Poly[[diaqua-bis(μ(2)-4,4'-bipyridine)-manganese(II)] bis-[2-(2-carboxy-phenyl-di-sulfanyl)benzoate]].

The title complex, {[Mn(C(10)H(8)N(2))(2)(H(2)O)(2)](C(14)H(9)O(4)S(2))(2)}(n), contains an octa-hedrally coordinated Mn(II) cation and 2-(2-carboxy-phenyl-disulfan-yl)benzoate anions. The Mn(II) center is situated on a crystallographic center of inversion and is coordinated by four 4,4'-bipyridine (4,4'-bipy) ligands and two water mol-ecules. The 4,4'-bipy ligands act as bridging ligands, producing a fishing-net-like two-dimensional framework. In the crystal structure, this positively charged framework is charge balanced by 2-(2-carboxy-phenyl-disulfan-yl)benzoate anions that form a separate anionic two-dimensional framework via inter-molecular O-H⋯O hydrogen bonds and C-H⋯π stacking inter-actions. Additional inter-molecular O-H⋯O hydrogen bonds link the cationic and anionic frameworks to form the three-dimensional crystal structure.

Related literature

For general background on the design and synthesis of coordination polymers, see: James (2003 ▶); Kitagawa et al. (2004 ▶); Steel (2005 ▶); Ye et al. (2005 ▶). For the crystal structures of related complexes with 4,4′-bipyridine ligands, see: Biradha et al. (2006 ▶); Denning et al. (2008 ▶); Hoffart et al. (2007 ▶); Noro et al. (2002 ▶); Qin et al. (2007 ▶); Zhang et al. (2007 ▶). For metal–organic framework materials containing 2,2′-dithio­dibenzoic acid, see: Humphrey et al. (2004 ▶); Murugavel et al. (2001 ▶); Wang et al. (2004 ▶); Zhao et al. (2004 ▶).

Experimental

Crystal data

[Mn(C10H8N2)2(H2O)2](C14H9O4S2)2

M = 1014.00

Triclinic,

a = 8.260 (5) Å

b = 11.771 (7) Å

c = 11.917 (7) Å

α = 94.334 (6)°

β = 102.339 (7)°

γ = 96.217 (7)°

V = 1119 (1) Å3

Z = 1

Mo Kα radiation

μ = 0.55 mm−1

T = 293 K

0.41 × 0.13 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.807, T max = 0.952

8248 measured reflections

3921 independent reflections

3242 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.081

S = 1.03

3921 reflections

304 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013646/im2106sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013646/im2106Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C10H8N2)2(H2O)2](C14H9O4S2)2	Z = 1
Mr = 1014.00	F(000) = 523
Triclinic, P1	Dx = 1.504 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.260 (5) Å	Cell parameters from 3063 reflections
b = 11.771 (7) Å	θ = 2.6–27.3°
c = 11.917 (7) Å	µ = 0.55 mm−1
α = 94.334 (6)°	T = 293 K
β = 102.339 (7)°	Prism, yellow
γ = 96.217 (7)°	0.41 × 0.13 × 0.09 mm
V = 1119 (1) Å3

Bruker SMART CCD area-detector diffractometer	3921 independent reflections
Radiation source: fine-focus sealed tube	3242 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.807, Tmax = 0.952	k = −14→14
8248 measured reflections	l = −14→13

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0338P)2 + 0.4902P] where P = (Fo2 + 2Fc2)/3
3921 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
Mn1	0.0000	0.0000	0.5000	0.02618 (12)
C1	0.1323 (3)	0.0099 (2)	0.26331 (18)	0.0413 (5)
H1	0.2313	0.0235	0.3195	0.050*
C2	0.1417 (3)	0.0171 (2)	0.14994 (18)	0.0426 (6)
H2	0.2450	0.0358	0.1321	0.051*
C3	−0.0016 (2)	−0.00339 (17)	0.06212 (16)	0.0288 (4)
C4	−0.1492 (3)	−0.03266 (19)	0.09752 (17)	0.0367 (5)
H4	−0.2496	−0.0490	0.0428	0.044*
C5	−0.1486 (3)	−0.03779 (19)	0.21322 (17)	0.0365 (5)
H5	−0.2499	−0.0580	0.2333	0.044*
C6	−0.0798 (3)	0.24339 (19)	0.4099 (2)	0.0470 (6)
H6	−0.1457	0.1943	0.3484	0.056*
C7	−0.0917 (3)	0.35907 (19)	0.4094 (2)	0.0499 (6)
H7	−0.1659	0.3853	0.3497	0.060*
C8	0.0067 (3)	0.43706 (17)	0.49789 (18)	0.0329 (5)
C9	0.1167 (3)	0.38947 (19)	0.58152 (19)	0.0420 (5)
H9	0.1880	0.4370	0.6419	0.050*
C10	0.1207 (3)	0.27247 (19)	0.57538 (19)	0.0418 (5)
H10	0.1977	0.2441	0.6318	0.050*
C11	0.4897 (3)	0.19836 (19)	0.37959 (18)	0.0366 (5)
C12	0.4734 (3)	0.29917 (18)	0.30933 (17)	0.0344 (5)
C13	0.4283 (3)	0.3990 (2)	0.3568 (2)	0.0488 (6)
H13	0.3984	0.3993	0.4278	0.059*
C14	0.4264 (4)	0.4974 (2)	0.3015 (2)	0.0626 (8)
H14	0.3949	0.5633	0.3344	0.075*
C15	0.4719 (4)	0.4971 (2)	0.1964 (2)	0.0560 (7)
H15	0.4741	0.5639	0.1595	0.067*
C16	0.5139 (3)	0.3989 (2)	0.14617 (19)	0.0429 (6)
H16	0.5428	0.3998	0.0749	0.051*
C17	0.5139 (2)	0.29761 (18)	0.20047 (17)	0.0330 (5)
C18	0.6650 (3)	0.2313 (2)	−0.25469 (19)	0.0427 (6)
C19	0.7963 (3)	0.26720 (19)	−0.14760 (19)	0.0400 (5)
C20	0.9572 (3)	0.3118 (2)	−0.1525 (2)	0.0571 (7)
H20	0.9828	0.3190	−0.2241	0.069*
C21	1.0794 (3)	0.3457 (3)	−0.0539 (3)	0.0704 (9)
H21	1.1863	0.3754	−0.0590	0.084*
C22	1.0418 (3)	0.3351 (3)	0.0525 (2)	0.0638 (8)
H22	1.1237	0.3575	0.1195	0.077*
C23	0.8834 (3)	0.2913 (2)	0.0595 (2)	0.0488 (6)
H23	0.8592	0.2850	0.1317	0.059*
C24	0.7592 (3)	0.25648 (18)	−0.03888 (18)	0.0369 (5)
N1	0.0201 (2)	0.19659 (14)	0.49270 (14)	0.0338 (4)
N2	−0.0105 (2)	−0.01530 (14)	0.29787 (14)	0.0309 (4)
O1	0.26802 (17)	0.02247 (12)	0.53842 (12)	0.0354 (3)
H11	0.3286	0.0809	0.5256	0.042*
H12	0.3335	−0.0201	0.5745	0.042*
O2	0.4542 (2)	0.20761 (14)	0.47789 (13)	0.0493 (4)
O3	0.5396 (2)	0.11191 (14)	0.33731 (13)	0.0466 (4)
O4	0.5199 (2)	0.20487 (17)	−0.25451 (14)	0.0602 (5)
O5	0.7208 (2)	0.23484 (17)	−0.35055 (14)	0.0606 (5)
H51	0.6376	0.2168	−0.4033	0.073*
S1	0.55261 (7)	0.19603 (5)	−0.03290 (5)	0.04397 (16)
S2	0.56728 (7)	0.16800 (5)	0.13681 (5)	0.03939 (15)

	U11	U22	U33	U12	U13	U23
Mn1	0.0335 (2)	0.0252 (2)	0.0210 (2)	0.00591 (17)	0.00676 (18)	0.00459 (17)
C1	0.0358 (12)	0.0617 (15)	0.0222 (11)	−0.0030 (11)	0.0030 (9)	0.0019 (10)
C2	0.0351 (12)	0.0648 (16)	0.0268 (11)	−0.0044 (11)	0.0104 (9)	0.0038 (11)
C3	0.0363 (11)	0.0293 (11)	0.0213 (10)	0.0047 (9)	0.0078 (8)	0.0014 (8)
C4	0.0318 (11)	0.0534 (14)	0.0227 (11)	0.0015 (10)	0.0037 (9)	0.0031 (9)
C5	0.0346 (12)	0.0489 (13)	0.0267 (11)	0.0024 (10)	0.0097 (9)	0.0042 (9)
C6	0.0566 (15)	0.0302 (12)	0.0442 (14)	0.0031 (11)	−0.0087 (11)	0.0018 (10)
C7	0.0539 (15)	0.0344 (13)	0.0501 (15)	0.0061 (11)	−0.0135 (12)	0.0054 (11)
C8	0.0329 (11)	0.0299 (11)	0.0357 (11)	0.0025 (9)	0.0080 (9)	0.0038 (9)
C9	0.0481 (14)	0.0352 (12)	0.0362 (12)	0.0066 (10)	−0.0035 (10)	−0.0016 (10)
C10	0.0500 (14)	0.0375 (13)	0.0361 (12)	0.0132 (10)	0.0007 (11)	0.0069 (10)
C11	0.0350 (12)	0.0436 (13)	0.0301 (12)	0.0033 (10)	0.0040 (9)	0.0091 (10)
C12	0.0338 (11)	0.0401 (12)	0.0293 (11)	0.0053 (9)	0.0055 (9)	0.0079 (9)
C13	0.0643 (16)	0.0508 (15)	0.0367 (13)	0.0151 (12)	0.0183 (12)	0.0072 (11)
C14	0.095 (2)	0.0449 (15)	0.0562 (17)	0.0262 (14)	0.0249 (16)	0.0083 (13)
C15	0.0811 (19)	0.0419 (14)	0.0492 (16)	0.0164 (13)	0.0145 (14)	0.0188 (12)
C16	0.0522 (14)	0.0476 (14)	0.0323 (12)	0.0096 (11)	0.0125 (11)	0.0129 (10)
C17	0.0298 (11)	0.0399 (12)	0.0282 (11)	0.0061 (9)	0.0019 (9)	0.0069 (9)
C18	0.0582 (16)	0.0414 (13)	0.0326 (12)	0.0110 (11)	0.0155 (11)	0.0073 (10)
C19	0.0455 (13)	0.0426 (13)	0.0353 (12)	0.0120 (10)	0.0124 (10)	0.0068 (10)
C20	0.0574 (17)	0.0724 (19)	0.0480 (15)	0.0075 (14)	0.0245 (13)	0.0110 (13)
C21	0.0445 (16)	0.098 (2)	0.068 (2)	−0.0070 (15)	0.0194 (15)	0.0086 (17)
C22	0.0462 (16)	0.086 (2)	0.0505 (16)	−0.0066 (14)	0.0019 (13)	0.0022 (15)
C23	0.0469 (14)	0.0637 (16)	0.0328 (12)	0.0006 (12)	0.0069 (11)	0.0014 (11)
C24	0.0404 (12)	0.0382 (12)	0.0326 (12)	0.0045 (10)	0.0099 (10)	0.0015 (9)
N1	0.0400 (10)	0.0308 (9)	0.0303 (9)	0.0072 (8)	0.0059 (8)	0.0032 (7)
N2	0.0366 (10)	0.0330 (9)	0.0242 (9)	0.0039 (7)	0.0091 (8)	0.0032 (7)
O1	0.0333 (8)	0.0389 (8)	0.0353 (8)	0.0072 (6)	0.0059 (6)	0.0141 (6)
O2	0.0654 (11)	0.0569 (11)	0.0292 (8)	0.0068 (8)	0.0160 (8)	0.0132 (7)
O3	0.0575 (10)	0.0477 (10)	0.0425 (9)	0.0208 (8)	0.0162 (8)	0.0204 (8)
O4	0.0569 (12)	0.0838 (14)	0.0348 (9)	−0.0073 (10)	0.0084 (8)	0.0034 (9)
O5	0.0658 (12)	0.0897 (14)	0.0305 (9)	0.0164 (10)	0.0168 (8)	0.0068 (9)
S1	0.0428 (3)	0.0576 (4)	0.0289 (3)	−0.0034 (3)	0.0082 (2)	0.0014 (3)
S2	0.0464 (3)	0.0420 (3)	0.0326 (3)	0.0074 (3)	0.0131 (2)	0.0070 (2)

Mn1—O1	2.1453 (18)	C11—C12	1.505 (3)
Mn1—O1i	2.1453 (18)	C12—C13	1.387 (3)
Mn1—N1i	2.312 (2)	C12—C17	1.407 (3)
Mn1—N1	2.312 (2)	C13—C14	1.376 (3)
Mn1—N2	2.384 (2)	C13—H13	0.9300
Mn1—N2i	2.384 (2)	C14—C15	1.381 (4)
C1—N2	1.341 (3)	C14—H14	0.9300
C1—C2	1.378 (3)	C15—C16	1.374 (3)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.388 (3)	C16—C17	1.399 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.391 (3)	C17—S2	1.792 (2)
C3—C3ii	1.495 (4)	C18—O4	1.206 (3)
C4—C5	1.384 (3)	C18—O5	1.322 (3)
C4—H4	0.9300	C18—C19	1.487 (3)
C5—N2	1.338 (3)	C19—C20	1.390 (3)
C5—H5	0.9300	C19—C24	1.405 (3)
C6—N1	1.338 (3)	C20—C21	1.376 (4)
C6—C7	1.376 (3)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.380 (4)
C7—C8	1.393 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.376 (4)
C8—C9	1.393 (3)	C22—H22	0.9300
C8—C8iii	1.495 (4)	C23—C24	1.385 (3)
C9—C10	1.378 (3)	C23—H23	0.9300
C9—H9	0.9300	C24—S1	1.794 (2)
C10—N1	1.347 (3)	O1—H11	0.8488
C10—H10	0.9300	O1—H12	0.8488
C11—O3	1.249 (3)	O5—H51	0.8220
C11—O2	1.267 (3)	S1—S2	2.0539 (14)
O1—Mn1—O1i	180.0	C17—C12—C11	121.76 (19)
O1—Mn1—N1i	93.78 (6)	C14—C13—C12	121.6 (2)
O1i—Mn1—N1i	86.22 (6)	C14—C13—H13	119.2
O1—Mn1—N1	86.22 (6)	C12—C13—H13	119.2
O1i—Mn1—N1	93.78 (6)	C13—C14—C15	119.2 (2)
N1i—Mn1—N1	180.0	C13—C14—H14	120.4
O1—Mn1—N2	91.06 (5)	C15—C14—H14	120.4
O1i—Mn1—N2	88.94 (5)	C16—C15—C14	120.5 (2)
N1i—Mn1—N2	93.20 (6)	C16—C15—H15	119.8
N1—Mn1—N2	86.80 (6)	C14—C15—H15	119.8
O1—Mn1—N2i	88.94 (5)	C15—C16—C17	121.0 (2)
O1i—Mn1—N2i	91.06 (5)	C15—C16—H16	119.5
N1i—Mn1—N2i	86.80 (6)	C17—C16—H16	119.5
N1—Mn1—N2i	93.20 (6)	C16—C17—C12	118.4 (2)
N2—Mn1—N2i	180.0	C16—C17—S2	122.06 (17)
N2—C1—C2	124.3 (2)	C12—C17—S2	119.51 (16)
N2—C1—H1	117.9	O4—C18—O5	122.9 (2)
C2—C1—H1	117.9	O4—C18—C19	123.2 (2)
C1—C2—C3	120.5 (2)	O5—C18—C19	113.9 (2)
C1—C2—H2	119.7	C20—C19—C24	118.7 (2)
C3—C2—H2	119.7	C20—C19—C18	121.1 (2)
C2—C3—C4	115.27 (18)	C24—C19—C18	120.2 (2)
C2—C3—C3ii	122.7 (2)	C21—C20—C19	121.6 (2)
C4—C3—C3ii	122.0 (2)	C21—C20—H20	119.2
C5—C4—C3	120.80 (19)	C19—C20—H20	119.2
C5—C4—H4	119.6	C20—C21—C22	119.3 (3)
C3—C4—H4	119.6	C20—C21—H21	120.3
N2—C5—C4	123.71 (19)	C22—C21—H21	120.3
N2—C5—H5	118.1	C23—C22—C21	120.1 (3)
C4—C5—H5	118.1	C23—C22—H22	119.9
N1—C6—C7	124.6 (2)	C21—C22—H22	119.9
N1—C6—H6	117.7	C22—C23—C24	121.2 (2)
C7—C6—H6	117.7	C22—C23—H23	119.4
C6—C7—C8	120.3 (2)	C24—C23—H23	119.4
C6—C7—H7	119.8	C23—C24—C19	119.0 (2)
C8—C7—H7	119.8	C23—C24—S1	122.39 (17)
C7—C8—C9	115.4 (2)	C19—C24—S1	118.59 (17)
C7—C8—C8iii	121.8 (2)	C6—N1—C10	114.97 (18)
C9—C8—C8iii	122.8 (2)	C6—N1—Mn1	121.51 (14)
C10—C9—C8	120.5 (2)	C10—N1—Mn1	123.27 (14)
C10—C9—H9	119.8	C5—N2—C1	115.39 (17)
C8—C9—H9	119.8	C5—N2—Mn1	126.19 (13)
N1—C10—C9	124.1 (2)	C1—N2—Mn1	118.17 (13)
N1—C10—H10	118.0	Mn1—O1—H11	124.9
C9—C10—H10	118.0	Mn1—O1—H12	127.9
O3—C11—O2	124.6 (2)	H11—O1—H12	106.9
O3—C11—C12	117.53 (19)	C18—O5—H51	105.1
O2—C11—C12	117.8 (2)	C24—S1—S2	105.21 (8)
C13—C12—C17	119.2 (2)	C17—S2—S1	104.13 (8)
C13—C12—C11	118.9 (2)
N2—C1—C2—C3	−0.7 (4)	C20—C19—C24—C23	0.4 (3)
C1—C2—C3—C4	−1.1 (3)	C18—C19—C24—C23	−179.5 (2)
C1—C2—C3—C3ii	179.9 (2)	C20—C19—C24—S1	−178.70 (18)
C2—C3—C4—C5	1.3 (3)	C18—C19—C24—S1	1.4 (3)
C3ii—C3—C4—C5	−179.7 (2)	C7—C6—N1—C10	−4.3 (4)
C3—C4—C5—N2	0.3 (3)	C7—C6—N1—Mn1	170.2 (2)
N1—C6—C7—C8	1.4 (4)	C9—C10—N1—C6	4.3 (3)
C6—C7—C8—C9	1.6 (4)	C9—C10—N1—Mn1	−170.04 (18)
C6—C7—C8—C8iii	−178.1 (3)	O1—Mn1—N1—C6	137.19 (18)
C7—C8—C9—C10	−1.6 (3)	O1i—Mn1—N1—C6	−42.81 (18)
C8iii—C8—C9—C10	178.1 (2)	N1i—Mn1—N1—C6	−123 (100)
C8—C9—C10—N1	−1.5 (4)	N2—Mn1—N1—C6	45.92 (18)
O3—C11—C12—C13	−176.1 (2)	N2i—Mn1—N1—C6	−134.08 (18)
O2—C11—C12—C13	3.0 (3)	O1—Mn1—N1—C10	−48.84 (17)
O3—C11—C12—C17	−0.6 (3)	O1i—Mn1—N1—C10	131.16 (17)
O2—C11—C12—C17	178.5 (2)	N1i—Mn1—N1—C10	51 (100)
C17—C12—C13—C14	−1.8 (4)	N2—Mn1—N1—C10	−140.12 (18)
C11—C12—C13—C14	173.8 (2)	N2i—Mn1—N1—C10	39.88 (18)
C12—C13—C14—C15	−0.5 (4)	C4—C5—N2—C1	−2.0 (3)
C13—C14—C15—C16	1.8 (4)	C4—C5—N2—Mn1	172.24 (16)
C14—C15—C16—C17	−0.9 (4)	C2—C1—N2—C5	2.2 (3)
C15—C16—C17—C12	−1.4 (3)	C2—C1—N2—Mn1	−172.51 (19)
C15—C16—C17—S2	179.74 (19)	O1—Mn1—N2—C5	176.09 (17)
C13—C12—C17—C16	2.7 (3)	O1i—Mn1—N2—C5	−3.91 (17)
C11—C12—C17—C16	−172.80 (19)	N1i—Mn1—N2—C5	82.25 (17)
C13—C12—C17—S2	−178.41 (17)	N1—Mn1—N2—C5	−97.75 (17)
C11—C12—C17—S2	6.1 (3)	N2i—Mn1—N2—C5	−142 (100)
O4—C18—C19—C20	−171.1 (2)	O1—Mn1—N2—C1	−9.86 (16)
O5—C18—C19—C20	6.7 (3)	O1i—Mn1—N2—C1	170.14 (16)
O4—C18—C19—C24	8.8 (4)	N1i—Mn1—N2—C1	−103.70 (16)
O5—C18—C19—C24	−173.4 (2)	N1—Mn1—N2—C1	76.30 (16)
C24—C19—C20—C21	−0.2 (4)	N2i—Mn1—N2—C1	33 (100)
C18—C19—C20—C21	179.8 (3)	C23—C24—S1—S2	−9.7 (2)
C19—C20—C21—C22	0.1 (5)	C19—C24—S1—S2	169.35 (16)
C20—C21—C22—C23	−0.2 (5)	C16—C17—S2—S1	−15.88 (19)
C21—C22—C23—C24	0.4 (4)	C12—C17—S2—S1	165.29 (15)
C22—C23—C24—C19	−0.5 (4)	C24—S1—S2—C17	91.50 (11)
C22—C23—C24—S1	178.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···O2	0.85	1.92	2.761 (3)	173
O1—H12···O3iv	0.85	1.82	2.667 (3)	174
O5—H51···O2v	0.82	1.83	2.637 (3)	169
C4—H4···S1vi	0.93	2.86	3.562 (3)	133
C23—H23···S2	0.93	2.66	3.191 (3)	117
C22—H22···Cg1vii	0.93	2.94	3.79 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11⋯O2	0.85	1.92	2.761 (3)	173
O1—H12⋯O3i	0.85	1.82	2.667 (3)	174
O5—H51⋯O2ii	0.82	1.83	2.637 (3)	169
C4—H4⋯S1iii	0.93	2.86	3.562 (3)	133
C23—H23⋯S2	0.93	2.66	3.191 (3)	117
C22—H22⋯Cg1iv	0.93	2.94	3.79 (2)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C12–C17 ring.