Crystal structure of strontium and barium acesulafame (6-methyl-4-oxo-4H-1,2,3-oxa-thia-zin-3-ide 2,2-dioxide).

Both strontium and barium acesulfames, namely poly[aqua-bis-(μ3-6-methyl-2,2-dioxo-1,2λ6,3-oxa-thia-zin-4-olato)strontium(II)], [Sr(C4H4NO4S)2(H2O)] n , and the barium(II) analogue, [Ba(C4H4NO4S)2(H2O)] n , crystallize in nearly identical isotypic forms, with barium-oxygen inter-atomic distances being longer due to the larger ionic radius of the barium(II) ion. The coordination number of the metal ion is 9; the coordination polyhedra can be described as distorted capped square anti-prisms [Johnson solid J10; Johnson (1966). Can. J. Math.18, 169-200]. The conformation of the acesulafame ions is a distorted envelope with an out-of-plane S atom. Metal and acesulfame ions are assembled into infinitive chains along the [100] axis. These chains are connected via hydrogen bonds into a three-dimensional network.

Chemical context

Acesulfame is one of the most common sweeteners; usually it is used in the form of a potassium salt. Salts with all alkali metals, ammonium, magnesium, and calcium ions, as well as its protonated mol­ecular form, are also known. The almost identical crystal structures of the strontium and barium salts are reported here.

Structural commentary

Both the strontium and barium compounds crystallize in nearly identical isotypic forms (Fig. 1 ▸), with the barium–oxygen inter­atomic distances being longer due to the larger ionic radius of the barium(II) ion (Tables 1 ▸ and 2 ▸). Because of the similarity of the structures, representations would be visually identical, and all figures are shown for the strontium salt only. In both cases, the coordination sphere of the metal ion contains a water mol­ecule, two O atoms from carbonyl groups, two O atoms from sulfonyl fragments, and two bidentate amide groups coordinated through both their carbonyl group and the adjacent deprotonated N atom (Fig. 2 ▸). The total coordination number is nine. This coordination polyhedron can be described as a distorted capped square anti­prism. The corresponding ideal polyhedron is a gyro­elongated square pyramid, a Johnson solid J10 (Johnson, 1966 ▸). In this case, the base of the polyhedron is not a square but a rectangle formed by two N and two O atoms from two bidentate amide groups. Nitro­gen–oxygen distances within each of the groups are practically the same: N1i⋯O2i = 2.232 (2) Å and N2iii⋯O6iii = 2.233 (2) Å (Sr); and N1i⋯O2i = 2.233 (3) Å and N2iii⋯O6iii = 2.239 (2) Å (Ba). The inter­atomic separations between these groups are much longer: N1i⋯O6iii = 3.0609 (19) (Sr) and 3.174 (3) Å (Ba), and N2iii⋯O2i = 3.0787 (18) (Sr) and 3.184 (3) Å (Ba) [symmetry codes: (i) −x + 1, −y + 1, −z + 1; (iii) −x + 2, −y + 1, −z + 1.]

Figure 1

The numbering scheme of strontium acesulfame monohydrate, shown with 50% probability displacement elipsoids.

Table 1

Selected bond lengths (Å) for Sr

Sr1—O1	2.6000 (14)	Sr1—O6iii	2.8070 (13)
Sr1—O2i	2.9039 (14)	Sr1—O9iv	2.5782 (12)
Sr1—O2	2.5026 (12)	Sr1—N1i	2.7553 (15)
Sr1—O5ii	2.5790 (13)	Sr1—N2iii	2.7447 (14)
Sr1—O6	2.5116 (12)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Table 2

Selected bond lengths (Å) for Ba

Ba1—O1	2.732 (2)	Ba1—O6iii	2.9192 (18)
Ba1—O2i	2.9714 (19)	Ba1—O9iv	2.7478 (18)
Ba1—O2	2.6812 (17)	Ba1—N1i	2.921 (2)
Ba1—O5ii	2.7560 (18)	Ba1—N2iii	2.9077 (19)
Ba1—O6	2.6788 (16)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Figure 2

The coordination polyhedron of the Sr metal ion. Symmetry codes for the base rectangle atoms are: N1 and O2 at (−x + 1, −y + 1, −z + 1), N2 and O6 at (−x + 2, −y + 1, −z + 1). For the upper rectangle: O9 is at (x − 1, y, z) and O5 is at (x + 1, y, z).

Deviations from exact right angles are around 5° for the Sr and 1.5° for the Ba structure. The upper square of the coordination polyhedron is less distorted, with angles very close (mostly within 1°) to 90°. The two average planes of the base rectangle and upper square are nearly coplanar, with the angles between them being 1.17 (4) (Sr) and 0.99 (6)° (Ba). The line between the metal ions and the capping oxygen of the water mol­ecules are nearly perpendicular to these planes: the angles between the upper plane normal and the connecting line are 4.90 (4) (Sr) and 5.58 (6)° (Ba).

The geometries of the two acesulfame anions in each structure are very similar to each other (Fig. 3 ▸), as well as to those of previously reported compounds. The six-membered rings have only one atom with a tetra­hedral environment (S). The other five atoms deviate only slightly from their average planes (Fig. 4 ▸). This conformation can be described as an envelope, slightly distorted toward a boat.

Figure 3

Overlay of the two acesulafame ions in the Sr structure.

Figure 4

View of the acesulafame anion in the Sr structure. Deviations from the average plane of five atoms in six-membered ring are 0.031 (N1), −0.010 (O3), −0.011 (C3), +0.042 (C2), −0.052 (C1) and 0.5377 (15) Å (S1).

Supra­molecular features

Each acesulfame anion is connected to three strontium (or barium) ions via a bridging O atom of the amide carbonyl group, an N atom of this group, and one of the O atoms of a sulfonyl group. Each metal ion is directly connected to six acesulfame anions. As a result, metal ions and acesulfame anions form infinite chains along the [100] axis (Fig. 5 ▸). The O atoms of the two sulfonyl groups that are not connected to metal ions form, instead, strong hydrogen bonds with both H atoms of the water mol­ecule. These hydrogen bonds (Tables 3 ▸ and 4 ▸) connect each chain to four neighboring parellel chains, thus creating a three-dimensional assembly (Fig. 6 ▸). There are also two short C—H⋯O contacts (Tables 3 ▸ and 4 ▸) which may additionally stabilize the crystal structures.

Figure 5

The infinite chain of metal ions and acesulafame anions along the [100] axis. The view is along the [010] vector.

Table 3

Hydrogen-bond geometry (Å, °) for Sr

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4v	0.79 (3)	2.18 (3)	2.899 (2)	151 (3)
O1—H1B⋯O8vi	0.83 (3)	2.22 (3)	2.9850 (19)	152 (3)
C4—H4B⋯O5v	0.98	2.37	3.273 (3)	153
C6—H6⋯O8vi	0.95	2.47	3.318 (2)	148

Symmetry codes: (v) ; (vi) .

Table 4

Hydrogen-bond geometry (Å, °) for Ba

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4v	0.74 (4)	2.12 (4)	2.829 (3)	162 (4)
O1—H1B⋯O8vi	0.74 (4)	2.20 (4)	2.889 (3)	156 (4)
C4—H4B⋯O5v	0.98	2.44	3.361 (4)	155
C6—H6⋯O8vi	0.95	2.52	3.357 (3)	147

Symmetry codes: (v) ; (vi) .

Figure 6

The packing of Sr acesulafame, viewed along the [100] axis.

Database survey

There are over 40 acesulfame structures deposited in the Cambridge Structural Database (CSD; Groom et al., 2016 ▸; Version 5.38). Of these structures, alkali metal, ammonium, and thallium salts FEQPUP (Piro et al., 2017 ▸), KMTOZD (Paulus, 1975 ▸), SUQTOP, SURCIT and SURCOZ (Piro et al., 2015 ▸), TOFPEL (Echeverría et al., 2014 ▸), OCAHUY (Baran et al., 2015 ▸), magnesium salt XAGVAF (Piro et al., 2016 ▸), calcium salt EXUCOR (Demirtas et al., 2012 ▸), and protonated forms WURMOM and WURMOM01 (Velaga et al., 2010 ▸) are closely related to the structures of the title compounds. Several other structures describe coordination compounds with transition-metal ions and various salts of bulky organic cations.

Synthesis and crystallization

The protonated form of acesulfame, 6-methyl-1,2,3-oxa­thia­zin-4(3H)-one 2,2-dioxide, was synthesized following a published procedure (Velaga et al., 2010 ▸). The starting compound, potassium acesulfame, was obtained at a stated purity of 99% and no attempt was made at further purification. 2 g (0.01 mol) of it were dissolved in water (10 ml), acidified with 10 ml of 6 M HCl, and extracted with several portions of methyl­ene chloride (15 ml each). Evaporation of the methyl­ene chloride extract resulted in crystals of protonated acesulfame (identified by X-ray diffraction; CSD refcode WURMOM). Both strontium oxide (100 mg, 0.001 mol) and barium oxide (150 mg, 0.001 mol) were treated with a small amount of water (ca 10 ml), forming the corresponding hydroxides. Stoichiometric amounts (0.002 mol, 320 mg) of 6-methyl-1,2,3-oxa­thia­zin-4(3H)-one 2,2-dioxide were added under gentle heating to neutralize the alkaline solutions. Slow evaporation of the filtrated solutions resulted in colorless crystals (around 100 mg), some of which were suitable for X-ray investigation. No attempts to optimize the reaction conditions or to recover more material were made. Several crystals were tested; the best results obtained are reported here. FT-IR-ATR, Sr–acesulfame (cm−1): 3620, 3550 (H2O), 1641 (amide), 1555, 1173 (SO2), 938.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5 ▸. All H atoms of water mol­ecules are refined in isotropic approximation. All other H atoms are refined with riding coordinates; methyl H atoms are refined as rotating idealized methyl groups and with U iso(H) = 1.5U iso(C).

Table 5

Experimental details

	Sr complex	Ba complex
Crystal data
Chemical formula	[Sr(C4H4NO4S)2(H2O)]	[Ba(C4H4NO4S)2(H2O)]
M r	429.92	479.64
Crystal system, space group	Monoclinic, P21/n	Monoclinic, P21/n
Temperature (K)	173	173
a, b, c (Å)	7.9695 (3), 18.5217 (8), 9.7310 (4)	8.2086 (5), 18.8899 (11), 9.8999 (6)
β (°)	99.651 (1)	99.5197 (10)
V (Å3)	1416.05 (10)	1513.93 (16)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm−1)	4.15	2.94
Crystal size (mm)	0.55 × 0.13 × 0.07	0.52 × 0.21 × 0.20
Data collection
Diffractometer	Bruker PHOTON-100 CMOS	Bruker PHOTON-100 CMOS
Absorption correction	Numerical (SADABS; Krause et al., 2015 ▸)	Numerical (SADABS; Krause et al., 2015 ▸)
T min, T max	0.228, 0.797	0.309, 0.635
No. of measured, independent and observed [I > 2σ(I)] reflections	54583, 5414, 4548	41654, 6324, 5218
R int	0.043	0.048
(sin θ/λ)max (Å−1)	0.771	0.794
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.027, 0.062, 1.04	0.032, 0.059, 1.09
No. of reflections	5414	6324
No. of parameters	209	209
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
Δρmax, Δρmin (e Å−3)	0.73, −0.46	1.02, −0.61

Computer programs: APEX2 and SAINT (Bruker, 2013 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2016 (Sheldrick, 2015b ▸) and OLEX2 (Dolomanov et al., 2009 ▸).

Crystal structure: contains datablock(s) Ba, Sr. DOI: 10.1107/S2056989018006059/zl2727sup1.cif

Structure factors: contains datablock(s) Sr. DOI: 10.1107/S2056989018006059/zl2727Srsup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989018006059/zl2727Srsup4.cdx

Structure factors: contains datablock(s) Ba. DOI: 10.1107/S2056989018006059/zl2727Basup3.hkl

CCDC references: 1838460, 1838459

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Sr(C4H4NO4S)2(H2O)]	F(000) = 856
Mr = 429.92	Dx = 2.017 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.9695 (3) Å	Cell parameters from 9082 reflections
b = 18.5217 (8) Å	θ = 3.1–33.3°
c = 9.7310 (4) Å	µ = 4.15 mm−1
β = 99.651 (1)°	T = 173 K
V = 1416.05 (10) Å3	Needle, colourless
Z = 4	0.55 × 0.13 × 0.07 mm

Bruker PHOTON-100 CMOS diffractometer	4548 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.043
Absorption correction: numerical (SADABS; Krause et al., 2015)	θmax = 33.2°, θmin = 3.1°
Tmin = 0.228, Tmax = 0.797	h = −12→12
54583 measured reflections	k = −28→28
5414 independent reflections	l = −14→14

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)] = 0.027	Hydrogen site location: mixed
wR(F2) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0247P)2 + 1.3759P] where P = (Fo2 + 2Fc2)/3
5414 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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.

	x	y	z	Uiso*/Ueq
Sr1	0.73894 (2)	0.46960 (2)	0.43922 (2)	0.01161 (4)
S1	0.07248 (5)	0.32528 (2)	0.53917 (4)	0.01432 (7)
S2	1.37055 (5)	0.52355 (2)	0.16245 (4)	0.01457 (8)
O1	0.69696 (19)	0.37734 (8)	0.23495 (15)	0.0236 (3)
H1A	0.703 (4)	0.3346 (16)	0.232 (3)	0.038 (8)*
H1B	0.656 (4)	0.3914 (17)	0.155 (3)	0.049 (9)*
O2	0.46642 (16)	0.41317 (7)	0.48048 (14)	0.0216 (3)
O3	0.04339 (16)	0.28794 (7)	0.38723 (14)	0.0207 (3)
O4	0.11859 (18)	0.26877 (7)	0.63821 (14)	0.0247 (3)
O5	−0.08823 (16)	0.35905 (7)	0.54351 (14)	0.0200 (2)
O6	1.00611 (16)	0.48946 (7)	0.33932 (13)	0.0185 (2)
O7	1.34454 (16)	0.44775 (8)	0.07948 (14)	0.0218 (3)
O8	1.31994 (17)	0.57900 (8)	0.06234 (13)	0.0223 (3)
O9	1.54716 (15)	0.52276 (7)	0.22320 (13)	0.0197 (2)
N1	0.21644 (18)	0.38308 (8)	0.53881 (15)	0.0159 (3)
N2	1.25495 (18)	0.51967 (8)	0.27867 (14)	0.0162 (3)
C1	0.3450 (2)	0.36951 (9)	0.46730 (17)	0.0149 (3)
C2	0.3318 (2)	0.30990 (10)	0.36758 (18)	0.0191 (3)
H2	0.4300	0.2956	0.3311	0.023*
C3	0.1853 (2)	0.27495 (10)	0.32641 (18)	0.0188 (3)
C4	0.1419 (3)	0.22384 (12)	0.2083 (2)	0.0310 (4)
H4A	0.0983	0.1789	0.2419	0.046*
H4B	0.2441	0.2135	0.1680	0.046*
H4C	0.0548	0.2454	0.1370	0.046*
C5	1.1042 (2)	0.48462 (9)	0.25133 (17)	0.0142 (3)
C6	1.0638 (2)	0.43825 (10)	0.12897 (17)	0.0175 (3)
H6	0.9511	0.4203	0.1040	0.021*
C7	1.1800 (2)	0.42032 (10)	0.05129 (17)	0.0186 (3)
C8	1.1604 (3)	0.36965 (12)	−0.0686 (2)	0.0312 (4)
H8A	1.1812	0.3954	−0.1521	0.047*
H8B	1.0446	0.3500	−0.0848	0.047*
H8C	1.2424	0.3301	−0.0480	0.047*

	U11	U22	U33	U12	U13	U23
Sr1	0.01046 (6)	0.01363 (7)	0.01116 (6)	−0.00146 (5)	0.00300 (4)	−0.00080 (5)
S1	0.01438 (17)	0.01221 (16)	0.01734 (18)	−0.00014 (13)	0.00547 (13)	−0.00002 (13)
S2	0.01118 (16)	0.0224 (2)	0.01036 (16)	−0.00041 (14)	0.00245 (12)	−0.00008 (14)
O1	0.0324 (7)	0.0183 (6)	0.0196 (6)	−0.0036 (5)	0.0034 (5)	−0.0044 (5)
O2	0.0156 (6)	0.0261 (7)	0.0230 (6)	−0.0074 (5)	0.0032 (5)	0.0018 (5)
O3	0.0161 (6)	0.0236 (6)	0.0235 (6)	−0.0044 (5)	0.0061 (5)	−0.0086 (5)
O4	0.0291 (7)	0.0179 (6)	0.0278 (7)	0.0027 (5)	0.0068 (5)	0.0079 (5)
O5	0.0156 (5)	0.0187 (6)	0.0280 (7)	0.0015 (5)	0.0101 (5)	0.0016 (5)
O6	0.0160 (5)	0.0223 (6)	0.0189 (6)	−0.0016 (5)	0.0085 (5)	−0.0008 (5)
O7	0.0185 (6)	0.0283 (7)	0.0202 (6)	−0.0013 (5)	0.0077 (5)	−0.0082 (5)
O8	0.0196 (6)	0.0301 (7)	0.0168 (6)	0.0013 (5)	0.0020 (5)	0.0068 (5)
O9	0.0113 (5)	0.0322 (7)	0.0153 (5)	−0.0004 (5)	0.0016 (4)	0.0019 (5)
N1	0.0139 (6)	0.0156 (6)	0.0190 (6)	−0.0005 (5)	0.0049 (5)	−0.0018 (5)
N2	0.0132 (6)	0.0233 (7)	0.0124 (6)	−0.0028 (5)	0.0029 (5)	−0.0021 (5)
C1	0.0129 (6)	0.0160 (7)	0.0155 (7)	0.0003 (5)	0.0014 (5)	0.0042 (5)
C2	0.0178 (7)	0.0211 (8)	0.0201 (8)	0.0020 (6)	0.0077 (6)	−0.0022 (6)
C3	0.0213 (8)	0.0174 (8)	0.0190 (8)	0.0012 (6)	0.0066 (6)	−0.0017 (6)
C4	0.0377 (11)	0.0292 (10)	0.0274 (10)	−0.0034 (9)	0.0092 (8)	−0.0135 (8)
C5	0.0120 (6)	0.0177 (7)	0.0130 (7)	0.0006 (5)	0.0024 (5)	0.0028 (5)
C6	0.0162 (7)	0.0220 (8)	0.0138 (7)	−0.0033 (6)	0.0008 (6)	−0.0008 (6)
C7	0.0217 (8)	0.0199 (8)	0.0137 (7)	−0.0022 (6)	0.0016 (6)	−0.0014 (6)
C8	0.0420 (12)	0.0308 (10)	0.0223 (9)	−0.0102 (9)	0.0099 (8)	−0.0113 (8)

Sr1—Sr1i	4.2816 (3)	O5—Sr1iv	2.5789 (13)
Sr1—O1	2.6000 (14)	O6—Sr1i	2.8070 (13)
Sr1—O2ii	2.9039 (14)	O6—C5	1.2556 (19)
Sr1—O2	2.5026 (12)	O7—C7	1.390 (2)
Sr1—O5iii	2.5790 (13)	O9—Sr1iii	2.5782 (12)
Sr1—O6	2.5116 (12)	N1—Sr1ii	2.7553 (15)
Sr1—O6i	2.8070 (13)	N1—C1	1.355 (2)
Sr1—O9iv	2.5782 (12)	N2—Sr1i	2.7448 (14)
Sr1—N1ii	2.7553 (15)	N2—C5	1.352 (2)
Sr1—N2i	2.7447 (14)	C1—Sr1ii	3.2186 (17)
Sr1—C1ii	3.2186 (17)	C1—C2	1.462 (2)
Sr1—C5i	3.1761 (16)	C2—H2	0.9500
S1—O3	1.6134 (13)	C2—C3	1.336 (2)
S1—O4	1.4285 (13)	C3—C4	1.484 (3)
S1—O5	1.4323 (13)	C4—H4A	0.9800
S1—N1	1.5697 (15)	C4—H4B	0.9800
S2—O7	1.6156 (14)	C4—H4C	0.9800
S2—O8	1.4264 (13)	C5—Sr1i	3.1762 (16)
S2—O9	1.4324 (13)	C5—C6	1.460 (2)
S2—N2	1.5755 (14)	C6—H6	0.9500
O1—H1A	0.79 (3)	C6—C7	1.332 (2)
O1—H1B	0.84 (3)	C7—C8	1.485 (3)
O2—Sr1ii	2.9040 (14)	C8—H8A	0.9800
O2—C1	1.251 (2)	C8—H8B	0.9800
O3—C3	1.383 (2)	C8—H8C	0.9800
O1—Sr1—Sr1i	112.25 (3)	O4—S1—O5	115.48 (8)
O1—Sr1—O2ii	133.71 (4)	O4—S1—N1	113.32 (8)
O1—Sr1—O6i	138.44 (4)	O5—S1—O3	102.85 (7)
O1—Sr1—N1ii	135.12 (5)	O5—S1—N1	111.08 (8)
O1—Sr1—N2i	142.25 (5)	N1—S1—O3	106.45 (7)
O1—Sr1—C1ii	144.92 (5)	O8—S2—O7	106.65 (8)
O1—Sr1—C5i	151.65 (5)	O8—S2—O9	115.79 (8)
O2—Sr1—Sr1i	153.49 (3)	O8—S2—N2	113.00 (8)
O2ii—Sr1—Sr1i	107.12 (3)	O9—S2—O7	103.43 (8)
O2—Sr1—O1	81.04 (5)	O9—S2—N2	110.83 (8)
O2—Sr1—O2ii	74.08 (5)	N2—S2—O7	106.12 (7)
O2—Sr1—O5iii	91.48 (4)	Sr1—O1—H1A	133 (2)
O2—Sr1—O6	159.74 (4)	Sr1—O1—H1B	119 (2)
O2—Sr1—O6i	121.71 (4)	H1A—O1—H1B	107 (3)
O2—Sr1—O9iv	83.02 (4)	Sr1—O2—Sr1ii	105.92 (5)
O2—Sr1—N1ii	120.35 (4)	C1—O2—Sr1	158.55 (12)
O2—Sr1—N2i	74.94 (4)	C1—O2—Sr1ii	92.84 (10)
O2ii—Sr1—C1ii	22.85 (4)	C3—O3—S1	117.69 (11)
O2—Sr1—C1ii	96.57 (4)	S1—O5—Sr1iv	139.14 (7)
O2ii—Sr1—C5i	72.26 (4)	Sr1—O6—Sr1i	107.09 (4)
O2—Sr1—C5i	100.00 (4)	C5—O6—Sr1i	95.14 (10)
O5iii—Sr1—Sr1i	70.73 (3)	C5—O6—Sr1	156.71 (12)
O5iii—Sr1—O1	76.75 (5)	C7—O7—S2	117.00 (11)
O5iii—Sr1—O2ii	140.87 (4)	S2—O9—Sr1iii	138.38 (8)
O5iii—Sr1—O6i	69.04 (4)	S1—N1—Sr1ii	139.48 (8)
O5iii—Sr1—N1ii	134.61 (4)	C1—N1—Sr1ii	97.17 (10)
O5iii—Sr1—N2i	75.24 (4)	C1—N1—S1	119.36 (12)
O5iii—Sr1—C1ii	138.28 (4)	S2—N2—Sr1i	143.15 (8)
O5iii—Sr1—C5i	74.90 (4)	C5—N2—Sr1i	95.61 (9)
O6i—Sr1—Sr1i	34.10 (2)	C5—N2—S2	119.20 (12)
O6—Sr1—Sr1i	38.80 (3)	O2—C1—Sr1ii	64.31 (9)
O6—Sr1—O1	79.00 (4)	O2—C1—N1	117.77 (16)
O6i—Sr1—O2ii	87.68 (4)	O2—C1—C2	121.63 (15)
O6—Sr1—O2ii	123.18 (4)	N1—C1—Sr1ii	58.14 (9)
O6—Sr1—O5iii	80.62 (4)	N1—C1—C2	120.30 (15)
O6—Sr1—O6i	72.91 (4)	C2—C1—Sr1ii	153.07 (11)
O6—Sr1—O9iv	93.08 (4)	C1—C2—H2	119.1
O6—Sr1—N1ii	77.19 (4)	C3—C2—C1	121.80 (15)
O6—Sr1—N2i	120.16 (4)	C3—C2—H2	119.1
O6i—Sr1—C1ii	71.99 (4)	O3—C3—C4	109.98 (16)
O6—Sr1—C1ii	101.74 (4)	C2—C3—O3	121.56 (16)
O6—Sr1—C5i	95.93 (4)	C2—C3—C4	128.27 (17)
O6i—Sr1—C5i	23.19 (4)	C3—C4—H4A	109.5
O9iv—Sr1—Sr1i	122.73 (3)	C3—C4—H4B	109.5
O9iv—Sr1—O1	69.20 (5)	C3—C4—H4C	109.5
O9iv—Sr1—O2ii	69.51 (4)	H4A—C4—H4B	109.5
O9iv—Sr1—O5iii	145.95 (4)	H4A—C4—H4C	109.5
O9iv—Sr1—O6i	140.95 (4)	H4B—C4—H4C	109.5
O9iv—Sr1—N1ii	74.71 (4)	O6—C5—Sr1i	61.67 (9)
O9iv—Sr1—N2i	134.15 (4)	O6—C5—N2	117.76 (15)
O9iv—Sr1—C1ii	75.76 (4)	O6—C5—C6	121.39 (15)
O9iv—Sr1—C5i	139.15 (4)	N2—C5—Sr1i	59.32 (8)
N1ii—Sr1—Sr1i	67.12 (3)	N2—C5—C6	120.67 (14)
N1ii—Sr1—O2ii	46.36 (4)	C6—C5—Sr1i	158.19 (11)
N1ii—Sr1—O6i	66.77 (4)	C5—C6—H6	119.0
N1ii—Sr1—C1ii	24.69 (4)	C7—C6—C5	122.03 (16)
N1ii—Sr1—C5i	68.71 (4)	C7—C6—H6	119.0
N2i—Sr1—Sr1i	81.44 (3)	O7—C7—C8	110.95 (16)
N2i—Sr1—O2ii	65.98 (4)	C6—C7—O7	121.31 (15)
N2i—Sr1—O6i	47.42 (4)	C6—C7—C8	127.71 (17)
N2i—Sr1—N1ii	82.54 (4)	C7—C8—H8A	109.5
N2i—Sr1—C1ii	67.66 (4)	C7—C8—H8B	109.5
N2i—Sr1—C5i	25.07 (4)	C7—C8—H8C	109.5
C1ii—Sr1—Sr1i	85.22 (3)	H8A—C8—H8B	109.5
C5i—Sr1—Sr1i	57.18 (3)	H8A—C8—H8C	109.5
C5i—Sr1—C1ii	63.40 (4)	H8B—C8—H8C	109.5
O4—S1—O3	106.58 (8)
Sr1—O2—C1—Sr1ii	−151.3 (3)	O3—S1—N1—C1	−35.06 (15)
Sr1—O2—C1—N1	−175.1 (2)	O4—S1—O3—C3	−82.71 (14)
Sr1ii—O2—C1—N1	−23.76 (15)	O4—S1—O5—Sr1iv	170.15 (11)
Sr1—O2—C1—C2	−1.4 (4)	O4—S1—N1—Sr1ii	−126.76 (12)
Sr1ii—O2—C1—C2	149.95 (14)	O4—S1—N1—C1	81.76 (15)
Sr1—O6—C5—Sr1i	−162.9 (3)	O5—S1—O3—C3	155.40 (13)
Sr1i—O6—C5—N2	−20.16 (16)	O5—S1—N1—Sr1ii	5.17 (15)
Sr1—O6—C5—N2	177.0 (2)	O5—S1—N1—C1	−146.30 (13)
Sr1—O6—C5—C6	−7.8 (4)	O6—C5—C6—C7	−165.34 (17)
Sr1i—O6—C5—C6	155.04 (14)	O7—S2—O9—Sr1iii	−82.06 (12)
Sr1ii—N1—C1—O2	25.31 (16)	O7—S2—N2—Sr1i	123.73 (13)
Sr1ii—N1—C1—C2	−148.50 (13)	O7—S2—N2—C5	−35.08 (15)
Sr1i—N2—C5—O6	20.65 (16)	O8—S2—O7—C7	−79.80 (14)
Sr1i—N2—C5—C6	−154.58 (13)	O8—S2—O9—Sr1iii	161.68 (10)
Sr1ii—C1—C2—C3	−67.2 (3)	O8—S2—N2—Sr1i	−119.74 (13)
Sr1i—C5—C6—C7	−73.7 (4)	O8—S2—N2—C5	81.44 (15)
S1—O3—C3—C2	−19.8 (2)	O9—S2—O7—C7	157.64 (12)
S1—O3—C3—C4	164.84 (13)	O9—S2—N2—Sr1i	12.10 (16)
S1—N1—C1—Sr1ii	161.78 (14)	O9—S2—N2—C5	−146.71 (13)
S1—N1—C1—O2	−172.91 (13)	N1—S1—O3—C3	38.52 (15)
S1—N1—C1—C2	13.3 (2)	N1—S1—O5—Sr1iv	39.33 (14)
S2—O7—C7—C6	−24.5 (2)	N1—C1—C2—C3	11.3 (3)
S2—O7—C7—C8	157.25 (14)	N2—S2—O7—C7	40.92 (14)
S2—N2—C5—Sr1i	167.42 (14)	N2—S2—O9—Sr1iii	31.28 (14)
S2—N2—C5—O6	−171.93 (13)	N2—C5—C6—C7	9.7 (3)
S2—N2—C5—C6	12.8 (2)	C1—C2—C3—O3	−7.2 (3)
O2—C1—C2—C3	−162.30 (17)	C1—C2—C3—C4	167.20 (19)
O3—S1—O5—Sr1iv	−74.19 (13)	C5—C6—C7—O7	−3.0 (3)
O3—S1—N1—Sr1ii	116.42 (12)	C5—C6—C7—C8	175.01 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4v	0.79 (3)	2.18 (3)	2.899 (2)	151 (3)
O1—H1B···O8vi	0.83 (3)	2.22 (3)	2.9850 (19)	152 (3)
C4—H4B···O5v	0.98	2.37	3.273 (3)	153
C6—H6···O8vi	0.95	2.47	3.318 (2)	148

[Ba(C4H4NO4S)2(H2O)]	F(000) = 928
Mr = 479.64	Dx = 2.104 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2086 (5) Å	Cell parameters from 9794 reflections
b = 18.8899 (11) Å	θ = 3.0–36.3°
c = 9.8999 (6) Å	µ = 2.94 mm−1
β = 99.5197 (10)°	T = 173 K
V = 1513.93 (16) Å3	Block, colourless
Z = 4	0.52 × 0.21 × 0.20 mm

Bruker PHOTON-100 CMOS diffractometer	5218 reflections with I > 2σ(I)
Radiation source: sealedtube	Rint = 0.048
φ and ω scans	θmax = 34.3°, θmin = 3.0°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −13→13
Tmin = 0.309, Tmax = 0.635	k = −29→29
41654 measured reflections	l = −15→15
6324 independent reflections

Refinement on F2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0158P)2 + 2.2204P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
6324 reflections	Δρmax = 1.02 e Å−3
209 parameters	Δρmin = −0.61 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
Ba1	0.73689 (2)	0.46819 (2)	0.43614 (2)	0.01376 (3)
S1	0.07538 (7)	0.32148 (3)	0.54490 (6)	0.01768 (10)
S2	1.36455 (6)	0.52303 (3)	0.15371 (6)	0.01847 (11)
O1	0.6927 (3)	0.37493 (12)	0.2222 (2)	0.0313 (4)
H1A	0.692 (5)	0.336 (2)	0.213 (4)	0.047 (12)*
H1B	0.664 (5)	0.389 (2)	0.153 (4)	0.041 (11)*
O2	0.4531 (2)	0.40981 (10)	0.48151 (19)	0.0255 (4)
O3	0.0469 (2)	0.28363 (10)	0.39659 (19)	0.0259 (4)
O4	0.1222 (3)	0.26718 (10)	0.6433 (2)	0.0314 (4)
O5	−0.0809 (2)	0.35404 (9)	0.5498 (2)	0.0260 (4)
O6	1.0152 (2)	0.48791 (10)	0.33283 (18)	0.0227 (4)
O7	1.3411 (2)	0.44828 (10)	0.07381 (19)	0.0270 (4)
O8	1.3107 (2)	0.57651 (11)	0.05494 (18)	0.0270 (4)
O9	1.5363 (2)	0.52380 (11)	0.21146 (18)	0.0257 (4)
N1	0.2129 (2)	0.37885 (10)	0.5425 (2)	0.0190 (4)
N2	1.2552 (2)	0.51888 (11)	0.27018 (19)	0.0190 (4)
C1	0.3361 (3)	0.36655 (12)	0.4691 (2)	0.0185 (4)
C2	0.3227 (3)	0.30894 (13)	0.3700 (3)	0.0240 (5)
H2	0.416716	0.296609	0.330515	0.029*
C3	0.1826 (3)	0.27297 (13)	0.3330 (3)	0.0233 (5)
C4	0.1416 (4)	0.22233 (17)	0.2179 (3)	0.0381 (7)
H4A	0.104320	0.177552	0.252407	0.057*
H4B	0.239932	0.213846	0.175937	0.057*
H4C	0.053596	0.242128	0.149386	0.057*
C5	1.1101 (3)	0.48350 (12)	0.2459 (2)	0.0169 (4)
C6	1.0711 (3)	0.43709 (13)	0.1272 (2)	0.0213 (4)
H6	0.962455	0.418511	0.104690	0.026*
C7	1.1828 (3)	0.41992 (14)	0.0493 (2)	0.0237 (5)
C8	1.1637 (5)	0.36907 (18)	−0.0670 (3)	0.0422 (8)
H8A	1.184568	0.393477	−0.149831	0.063*
H8B	1.051152	0.350013	−0.082391	0.063*
H8C	1.242929	0.330240	−0.045421	0.063*

	U11	U22	U33	U12	U13	U23
Ba1	0.01155 (5)	0.01638 (6)	0.01386 (6)	−0.00196 (5)	0.00359 (4)	−0.00155 (5)
S1	0.0171 (2)	0.0136 (2)	0.0238 (3)	0.00023 (19)	0.0076 (2)	0.0012 (2)
S2	0.0133 (2)	0.0298 (3)	0.0126 (2)	−0.0002 (2)	0.00297 (18)	0.0006 (2)
O1	0.0517 (13)	0.0203 (10)	0.0211 (10)	−0.0050 (9)	0.0039 (9)	−0.0042 (8)
O2	0.0182 (8)	0.0281 (9)	0.0304 (10)	−0.0065 (7)	0.0049 (7)	0.0006 (8)
O3	0.0212 (8)	0.0291 (9)	0.0286 (9)	−0.0067 (7)	0.0076 (7)	−0.0093 (8)
O4	0.0402 (11)	0.0195 (9)	0.0348 (11)	0.0034 (8)	0.0072 (9)	0.0098 (8)
O5	0.0188 (8)	0.0224 (8)	0.0397 (11)	0.0023 (7)	0.0135 (7)	0.0028 (8)
O6	0.0171 (7)	0.0319 (9)	0.0211 (8)	−0.0024 (7)	0.0093 (6)	−0.0025 (7)
O7	0.0230 (8)	0.0367 (10)	0.0232 (9)	0.0001 (7)	0.0098 (7)	−0.0092 (8)
O8	0.0237 (8)	0.0377 (11)	0.0195 (9)	0.0005 (8)	0.0026 (7)	0.0089 (8)
O9	0.0139 (7)	0.0438 (11)	0.0193 (8)	−0.0010 (7)	0.0023 (6)	0.0032 (8)
N1	0.0163 (8)	0.0172 (9)	0.0244 (10)	−0.0023 (7)	0.0065 (7)	−0.0016 (7)
N2	0.0154 (8)	0.0290 (11)	0.0131 (8)	−0.0037 (7)	0.0045 (7)	−0.0021 (7)
C1	0.0146 (9)	0.0190 (10)	0.0217 (11)	0.0016 (8)	0.0021 (8)	0.0032 (8)
C2	0.0227 (11)	0.0232 (12)	0.0282 (13)	0.0035 (9)	0.0109 (10)	−0.0014 (10)
C3	0.0263 (12)	0.0225 (11)	0.0220 (11)	0.0014 (9)	0.0072 (9)	−0.0030 (9)
C4	0.0475 (18)	0.0343 (15)	0.0342 (16)	−0.0044 (13)	0.0123 (14)	−0.0140 (13)
C5	0.0154 (9)	0.0202 (10)	0.0153 (10)	0.0007 (8)	0.0028 (8)	0.0020 (8)
C6	0.0197 (10)	0.0264 (12)	0.0172 (11)	−0.0047 (9)	0.0014 (8)	−0.0023 (9)
C7	0.0283 (12)	0.0256 (12)	0.0171 (11)	−0.0021 (10)	0.0036 (9)	−0.0017 (9)
C8	0.058 (2)	0.0421 (18)	0.0293 (15)	−0.0127 (15)	0.0151 (14)	−0.0172 (13)

Ba1—Ba1i	4.4491 (3)	O1—H1B	0.74 (4)
Ba1—O1	2.732 (2)	O2—C1	1.252 (3)
Ba1—O2i	2.9714 (19)	O3—C3	1.382 (3)
Ba1—O2	2.6812 (17)	O6—C5	1.256 (3)
Ba1—O5ii	2.7560 (18)	O7—C7	1.389 (3)
Ba1—O6	2.6788 (16)	N1—C1	1.359 (3)
Ba1—O6iii	2.9192 (18)	N2—C5	1.352 (3)
Ba1—O9iv	2.7478 (18)	C1—C2	1.457 (3)
Ba1—N1i	2.921 (2)	C2—H2	0.9500
Ba1—N2iii	2.9077 (19)	C2—C3	1.334 (4)
Ba1—C1i	3.342 (2)	C3—C4	1.483 (4)
Ba1—C5iii	3.318 (2)	C4—H4A	0.9800
S1—O3	1.6149 (19)	C4—H4B	0.9800
S1—O4	1.4232 (19)	C4—H4C	0.9800
S1—O5	1.4309 (17)	C5—C6	1.459 (3)
S1—N1	1.568 (2)	C6—H6	0.9500
S2—O7	1.6143 (19)	C6—C7	1.332 (3)
S2—O8	1.4245 (19)	C7—C8	1.488 (4)
S2—O9	1.4313 (17)	C8—H8A	0.9800
S2—N2	1.5758 (19)	C8—H8B	0.9800
O1—H1A	0.75 (4)	C8—H8C	0.9800
O1—Ba1—Ba1i	112.59 (5)	O4—S1—O5	115.39 (12)
O1—Ba1—O2i	134.76 (6)	O4—S1—N1	113.25 (12)
O1—Ba1—O5ii	78.79 (7)	O5—S1—O3	103.03 (11)
O1—Ba1—O6iii	140.94 (6)	O5—S1—N1	110.81 (11)
O1—Ba1—O9iv	68.53 (7)	N1—S1—O3	106.77 (10)
O1—Ba1—N1i	133.85 (6)	O8—S2—O7	106.60 (11)
O1—Ba1—N2iii	143.83 (6)	O8—S2—O9	116.14 (11)
O1—Ba1—C1i	144.37 (7)	O8—S2—N2	112.82 (11)
O1—Ba1—C5iii	153.32 (7)	O9—S2—O7	103.55 (11)
O2i—Ba1—Ba1i	35.84 (3)	O9—S2—N2	110.54 (10)
O2—Ba1—Ba1i	40.45 (4)	N2—S2—O7	106.20 (10)
O2—Ba1—O1	81.78 (6)	Ba1—O1—H1A	137 (3)
O2—Ba1—O2i	76.29 (6)	Ba1—O1—H1B	118 (3)
O2—Ba1—O5ii	92.16 (5)	H1A—O1—H1B	105 (4)
O2—Ba1—O6iii	119.87 (5)	Ba1—O2—Ba1i	103.71 (6)
O2—Ba1—O9iv	82.65 (5)	C1—O2—Ba1	157.81 (16)
O2—Ba1—N1i	120.71 (5)	C1—O2—Ba1i	95.98 (14)
O2—Ba1—N2iii	75.13 (5)	C3—O3—S1	118.19 (16)
O2i—Ba1—C1i	21.87 (5)	S1—O5—Ba1iv	138.72 (10)
O2—Ba1—C1i	97.82 (6)	Ba1—O6—Ba1iii	105.57 (5)
O2—Ba1—C5iii	99.04 (5)	C5—O6—Ba1iii	97.13 (14)
O2i—Ba1—C5iii	70.11 (5)	C5—O6—Ba1	156.59 (16)
O5ii—Ba1—Ba1i	122.42 (4)	C7—O7—S2	117.07 (15)
O5ii—Ba1—O2i	140.25 (5)	S2—O9—Ba1ii	137.59 (10)
O5ii—Ba1—O6iii	68.99 (5)	S1—N1—Ba1i	140.88 (10)
O5ii—Ba1—N1i	133.14 (6)	C1—N1—Ba1i	95.70 (13)
O5ii—Ba1—N2iii	74.73 (6)	C1—N1—S1	119.41 (17)
O5ii—Ba1—C1i	136.60 (6)	S2—N2—Ba1iii	143.73 (10)
O5ii—Ba1—C5iii	74.53 (6)	C5—N2—Ba1iii	95.30 (13)
O6—Ba1—Ba1i	155.73 (4)	C5—N2—S2	119.09 (16)
O6iii—Ba1—Ba1i	103.27 (3)	O2—C1—Ba1i	62.15 (13)
O6—Ba1—O1	78.82 (6)	O2—C1—N1	117.5 (2)
O6iii—Ba1—O2i	83.93 (5)	O2—C1—C2	121.7 (2)
O6—Ba1—O2	160.13 (6)	N1—C1—Ba1i	60.43 (12)
O6—Ba1—O2i	121.09 (5)	N1—C1—C2	120.5 (2)
O6—Ba1—O5ii	79.94 (5)	C2—C1—Ba1i	152.82 (16)
O6—Ba1—O6iii	74.43 (5)	C1—C2—H2	119.0
O6—Ba1—O9iv	94.15 (5)	C3—C2—C1	122.1 (2)
O6iii—Ba1—N1i	65.83 (5)	C3—C2—H2	119.0
O6—Ba1—N1i	76.77 (5)	O3—C3—C4	110.3 (2)
O6—Ba1—N2iii	119.39 (5)	C2—C3—O3	121.6 (2)
O6iii—Ba1—C1i	69.44 (5)	C2—C3—C4	128.0 (2)
O6—Ba1—C1i	100.43 (5)	C3—C4—H4A	109.5
O6—Ba1—C5iii	96.38 (5)	C3—C4—H4B	109.5
O6iii—Ba1—C5iii	22.06 (5)	C3—C4—H4C	109.5
O9iv—Ba1—Ba1i	72.06 (4)	H4A—C4—H4B	109.5
O9iv—Ba1—O2i	69.77 (5)	H4A—C4—H4C	109.5
O9iv—Ba1—O5ii	147.31 (6)	H4B—C4—H4C	109.5
O9iv—Ba1—O6iii	140.57 (6)	O6—C5—Ba1iii	60.81 (12)
O9iv—Ba1—N1i	74.86 (6)	O6—C5—N2	118.3 (2)
O9iv—Ba1—N2iii	133.52 (6)	O6—C5—C6	120.9 (2)
O9iv—Ba1—C1i	76.05 (6)	N2—C5—Ba1iii	60.77 (11)
O9iv—Ba1—C5iii	138.14 (6)	N2—C5—C6	120.65 (19)
N1i—Ba1—Ba1i	80.31 (4)	C6—C5—Ba1iii	158.10 (16)
N1i—Ba1—O2i	44.54 (5)	C5—C6—H6	118.9
N1i—Ba1—C1i	23.87 (5)	C7—C6—C5	122.1 (2)
N1i—Ba1—C5iii	68.44 (6)	C7—C6—H6	118.9
N2iii—Ba1—Ba1i	64.48 (4)	O7—C7—C8	111.1 (2)
N2iii—Ba1—O2i	65.57 (5)	C6—C7—O7	121.2 (2)
N2iii—Ba1—O6iii	45.20 (5)	C6—C7—C8	127.6 (3)
N2iii—Ba1—N1i	82.24 (6)	C7—C8—H8A	109.5
N2iii—Ba1—C1i	67.43 (6)	C7—C8—H8B	109.5
N2iii—Ba1—C5iii	23.94 (5)	C7—C8—H8C	109.5
C1i—Ba1—Ba1i	57.47 (4)	H8A—C8—H8B	109.5
C5iii—Ba1—Ba1i	82.39 (4)	H8A—C8—H8C	109.5
C5iii—Ba1—C1i	62.23 (6)	H8B—C8—H8C	109.5
O4—S1—O3	106.60 (11)
Ba1—O2—C1—Ba1i	−152.6 (4)	O3—S1—N1—C1	−33.6 (2)
Ba1—O2—C1—N1	−177.7 (3)	O4—S1—O3—C3	−84.9 (2)
Ba1i—O2—C1—N1	−25.2 (2)	O4—S1—O5—Ba1iv	170.65 (15)
Ba1—O2—C1—C2	−3.7 (6)	O4—S1—N1—Ba1i	−125.67 (17)
Ba1i—O2—C1—C2	148.9 (2)	O4—S1—N1—C1	83.4 (2)
Ba1—O6—C5—Ba1iii	−165.9 (4)	O5—S1—O3—C3	153.20 (18)
Ba1iii—O6—C5—N2	−20.6 (2)	O5—S1—N1—Ba1i	5.8 (2)
Ba1—O6—C5—N2	173.5 (3)	O5—S1—N1—C1	−145.06 (19)
Ba1—O6—C5—C6	−11.1 (5)	O6—C5—C6—C7	−165.8 (2)
Ba1iii—O6—C5—C6	154.73 (19)	O7—S2—O9—Ba1ii	−80.89 (17)
Ba1i—N1—C1—O2	25.6 (2)	O7—S2—N2—Ba1iii	124.24 (18)
Ba1i—N1—C1—C2	−148.52 (19)	O7—S2—N2—C5	−35.3 (2)
Ba1iii—N2—C5—O6	20.6 (2)	O8—S2—O7—C7	−79.77 (19)
Ba1iii—N2—C5—C6	−154.73 (19)	O8—S2—O9—Ba1ii	162.65 (14)
Ba1i—C1—C2—C3	−74.1 (4)	O8—S2—N2—Ba1iii	−119.34 (18)
Ba1iii—C5—C6—C7	−77.8 (5)	O8—S2—N2—C5	81.1 (2)
S1—O3—C3—C2	−18.7 (3)	O9—S2—O7—C7	157.23 (18)
S1—O3—C3—C4	165.55 (19)	O9—S2—N2—Ba1iii	12.6 (2)
S1—N1—C1—Ba1i	162.0 (2)	O9—S2—N2—C5	−146.95 (19)
S1—N1—C1—O2	−172.35 (18)	N1—S1—O3—C3	36.4 (2)
S1—N1—C1—C2	13.5 (3)	N1—S1—O5—Ba1iv	40.3 (2)
S2—O7—C7—C6	−24.1 (3)	N1—C1—C2—C3	9.8 (4)
S2—O7—C7—C8	157.7 (2)	N2—S2—O7—C7	40.8 (2)
S2—N2—C5—Ba1iii	168.0 (2)	N2—S2—O9—Ba1ii	32.5 (2)
S2—N2—C5—O6	−171.40 (18)	N2—C5—C6—C7	9.4 (4)
S2—N2—C5—C6	13.3 (3)	C1—C2—C3—O3	−6.5 (4)
O2—C1—C2—C3	−164.1 (2)	C1—C2—C3—C4	168.5 (3)
O3—S1—O5—Ba1iv	−73.61 (18)	C5—C6—C7—O7	−3.1 (4)
O3—S1—N1—Ba1i	117.32 (17)	C5—C6—C7—C8	174.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4v	0.74 (4)	2.12 (4)	2.829 (3)	162 (4)
O1—H1B···O8vi	0.74 (4)	2.20 (4)	2.889 (3)	156 (4)
C4—H4B···O5v	0.98	2.44	3.361 (4)	155
C6—H6···O8vi	0.95	2.52	3.357 (3)	147