Tetra­aqua­bis(4,4′-bipyridine)cobalt(II) 2-aminona­phthalene-1-sulfonate hexa­hydrate

The title compound, [Co(C₁₀H₈N₂)₂(H₂O)₄](C₁₀H₈NO₃S)₂·6H₂O, contains a tetra­aqua­bis(4,4′-bipyridine)­cobalt(II) cation, two ANS⁻ anions (HANS = 2-amino­naphthalene-1-sulfonic acid) and six solvent water mol­ecules. The Co^II atom lies on an inversion centre and is coordinated octahedrally by two mutually trans 4,4′-bipyridine mol­ecules bound in a monodentate fashion and by four water mol­ecules in the equatorial plane. The cations and water mol­ecules are arranged into infinite two-dimensional layers by an extensive network of hydrogen bonds. The ANS⁻ anions are trapped between these layers via N—H...O inter­actions between the amino groups and the solvent and coordinated water mol­ecules. Adjacent layers are stacked via weak π–π inter­actions between 4,4′-bipyridine mol­ecules [nearest centroid-to-centroid distance 3.662 (0) Å].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.109
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.84
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B    ..  S1      ..       2.93 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B    ..  S1      ..       3.03 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            N1  -CO1 -N1  -C3      9.00  0.00   3.666   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N1  -CO1 -N1  -C2      8.00  0.00   3.666   1.555   1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (2)       1.83

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

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

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S1. Comment

The asymmetric unit of the title complex (Fig. 1) contains half of a Co^II center, one monodentate 4,4'-bipyridine ligand, one free ANS^- anion, two coordinated water (O1 and O2) and three lattice water molecules (O6, O7 and O8). The Co^II atom, which lies on an inversion center, is six-coordinated to four oxygen atoms from four coordinated water molecules and two nitrogen atoms from two 4,4'-bipyridine ligands, exhibiting a nearly ideal octahedral coordination geometry. The isolated cations are connected to three lattice water molecules by extensive O—H···O hydrogen bonds interactions to generate a two-dimensional Co^II–H₂O layer (Fig. 2 and Table 1). And these adjacent two-dimensional layers are further stacked together by weak π–π interactions between interlayer 4,4'-bipy, exhibiting three-dimensional interdigitated supramoleuclar architectures. The nearest centroid-to-centroid distance is 3.662 (0) Å. Free ANS anions are tightly encapsulated in the channels of the three-dimensional packing structure via N—H···O interactions between amino groups and the lattice as well as coordinated water molecules (Fig. 3 and Table 2).

Related literature

For details of the role of water molecules in self-assembly processes, see Tajkhorshid et al. (2002). For investigations of water-based clusters assembled by hydrogen bonds, see: Yoshizawa et al. (2005); Sreenivasulu & Vittal (2004).

S2. Experimental

The title complex was synthesized by dissolving Co(CH₃COO)₂4H₂O (99.6 mg, 0.4 mmol), 4,4'-bipyridine (38.4 mg, 0.2 mmol), HANS (89.3 mg, 0.4 mmol), NaOH (24 mg, 0.6 mmol), and H₂O (15 ml) in a 23 ml Teflon lined autoclave under autogenous pressure at 140°C for 2 days. The mixture was slowly cooled to room temperature at a rate of 5 K h^-1, pale-red block-shaped crystals suitable for X-ray analysis were obtained in 33% yield. Analysis calculated for C₄₀H₅₂CoN₆O₁₆S₂: C 48.24, H 5.26, N 8.44%; found: C 48.20, H 5.38, N 8.62%.

S3. Refinement

H atoms were initially located in difference maps, but were subsequently introduced in calculated positions and treated as riding, with C—H = 0.93, O—H = 0.85 and N—H = 0.86 Å. All H atoms were allocated displacement parameters related to those of their parent atoms [U_iso(H) = 1.2U_eq(C, N), or 1.5U_eq(O)].

Computing details

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2; data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL and DIAMOND (Brandenburg & Berndt, 1999).

Figures

	Fig. 1. The structure of the title compound with thermal ellipsoids drawn at the 30% probability level.
	Fig. 2. The two dimensional layer structure formed by O—H···O hydrogen bonds (dashed lines) between the complex molecules and the water solvates.
	Fig. 3. Packing diagram for the title complex.

Tetraaquabis(4,4'-bipyridine)cobalt(II) 2-aminonaphthalene-1-sulfonate hexahydrate

Crystal data

[Co(C10H8N2)2(H2O)4](C10H8NO3S)2·6H2O	F(000) = 1042
Mr = 995.93	Dx = 1.450 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3808 reflections
a = 12.4737 (14) Å	θ = 2.3–25.1°
b = 18.358 (2) Å	µ = 0.54 mm^−1
c = 10.9196 (13) Å	T = 293 K
β = 114.148 (1)°	Block, pale red
V = 2281.7 (5) Å^3	0.32 × 0.28 × 0.22 mm
Z = 2

Data collection

Bruker APEXII CCD area-detector diffractometer	4021 independent reflections
Radiation source: fine-focus sealed tube	3270 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→12
Tmin = 0.840, Tmax = 0.887	k = −19→21
12190 measured reflections	l = −12→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0583P)^2 + 1.0964P] where P = (Fo^2 + 2Fc^2)/3
4021 reflections	(Δ/σ)max = 0.001
295 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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
Co1	0.5000	0.5000	0.5000	0.03414 (14)
S1	0.68106 (5)	0.61872 (4)	−0.02091 (6)	0.04513 (18)
O1	0.44371 (14)	0.57897 (9)	0.34621 (16)	0.0459 (4)
H1A	0.4393	0.5695	0.2681	0.069*
H1B	0.4480	0.6239	0.3668	0.069*
O2	0.48301 (14)	0.57884 (10)	0.62652 (17)	0.0498 (4)
H2A	0.4184	0.5872	0.6326	0.075*
H2B	0.5442	0.5939	0.6919	0.075*
O3	0.7056 (2)	0.54311 (11)	0.0094 (2)	0.0897 (8)
O4	0.67303 (18)	0.63600 (12)	−0.15273 (18)	0.0664 (6)
O5	0.57611 (19)	0.64226 (16)	−0.0080 (3)	0.0948 (8)
N1	0.31765 (16)	0.46586 (11)	0.44211 (19)	0.0387 (4)
N2	−0.27372 (18)	0.40516 (14)	0.3473 (2)	0.0551 (6)
N3	0.6869 (3)	0.73128 (17)	0.1974 (3)	0.0915 (10)
H3A	0.6234	0.7088	0.1481	0.110*
H3B	0.6862	0.7629	0.2551	0.110*
C1	0.1718 (2)	0.39321 (19)	0.4720 (4)	0.0805 (11)
H1	0.1558	0.3521	0.5115	0.097*
C2	0.2858 (2)	0.40909 (18)	0.4935 (4)	0.0777 (11)
H2	0.3444	0.3777	0.5479	0.093*
C3	0.2301 (2)	0.50586 (18)	0.3617 (3)	0.0679 (9)
H3	0.2479	0.5451	0.3193	0.081*
C4	0.1139 (2)	0.49405 (18)	0.3355 (3)	0.0661 (9)
H4	0.0567	0.5251	0.2777	0.079*
C5	0.08187 (19)	0.43739 (13)	0.3932 (2)	0.0378 (5)
C6	−0.04222 (19)	0.42505 (13)	0.3733 (2)	0.0388 (5)
C7	−0.1325 (2)	0.4684 (2)	0.2911 (3)	0.0686 (9)
H7	−0.1181	0.5056	0.2421	0.082*
C8	−0.2450 (2)	0.4563 (2)	0.2816 (3)	0.0740 (10)
H8	−0.3046	0.4865	0.2250	0.089*
C9	−0.1865 (3)	0.36315 (18)	0.4241 (4)	0.0726 (9)
H9	−0.2035	0.3259	0.4711	0.087*
C10	−0.0719 (2)	0.37078 (16)	0.4394 (4)	0.0661 (9)
H10	−0.0146	0.3389	0.4948	0.079*
C11	0.8024 (2)	0.66754 (12)	0.0958 (2)	0.0384 (5)
C12	0.9161 (2)	0.65456 (12)	0.0952 (2)	0.0389 (5)
C13	0.9385 (2)	0.60407 (14)	0.0116 (3)	0.0482 (6)
H13	0.8773	0.5756	−0.0468	0.058*
C14	1.0489 (3)	0.59610 (18)	0.0148 (3)	0.0685 (9)
H14	1.0611	0.5625	−0.0421	0.082*
C15	1.1428 (3)	0.6372 (2)	0.1010 (4)	0.0785 (11)
H15	1.2172	0.6313	0.1020	0.094*
C16	1.1250 (3)	0.6855 (2)	0.1833 (4)	0.0723 (10)
H16	1.1880	0.7130	0.2413	0.087*
C17	1.0133 (2)	0.69561 (15)	0.1836 (3)	0.0525 (7)
C18	0.9945 (3)	0.74661 (16)	0.2700 (3)	0.0676 (9)
H18	1.0575	0.7742	0.3277	0.081*
C19	0.8892 (3)	0.75618 (16)	0.2710 (3)	0.0695 (9)
H19	0.8811	0.7897	0.3304	0.083*
C20	0.7885 (3)	0.71681 (15)	0.1840 (3)	0.0544 (7)
O6	0.4298 (2)	0.57428 (12)	0.0930 (2)	0.0804 (7)
H6A	0.4992	0.5625	0.1042	0.121*
H6B	0.3781	0.5419	0.0552	0.121*
O7	0.4464 (2)	0.73225 (13)	0.3298 (3)	0.0924 (8)
H7A	0.4282	0.7334	0.2458	0.139*
H7B	0.5077	0.7554	0.3798	0.139*
O8	0.3637 (3)	0.72911 (17)	0.0418 (3)	0.1175 (11)
H8A	0.3643	0.6869	0.0100	0.176*
H8B	0.4063	0.7611	0.0272	0.176*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0231 (2)	0.0467 (3)	0.0319 (2)	−0.00243 (18)	0.01052 (17)	−0.00211 (18)
S1	0.0398 (3)	0.0500 (4)	0.0410 (3)	−0.0111 (3)	0.0118 (3)	0.0024 (3)
O1	0.0433 (10)	0.0538 (10)	0.0381 (9)	−0.0024 (8)	0.0142 (8)	0.0024 (7)
O2	0.0274 (8)	0.0727 (12)	0.0491 (10)	−0.0074 (8)	0.0156 (7)	−0.0223 (9)
O3	0.0922 (17)	0.0486 (12)	0.0858 (16)	−0.0270 (12)	−0.0068 (13)	0.0134 (11)
O4	0.0602 (12)	0.0839 (14)	0.0397 (10)	−0.0284 (11)	0.0045 (9)	0.0050 (9)
O5	0.0512 (13)	0.140 (2)	0.0998 (18)	−0.0185 (14)	0.0372 (13)	−0.0230 (17)
N1	0.0286 (10)	0.0476 (12)	0.0395 (10)	−0.0019 (9)	0.0137 (8)	−0.0020 (9)
N2	0.0327 (12)	0.0803 (16)	0.0553 (13)	−0.0074 (11)	0.0210 (10)	−0.0121 (12)
N3	0.088 (2)	0.096 (2)	0.108 (2)	0.0034 (17)	0.0578 (19)	−0.0365 (19)
C1	0.0311 (14)	0.081 (2)	0.118 (3)	0.0009 (14)	0.0194 (16)	0.052 (2)
C2	0.0289 (14)	0.073 (2)	0.119 (3)	0.0047 (14)	0.0177 (16)	0.042 (2)
C3	0.0308 (14)	0.094 (2)	0.0695 (19)	−0.0048 (14)	0.0112 (13)	0.0424 (17)
C4	0.0277 (13)	0.088 (2)	0.0715 (19)	0.0032 (13)	0.0088 (13)	0.0391 (17)
C5	0.0274 (11)	0.0475 (13)	0.0384 (12)	−0.0032 (10)	0.0134 (10)	−0.0062 (10)
C6	0.0286 (11)	0.0496 (14)	0.0386 (12)	−0.0023 (10)	0.0141 (10)	−0.0088 (10)
C7	0.0346 (14)	0.116 (3)	0.0572 (17)	0.0102 (16)	0.0207 (13)	0.0350 (18)
C8	0.0301 (14)	0.134 (3)	0.0538 (17)	0.0148 (17)	0.0131 (13)	0.0266 (19)
C9	0.0471 (17)	0.0645 (19)	0.119 (3)	−0.0043 (15)	0.0465 (19)	0.0164 (19)
C10	0.0398 (15)	0.0577 (17)	0.106 (2)	0.0045 (13)	0.0355 (16)	0.0215 (17)
C11	0.0403 (13)	0.0358 (12)	0.0348 (12)	−0.0024 (10)	0.0110 (10)	0.0018 (10)
C12	0.0398 (13)	0.0364 (12)	0.0350 (12)	−0.0005 (10)	0.0095 (10)	0.0108 (10)
C13	0.0502 (15)	0.0450 (14)	0.0478 (14)	0.0072 (12)	0.0186 (12)	0.0082 (11)
C14	0.072 (2)	0.072 (2)	0.073 (2)	0.0298 (18)	0.0413 (18)	0.0262 (17)
C15	0.0443 (18)	0.097 (3)	0.096 (3)	0.0162 (18)	0.0308 (19)	0.047 (2)
C16	0.0393 (16)	0.081 (2)	0.079 (2)	−0.0086 (15)	0.0064 (15)	0.0287 (19)
C17	0.0467 (16)	0.0482 (15)	0.0477 (14)	−0.0069 (12)	0.0043 (12)	0.0140 (12)
C18	0.073 (2)	0.0526 (18)	0.0506 (16)	−0.0213 (15)	−0.0014 (15)	−0.0064 (14)
C19	0.093 (3)	0.0526 (18)	0.0548 (17)	−0.0071 (17)	0.0224 (17)	−0.0175 (14)
C20	0.0661 (18)	0.0461 (15)	0.0519 (15)	0.0029 (13)	0.0252 (14)	−0.0023 (12)
O6	0.1082 (18)	0.0777 (15)	0.0730 (14)	−0.0410 (13)	0.0551 (14)	−0.0252 (12)
O7	0.1018 (19)	0.0765 (16)	0.1005 (19)	−0.0156 (14)	0.0430 (16)	−0.0103 (14)
O8	0.127 (3)	0.102 (2)	0.161 (3)	0.0241 (18)	0.098 (2)	0.018 (2)

Geometric parameters (Å, º)

Co1—O2^i	2.0708 (16)	C6—C7	1.371 (4)
Co1—O2	2.0708 (16)	C7—C8	1.382 (4)
Co1—O1^i	2.1096 (16)	C7—H7	0.9300
Co1—O1	2.1096 (16)	C8—H8	0.9300
Co1—N1^i	2.1885 (18)	C9—C10	1.377 (4)
Co1—N1	2.1885 (18)	C9—H9	0.9300
S1—O3	1.431 (2)	C10—H10	0.9300
S1—O4	1.4369 (19)	C11—C20	1.383 (3)
S1—O5	1.439 (2)	C11—C12	1.441 (3)
S1—C11	1.772 (2)	C12—C13	1.406 (4)
O1—H1A	0.8499	C12—C17	1.419 (3)
O1—H1B	0.8500	C13—C14	1.372 (4)
O2—H2A	0.8501	C13—H13	0.9300
O2—H2B	0.8500	C14—C15	1.387 (5)
N1—C3	1.311 (3)	C14—H14	0.9300
N1—C2	1.320 (3)	C15—C16	1.345 (5)
N2—C9	1.317 (4)	C15—H15	0.9300
N2—C8	1.318 (4)	C16—C17	1.406 (4)
N3—C20	1.360 (4)	C16—H16	0.9300
N3—H3A	0.8600	C17—C18	1.416 (4)
N3—H3B	0.8600	C18—C19	1.329 (5)
C1—C5	1.367 (4)	C18—H18	0.9300
C1—C2	1.374 (4)	C19—C20	1.424 (4)
C1—H1	0.9300	C19—H19	0.9300
C2—H2	0.9300	O6—H6A	0.8505
C3—C4	1.375 (4)	O6—H6B	0.8502
C3—H3	0.9300	O7—H7A	0.8501
C4—C5	1.358 (4)	O7—H7B	0.8500
C4—H4	0.9300	O8—H8A	0.8501
C5—C6	1.490 (3)	O8—H8B	0.8501
C6—C10	1.368 (4)
O2^i—Co1—O2	180.0	C10—C6—C7	116.2 (2)
O2^i—Co1—O1^i	87.66 (7)	C10—C6—C5	121.6 (2)
O2—Co1—O1^i	92.34 (7)	C7—C6—C5	122.2 (2)
O2^i—Co1—O1	92.34 (7)	C6—C7—C8	119.6 (3)
O2—Co1—O1	87.66 (7)	C6—C7—H7	120.2
O1^i—Co1—O1	180.0	C8—C7—H7	120.2
O2^i—Co1—N1^i	90.85 (7)	N2—C8—C7	124.6 (3)
O2—Co1—N1^i	89.15 (7)	N2—C8—H8	117.7
O1^i—Co1—N1^i	89.93 (7)	C7—C8—H8	117.7
O1—Co1—N1^i	90.07 (7)	N2—C9—C10	124.3 (3)
O2^i—Co1—N1	89.15 (7)	N2—C9—H9	117.9
O2—Co1—N1	90.85 (7)	C10—C9—H9	117.9
O1^i—Co1—N1	90.07 (7)	C6—C10—C9	120.2 (3)
O1—Co1—N1	89.93 (7)	C6—C10—H10	119.9
N1^i—Co1—N1	180.00 (11)	C9—C10—H10	119.9
O3—S1—O4	111.52 (15)	C20—C11—C12	121.0 (2)
O3—S1—O5	112.69 (17)	C20—C11—S1	121.2 (2)
O4—S1—O5	109.78 (15)	C12—C11—S1	117.77 (17)
O3—S1—C11	106.57 (12)	C13—C12—C17	116.8 (2)
O4—S1—C11	107.32 (11)	C13—C12—C11	124.6 (2)
O5—S1—C11	108.73 (13)	C17—C12—C11	118.6 (2)
Co1—O1—H1A	121.5	C14—C13—C12	121.2 (3)
Co1—O1—H1B	119.4	C14—C13—H13	119.4
H1A—O1—H1B	115.7	C12—C13—H13	119.4
Co1—O2—H2A	122.6	C13—C14—C15	121.3 (3)
Co1—O2—H2B	119.1	C13—C14—H14	119.4
H2A—O2—H2B	115.5	C15—C14—H14	119.4
C3—N1—C2	114.4 (2)	C16—C15—C14	119.2 (3)
C3—N1—Co1	121.05 (17)	C16—C15—H15	120.4
C2—N1—Co1	124.17 (17)	C14—C15—H15	120.4
C9—N2—C8	115.3 (2)	C15—C16—C17	121.5 (3)
C20—N3—H3A	120.0	C15—C16—H16	119.2
C20—N3—H3B	120.0	C17—C16—H16	119.2
H3A—N3—H3B	120.0	C16—C17—C18	121.5 (3)
C5—C1—C2	120.5 (3)	C16—C17—C12	120.0 (3)
C5—C1—H1	119.8	C18—C17—C12	118.4 (3)
C2—C1—H1	119.8	C19—C18—C17	121.8 (3)
N1—C2—C1	124.4 (3)	C19—C18—H18	119.1
N1—C2—H2	117.8	C17—C18—H18	119.1
C1—C2—H2	117.8	C18—C19—C20	122.2 (3)
N1—C3—C4	124.7 (2)	C18—C19—H19	118.9
N1—C3—H3	117.6	C20—C19—H19	118.9
C4—C3—H3	117.6	N3—C20—C11	126.2 (3)
C5—C4—C3	120.6 (2)	N3—C20—C19	115.8 (3)
C5—C4—H4	119.7	C11—C20—C19	118.0 (3)
C3—C4—H4	119.7	H6A—O6—H6B	114.7
C4—C5—C1	115.2 (2)	H7A—O7—H7B	116.9
C4—C5—C6	122.3 (2)	H8A—O8—H8B	116.3
C1—C5—C6	122.5 (2)
O2^i—Co1—N1—C3	−106.1 (2)	N2—C9—C10—C6	0.5 (6)
O2—Co1—N1—C3	73.9 (2)	O3—S1—C11—C20	−119.3 (2)
O1^i—Co1—N1—C3	166.3 (2)	O4—S1—C11—C20	121.1 (2)
O1—Co1—N1—C3	−13.7 (2)	O5—S1—C11—C20	2.4 (3)
N1^i—Co1—N1—C3	94 (100)	O3—S1—C11—C12	61.1 (2)
O2^i—Co1—N1—C2	81.0 (3)	O4—S1—C11—C12	−58.5 (2)
O2—Co1—N1—C2	−99.0 (3)	O5—S1—C11—C12	−177.19 (19)
O1^i—Co1—N1—C2	−6.7 (3)	C20—C11—C12—C13	178.2 (2)
O1—Co1—N1—C2	173.3 (3)	S1—C11—C12—C13	−2.2 (3)
N1^i—Co1—N1—C2	−79 (100)	C20—C11—C12—C17	−2.5 (3)
C3—N1—C2—C1	−2.9 (5)	S1—C11—C12—C17	177.12 (17)
Co1—N1—C2—C1	170.4 (3)	C17—C12—C13—C14	−1.0 (3)
C5—C1—C2—N1	−0.1 (6)	C11—C12—C13—C14	178.4 (2)
C2—N1—C3—C4	3.3 (5)	C12—C13—C14—C15	0.4 (4)
Co1—N1—C3—C4	−170.3 (3)	C13—C14—C15—C16	0.2 (5)
N1—C3—C4—C5	−0.6 (6)	C14—C15—C16—C17	−0.2 (5)
C3—C4—C5—C1	−2.5 (5)	C15—C16—C17—C18	−179.9 (3)
C3—C4—C5—C6	176.6 (3)	C15—C16—C17—C12	−0.4 (4)
C2—C1—C5—C4	2.8 (5)	C13—C12—C17—C16	0.9 (3)
C2—C1—C5—C6	−176.3 (3)	C11—C12—C17—C16	−178.5 (2)
C4—C5—C6—C10	−175.4 (3)	C13—C12—C17—C18	−179.5 (2)
C1—C5—C6—C10	3.7 (4)	C11—C12—C17—C18	1.1 (3)
C4—C5—C6—C7	2.7 (4)	C16—C17—C18—C19	−179.8 (3)
C1—C5—C6—C7	−178.2 (3)	C12—C17—C18—C19	0.7 (4)
C10—C6—C7—C8	1.3 (5)	C17—C18—C19—C20	−1.0 (5)
C5—C6—C7—C8	−176.9 (3)	C12—C11—C20—N3	−177.1 (3)
C9—N2—C8—C7	−1.3 (5)	S1—C11—C20—N3	3.3 (4)
C6—C7—C8—N2	0.2 (6)	C12—C11—C20—C19	2.1 (4)
C8—N2—C9—C10	0.9 (5)	S1—C11—C20—C19	−177.4 (2)
C7—C6—C10—C9	−1.6 (5)	C18—C19—C20—N3	179.0 (3)
C5—C6—C10—C9	176.6 (3)	C18—C19—C20—C11	−0.4 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6	0.85	1.87	2.700 (3)	166
O1—H1B···O7	0.85	2.03	2.821 (3)	155
O2—H2A···N2^ii	0.85	1.91	2.756 (3)	174
O2—H2B···O4^iii	0.85	1.96	2.803 (2)	173
O2—H2B···S1^iii	0.85	2.93	3.6985 (18)	152
N3—H3A···O5	0.86	1.98	2.660 (4)	135
N3—H3B···O4^iv	0.86	2.15	2.980 (3)	162
O6—H6A···O5	0.85	2.35	2.784 (3)	112
O6—H6B···O3^v	0.85	1.85	2.684 (3)	167
O6—H6B···S1^v	0.85	3.03	3.768 (2)	147
O7—H7A···O8	0.85	2.04	2.881 (5)	172
O7—H7B···O5^iv	0.85	2.21	2.953 (4)	145
O8—H8A···O6	0.85	2.27	2.949 (4)	137
O8—H8B···O7^vi	0.85	2.41	2.980 (4)	125

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