Poly[[diaqua-tris(μ2-4,4'-bi-pyridine)-bis[μ2-2-(carb-oxylato-methyl-sulfan-yl)nicotinato]dicobalt(II)] 1.3-hydrate].

The title complex, [Co2(C8H5NO4S)2(C10H8N2)3(H2O)2]·1.3H2O, was synthesized under hydro-thermal conditions. The Co(II) ion is six-coordinated in a slightly distorted octa-hedral environment resulting from two carboxyl-ate O atoms of two 2-carb-oxy-methyl-sulfanyl nicotinate (2-CMSN(2-)) anions, one water mol-ecule and three N atoms of three 4,4'-bi-pyridine ligands, with one 4,4'-bi-pyridine ligand situated on a centre of inversion. Two neighboring Co(II) ions are linked by two anions, giving a dinuclear [Co2(2-CMSN)2] subunit with a Co⋯Co separation of 6.8600 (3) Å. The dinuclear subunits are joined by bridging 4,4'-bi-pyridine linkers, generating a three-dimensional network structure. Disordered water mol-ecules are situated in the free space of this network. O-H⋯O hydrogen bonding within and between the subunits enhances the stability of the structure.

Related literature

For general background to coordination polymers, see: Wang et al. (2004 ▶). For crystal structures of related compounds based on 2-mercaptonicotinic acid, see: Sun et al. (2011 ▶). For complexes derived from the 2-H2CMSN ligand, see: Jiang et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

[Co2(C8H5NO4S)2(C10H8N2)3(H2O)2]·1.3H2O

M = 534.13

Monoclinic,

a = 10.2211 (1) Å

b = 17.1355 (2) Å

c = 16.4142 (2) Å

β = 125.484 (1)°

V = 2340.92 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.87 mm−1

T = 296 K

0.34 × 0.20 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.814, T max = 0.912

38093 measured reflections

5439 independent reflections

4772 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.093

S = 1.05

5439 reflections

315 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813015262/wm2744sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015262/wm2744Isup2.hkl

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

[Co2(C8H5NO4S)2(C10H8N2)3(H2O)2]·1.3H2O	F(000) = 1092.9
Mr = 1068.26	V=2340.92(5)Å3
Monoclinic, P21/c	Dx = 1.516 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.2211 (1) Å	θ = 1.9–27.6°
b = 17.1355 (2) Å	µ = 0.87 mm−1
c = 16.4142 (2) Å	T = 296 K
β = 125.484 (1)°	Block, red
V = 2340.92 (5) Å3	0.34 × 0.20 × 0.11 mm
Z = 2

Bruker APEXII CCD diffractometer	5439 independent reflections
Radiation source: fine-focus sealed tube	4772 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 27.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −13→13
Tmin = 0.814, Tmax = 0.912	k = −22→22
38093 measured reflections	l = −21→21

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0477P)2 + 1.3453P] where P = (Fo2 + 2Fc2)/3
5439 reflections	(Δ/σ)max = 0.001
315 parameters	Δρmax = 0.68 e Å−3
3 restraints	Δρmin = −0.53 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	Occ. (<1)
Co1	0.22673 (3)	−0.467750 (13)	0.253178 (16)	0.02436 (8)
S1	−0.26808 (6)	−0.54790 (4)	0.03145 (4)	0.04356 (14)
N1	−0.3385 (2)	−0.68541 (12)	−0.05863 (14)	0.0512 (5)
N2	0.04982 (18)	−0.38323 (9)	0.15601 (11)	0.0316 (3)
N3	−0.60092 (18)	−0.12730 (9)	−0.15781 (11)	0.0317 (3)
N4	0.14149 (18)	−0.47934 (10)	0.34767 (11)	0.0324 (3)
O1	0.06128 (15)	−0.55683 (8)	0.16874 (10)	0.0366 (3)
O2	0.20011 (18)	−0.66643 (9)	0.23590 (11)	0.0506 (4)
O3	−0.54191 (18)	−0.48099 (12)	−0.24881 (12)	0.0595 (5)
O4	−0.29489 (15)	−0.53055 (8)	−0.15622 (10)	0.0327 (3)
O1W	0.41017 (15)	−0.55208 (8)	0.34497 (9)	0.0344 (3)
H1WB	0.3686	−0.5973	0.3268	0.041*
H1WA	0.4812	−0.5482	0.3336	0.041*
O2W	0.3056 (6)	−0.8235 (3)	0.2968 (4)	0.0716 (13)*	0.40
O3W	−0.7292 (11)	−0.3553 (6)	−0.2320 (7)	0.082 (2)*	0.25
C1	−0.0421 (3)	−0.75259 (13)	0.07695 (19)	0.0537 (6)
H1A	0.0564	−0.7762	0.1229	0.064*
C2	−0.1648 (4)	−0.79492 (14)	−0.0044 (2)	0.0737 (9)
H2A	−0.1496	−0.8467	−0.0141	0.088*
C3	−0.3083 (4)	−0.75831 (15)	−0.0694 (2)	0.0661 (8)
H3A	−0.3895	−0.7863	−0.1245	0.079*
C4	−0.2204 (2)	−0.64420 (12)	0.01904 (13)	0.0350 (4)
C5	−0.0664 (2)	−0.67566 (11)	0.08956 (14)	0.0345 (4)
C6	0.0760 (2)	−0.62946 (11)	0.17223 (13)	0.0314 (4)
C7	−0.4499 (3)	−0.52819 (15)	−0.09011 (16)	0.0474 (5)
H7A	−0.5211	−0.5727	−0.1103	0.057*
H7B	−0.5031	−0.4837	−0.0847	0.057*
C8	−0.4259 (2)	−0.51158 (12)	−0.17142 (14)	0.0347 (4)
C9	−0.1027 (3)	−0.26859 (15)	0.12914 (17)	0.0637 (8)
H9A	−0.1169	−0.2245	0.1563	0.076*
C10	0.0229 (3)	−0.31873 (14)	0.18932 (16)	0.0563 (7)
H10A	0.0930	−0.3069	0.2570	0.068*
C11	−0.0478 (2)	−0.39688 (11)	0.05773 (13)	0.0334 (4)
H11A	−0.0282	−0.4403	0.0323	0.040*
C12	−0.1767 (2)	−0.34941 (11)	−0.00793 (13)	0.0346 (4)
H12A	−0.2421	−0.3614	−0.0758	0.042*
C13	−0.2083 (2)	−0.28423 (11)	0.02741 (14)	0.0369 (4)
C14	−0.4239 (3)	−0.19437 (14)	−0.00281 (15)	0.0474 (5)
H14A	−0.3913	−0.2030	0.0624	0.057*
C15	−0.3472 (2)	−0.23228 (11)	−0.03857 (14)	0.0359 (4)
C16	−0.5485 (2)	−0.14378 (13)	−0.06392 (14)	0.0421 (5)
H16A	−0.5990	−0.1197	−0.0383	0.051*
C17	−0.5296 (3)	−0.16573 (12)	−0.19305 (15)	0.0422 (5)
H17A	−0.5660	−0.1568	−0.2590	0.051*
C18	−0.4046 (3)	−0.21800 (12)	−0.13694 (15)	0.0439 (5)
H18A	−0.3595	−0.2434	−0.1652	0.053*
C19	−0.0124 (3)	−0.46731 (18)	0.31159 (16)	0.0580 (7)
H19A	−0.0828	−0.4523	0.2450	0.070*
C20	−0.0725 (2)	−0.47589 (19)	0.36765 (16)	0.0623 (8)
H20A	−0.1810	−0.4673	0.3384	0.075*
C21	0.1870 (2)	−0.51257 (11)	0.50404 (14)	0.0342 (4)
H21A	0.2596	−0.5290	0.5698	0.041*
C22	0.2363 (2)	−0.50319 (11)	0.44222 (14)	0.0334 (4)
H22A	0.3429	−0.5143	0.4684	0.040*
C23	0.0286 (2)	−0.49728 (11)	0.46761 (13)	0.0319 (4)

	U11	U22	U33	U12	U13	U23
Co1	0.01954 (12)	0.02930 (13)	0.02172 (12)	0.00108 (8)	0.01053 (10)	0.00026 (8)
S1	0.0376 (3)	0.0610 (3)	0.0279 (2)	0.0119 (2)	0.0166 (2)	−0.0005 (2)
N1	0.0453 (10)	0.0565 (11)	0.0372 (9)	−0.0174 (9)	0.0156 (8)	−0.0018 (8)
N2	0.0287 (7)	0.0332 (7)	0.0277 (7)	0.0085 (6)	0.0133 (6)	0.0012 (6)
N3	0.0272 (7)	0.0340 (8)	0.0269 (7)	0.0054 (6)	0.0118 (6)	0.0025 (6)
N4	0.0243 (7)	0.0467 (9)	0.0270 (7)	−0.0038 (6)	0.0153 (6)	−0.0027 (6)
O1	0.0280 (7)	0.0316 (6)	0.0355 (7)	−0.0012 (5)	0.0100 (6)	−0.0022 (5)
O2	0.0419 (8)	0.0390 (8)	0.0445 (8)	0.0039 (6)	0.0101 (7)	0.0102 (6)
O3	0.0285 (8)	0.1104 (15)	0.0385 (8)	0.0196 (8)	0.0188 (7)	0.0218 (9)
O4	0.0257 (6)	0.0449 (7)	0.0285 (6)	0.0045 (5)	0.0163 (5)	−0.0001 (5)
O1W	0.0265 (6)	0.0432 (7)	0.0298 (6)	0.0052 (5)	0.0142 (5)	0.0048 (5)
C1	0.0587 (14)	0.0325 (10)	0.0540 (13)	−0.0024 (10)	0.0237 (12)	0.0045 (9)
C2	0.095 (2)	0.0312 (11)	0.0711 (18)	−0.0167 (13)	0.0345 (17)	−0.0085 (11)
C3	0.0711 (18)	0.0491 (14)	0.0481 (13)	−0.0264 (13)	0.0174 (13)	−0.0067 (11)
C4	0.0346 (10)	0.0435 (10)	0.0276 (8)	−0.0089 (8)	0.0184 (8)	0.0004 (7)
C5	0.0379 (10)	0.0326 (9)	0.0317 (9)	−0.0069 (7)	0.0196 (8)	0.0025 (7)
C6	0.0324 (9)	0.0345 (9)	0.0262 (8)	−0.0014 (7)	0.0164 (7)	0.0043 (7)
C7	0.0287 (10)	0.0808 (16)	0.0351 (10)	0.0118 (10)	0.0198 (9)	0.0087 (10)
C8	0.0239 (9)	0.0502 (11)	0.0280 (8)	−0.0007 (8)	0.0140 (7)	−0.0029 (8)
C9	0.0586 (15)	0.0597 (14)	0.0353 (11)	0.0329 (12)	0.0057 (10)	−0.0140 (10)
C10	0.0495 (13)	0.0581 (14)	0.0293 (10)	0.0250 (11)	0.0046 (9)	−0.0102 (9)
C11	0.0403 (10)	0.0324 (9)	0.0287 (8)	0.0094 (7)	0.0207 (8)	0.0026 (7)
C12	0.0402 (10)	0.0353 (9)	0.0240 (8)	0.0088 (8)	0.0162 (8)	0.0023 (7)
C13	0.0360 (10)	0.0374 (10)	0.0292 (9)	0.0131 (8)	0.0143 (8)	0.0026 (7)
C14	0.0505 (12)	0.0582 (13)	0.0276 (9)	0.0263 (10)	0.0193 (9)	0.0095 (9)
C15	0.0335 (10)	0.0350 (9)	0.0294 (9)	0.0100 (7)	0.0127 (8)	0.0010 (7)
C16	0.0421 (11)	0.0503 (11)	0.0334 (10)	0.0189 (9)	0.0216 (9)	0.0063 (8)
C17	0.0502 (12)	0.0444 (11)	0.0301 (9)	0.0165 (9)	0.0222 (9)	0.0083 (8)
C18	0.0508 (12)	0.0454 (11)	0.0371 (10)	0.0202 (9)	0.0265 (10)	0.0073 (9)
C19	0.0243 (10)	0.123 (2)	0.0231 (9)	−0.0001 (11)	0.0117 (8)	0.0058 (11)
C20	0.0190 (9)	0.137 (3)	0.0276 (10)	−0.0005 (12)	0.0119 (8)	0.0040 (12)
C21	0.0314 (9)	0.0408 (10)	0.0322 (9)	0.0058 (7)	0.0195 (8)	0.0088 (7)
C22	0.0272 (9)	0.0401 (10)	0.0358 (9)	0.0055 (7)	0.0200 (8)	0.0067 (8)
C23	0.0258 (9)	0.0428 (10)	0.0286 (8)	−0.0074 (7)	0.0166 (7)	−0.0042 (7)

Co1—O4i	2.0752 (13)	C5—C6	1.514 (3)
Co1—O1	2.0951 (13)	C7—C8	1.518 (3)
Co1—N2	2.1361 (14)	C7—H7A	0.9700
Co1—O1W	2.1434 (13)	C7—H7B	0.9700
Co1—N4	2.1847 (15)	C9—C10	1.375 (3)
Co1—N3ii	2.2141 (15)	C9—C13	1.390 (3)
S1—C4	1.765 (2)	C9—H9A	0.9300
S1—C7	1.801 (2)	C10—H10A	0.9300
N1—C3	1.323 (4)	C11—C12	1.382 (2)
N1—C4	1.340 (3)	C11—H11A	0.9300
N2—C10	1.331 (2)	C12—C13	1.380 (3)
N2—C11	1.336 (2)	C12—H12A	0.9300
N3—C16	1.335 (2)	C13—C15	1.482 (3)
N3—C17	1.338 (2)	C14—C16	1.377 (3)
N3—Co1iii	2.2141 (14)	C14—C15	1.384 (3)
N4—C22	1.330 (2)	C14—H14A	0.9300
N4—C19	1.336 (3)	C15—C18	1.382 (3)
O1—C6	1.251 (2)	C16—H16A	0.9300
O2—C6	1.251 (2)	C17—C18	1.384 (3)
O3—C8	1.243 (2)	C17—H17A	0.9300
O4—C8	1.254 (2)	C18—H18A	0.9300
O4—Co1i	2.0752 (13)	C19—C20	1.379 (3)
O1W—H1WB	0.8500	C19—H19A	0.9300
O1W—H1WA	0.8500	C20—C23	1.388 (3)
C1—C5	1.379 (3)	C20—H20A	0.9300
C1—C2	1.392 (4)	C21—C22	1.379 (2)
C1—H1A	0.9300	C21—C23	1.387 (2)
C2—C3	1.366 (4)	C21—H21A	0.9300
C2—H2A	0.9300	C22—H22A	0.9300
C3—H3A	0.9300	C23—C23iv	1.484 (3)
C4—C5	1.412 (3)
O4i—Co1—O1	89.07 (5)	C8—C7—H7B	108.6
O4i—Co1—N2	87.27 (5)	S1—C7—H7B	108.6
O1—Co1—N2	89.52 (6)	H7A—C7—H7B	107.5
O4i—Co1—O1W	89.06 (5)	O3—C8—O4	125.96 (18)
O1—Co1—O1W	90.84 (5)	O3—C8—C7	115.63 (17)
N2—Co1—O1W	176.31 (5)	O4—C8—C7	118.40 (17)
O4i—Co1—N4	173.20 (6)	C10—C9—C13	119.52 (19)
O1—Co1—N4	84.38 (6)	C10—C9—H9A	120.2
N2—Co1—N4	94.48 (6)	C13—C9—H9A	120.2
O1W—Co1—N4	89.21 (5)	N2—C10—C9	123.60 (19)
O4i—Co1—N3ii	91.36 (5)	N2—C10—H10A	118.2
O1—Co1—N3ii	179.27 (6)	C9—C10—H10A	118.2
N2—Co1—N3ii	89.91 (6)	N2—C11—C12	122.98 (16)
O1W—Co1—N3ii	89.76 (6)	N2—C11—H11A	118.5
N4—Co1—N3ii	95.21 (6)	C12—C11—H11A	118.5
C4—S1—C7	102.94 (11)	C13—C12—C11	119.87 (17)
C3—N1—C4	118.3 (2)	C13—C12—H12A	120.1
C10—N2—C11	117.00 (16)	C11—C12—H12A	120.1
C10—N2—Co1	122.93 (13)	C12—C13—C9	116.92 (17)
C11—N2—Co1	119.88 (12)	C12—C13—C15	122.51 (17)
C16—N3—C17	116.14 (16)	C9—C13—C15	120.57 (17)
C16—N3—Co1iii	123.35 (12)	C16—C14—C15	119.91 (18)
C17—N3—Co1iii	120.09 (12)	C16—C14—H14A	120.0
C22—N4—C19	115.95 (16)	C15—C14—H14A	120.0
C22—N4—Co1	122.38 (12)	C18—C15—C14	116.83 (17)
C19—N4—Co1	121.55 (13)	C18—C15—C13	122.48 (18)
C6—O1—Co1	131.70 (12)	C14—C15—C13	120.68 (18)
C8—O4—Co1i	130.24 (12)	N3—C16—C14	123.75 (18)
Co1—O1W—H1WB	108.2	N3—C16—H16A	118.1
Co1—O1W—H1WA	107.6	C14—C16—H16A	118.1
H1WB—O1W—H1WA	108.2	N3—C17—C18	123.70 (18)
C5—C1—C2	120.1 (2)	N3—C17—H17A	118.1
C5—C1—H1A	119.9	C18—C17—H17A	118.1
C2—C1—H1A	119.9	C15—C18—C17	119.59 (18)
C3—C2—C1	118.1 (2)	C15—C18—H18A	120.2
C3—C2—H2A	121.0	C17—C18—H18A	120.2
C1—C2—H2A	121.0	N4—C19—C20	123.60 (19)
N1—C3—C2	123.9 (2)	N4—C19—H19A	118.2
N1—C3—H3A	118.1	C20—C19—H19A	118.2
C2—C3—H3A	118.1	C19—C20—C23	120.19 (19)
N1—C4—C5	122.6 (2)	C19—C20—H20A	119.9
N1—C4—S1	116.49 (16)	C23—C20—H20A	119.9
C5—C4—S1	120.88 (14)	C22—C21—C23	119.62 (17)
C1—C5—C4	117.00 (19)	C22—C21—H21A	120.2
C1—C5—C6	118.12 (19)	C23—C21—H21A	120.2
C4—C5—C6	124.70 (17)	N4—C22—C21	124.35 (17)
O2—C6—O1	125.36 (17)	N4—C22—H22A	117.8
O2—C6—C5	117.72 (17)	C21—C22—H22A	117.8
O1—C6—C5	116.86 (16)	C21—C23—C20	116.18 (17)
C8—C7—S1	114.81 (14)	C21—C23—C23iv	121.7 (2)
C8—C7—H7A	108.6	C20—C23—C23iv	122.1 (2)
S1—C7—H7A	108.6
O4i—Co1—N2—C10	−135.1 (2)	C1—C5—C6—O1	164.59 (19)
O1—Co1—N2—C10	135.8 (2)	C4—C5—C6—O1	−10.3 (3)
N4—Co1—N2—C10	51.5 (2)	C4—S1—C7—C8	−75.84 (19)
N3ii—Co1—N2—C10	−43.7 (2)	Co1i—O4—C8—O3	−8.2 (3)
O4i—Co1—N2—C11	49.97 (15)	Co1i—O4—C8—C7	170.55 (14)
O1—Co1—N2—C11	−39.12 (15)	S1—C7—C8—O3	−164.40 (18)
O1W—Co1—N2—C11	56.5 (9)	S1—C7—C8—O4	16.8 (3)
N4—Co1—N2—C11	−123.44 (15)	C11—N2—C10—C9	3.2 (4)
N3ii—Co1—N2—C11	141.34 (15)	Co1—N2—C10—C9	−171.9 (2)
O4i—Co1—N4—C22	99.9 (4)	C13—C9—C10—N2	−0.7 (5)
O1—Co1—N4—C22	115.53 (15)	C10—N2—C11—C12	−3.0 (3)
N2—Co1—N4—C22	−155.40 (15)	Co1—N2—C11—C12	172.19 (15)
O1W—Co1—N4—C22	24.61 (15)	N2—C11—C12—C13	0.5 (3)
N3ii—Co1—N4—C22	−65.08 (16)	C11—C12—C13—C9	2.0 (3)
O4i—Co1—N4—C19	−76.0 (5)	C11—C12—C13—C15	−178.22 (19)
O1—Co1—N4—C19	−60.33 (19)	C10—C9—C13—C12	−1.9 (4)
N2—Co1—N4—C19	28.75 (19)	C10—C9—C13—C15	178.3 (3)
O1W—Co1—N4—C19	−151.25 (19)	C16—C14—C15—C18	−1.5 (3)
N3ii—Co1—N4—C19	119.06 (19)	C16—C14—C15—C13	177.3 (2)
O4i—Co1—O1—C6	85.94 (17)	C12—C13—C15—C18	−33.7 (3)
N2—Co1—O1—C6	173.22 (17)	C9—C13—C15—C18	146.1 (3)
O1W—Co1—O1—C6	−3.11 (17)	C12—C13—C15—C14	147.5 (2)
N4—Co1—O1—C6	−92.23 (17)	C9—C13—C15—C14	−32.7 (3)
N3ii—Co1—O1—C6	−148 (4)	C17—N3—C16—C14	2.8 (3)
C5—C1—C2—C3	−0.8 (4)	Co1iii—N3—C16—C14	−169.71 (18)
C4—N1—C3—C2	1.9 (4)	C15—C14—C16—N3	−1.0 (4)
C1—C2—C3—N1	−1.3 (5)	C16—N3—C17—C18	−2.2 (3)
C3—N1—C4—C5	−0.4 (3)	Co1iii—N3—C17—C18	170.62 (18)
C3—N1—C4—S1	−178.79 (19)	C14—C15—C18—C17	2.1 (3)
C7—S1—C4—N1	−16.68 (17)	C13—C15—C18—C17	−176.7 (2)
C7—S1—C4—C5	164.86 (15)	N3—C17—C18—C15	−0.3 (4)
C2—C1—C5—C4	2.1 (3)	C22—N4—C19—C20	2.2 (4)
C2—C1—C5—C6	−173.2 (2)	Co1—N4—C19—C20	178.3 (2)
N1—C4—C5—C1	−1.6 (3)	N4—C19—C20—C23	0.8 (5)
S1—C4—C5—C1	176.78 (16)	C19—N4—C22—C21	−2.8 (3)
N1—C4—C5—C6	173.38 (18)	Co1—N4—C22—C21	−178.90 (15)
S1—C4—C5—C6	−8.3 (3)	C23—C21—C22—N4	0.6 (3)
Co1—O1—C6—O2	4.9 (3)	C22—C21—C23—C20	2.4 (3)
Co1—O1—C6—C5	−172.18 (12)	C22—C21—C23—C23iv	−177.0 (2)
C1—C5—C6—O2	−12.7 (3)	C19—C20—C23—C21	−3.0 (4)
C4—C5—C6—O2	172.36 (18)	C19—C20—C23—C23iv	176.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3i	0.85	1.89	2.663 (2)	150
O1W—H1WB···O2	0.85	1.90	2.682 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3i	0.85	1.89	2.663 (2)	150
O1W—H1WB⋯O2	0.85	1.90	2.682 (2)	152

Symmetry code: (i) .