Poly[aqua­bis­[μ₃-4-(3-pyrid­yl)pyrimidine-2-sulfonato-κ⁴N⁴:N¹,O:O][μ₂-4-(3-pyrid­yl)pyrimidine-2-sulfonato-κ³N⁴:N¹,O]tris­ilver(I)]

In the crystal structure of the title compound, [Ag₃(C₉H₆N₃O₃S)₃(H₂O)₂]_n, the mol­ecules are linked into three-decked polymeric zigzag chains propagating in [100]. On the middle deck, the Ag atom is five-coordinated by three O atoms from three 4-(3-pyrid­yl)pyrimidine-2-sulfonate (L) ligands, one of which lies on a mirror plane with the sulfonate group disordered over two orientations in a 1:1 ratio, and two N atoms from two L ligands, which lie on the same mirror plane. On the upper and lower decks, the Ag atom is four-coordinated by an aqua ligand, one O and two N atoms from two L ligands with the pyridyl and pyrimidine rings twisted at 19.8 (2)°. In the polymeric chain, there are π–π inter­actions between six-membered rings of L ligands from different decks with centroid–centroid distances of 3.621 (7) and 3.721 (3) Å. In the crystal, inter­molecular O—H...O hydrogen bonds link further these three-decked chains into layers parallel to (010).

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.011 Å
• Disorder in main residue
• R factor = 0.052
• wR factor = 0.119
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     --  O3      ..        5.7 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     --  C4      ..        5.2 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     --  C2      ..        5.8 su
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0106 Ang
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          4
PLAT918_ALERT_3_C Reflection(s) # with I(obs) much smaller I(calc)          1
PLAT974_ALERT_2_C Large Calcd. Negative Residual Density on    Ag2      -1.25 eA-3

Alert level G
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          1
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ag1    --  O4      ..        6.3 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ag2    --  N4      ..        9.8 su
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................          6 Perc.
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......          !

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

S1. Comment

Remarkable attention has been paid to the rational design and assembly of new coordination polymers with thioethers in recent years (Dong et al., 2009; Fang et al., 2010; Zhu, 2010). Herein we present the title compound, (I) - the newly synthesized compound derived from 4-(2-pyridinyl)pyrimidine-2-thiol.

The molecular structure of title compound with the atom-numbering scheme is shown in Fig. 1. It crystallizes in the centrosymmetric space group \'-P 2ac 2n'. Ag1 is tetracoordinated and Ag2 is pentacoordinate. Ag1 is coordinated by two N atom from two L ligands and one coordinated water molecule as well as one O atom from the SO₃ group. The two N atoms from different ligands are in a slightly distorted linear geometry with an N—Ag—N bond angle of 160.8°. Ag2 is bound by two different N atoms located from two ligands, and thee O donors from the three different SO3 group.

In (I) (Fig. 1), each ligand L (L = 4-(2-pyridyl)-pyrimidine-2-sulfonato) exhibits a chelating-bridging tridentate mode. The molecules are linked into three-decked polymeric zigzag chains propagated in [100]. On the middle deck, which is situated on a mirror plane, the Ag centre is five-coordinated by three O atoms from three ligands L, one of which lies on a mirror plane with the disordered sulfonato group over two orientations in a 1:1 ratio, and two N atoms from two ligands L, which lie on the same mirror plane. On the upper and lower decks, each Ag centre is four-coordinated by aqua ligand, one O and two N atoms from two ligands L with the pyridyl and pyrimidine rings twisted at 19.8 (2)°. In the polymeric chain, there are π–π interactions between six-membered rings of ligands L from different decks (Table 1).

In the crystal structure, intermolecular O—H···O hydrogen bonds l(Table 2) ink further these three-decked chains into layers parallel to ac plane.

Related literature

For backgroud to coordination polymers with thioethers, see: Dong et al. (2009); Fang et al. (2010). For the crystal structure of the related compound catena- poly[[µ-4-(2-pyridyl)-pyrimidine-2-sulfonato)-silver(I)] monohydrate], see: Zhu (2010).

S2. Experimental

All solvents and chemicals were of analytical grade and were used without further purification. The title compound was prepared by similar procedure reported in the literature (Dong et al., 2009; Fang et al., 2010; Zhu, 2010). To a suspension of NaL₂ (26.0 mg, 0.1 mmol) in water (5 ml) in a tube, a solution of AgNO₃ (8.5 mg, 0.05 mmol) in acetonitrile (5 ml) was very slowly dropped. Crystal products formed after two weeks standing in a dark. Single crystals suitable for X-ray diffraction were grown from methanol solution by slow evaporation in air at room temperature.

S3. Refinement

All hydrogen atoms were geometrically positioned (C—H 0.93 Å; O—H 0.96 Å) and refined as riding, with U_iso(H)=1.2–1.5 U_eq of the parent atom.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

Fig. 1. A portion of the polymeric structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids [symmetry code: (a) x, 0.5 - y, z]. For the disordered sulfonato group with the atoms O5, O6 and O7 only one orientation is shown.

Poly[aquabis[µ₃-4-(3-pyridyl)pyrimidine-2-sulfonato- κ⁴N⁴:N¹,O:O][µ₂-4-(3-pyridyl)pyrimidine- 2-sulfonato-κ³N⁴:N¹,O]trisilver(I)]

Crystal data

[Ag3(C9H6N3O3S)3(H2O)2]	F(000) = 2096
Mr = 1068.36	Dx = 2.158 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 3327 reflections
a = 19.0738 (16) Å	θ = 2.1–26.0°
b = 19.9598 (17) Å	µ = 2.04 mm^−1
c = 8.6372 (7) Å	T = 291 K
V = 3288.3 (5) Å^3	Block, colourless
Z = 4	0.30 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3327 independent reflections
Radiation source: fine-focus sealed tube	2555 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
ϕ and ω scan	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→23
Tmin = 0.56, Tmax = 0.64	k = −24→24
16896 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 1.55P] where P = (Fo^2 + 2Fc^2)/3
3327 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 0.80 e Å^−3
0 restraints	Δρmin = −1.25 e Å^−3

Special details

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.13631 (3)	0.41025 (2)	0.94740 (6)	0.03754 (16)
Ag2	0.17483 (3)	0.2500	0.82162 (8)	0.03481 (19)
C1	0.2943 (4)	0.4436 (3)	0.8566 (7)	0.0408 (15)
H1	0.2986	0.4544	0.9609	0.049*
C2	0.3536 (4)	0.4436 (3)	0.7610 (7)	0.0374 (14)
H2	0.3972	0.4546	0.8018	0.045*
C3	0.3474 (4)	0.4272 (3)	0.6065 (8)	0.0381 (15)
C4	0.2242 (3)	0.4108 (3)	0.6403 (7)	0.0335 (13)
C5	0.4053 (4)	0.4241 (3)	0.4987 (8)	0.0384 (14)
C6	0.3956 (3)	0.4261 (3)	0.3385 (8)	0.0396 (15)
H6	0.3507	0.4293	0.2971	0.047*
C7	0.4540 (3)	0.4234 (3)	0.2411 (7)	0.0326 (13)
H7	0.4479	0.4252	0.1344	0.039*
C8	0.5201 (3)	0.4181 (3)	0.3014 (7)	0.0392 (14)
H8	0.5587	0.4162	0.2357	0.047*
C9	0.4730 (3)	0.4183 (3)	0.5592 (7)	0.0351 (14)
H9	0.4795	0.4163	0.6658	0.042*
C10	0.2727 (5)	0.2500	0.5262 (11)	0.044 (2)
H10	0.2316	0.2500	0.4683	0.053*
C11	0.3369 (4)	0.2500	0.4532 (10)	0.0311 (18)
H11	0.3390	0.2500	0.3456	0.037*
C12	0.3972 (4)	0.2500	0.5375 (10)	0.0330 (19)
C13	0.3317 (5)	0.2500	0.7715 (10)	0.0348 (19)
C14	0.4694 (4)	0.2500	0.4665 (9)	0.0329 (19)
C15	0.4792 (5)	0.2500	0.3072 (11)	0.041 (2)
H15	0.4407	0.2500	0.2410	0.049*
C16	0.5466 (5)	0.2500	0.2474 (11)	0.044 (2)
H16	0.5530	0.2500	0.1406	0.053*
C17	0.6043 (5)	0.2500	0.3432 (9)	0.0337 (19)
H17	0.6493	0.2500	0.3022	0.040*
C18	0.5278 (5)	0.2500	0.5643 (11)	0.0345 (19)
H18	0.5216	0.2500	0.6712	0.041*
N1	0.2295 (3)	0.4278 (3)	0.7962 (6)	0.0409 (13)
N2	0.2817 (3)	0.4101 (3)	0.5462 (6)	0.0421 (13)
N3	0.5297 (3)	0.4155 (2)	0.4619 (6)	0.0323 (11)
N4	0.2698 (4)	0.2500	0.6895 (8)	0.0366 (17)
N5	0.3958 (4)	0.2500	0.6979 (9)	0.0358 (17)
N6	0.5937 (4)	0.2500	0.5036 (9)	0.0394 (18)
O1	0.1096 (2)	0.4554 (2)	0.5436 (5)	0.0450 (12)
O2	0.1566 (3)	0.3564 (2)	0.4227 (5)	0.0458 (11)
O3	0.1103 (2)	0.3505 (2)	0.6811 (5)	0.0432 (11)
O4	0.2270 (2)	0.3934 (2)	1.1536 (5)	0.0415 (11)
H4B	0.2560	0.3560	1.1266	0.062*
H4C	0.2041	0.3848	1.2506	0.062*
O5	0.2702 (5)	0.2734 (5)	1.0142 (10)	0.045 (2)	0.50
O6	0.3935 (6)	0.2966 (6)	1.0009 (12)	0.048 (3)	0.50
O7	0.3524 (6)	0.1854 (5)	1.0227 (10)	0.039 (2)	0.50
S1	0.14301 (9)	0.39214 (9)	0.5640 (2)	0.0420 (4)
S2	0.33833 (12)	0.2500	0.9713 (3)	0.0387 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0395 (3)	0.0334 (3)	0.0398 (3)	−0.0030 (2)	0.0070 (2)	−0.0051 (2)
Ag2	0.0272 (3)	0.0338 (3)	0.0434 (4)	0.000	0.0094 (3)	0.000
C1	0.048 (4)	0.038 (4)	0.036 (3)	−0.009 (3)	−0.012 (3)	−0.004 (3)
C2	0.037 (4)	0.042 (3)	0.033 (3)	0.000 (3)	0.010 (3)	−0.005 (3)
C3	0.036 (4)	0.037 (3)	0.041 (3)	0.004 (3)	0.007 (3)	0.004 (3)
C4	0.037 (3)	0.029 (3)	0.034 (3)	−0.001 (3)	0.007 (3)	−0.007 (2)
C5	0.046 (4)	0.029 (3)	0.040 (3)	0.001 (3)	−0.004 (3)	−0.005 (3)
C6	0.029 (3)	0.051 (4)	0.038 (3)	0.003 (3)	0.006 (3)	0.002 (3)
C7	0.043 (4)	0.029 (3)	0.026 (3)	0.002 (3)	0.011 (3)	0.003 (2)
C8	0.033 (3)	0.047 (4)	0.037 (3)	−0.004 (3)	0.000 (3)	0.002 (3)
C9	0.047 (4)	0.027 (3)	0.032 (3)	−0.003 (3)	0.010 (3)	0.001 (2)
C10	0.032 (5)	0.063 (7)	0.037 (5)	0.000	0.002 (4)	0.000
C11	0.026 (4)	0.030 (4)	0.037 (5)	0.000	−0.010 (3)	0.000
C12	0.027 (5)	0.040 (5)	0.033 (5)	0.000	−0.004 (3)	0.000
C13	0.031 (5)	0.034 (4)	0.039 (5)	0.000	0.008 (4)	0.000
C14	0.031 (5)	0.036 (5)	0.032 (4)	0.000	−0.019 (3)	0.000
C15	0.038 (5)	0.035 (5)	0.050 (6)	0.000	−0.015 (4)	0.000
C16	0.040 (6)	0.058 (6)	0.035 (5)	0.000	−0.013 (4)	0.000
C17	0.040 (5)	0.040 (5)	0.021 (4)	0.000	0.006 (3)	0.000
C18	0.034 (5)	0.030 (4)	0.040 (5)	0.000	−0.019 (4)	0.000
N1	0.039 (3)	0.048 (3)	0.036 (3)	0.001 (2)	0.001 (2)	−0.010 (2)
N2	0.048 (3)	0.045 (3)	0.034 (3)	0.008 (3)	−0.007 (2)	0.003 (2)
N3	0.025 (3)	0.028 (3)	0.044 (3)	−0.002 (2)	−0.004 (2)	−0.002 (2)
N4	0.047 (5)	0.034 (4)	0.029 (4)	0.000	−0.022 (3)	0.000
N5	0.036 (4)	0.034 (4)	0.038 (4)	0.000	−0.011 (3)	0.000
N6	0.035 (4)	0.049 (5)	0.035 (4)	0.000	−0.006 (3)	0.000
O1	0.048 (3)	0.050 (3)	0.038 (2)	0.016 (2)	−0.010 (2)	0.011 (2)
O2	0.046 (3)	0.042 (3)	0.049 (3)	−0.007 (2)	0.001 (2)	−0.014 (2)
O3	0.045 (3)	0.049 (3)	0.036 (2)	−0.019 (2)	−0.008 (2)	0.017 (2)
O4	0.043 (3)	0.053 (3)	0.029 (2)	−0.005 (2)	−0.0050 (19)	0.0173 (19)
O5	0.039 (5)	0.051 (6)	0.045 (5)	0.013 (4)	−0.004 (4)	−0.009 (4)
O6	0.033 (6)	0.069 (8)	0.042 (6)	−0.016 (5)	−0.009 (5)	−0.010 (5)
O7	0.054 (7)	0.039 (5)	0.025 (5)	−0.004 (5)	0.004 (4)	−0.003 (4)
S1	0.0421 (10)	0.0402 (9)	0.0438 (9)	−0.0010 (7)	−0.0005 (7)	0.0014 (7)
S2	0.0260 (11)	0.0504 (14)	0.0396 (12)	0.000	0.0029 (9)	0.000

Geometric parameters (Å, º)

Ag1—N3^i	2.182 (5)	C12—C14	1.508 (13)
Ag1—N1	2.234 (6)	C13—N5	1.377 (12)
Ag1—O4	2.505 (4)	C13—N4	1.377 (11)
Ag2—N4	2.140 (8)	C13—S2	1.730 (9)
Ag2—N6^i	2.162 (8)	C14—C15	1.389 (13)
Ag2—O5	2.508 (9)	C14—C18	1.397 (11)
Ag2—O5^ii	2.508 (9)	C15—C16	1.386 (14)
C1—N1	1.378 (8)	C15—H15	0.9300
C1—C2	1.400 (9)	C16—C17	1.376 (13)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.380 (9)	C17—N6	1.400 (11)
C2—H2	0.9300	C17—H17	0.9300
C3—N2	1.401 (9)	C18—N6	1.363 (12)
C3—C5	1.445 (9)	C18—H18	0.9300
C4—N2	1.364 (8)	N3—Ag1^iii	2.182 (5)
C4—N1	1.392 (8)	N6—Ag2^iii	2.162 (8)
C4—S1	1.724 (6)	O1—S1	1.424 (5)
C5—C6	1.396 (9)	O2—S1	1.438 (5)
C5—C9	1.397 (9)	O3—S1	1.449 (4)
C6—C7	1.397 (9)	O4—H4B	0.9600
C6—H6	0.9300	O4—H4C	0.9600
C7—C8	1.368 (9)	O5—O5^ii	0.934 (18)
C7—H7	0.9300	O5—S2	1.431 (9)
C8—N3	1.399 (8)	O5—O7^ii	1.773 (14)
C8—H8	0.9300	O6—O7^ii	0.882 (12)
C9—N3	1.371 (8)	O6—S2	1.428 (10)
C9—H9	0.9300	O7—O6^ii	0.882 (12)
C10—C11	1.377 (12)	O7—S2	1.389 (10)
C10—N4	1.412 (11)	O7—O5^ii	1.773 (14)
C10—H10	0.9300	S2—O7^ii	1.389 (10)
C11—C12	1.362 (11)	S2—O6^ii	1.428 (10)
C11—H11	0.9300	S2—O5^ii	1.431 (9)
C12—N5	1.386 (11)
Cg1···Cg1^ii	3.621 (7)	Cg2···Cg2^ii	3.721 (3)
N3^i—Ag1—N1	160.8 (2)	C16—C17—N6	118.7 (8)
N3^i—Ag1—O4	113.25 (17)	C16—C17—H17	120.6
N1—Ag1—O4	83.53 (17)	N6—C17—H17	120.6
N4—Ag2—N6^i	167.9 (3)	N6—C18—C14	120.1 (8)
N4—Ag2—O5	74.9 (3)	N6—C18—H18	119.9
N6^i—Ag2—O5	93.2 (3)	C14—C18—H18	119.9
N4—Ag2—O5^ii	74.9 (3)	C1—N1—C4	119.2 (5)
N6^i—Ag2—O5^ii	93.2 (3)	C1—N1—Ag1	121.9 (4)
O5—Ag2—O5^ii	21.5 (4)	C4—N1—Ag1	118.0 (4)
N1—C1—C2	120.0 (5)	C4—N2—C3	119.7 (5)
N1—C1—H1	120.0	C9—N3—C8	120.2 (5)
C2—C1—H1	120.0	C9—N3—Ag1^iii	121.2 (4)
C3—C2—C1	120.1 (6)	C8—N3—Ag1^iii	118.6 (4)
C3—C2—H2	119.9	C13—N4—C10	118.7 (8)
C1—C2—H2	119.9	C13—N4—Ag2	116.8 (5)
C2—C3—N2	119.6 (6)	C10—N4—Ag2	124.5 (6)
C2—C3—C5	124.6 (6)	C13—N5—C12	118.7 (7)
N2—C3—C5	115.7 (6)	C18—N6—C17	120.9 (8)
N2—C4—N1	121.4 (6)	C18—N6—Ag2^iii	113.0 (6)
N2—C4—S1	119.5 (4)	C17—N6—Ag2^iii	126.0 (6)
N1—C4—S1	119.2 (5)	Ag1—O4—H4B	109.3
C6—C5—C9	119.7 (6)	Ag1—O4—H4C	109.4
C6—C5—C3	122.4 (6)	H4B—O4—H4C	109.5
C9—C5—C3	117.9 (6)	O5^ii—O5—S2	70.9 (4)
C5—C6—C7	119.3 (6)	O5^ii—O5—O7^ii	117.6 (4)
C5—C6—H6	120.3	S2—O5—O7^ii	50.0 (4)
C7—C6—H6	120.3	O5^ii—O5—Ag2	79.3 (2)
C8—C7—C6	120.6 (6)	S2—O5—Ag2	115.2 (5)
C8—C7—H7	119.7	O7^ii—O5—Ag2	139.1 (6)
C6—C7—H7	119.7	O7^ii—O6—S2	69.4 (9)
C7—C8—N3	120.0 (6)	O6^ii—O7—S2	74.2 (10)
C7—C8—H8	120.0	O6^ii—O7—O5^ii	126.1 (12)
N3—C8—H8	120.0	S2—O7—O5^ii	52.1 (4)
N3—C9—C5	120.2 (6)	O1—S1—O2	114.5 (3)
N3—C9—H9	119.9	O1—S1—O3	113.7 (3)
C5—C9—H9	119.9	O2—S1—O3	112.7 (3)
C11—C10—N4	119.5 (9)	O1—S1—C4	104.9 (3)
C11—C10—H10	120.2	O2—S1—C4	105.7 (3)
N4—C10—H10	120.2	O3—S1—C4	104.1 (3)
C12—C11—C10	120.4 (8)	O7^ii—S2—O7	136.2 (8)
C12—C11—H11	119.8	O7—S2—O6	113.9 (8)
C10—C11—H11	119.8	O7^ii—S2—O6^ii	113.9 (8)
C11—C12—N5	121.2 (8)	O6—S2—O6^ii	81.3 (10)
C11—C12—C14	123.7 (8)	O7^ii—S2—O5^ii	113.3 (6)
N5—C12—C14	115.1 (7)	O7—S2—O5^ii	77.9 (6)
N5—C13—N4	121.5 (8)	O6—S2—O5^ii	146.8 (6)
N5—C13—S2	113.3 (7)	O6^ii—S2—O5^ii	114.3 (6)
N4—C13—S2	125.1 (7)	O7^ii—S2—O5	77.9 (6)
C15—C14—C18	119.5 (9)	O7—S2—O5	113.3 (6)
C15—C14—C12	121.7 (7)	O6—S2—O5	114.3 (6)
C18—C14—C12	118.8 (8)	O6^ii—S2—O5	146.8 (6)
C16—C15—C14	119.6 (8)	O7^ii—S2—C13	109.4 (4)
C16—C15—H15	120.2	O7—S2—C13	109.4 (4)
C14—C15—H15	120.2	O6—S2—C13	103.4 (5)
C17—C16—C15	121.1 (9)	O6^ii—S2—C13	103.4 (5)
C17—C16—H16	119.4	O5^ii—S2—C13	101.1 (5)
C15—C16—H16	119.4	O5—S2—C13	101.1 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4C···O2^iv	0.96	1.83	2.784 (6)	171

Symmetry code: (iv) x, y, z+1.