed in the range 25–600°C under air atmosphere at a flow rate of 5°C/min (Fig. 6). The pyrolytic processes for compound (I) occurs in two main steps. The first step corresponds to the release of four water molecules (2 bridging water molecules and 2 monodentate) (scheme1) between 90°C and 200°C, which corresponds to approximately 18% of the weight of (I). Subsequently, the ligands undergo pyrolysis to result in decomposition (32% by weight) in the range of 200 to 600°C. In compound (II), the pyrolytic processes also go through two stages. The first step corresponds to the release of three water molecules (1 bridging water molecule and 2 monodentate) (scheme1) between 100°C and 160°C, which corresponds to approximately 16% of the weight of (II). The second step corresponding to a weight loss of 44% of (II) is attributed to the decomposition of the ligand 160 and 600°C.

Figure 6
Thermogravimetric analysis of compounds (I)

and (II)

7. Thermogravimetric analysis

The thermogravimetric analysis (TGA) was performed in the range 25–600°C under an air atmosphere at a flow rate of 5°C min⁻¹ (Fig. 6). The pyrolytic processes for compound (I) occur in two main steps. The first step corresponds to the release of four water molecules (two bridging water molecules and two monodentate) between 90°C and 200°C, which corresponds to approximately 18% of the weight of (I). Subsequently, the ligands undergo pyrolysis to result in decomposition (32% by weight) in the range 200–600°C. In compound (II), the pyrolytic processes also go through two stages. The first step corresponds to the release of three water molecules (one bridging water molecule and two monodentate) between 100°C and 160°C, which corresponds to approximately 16% of the weight of (II). The second step corresponding to a weight loss of 44% of (II) is attributed to the decomposition of the ligand between 160 and 600°C.

8. Fluorescence properties

The fluorescence properties of compounds (I) and (II) were determined from the emission spectra at the same excitation wavelength (eX = 322 nm) on an Agilent Cary Eclipse Fluorescence Spectrophotometer at room temperature. Excitation of the two compounds after dissolution in DMSO leads to similar fluorescence emission spectra. The emission maximum of (I) is observed to shift from 368 to 377 nm and from 371 to 378 nm for II (see Fig. S2 in the supporting information), probably corresponding to π* → π or π*→n electronic transition of the aromatic ring ttzbenz ligands (Koşar et al., 2012 ), due to the close resemblance of the emission band of the two compounds. We also note downward absorption values ranging from compound (I) to (II), which may be due to the increase in the atomic number from Sr²⁺ to Ba²⁺.

9. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. The water H atoms were located in a difference-Fourier map and their positions and isotropic displacement parameters were refined. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms (C—H = 0.93 Å) with U_iso(H) = 1.2U_eq(C).

Table 5
Experimental details

	(I)	(II)
Crystal data
Chemical formula	[Ba(C₈H₄N₄O₂)(H₂O)₄]	[Sr(C₈H₄N₄O₂)(H₂O)₃]
M_r	397.55	329.82
Crystal system, space group	Orthorhombic, Imma	Orthorhombic, Pmna
Temperature (K)	298	150
a, b, c (Å)	7.5012 (1), 7.1444 (1), 24.7457 (5)	6.914 (6), 7.018 (7), 24.164 (2)
V (Å³)	1326.16 (4)	1172.5 (16)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	3.02	4.62
Crystal size (mm)	0.6 × 0.5 × 0.22	0.20 × 0.1 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2011 )	Multi-scan (SADABS; Bruker, 2011)
T_min, T_max	0.670, 0.747	0.67, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	5216, 952, 920	9495, 2091, 1740
R_int	0.032	0.038
(sin θ/λ)_max (Å⁻¹)	0.667	0.735

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.016, 0.039, 1.07	0.028, 0.062, 1.07
No. of reflections	937	2091
No. of parameters	70	105
No. of restraints	0	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.91, −0.31	0.65, −0.44
Computer programs: APEX2 and SAINT (Bruker, 2011), CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SIR92 (Altomare et al., 1993 ), SHELXL (Sheldrick, 2015b ), SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ), OLEX2 (Dolomanov et al., 2009 ), Mercury (Macrae et al., 2020 ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 2003538; 2003537

Crystal structure: contains datablocks TTZBENZ_AE, I, II. DOI: https://doi.org/10.1107/S2056989020006386/tx2021sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020006386/tx2021Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989020006386/tx2021IIsup3.hkl

Infrared spectra. DOI: https://doi.org/10.1107/S2056989020006386/tx2021sup4.jpg

Photoluminescent spectra. DOI: https://doi.org/10.1107/S2056989020006386/tx2021sup5.jpg

Table S1. Comparative shape analysis of two polymers. DOI: https://doi.org/10.1107/S2056989020006386/tx2021sup6.doc

checkCIF report

Computing details top

For both structures, data collection: APEX2 (Bruker, 2011). Cell refinement: SAINT (Bruker, 2011) for (I); CrysAlis PRO (Rigaku OD, 2015) for (II). Data reduction: SAINT (Bruker, 2011) for (I); CrysAlis PRO (Rigaku OD, 2015) for (II). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (I); SIR92 (Altomare et al., 1993) for (II). Program(s) used to refine structure: SHELXL (Sheldrick, 2015b) for (I); SHELXL97 (Sheldrick, 2008) for (II). Molecular graphics: OLEX2 (Dolomanov et al., 2009) for (I); ORTEP-3 for Windows (Farrugia, 2012), OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2020) for (II). Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) for (I); PLATON (Spek, 2020); publCIF (Westrip, 2010) for (II).

Poly[di-µ-aqua-diaqua[µ₃-5-(4-carboxylatophenyl)-1H-1,2,3,4-tetrazol-1-ido-κ⁴O:O,O':O']barium(II)] (I) top

Crystal data top

[Ba(C₈H₄N₄O₂)(H₂O)₄]	F(000) = 768
M_r = 397.55	D_x = 1.991 Mg m⁻³
Orthorhombic, Imma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2b 2	Cell parameters from 9092 reflections
a = 7.5012 (1) Å	θ = 4.3–51.0°
b = 7.1444 (1) Å	µ = 3.02 mm⁻¹
c = 24.7457 (5) Å	T = 298 K
V = 1326.16 (4) Å³	Block, colorless
Z = 4	0.6 × 0.5 × 0.22 mm

Data collection top

Bruker APEXII CCD diffractometer	920 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.032
Absorption correction: multi-scan (SADABS; Bruker, 2011)	θ_max = 28.3°, θ_min = 4.9°
T_min = 0.670, T_max = 0.747	h = −10→7
5216 measured reflections	k = −9→7
952 independent reflections	l = −30→32

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)] = 0.016	Hydrogen site location: mixed
wR(F²) = 0.039	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0155P)² + 1.5691P] where P = (F_o² + 2F_c²)/3
937 reflections	(Δ/σ)_max = 0.002
70 parameters	Δρ_max = 0.91 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ba1	0.5000	0.7500	0.462655 (6)	0.02050 (7)
O2	0.7739 (2)	0.5000	0.5000	0.0309 (3)
O1	0.5000	0.4029 (2)	0.42376 (7)	0.0385 (4)
O3	0.2356 (3)	0.7500	0.38160 (10)	0.0458 (5)
N2	0.5000	0.1584 (3)	0.08485 (7)	0.0312 (4)
C1	0.5000	0.2500	0.39934 (11)	0.0197 (5)
N1	0.5000	0.0959 (3)	0.13588 (7)	0.0313 (4)
C2	0.5000	0.2500	0.33851 (11)	0.0221 (5)
C3	0.5000	0.0832 (3)	0.31016 (9)	0.0343 (5)
H3A	0.5000	−0.0298	0.3288	0.041*
C5	0.5000	0.2500	0.22580 (12)	0.0243 (6)
C6	0.5000	0.2500	0.16639 (12)	0.0233 (5)
C4	0.5000	0.0829 (3)	0.25423 (9)	0.0369 (6)
H4	0.5000	−0.0302	0.2356	0.044*
H3	0.175 (4)	0.665 (4)	0.3725 (13)	0.072 (9)*
H2	0.834 (3)	0.464 (4)	0.4761 (9)	0.046 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ba1	0.02865 (11)	0.01345 (10)	0.01940 (11)	0.000	0.000	0.000
O2	0.0294 (7)	0.0369 (9)	0.0265 (8)	0.000	0.000	−0.0053 (7)
O1	0.0744 (12)	0.0226 (8)	0.0184 (7)	0.000	0.000	−0.0041 (6)
O3	0.0508 (11)	0.0293 (9)	0.0571 (13)	0.000	−0.0202 (10)	0.000
N2	0.0469 (11)	0.0283 (10)	0.0183 (8)	0.000	0.000	−0.0020 (7)
C1	0.0246 (12)	0.0172 (12)	0.0173 (13)	0.000	0.000	0.000
N1	0.0527 (11)	0.0240 (9)	0.0171 (8)	0.000	0.000	−0.0010 (7)
C2	0.0319 (14)	0.0213 (13)	0.0132 (12)	0.000	0.000	0.000
C3	0.0659 (15)	0.0190 (9)	0.0180 (10)	0.000	0.000	0.0022 (8)
C5	0.0337 (14)	0.0231 (14)	0.0162 (13)	0.000	0.000	0.000
C6	0.0298 (13)	0.0223 (13)	0.0179 (13)	0.000	0.000	0.000
C4	0.0718 (17)	0.0193 (9)	0.0196 (10)	0.000	0.000	−0.0033 (8)

Geometric parameters (Å, º) top

Ba1—O1	2.6598 (17)	N2—N1	1.339 (3)
Ba1—O1ⁱ	2.6598 (17)	C1—O1^iv	1.249 (2)
Ba1—O3ⁱ	2.821 (2)	C1—C2	1.505 (4)
Ba1—O3	2.821 (2)	N1—C6	1.335 (2)
Ba1—O2ⁱⁱ	2.8750 (12)	C2—C3^iv	1.383 (3)
Ba1—O2	2.8750 (12)	C2—C3	1.383 (3)
Ba1—O2ⁱⁱⁱ	2.8750 (12)	C3—C4	1.384 (3)
Ba1—O2ⁱ	2.8750 (12)	C3—H3A	0.9300
Ba1—O1ⁱⁱ	3.0157 (17)	C5—C4	1.386 (3)
Ba1—O1ⁱⁱⁱ	3.0157 (17)	C5—C4^iv	1.386 (3)
O2—H2	0.78 (2)	C5—C6	1.470 (4)
O1—C1	1.249 (2)	C6—N1^iv	1.335 (2)
O3—H3	0.80 (3)	C4—H4	0.9300
N2—N2^iv	1.308 (4)

O1—Ba1—O1ⁱ	137.57 (7)	Ba1ⁱⁱⁱ—O2—Ba1	88.77 (5)
O1—Ba1—O3ⁱ	75.09 (3)	Ba1^v—O2—H2	117 (2)
O1ⁱ—Ba1—O3ⁱ	75.09 (3)	Ba1^vi—O2—H2	117 (2)
O1—Ba1—O3	75.09 (3)	Ba1^vii—O2—H2	117 (2)
O1ⁱ—Ba1—O3	75.09 (3)	Ba1ⁱⁱⁱ—O2—H2	117 (2)
O3ⁱ—Ba1—O3	89.36 (11)	Ba1—O2—H2	111.5 (19)
O1—Ba1—O2ⁱⁱ	134.06 (2)	C1—O1—Ba1	172.27 (16)
O1ⁱ—Ba1—O2ⁱⁱ	62.43 (2)	C1—O1—Ba1^v	97.70 (14)
O3ⁱ—Ba1—O2ⁱⁱ	74.10 (4)	Ba1—O1—Ba1^v	90.03 (5)
O3—Ba1—O2ⁱⁱ	136.98 (2)	C1—O1—Ba1^vii	97.70 (14)
O1—Ba1—O2	62.43 (2)	Ba1—O1—Ba1^vii	90.03 (5)
O1ⁱ—Ba1—O2	134.06 (2)	C1—O1—Ba1ⁱⁱⁱ	97.70 (14)
O3ⁱ—Ba1—O2	74.10 (4)	Ba1—O1—Ba1ⁱⁱⁱ	90.03 (5)
O3—Ba1—O2	136.98 (2)	C1—O1—Ba1^vi	97.70 (14)
O2ⁱⁱ—Ba1—O2	76.81 (4)	Ba1—O1—Ba1^vi	90.03 (5)
O1—Ba1—O2ⁱⁱⁱ	62.43 (2)	Ba1—O3—H3	127 (2)
O1ⁱ—Ba1—O2ⁱⁱⁱ	134.06 (2)	N2^iv—N2—N1	109.49 (12)
O3ⁱ—Ba1—O2ⁱⁱⁱ	136.98 (2)	O1—C1—O1^iv	122.1 (3)
O3—Ba1—O2ⁱⁱⁱ	74.10 (4)	O1—C1—C2	118.95 (13)
O2ⁱⁱ—Ba1—O2ⁱⁱⁱ	142.501 (17)	O1^iv—C1—C2	118.95 (13)
O2—Ba1—O2ⁱⁱⁱ	91.23 (5)	O1—C1—Ba1^vii	61.05 (13)
O1—Ba1—O2ⁱ	134.06 (2)	O1^iv—C1—Ba1^vii	61.05 (13)
O1ⁱ—Ba1—O2ⁱ	62.43 (2)	C2—C1—Ba1^vii	180.0
O3ⁱ—Ba1—O2ⁱ	136.98 (2)	O1—C1—Ba1ⁱⁱⁱ	61.05 (13)
O3—Ba1—O2ⁱ	74.10 (4)	O1^iv—C1—Ba1ⁱⁱⁱ	61.05 (13)
O2ⁱⁱ—Ba1—O2ⁱ	91.23 (5)	C2—C1—Ba1ⁱⁱⁱ	180.0
O2—Ba1—O2ⁱ	142.501 (17)	O1—C1—Ba1^vi	61.05 (13)
O2ⁱⁱⁱ—Ba1—O2ⁱ	76.81 (4)	O1^iv—C1—Ba1^vi	61.05 (13)
O1—Ba1—O1ⁱⁱ	132.46 (5)	C2—C1—Ba1^vi	180.0
O1ⁱ—Ba1—O1ⁱⁱ	89.97 (5)	O1—C1—Ba1^v	61.05 (13)
O3ⁱ—Ba1—O1ⁱⁱ	131.51 (5)	O1^iv—C1—Ba1^v	61.05 (13)
O3—Ba1—O1ⁱⁱ	131.51 (5)	C2—C1—Ba1^v	180.0
O2ⁱⁱ—Ba1—O1ⁱⁱ	58.35 (2)	C6—N1—N2	104.94 (19)
O2—Ba1—O1ⁱⁱ	85.73 (2)	C3^iv—C2—C3	119.0 (3)
O2ⁱⁱⁱ—Ba1—O1ⁱⁱ	85.73 (2)	C3^iv—C2—C1	120.48 (13)
O2ⁱ—Ba1—O1ⁱⁱ	58.35 (2)	C3—C2—C1	120.48 (13)
O1—Ba1—O1ⁱⁱⁱ	89.97 (5)	C2—C3—C4	120.6 (2)
O1ⁱ—Ba1—O1ⁱⁱⁱ	132.46 (5)	C2—C3—H3A	119.7
O3ⁱ—Ba1—O1ⁱⁱⁱ	131.51 (5)	C4—C3—H3A	119.7
O3—Ba1—O1ⁱⁱⁱ	131.51 (5)	C4—C5—C4^iv	119.0 (3)
O2ⁱⁱ—Ba1—O1ⁱⁱⁱ	85.73 (2)	C4—C5—C6	120.50 (14)
O2—Ba1—O1ⁱⁱⁱ	58.35 (2)	C4^iv—C5—C6	120.50 (14)
O2ⁱⁱⁱ—Ba1—O1ⁱⁱⁱ	58.35 (2)	N1^iv—C6—N1	111.1 (3)
O2ⁱ—Ba1—O1ⁱⁱⁱ	85.73 (2)	N1^iv—C6—C5	124.44 (13)
O1ⁱⁱ—Ba1—O1ⁱⁱⁱ	42.49 (6)	N1—C6—C5	124.44 (13)
Ba1^v—O2—Ba1	88.77 (5)	C3—C4—C5	120.4 (2)
Ba1^vi—O2—Ba1	88.77 (5)	C3—C4—H4	119.8
Ba1^vii—O2—Ba1	88.77 (5)	C5—C4—H4	119.8

O1—Ba1—O2—Ba1^v	−57.76 (3)	O1ⁱⁱ—Ba1—O2—Ba1^vii	85.62 (2)
O1ⁱ—Ba1—O2—Ba1^v	171.44 (5)	O1ⁱⁱⁱ—Ba1—O2—Ba1^vii	50.97 (3)
O3ⁱ—Ba1—O2—Ba1^v	−138.96 (4)	O1—Ba1—O2—Ba1ⁱⁱⁱ	−57.76 (3)
O3—Ba1—O2—Ba1^v	−67.75 (7)	O1ⁱ—Ba1—O2—Ba1ⁱⁱⁱ	171.44 (5)
O2ⁱⁱ—Ba1—O2—Ba1^v	144.096 (12)	O3ⁱ—Ba1—O2—Ba1ⁱⁱⁱ	−138.96 (4)
O2ⁱ—Ba1—O2—Ba1^v	69.71 (4)	O3—Ba1—O2—Ba1ⁱⁱⁱ	−67.75 (7)
O1ⁱⁱ—Ba1—O2—Ba1^v	85.62 (2)	O2ⁱⁱ—Ba1—O2—Ba1ⁱⁱⁱ	144.096 (12)
O1ⁱⁱⁱ—Ba1—O2—Ba1^v	50.97 (3)	O2ⁱ—Ba1—O2—Ba1ⁱⁱⁱ	69.71 (4)
O1—Ba1—O2—Ba1^vi	−57.76 (3)	O1ⁱⁱ—Ba1—O2—Ba1ⁱⁱⁱ	85.62 (2)
O1ⁱ—Ba1—O2—Ba1^vi	171.44 (5)	O1ⁱⁱⁱ—Ba1—O2—Ba1ⁱⁱⁱ	50.97 (3)
O3ⁱ—Ba1—O2—Ba1^vi	−138.96 (4)	O3ⁱ—Ba1—O1—Ba1^v	133.31 (5)
O3—Ba1—O2—Ba1^vi	−67.75 (7)	O2ⁱⁱ—Ba1—O1—Ba1^v	84.02 (4)
O2ⁱⁱ—Ba1—O2—Ba1^vi	144.096 (12)	O2—Ba1—O1—Ba1^v	53.73 (3)
O2ⁱ—Ba1—O2—Ba1^vi	69.71 (4)	O3ⁱ—Ba1—O1—Ba1^vii	133.31 (5)
O1ⁱⁱ—Ba1—O2—Ba1^vi	85.62 (2)	O2ⁱⁱ—Ba1—O1—Ba1^vii	84.02 (4)
O1ⁱⁱⁱ—Ba1—O2—Ba1^vi	50.97 (3)	O2—Ba1—O1—Ba1^vii	53.73 (3)
O1—Ba1—O2—Ba1^vii	−57.76 (3)	O3ⁱ—Ba1—O1—Ba1ⁱⁱⁱ	133.31 (5)
O1ⁱ—Ba1—O2—Ba1^vii	171.44 (5)	O2ⁱⁱ—Ba1—O1—Ba1ⁱⁱⁱ	84.02 (4)
O3ⁱ—Ba1—O2—Ba1^vii	−138.96 (4)	O2—Ba1—O1—Ba1ⁱⁱⁱ	53.73 (3)
O3—Ba1—O2—Ba1^vii	−67.75 (7)	O3ⁱ—Ba1—O1—Ba1^vi	133.31 (5)
O2ⁱⁱ—Ba1—O2—Ba1^vii	144.096 (12)	O2ⁱⁱ—Ba1—O1—Ba1^vi	84.02 (4)
O2ⁱ—Ba1—O2—Ba1^vii	69.71 (4)	O2—Ba1—O1—Ba1^vi	53.73 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2^viii	0.79 (2)	2.14 (2)	2.927 (2)	175 (3)
O3—H3···N1^ix	0.79 (3)	2.29 (3)	3.069 (2)	169 (3)

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

Poly[µ-aqua-diaqua[µ₃-5-(4-carboxylatophenyl)-1H-1,2,3,4-tetrazol-1-ido-κ⁴O:O,O':O']strontium(II)] (II) top

Crystal data top

[Sr(C₈H₄N₄O₂)(H₂O)₃]	F(000) = 656
M_r = 329.82	D_x = 1.874 Mg m⁻³
Orthorhombic, Pmna	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2	Cell parameters from 10707 reflections
a = 6.914 (6) Å	θ = 4.9–34.3°
b = 7.018 (7) Å	µ = 4.62 mm⁻¹
c = 24.164 (2) Å	T = 150 K
V = 1172.5 (16) Å³	Prism, colorless
Z = 4	0.20 × 0.1 × 0.07 mm

Data collection top

Bruker APEXII CCD diffractometer	2091 independent reflections
Radiation source: fine-focus sealed tube	1740 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 31.5°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −10→8
T_min = 0.67, T_max = 0.747	k = −10→8
9495 measured reflections	l = −34→35

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.028	w = 1/[σ²(F_o²) + (0.0253P)² + 0.7105P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.062	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 0.65 e Å⁻³
2091 reflections	Δρ_min = −0.44 e Å⁻³
105 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sr	0.5000	0.41161 (3)	0.285826 (9)	0.01071 (7)
O4	0.7500	0.6752 (3)	0.2500	0.0148 (4)
O2	0.5000	0.0703 (3)	0.32193 (13)	0.0341 (6)
O3	0.5000	0.6090 (3)	0.37304 (8)	0.0201 (4)
O1	0.84065 (19)	0.3310 (2)	0.31160 (5)	0.0157 (3)
C2	1.0000	0.2947 (3)	0.39842 (10)	0.0112 (5)
N1	1.1596 (2)	0.1898 (2)	0.60389 (6)	0.0155 (3)
C4	0.8268 (3)	0.2547 (3)	0.48414 (7)	0.0166 (4)
H4A	0.7101	0.2459	0.5031	0.020*
C5	1.0000	0.2407 (4)	0.51296 (10)	0.0120 (5)
N2	1.0952 (2)	0.1577 (2)	0.65534 (6)	0.0167 (3)
C6	1.0000	0.2079 (3)	0.57327 (10)	0.0120 (5)
C3	0.8269 (3)	0.2818 (3)	0.42714 (7)	0.0166 (4)
H3A	0.7102	0.2912	0.4082	0.020*
C1	1.0000	0.3206 (4)	0.33702 (10)	0.0113 (5)
H3	0.600 (3)	0.668 (4)	0.3839 (10)	0.037 (7)*
H4	0.709 (4)	0.743 (4)	0.2212 (9)	0.036 (8)*
H2	0.584 (4)	0.014 (5)	0.3353 (12)	0.058 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sr	0.00658 (11)	0.01630 (11)	0.00923 (10)	0.000	0.000	0.00006 (10)
O4	0.0141 (10)	0.0173 (8)	0.0131 (9)	0.000	−0.0015 (7)	0.000
O2	0.0211 (13)	0.0223 (12)	0.0590 (18)	0.000	0.000	0.0144 (12)
O3	0.0102 (10)	0.0302 (11)	0.0200 (10)	0.000	0.000	−0.0087 (9)
O1	0.0088 (6)	0.0258 (7)	0.0124 (6)	0.0014 (6)	−0.0017 (5)	0.0045 (5)
C2	0.0120 (12)	0.0107 (10)	0.0107 (11)	0.000	0.000	0.0017 (9)
N1	0.0144 (8)	0.0215 (8)	0.0106 (7)	−0.0015 (6)	−0.0014 (6)	0.0002 (6)
C4	0.0101 (9)	0.0251 (9)	0.0146 (8)	0.0019 (8)	0.0022 (7)	0.0017 (7)
C5	0.0140 (12)	0.0126 (11)	0.0093 (11)	0.000	0.000	−0.0019 (9)
N2	0.0186 (8)	0.0206 (7)	0.0110 (7)	−0.0015 (7)	−0.0010 (6)	0.0000 (6)
C6	0.0134 (12)	0.0112 (10)	0.0114 (11)	0.000	0.000	−0.0019 (9)
C3	0.0102 (9)	0.0260 (9)	0.0137 (8)	0.0023 (7)	−0.0009 (7)	0.0026 (7)
C1	0.0084 (12)	0.0124 (11)	0.0132 (11)	0.000	0.000	0.0007 (9)

Geometric parameters (Å, º) top

Sr—O1	2.501 (2)	C2—C3	1.387 (2)
Sr—O1ⁱ	2.501 (2)	C2—C1	1.495 (3)
Sr—O3	2.522 (2)	N1—C6	1.335 (2)
Sr—O2	2.549 (3)	N1—N2	1.340 (2)
Sr—O1ⁱⁱ	2.6602 (14)	C4—C5	1.389 (2)
Sr—O1ⁱⁱⁱ	2.6602 (14)	C4—C3	1.390 (2)
Sr—O4	2.6757 (18)	C4—H4A	0.9300
Sr—O4ⁱⁱ	2.6757 (18)	C5—C4^iv	1.389 (2)
O4—H4	0.89 (2)	C5—C6	1.475 (3)
O2—H2	0.77 (3)	N2—N2^iv	1.316 (4)
O3—H3	0.846 (16)	C6—N1^iv	1.335 (2)
O1—C1	1.2635 (19)	C3—H3A	0.9300
C2—C3^iv	1.387 (2)	C1—O1^iv	1.2635 (19)

O1—Sr—O1ⁱ	140.67 (7)	O4ⁱⁱ—Sr—Srⁱⁱ	43.74 (4)
O1—Sr—O3	85.19 (4)	C1ⁱⁱ—Sr—Srⁱⁱ	64.037 (19)
O1ⁱ—Sr—O3	85.20 (4)	O1—Sr—Sr^v	43.07 (4)
O1—Sr—O2	72.67 (4)	O1ⁱ—Sr—Sr^v	162.46 (3)
O1ⁱ—Sr—O2	72.67 (4)	O3—Sr—Sr^v	111.97 (2)
O3—Sr—O2	103.31 (9)	O2—Sr—Sr^v	98.82 (3)
O1—Sr—O1ⁱⁱ	124.21 (4)	O1ⁱⁱ—Sr—Sr^v	88.51 (4)
O1ⁱ—Sr—O1ⁱⁱ	77.42 (5)	O1ⁱⁱⁱ—Sr—Sr^v	39.95 (3)
O3—Sr—O1ⁱⁱ	148.91 (4)	O4—Sr—Sr^v	43.74 (4)
O2—Sr—O1ⁱⁱ	95.91 (7)	O4ⁱⁱ—Sr—Sr^v	115.64 (3)
O1—Sr—O1ⁱⁱⁱ	77.42 (5)	C1ⁱⁱ—Sr—Sr^v	64.037 (19)
O1ⁱ—Sr—O1ⁱⁱⁱ	124.21 (5)	Srⁱⁱ—Sr—Sr^v	126.79 (4)
O3—Sr—O1ⁱⁱⁱ	148.91 (4)	Sr—O4—Sr^v	92.52 (8)
O2—Sr—O1ⁱⁱⁱ	95.91 (7)	Sr—O4—H4	114.6 (18)
O1ⁱⁱ—Sr—O1ⁱⁱⁱ	48.93 (6)	Sr^v—O4—H4	108.9 (17)
O1—Sr—O4	68.20 (5)	Sr—O2—H2	129 (2)
O1ⁱ—Sr—O4	147.71 (5)	Sr—O3—H3	121.9 (18)
O3—Sr—O4	83.72 (5)	C1—O1—Sr	162.79 (14)
O2—Sr—O4	139.50 (4)	C1—O1—Sr^v	94.66 (12)
O1ⁱⁱ—Sr—O4	97.37 (4)	Sr—O1—Sr^v	96.98 (5)
O1ⁱⁱⁱ—Sr—O4	66.00 (5)	C3^iv—C2—C3	119.4 (2)
O1—Sr—O4ⁱⁱ	147.71 (5)	C3^iv—C2—C1	120.32 (11)
O1ⁱ—Sr—O4ⁱⁱ	68.20 (5)	C3—C2—C1	120.32 (11)
O3—Sr—O4ⁱⁱ	83.72 (5)	C6—N1—N2	104.81 (16)
O2—Sr—O4ⁱⁱ	139.50 (4)	C5—C4—C3	120.41 (18)
O1ⁱⁱ—Sr—O4ⁱⁱ	66.00 (5)	C5—C4—H4A	119.8
O1ⁱⁱⁱ—Sr—O4ⁱⁱ	97.37 (4)	C3—C4—H4A	119.8
O4—Sr—O4ⁱⁱ	80.48 (7)	C4—C5—C4^iv	119.1 (2)
O1—Sr—C1ⁱⁱ	101.29 (3)	C4—C5—C6	120.42 (11)
O1ⁱ—Sr—C1ⁱⁱ	101.29 (3)	C4^iv—C5—C6	120.42 (11)
O3—Sr—C1ⁱⁱ	158.83 (7)	N2^iv—N2—N1	109.42 (10)
O2—Sr—C1ⁱⁱ	97.87 (9)	N1^iv—C6—N1	111.5 (2)
O1ⁱⁱ—Sr—C1ⁱⁱ	24.50 (3)	N1^iv—C6—C5	124.22 (11)
O1ⁱⁱⁱ—Sr—C1ⁱⁱ	24.50 (3)	N1—C6—C5	124.22 (11)
O4—Sr—C1ⁱⁱ	80.16 (4)	C2—C3—C4	120.34 (18)
O4ⁱⁱ—Sr—C1ⁱⁱ	80.16 (4)	C2—C3—H3A	119.8
O1—Sr—Srⁱⁱ	162.46 (3)	C4—C3—H3A	119.8
O1ⁱ—Sr—Srⁱⁱ	43.07 (4)	O1—C1—O1^iv	121.4 (2)
O3—Sr—Srⁱⁱ	111.97 (2)	O1—C1—C2	119.31 (11)
O2—Sr—Srⁱⁱ	98.82 (3)	O1^iv—C1—C2	119.31 (11)
O1ⁱⁱ—Sr—Srⁱⁱ	39.95 (3)	O1—C1—Sr^v	60.84 (11)
O1ⁱⁱⁱ—Sr—Srⁱⁱ	88.51 (4)	O1^iv—C1—Sr^v	60.84 (11)
O4—Sr—Srⁱⁱ	115.64 (3)	C2—C1—Sr^v	174.84 (17)

O1—Sr—O4—Sr^v	43.94 (4)	O4ⁱⁱ—Sr—O1—Sr^v	−59.57 (8)
O1ⁱ—Sr—O4—Sr^v	−158.12 (6)	C1ⁱⁱ—Sr—O1—Sr^v	29.86 (6)
O3—Sr—O4—Sr^v	131.27 (4)	Srⁱⁱ—Sr—O1—Sr^v	61.70 (12)
O2—Sr—O4—Sr^v	28.11 (11)	C3—C4—C5—C4^iv	0.2 (4)
O1ⁱⁱ—Sr—O4—Sr^v	−80.03 (4)	C3—C4—C5—C6	−178.7 (2)
O1ⁱⁱⁱ—Sr—O4—Sr^v	−41.54 (3)	C6—N1—N2—N2^iv	−0.35 (16)
O4ⁱⁱ—Sr—O4—Sr^v	−144.08 (2)	N2—N1—C6—N1^iv	0.6 (3)
C1ⁱⁱ—Sr—O4—Sr^v	−62.52 (4)	N2—N1—C6—C5	−178.6 (2)
Srⁱⁱ—Sr—O4—Sr^v	−117.34 (3)	C4—C5—C6—N1^iv	−0.1 (4)
O1ⁱ—Sr—O1—C1	−74.0 (5)	C4^iv—C5—C6—N1^iv	−179.0 (2)
O3—Sr—O1—C1	2.4 (5)	C4—C5—C6—N1	179.0 (2)
O2—Sr—O1—C1	−103.1 (5)	C4^iv—C5—C6—N1	0.1 (4)
O1ⁱⁱ—Sr—O1—C1	171.6 (5)	C3^iv—C2—C3—C4	−0.5 (4)
O1ⁱⁱⁱ—Sr—O1—C1	156.5 (5)	C1—C2—C3—C4	179.0 (2)
O4—Sr—O1—C1	87.6 (5)	C5—C4—C3—C2	0.1 (3)
O4ⁱⁱ—Sr—O1—C1	72.7 (5)	Sr—O1—C1—O1^iv	−138.6 (3)
C1ⁱⁱ—Sr—O1—C1	162.1 (5)	Sr^v—O1—C1—O1^iv	−6.2 (3)
Srⁱⁱ—Sr—O1—C1	−166.1 (4)	Sr—O1—C1—C2	41.6 (6)
Sr^v—Sr—O1—C1	132.2 (5)	Sr^v—O1—C1—C2	174.1 (2)
O1ⁱ—Sr—O1—Sr^v	153.83 (6)	Sr—O1—C1—Sr^v	−132.5 (5)
O3—Sr—O1—Sr^v	−129.77 (7)	C3^iv—C2—C1—O1	179.6 (2)
O2—Sr—O1—Sr^v	124.67 (8)	C3—C2—C1—O1	0.1 (4)
O1ⁱⁱ—Sr—O1—Sr^v	39.36 (9)	C3^iv—C2—C1—O1^iv	−0.1 (4)
O1ⁱⁱⁱ—Sr—O1—Sr^v	24.29 (6)	C3—C2—C1—O1^iv	−179.6 (2)
O4—Sr—O1—Sr^v	−44.63 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1^vi	0.85 (2)	1.96 (2)	2.800 (2)	171 (3)
O3—H3···N2^vi	0.85 (2)	2.62 (2)	3.314 (3)	141 (2)
O2—H2···N2^vii	0.77 (3)	2.53 (3)	3.270 (3)	160 (3)
O4—H4···N2^viii	0.87 (2)	1.93 (2)	2.784 (2)	166 (2)

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

Acknowledgements

We would like to thank S. Maza and the Fluorescence Spectroscopy staff at the National Biotechnology Research Center, Constantine, Algeria.

Funding information

Funding for this research was provided by: Unité de Recherche de Chimie Moléculaire et Structurale (UR.CHEMS); Direction Générale de la Recherche Scientifique et du Developpement Technologique (DGRSDT) Algérie.

References

Alexandrov, E. V., Blatov, V. A., Kochetkov, A. V. & Proserpio, D. M. (2011). CrystEngComm, 13, 3947–3958. Web of Science CrossRef CAS Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Baggio, R., Stoilova, D., Polla, G., Leyva, G. & Garland, M. T. (2004). J. Mol. Struct. 697, 173–180. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Casanova, D., Llunell, M., Alemany, P. & Alvarez, S. (2005). Chem. Eur. J. 11, 1479–1494. Web of Science CrossRef PubMed CAS Google Scholar
Cheng, M., Ding, Y.-S., Zhang, Z. & Jia, Q.-X. (2016). Inorg. Chim. Acta, 450, 1–7. CSD CrossRef CAS Google Scholar
Damavarapu, R., Klapötke, T. M., Stierstorfer, J. & Tarantik, K. R. (2010). Propellants, Explosives, Pyrotech. 35, 395–406. Google Scholar
Demko, Z. P. & Sharpless, K. B. (2001). J. Org. Chem. 66, 7945–7950. Web of Science CrossRef PubMed CAS Google Scholar
Divya, R., Nair, L. P., Bijini, B. R., Nair, C. M. K., Gopakumar, N. & Babu, K. R. (2017). Physica B, 526, 37–44. CSD CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fischer, N., Klapötke, T. M., Peters, K., Rusan, M. & Stierstorfer, J. (2011). Z. Anorg. Allg. Chem. 637, 1693–1701. CSD CrossRef CAS Google Scholar
Fu, D.-W., Dai, J., Ge, J.-Z., Ye, H.-Y. & Qu, Z.-R. (2010). Inorg. Chem. Commun. 13, 282–285. Web of Science CSD CrossRef CAS Google Scholar
Gao, J.-X., Xiong, J. B., Xu, Q., Tan, Y. H., Liu, Y., Wen, H. R. & Tang, Y. Z. (2016). Cryst. Growth Des. 16, 1559–1564. CSD CrossRef CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hammerl, A., Holl, G., Kaiser, M., Klapötke, Th. M. & Piotrowski, H. (2003). Z. Anorg. Allg. Chem. 629, 2117–2121. CSD CrossRef CAS Google Scholar
Hammerl, A., Holl, G., Klapötke, Th. M., Mayer, P., Nöth, H., Piotrowski, H. & Warchhold, M. (2002). Eur. J. Inorg. Chem. pp. 834–845. CSD CrossRef Google Scholar
Hari, N., Jana, A. & Mohanta, S. (2017). Inorg. Chim. Acta, 467, 11–20. CSD CrossRef CAS Google Scholar
Hartdegen, V., Klapötke, T. M. & Sproll, S. M. (2009). Inorg. Chem. 48, 9549–9556. Web of Science CSD CrossRef PubMed CAS Google Scholar
Jiang, T., Zhao, Y.-F. & Zhang, X.-M. (2007). Inorg. Chem. Commun. 10, 1194–1197. Web of Science CSD CrossRef CAS Google Scholar
Klapötke, T. M. & Stierstorfer, J. (2009). J. Am. Chem. Soc. 131, 1122–1134. PubMed Google Scholar
Koşar, B., Albayrak, C., Ersanlı, C. C., Odabaşoğlu, M. & Büyükgüngör, O. (2012). Spectrochim. Acta A Mol. Biomol. Spectrosc. 93, 1–9. PubMed Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ouellette, W., Darling, K. & Zubieta, J. (2012). Inorg. Chim. Acta, 391, 36–43. CSD CrossRef CAS Google Scholar
Ouellette, W., Liu, H., O'Connor, C. J. & Zubieta, J. (2009). Inorg. Chem. 48, 4655–4657. CSD CrossRef PubMed CAS Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheng, D.-H., Dan, W.-Y., Luo, G.-X. & Deng, M.-L. (2016). Chin. J. Struct. Chem. 35, 264–270. CAS Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Sun, J.-Y., Wang, L., Zhang, D.-J., Li, D., Cao, Y., Zhang, L.-Y., Zeng, S.-L., Pang, G.-S., Fan, Y., Xu, J.-N. & Song, T.-Y. (2013). CrystEngComm, 15, 3402–3411. CSD CrossRef CAS Google Scholar
Wang, D., Zhang, L., Li, G., Huo, Q. & Liu, Y. (2015). RSC Adv. 5, 18087–18091. CSD CrossRef CAS Google Scholar
Wang, J., Nie, J. & Dai, C. (2011). J. Coord. Chem. 64, 1645–1653. CSD CrossRef CAS Google Scholar
Wei, Q., Yang, D., Larson, T. E., Kinnibrugh, T. L., Zou, R., Henson, N. J., Timofeeva, T., Xu, H., Zhao, Y. & Mattes, B. R. (2012). J. Mater. Chem. 22, 10166–10171. CSD CrossRef CAS Google Scholar
Werrett, M. V., Huff, G. S., Muzzioli, S., Fiorini, V., Zacchini, S., Skelton, B. W., Maggiore, A., Malicka, J. M., Cocchi, M., Gordon, K. C., Stagni, S. & Massi, M. (2015). Dalton Trans. 44, 8379–8393. CSD CrossRef CAS PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, H.-Y., Li, Y.-Z., Shi, W.-J., Hou, L., Wang, Y. & Zhu, Z. (2017). Dalton Trans. 46, 11722–11727. CSD CrossRef CAS PubMed Google Scholar
Yao, R.-X., Qin, Y.-L., Ji, F., Zhao, Y.-F. & Zhang, X.-M. (2013). Dalton Trans. 42, 6611–6618. CSD CrossRef CAS PubMed Google Scholar
Yu, Z.-P., Xiong, S.-S., Yong, G.-P. & Wang, Z.-Y. (2009). J. Coord. Chem. 62, 242–248. CSD CrossRef CAS Google Scholar
Zhang, T., Li, R. F., Tian, A. Q., Feng, X. & Tian, P. H. (2016). Chin. J. Struct. Chem. 35, 1122–1128. CAS Google Scholar
Zhang, X. B., Ren, Y. H., Li, W., Zhao, F. Q., Yi, J. H., Wang, B. Z. & Song, J. R. (2013). J. Coord. Chem. 66, 2051–2064. CSD CrossRef CAS Google Scholar
Zhao, H., Qu, Z.-R., Ye, H.-Y. & Xiong, R.-G. (2008). Chem. Soc. Rev. 37, 84–100. Web of Science CrossRef PubMed Google Scholar
Zheng, S.-L., Wang, Y., Yu, Z., Lin, Q. & Coppens, P. (2009). J. Am. Chem. Soc. 131, 18036–18037. CSD CrossRef PubMed CAS Google Scholar

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Volume 76| Part 6| June 2020| Pages 877-883

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