Tetra­aqua­bis[1,1′-(4-methoxy­naph­thalene-1,3-diyldimethyl­ene)pyridinium-3-carboxyl­ate-κO]cobalt(II) bis­(perchlorate) hexa­hydrate

Abstract

In the molecule of the centrosymmetric title compound, [Co(C₂₅H₂₀N₂O₅)₂(H₂O)₄](ClO₄)₂·6H₂O, the Co atom is octa­hedrally coordinated by four water mol­ecules lying in the equatorial plane and two monodentate carboxyl­ate groups from two dicarboxylate ligands. The crystal structure involves O—H⋯O and O—H⋯Cl hydrogen bonds..

Related literature

For related literature, see: Li et al. (2006 ▶).

Experimental

Crystal data

• [Co(C₂₅H₂₀N₂O₅)₂(H₂O)₄](ClO₄)₂·6H₂O

• M _r = 1294.86

• Triclinic,

• a = 7.9162 (19) Å

• b = 12.703 (3) Å

• c = 14.757 (3) Å

• α = 71.159 (6)°

• β = 89.759 (8)°

• γ = 77.175 (7)°

• V = 1365.7 (5) ų

• Z = 1

• Mo Kα radiation

• μ = 0.51 mm⁻¹

• T = 113 (2) K

• 0.18 × 0.16 × 0.14 mm

Data collection

• Rigaku Saturn diffractometer

• Absorption correction: multi-scan (Jacobson, 1998 ▶) T _min = 0.914, T _max = 0.932

• 12559 measured reflections

• 4738 independent reflections

• 4261 reflections with I > 2σ(I)

• R _int = 0.024

Refinement

• R[F ² > 2σ(F ²)] = 0.057

• wR(F ²) = 0.128

• S = 1.08

• 4738 reflections

• 417 parameters

• 17 restraints

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 1.27 e Å⁻³

• Δρ_min = −0.45 e Å⁻³

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2002 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10A⋯O13i	0.84 (4)	1.83 (4)	2.665 (5)	171 (6)
O10—H10B⋯O1ii	0.85 (4)	1.84 (4)	2.668 (6)	166 (6)
O11—H11A⋯O12i	0.87 (4)	1.83 (4)	2.690 (6)	174 (7)
O11—H11B⋯O14iii	0.86 (4)	1.85 (4)	2.701 (5)	173 (6)
O12—H12A⋯O1	0.83 (4)	1.84 (5)	2.654 (6)	164 (8)
O12—H12B⋯O4	0.87 (4)	1.91 (4)	2.772 (6)	173 (8)
O13—H13A⋯O5iv	0.86 (4)	1.94 (4)	2.787 (6)	172 (7)
O13—H13B⋯O9v	0.86 (4)	1.95 (4)	2.815 (6)	175 (7)
O13—H13B⋯Cl1v	0.86 (4)	2.69 (6)	3.451 (4)	147 (6)
O14—H14A⋯O4i	0.86 (4)	1.88 (4)	2.724 (6)	165 (7)
O14—H14B⋯O5vi	0.86 (4)	1.98 (4)	2.811 (6)	160 (7)

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

supplementary crystallographic information

Comment

Recently, corrdination chemistry becomes more and more important in the structural design of supramolecular chemistry. The deprotonated carboxyl group, which easily coordinated to metal atoms and can be used to prepare soluble metal complexes. During the synthesis of polymeric complexes using 3-methoxyl-1,3-pyridinium-3-carboxylate (L) as bridging ligand, to our surprise, the title monomeric Co complex was obtained.

As shown in Fig. 1, the stucture of the title compound, (I), four water molecules and two monodentate carboxylate groups from L ligands corrdinate to Co. the other three water molecules and carboxylate group of the ligand L and the perchlorate anion are free from corrdination.

For related literature, see: Li et al. (2006).

Experimental

An aqueous and water (V/V=1:1) solution of L (0.042 g, 0.1 mmol)and Co(ClO4)6H2O (0.11 g, 0.3 mmol) was stirred at 333 K for 10 min and then left to stand at room temperature. Single crystals of (I) were obtained after 3 d.

Refinement

(type here to add refinement details)

Figures

Fig. 1.

The molecular structure of (I), shown with 30% probability displacement ellipsoids.

Crystal data

[Co(C25H20N2O5)2(H2O)4](ClO4)2·6H2O	Z = 1
Mr = 1294.86	F000 = 673
Triclinic, P1	Dx = 1.574 Mg m−3
a = 7.9162 (19) Å	Mo Kα radiation λ = 0.71070 Å
b = 12.703 (3) Å	Cell parameters from 4046 reflections
c = 14.757 (3) Å	θ = 2.6–27.8º
α = 71.159 (6)º	µ = 0.51 mm−1
β = 89.759 (8)º	T = 113 (2) K
γ = 77.175 (7)º	Prism, colorless
V = 1365.7 (5) Å3	0.18 × 0.16 × 0.14 mm

Data collection

Rigaku Saturn diffractometer	4738 independent reflections
Radiation source: fine-focus sealed tube	4261 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
Detector resolution: 7.31 pixels mm-1	θmax = 25.0º
T = 113(2) K	θmin = 2.7º
ω scans	h = −9→9
Absorption correction: multi-scan(Jacobson, 1998)	k = −13→15
Tmin = 0.914, Tmax = 0.932	l = −17→17
12559 measured reflections

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0385P)2 + 4.0784P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.004
4738 reflections	Δρmax = 1.27 e Å−3
417 parameters	Δρmin = −0.45 e Å−3
17 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (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	1.5000	0.5000	0.5000	0.0166 (3)
N1	0.7742 (5)	0.6740 (4)	0.2020 (3)	0.0175 (9)
N2	0.7187 (6)	0.1380 (4)	0.2728 (3)	0.0228 (10)
O1	1.1365 (7)	0.4585 (4)	0.4208 (5)	0.073 (2)
O2	1.2985 (5)	0.5855 (3)	0.3906 (3)	0.0245 (9)
O3	0.6931 (6)	0.2768 (4)	0.0159 (4)	0.0443 (12)
O4	1.1873 (5)	0.1697 (3)	0.3646 (3)	0.0325 (10)
O5	1.2889 (5)	−0.0172 (3)	0.4167 (3)	0.0321 (10)
C1	1.1687 (7)	0.5520 (5)	0.3763 (4)	0.0277 (13)
C2	1.0353 (7)	0.6348 (5)	0.2975 (4)	0.0220 (12)
C3	1.0486 (7)	0.7466 (5)	0.2532 (4)	0.0268 (13)
H3	1.1446	0.7717	0.2701	0.032*
C4	0.9214 (7)	0.8213 (5)	0.1842 (4)	0.0266 (13)
H4	0.9292	0.8982	0.1538	0.032*
C5	0.7833 (7)	0.7839 (4)	0.1596 (4)	0.0217 (11)
H5	0.6946	0.8352	0.1130	0.026*
C6	0.8963 (7)	0.6001 (4)	0.2702 (4)	0.0203 (11)
H6	0.8862	0.5235	0.2997	0.024*
C7	0.6205 (7)	0.6347 (5)	0.1771 (4)	0.0222 (12)
H7A	0.5414	0.7000	0.1288	0.027*
H7B	0.5567	0.6114	0.2354	0.027*
C8	0.6653 (7)	0.5364 (4)	0.1382 (4)	0.0213 (12)
C9	0.7197 (7)	0.5518 (5)	0.0436 (4)	0.0238 (12)
C10	0.7556 (11)	0.6557 (5)	−0.0161 (4)	0.0432 (19)
H10	0.7389	0.7190	0.0066	0.052*
C11	0.8159 (8)	0.6675 (6)	−0.1092 (5)	0.0381 (15)
H11	0.8491	0.7356	−0.1454	0.046*
C12	0.8263 (8)	0.5787 (6)	−0.1474 (5)	0.0387 (15)
H12	0.8620	0.5871	−0.2104	0.046*
C13	0.7823 (8)	0.4757 (5)	−0.0902 (4)	0.0307 (14)
H13	0.7852	0.4160	−0.1161	0.037*
C14	0.7340 (7)	0.4612 (5)	0.0052 (4)	0.0243 (12)
C15	0.6947 (7)	0.3564 (5)	0.0618 (5)	0.0260 (13)
C16	0.6448 (7)	0.3420 (4)	0.1539 (5)	0.0278 (14)
C17	0.6314 (7)	0.4329 (5)	0.1918 (4)	0.0243 (12)
H17	0.5982	0.4223	0.2555	0.029*
C18	0.8347 (13)	0.1867 (7)	0.0329 (7)	0.068 (3)
H18A	0.9385	0.2157	0.0128	0.082*
H18B	0.8166	0.1373	−0.0035	0.082*
H18C	0.8504	0.1427	0.1016	0.082*
C19	0.5813 (7)	0.2382 (5)	0.2098 (5)	0.0327 (15)
H19A	0.5253	0.2121	0.1638	0.039*
H19B	0.4911	0.2610	0.2508	0.039*
C20	0.6727 (7)	0.0366 (5)	0.3076 (4)	0.0261 (12)
H20	0.5597	0.0311	0.2914	0.031*
C21	0.7884 (8)	−0.0581 (5)	0.3660 (4)	0.0280 (13)
H21	0.7556	−0.1290	0.3907	0.034*
C22	0.9537 (7)	−0.0498 (5)	0.3889 (4)	0.0249 (12)
H22	1.0363	−0.1157	0.4272	0.030*
C23	0.9980 (7)	0.0553 (4)	0.3556 (4)	0.0209 (11)
C24	0.8756 (7)	0.1483 (4)	0.2974 (4)	0.0223 (12)
H24	0.9033	0.2210	0.2744	0.027*
C25	1.1779 (7)	0.0706 (5)	0.3813 (4)	0.0241 (12)
Cl1	0.30440 (18)	0.00621 (11)	0.11433 (10)	0.0254 (4)
O6	0.2137 (9)	0.0363 (5)	0.1891 (3)	0.072 (2)
O7	0.4485 (8)	0.0568 (5)	0.0958 (6)	0.075 (2)
O8	0.1939 (7)	0.0440 (4)	0.0298 (3)	0.0463 (13)
O9	0.3657 (6)	−0.1168 (3)	0.1445 (3)	0.0324 (10)
O10	1.6526 (5)	0.6076 (3)	0.4204 (3)	0.0222 (8)
H10A	1.604 (7)	0.678 (4)	0.399 (4)	0.033*
H10B	1.724 (7)	0.597 (5)	0.467 (4)	0.033*
O11	1.4046 (5)	0.6184 (3)	0.5691 (3)	0.0241 (9)
H11A	1.293 (5)	0.645 (5)	0.563 (5)	0.036*
H11B	1.447 (7)	0.676 (5)	0.566 (5)	0.036*
O12	0.9425 (6)	0.3085 (4)	0.4369 (4)	0.0470 (14)
H12A	0.985 (10)	0.365 (5)	0.431 (6)	0.070*
H12B	1.017 (9)	0.260 (5)	0.418 (6)	0.070*
O13	0.5220 (6)	0.1760 (3)	0.6610 (3)	0.0319 (10)
H13A	0.589 (8)	0.128 (5)	0.639 (4)	0.048*
H13B	0.562 (9)	0.160 (6)	0.720 (3)	0.048*
O14	0.5114 (6)	0.8080 (3)	0.5631 (4)	0.0372 (11)
H14A	0.598 (7)	0.828 (6)	0.582 (5)	0.056*
H14B	0.444 (8)	0.871 (5)	0.528 (5)	0.056*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Co1	0.0134 (5)	0.0155 (5)	0.0214 (6)	−0.0038 (4)	−0.0016 (4)	−0.0065 (4)
N1	0.018 (2)	0.018 (2)	0.017 (2)	−0.0025 (17)	−0.0011 (17)	−0.0080 (18)
N2	0.017 (2)	0.017 (2)	0.034 (3)	−0.0035 (18)	0.001 (2)	−0.008 (2)
O1	0.064 (4)	0.032 (3)	0.097 (5)	−0.031 (3)	−0.062 (3)	0.027 (3)
O2	0.0179 (19)	0.024 (2)	0.031 (2)	−0.0065 (15)	−0.0067 (16)	−0.0058 (17)
O3	0.043 (3)	0.034 (2)	0.063 (3)	−0.006 (2)	−0.001 (2)	−0.028 (2)
O4	0.018 (2)	0.027 (2)	0.054 (3)	−0.0024 (16)	−0.0073 (19)	−0.017 (2)
O5	0.028 (2)	0.028 (2)	0.035 (2)	0.0062 (18)	−0.0103 (18)	−0.0130 (19)
C1	0.027 (3)	0.018 (3)	0.036 (3)	−0.006 (2)	−0.013 (3)	−0.005 (2)
C2	0.020 (3)	0.020 (3)	0.026 (3)	−0.004 (2)	−0.006 (2)	−0.007 (2)
C3	0.024 (3)	0.025 (3)	0.032 (3)	−0.010 (2)	−0.006 (2)	−0.007 (2)
C4	0.029 (3)	0.018 (3)	0.031 (3)	−0.008 (2)	−0.004 (2)	−0.003 (2)
C5	0.023 (3)	0.020 (3)	0.020 (3)	0.000 (2)	−0.001 (2)	−0.007 (2)
C6	0.020 (3)	0.017 (3)	0.023 (3)	−0.004 (2)	−0.003 (2)	−0.005 (2)
C7	0.018 (3)	0.024 (3)	0.026 (3)	−0.005 (2)	−0.005 (2)	−0.011 (2)
C8	0.018 (3)	0.018 (3)	0.026 (3)	−0.002 (2)	−0.012 (2)	−0.006 (2)
C9	0.022 (3)	0.021 (3)	0.025 (3)	−0.001 (2)	−0.015 (2)	−0.005 (2)
C10	0.089 (6)	0.010 (3)	0.022 (3)	0.005 (3)	−0.034 (3)	−0.004 (2)
C11	0.032 (3)	0.042 (4)	0.036 (4)	−0.009 (3)	0.001 (3)	−0.007 (3)
C12	0.033 (3)	0.046 (4)	0.032 (4)	−0.001 (3)	0.000 (3)	−0.011 (3)
C13	0.029 (3)	0.031 (3)	0.032 (3)	0.005 (2)	−0.012 (3)	−0.018 (3)
C14	0.014 (3)	0.021 (3)	0.035 (3)	0.002 (2)	−0.010 (2)	−0.010 (2)
C15	0.016 (3)	0.020 (3)	0.044 (4)	−0.001 (2)	−0.005 (2)	−0.015 (3)
C16	0.014 (3)	0.013 (3)	0.051 (4)	0.000 (2)	−0.013 (3)	−0.005 (3)
C17	0.017 (3)	0.023 (3)	0.029 (3)	−0.002 (2)	−0.011 (2)	−0.005 (2)
C18	0.081 (6)	0.050 (5)	0.069 (6)	0.020 (4)	−0.024 (5)	−0.036 (5)
C19	0.018 (3)	0.020 (3)	0.054 (4)	−0.002 (2)	−0.007 (3)	−0.005 (3)
C20	0.025 (3)	0.021 (3)	0.036 (3)	−0.011 (2)	0.003 (2)	−0.011 (2)
C21	0.034 (3)	0.019 (3)	0.032 (3)	−0.012 (2)	0.003 (3)	−0.006 (2)
C22	0.029 (3)	0.019 (3)	0.022 (3)	0.000 (2)	−0.002 (2)	−0.006 (2)
C23	0.024 (3)	0.019 (3)	0.020 (3)	−0.003 (2)	0.001 (2)	−0.008 (2)
C24	0.017 (3)	0.018 (3)	0.033 (3)	−0.005 (2)	0.001 (2)	−0.009 (2)
C25	0.023 (3)	0.023 (3)	0.025 (3)	0.002 (2)	−0.003 (2)	−0.012 (2)
Cl1	0.0301 (7)	0.0203 (7)	0.0229 (7)	0.0008 (5)	−0.0019 (6)	−0.0076 (5)
O6	0.110 (5)	0.048 (3)	0.025 (3)	0.039 (3)	0.012 (3)	−0.006 (2)
O7	0.058 (4)	0.046 (3)	0.133 (6)	−0.031 (3)	0.002 (4)	−0.034 (4)
O8	0.053 (3)	0.043 (3)	0.032 (3)	0.006 (2)	−0.018 (2)	−0.008 (2)
O9	0.041 (2)	0.018 (2)	0.034 (2)	0.0019 (18)	−0.0040 (19)	−0.0081 (18)
O10	0.0179 (19)	0.0174 (19)	0.028 (2)	−0.0036 (15)	−0.0002 (16)	−0.0041 (16)
O11	0.0197 (19)	0.024 (2)	0.034 (2)	−0.0066 (16)	0.0017 (17)	−0.0143 (18)
O12	0.025 (2)	0.026 (2)	0.098 (4)	−0.0120 (19)	0.014 (2)	−0.027 (3)
O13	0.036 (2)	0.022 (2)	0.031 (2)	0.0036 (18)	−0.0073 (19)	−0.0067 (18)
O14	0.032 (2)	0.022 (2)	0.055 (3)	−0.0050 (18)	−0.020 (2)	−0.010 (2)

Geometric parameters (Å, °)

Co1—O11	2.086 (4)	C12—C13	1.426 (9)
Co1—O11i	2.086 (4)	C12—H12	0.9500
Co1—O10	2.096 (4)	C13—C14	1.422 (9)
Co1—O10i	2.096 (4)	C13—H13	0.9500
Co1—O2i	2.110 (4)	C14—C15	1.425 (8)
Co1—O2	2.110 (4)	C15—C16	1.380 (9)
N1—C6	1.351 (7)	C16—C17	1.422 (8)
N1—C5	1.350 (7)	C16—C19	1.503 (8)
N1—C7	1.502 (6)	C17—H17	0.9500
N2—C24	1.340 (7)	C18—H18A	0.9800
N2—C20	1.355 (7)	C18—H18B	0.9800
N2—C19	1.516 (7)	C18—H18C	0.9800
O1—C1	1.240 (7)	C19—H19A	0.9900
O2—C1	1.240 (7)	C19—H19B	0.9900
O3—C18	1.370 (9)	C20—C21	1.370 (8)
O3—C15	1.389 (7)	C20—H20	0.9500
O4—C25	1.222 (7)	C21—C22	1.388 (8)
O5—C25	1.217 (7)	C21—H21	0.9500
C1—C2	1.517 (8)	C22—C23	1.389 (8)
C2—C6	1.379 (7)	C22—H22	0.9500
C2—C3	1.386 (8)	C23—C24	1.384 (8)
C3—C4	1.383 (8)	C23—C25	1.544 (8)
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.378 (8)	Cl1—O8	1.410 (5)
C4—H4	0.9500	Cl1—O7	1.413 (5)
C5—H5	0.9500	Cl1—O6	1.423 (5)
C6—H6	0.9500	Cl1—O9	1.446 (4)
C7—C8	1.509 (7)	O10—H10A	0.84 (4)
C7—H7A	0.9900	O10—H10B	0.85 (4)
C7—H7B	0.9900	O11—H11A	0.87 (4)
C8—C17	1.382 (8)	O11—H11B	0.86 (4)
C8—C9	1.424 (8)	O12—H12A	0.83 (4)
C9—C10	1.419 (9)	O12—H12B	0.87 (4)
C9—C14	1.421 (8)	O13—H13A	0.86 (4)
C10—C11	1.425 (10)	O13—H13B	0.86 (4)
C10—H10	0.9500	O14—H14A	0.86 (4)
C11—C12	1.402 (10)	O14—H14B	0.86 (4)
C11—H11	0.9500
O11—Co1—O11i	180.0	C13—C12—H12	120.5
O11—Co1—O10	89.89 (15)	C14—C13—C12	120.8 (5)
O11i—Co1—O10	90.11 (15)	C14—C13—H13	119.6
O11—Co1—O10i	90.11 (15)	C12—C13—H13	119.6
O11i—Co1—O10i	89.89 (15)	C9—C14—C13	120.4 (5)
O10—Co1—O10i	179.999 (1)	C9—C14—C15	119.7 (5)
O11—Co1—O2i	90.63 (15)	C13—C14—C15	119.8 (5)
O11i—Co1—O2i	89.37 (15)	C16—C15—O3	123.0 (5)
O10—Co1—O2i	91.78 (15)	C16—C15—C14	120.4 (5)
O10i—Co1—O2i	88.22 (15)	O3—C15—C14	116.3 (6)
O11—Co1—O2	89.37 (15)	C15—C16—C17	119.5 (5)
O11i—Co1—O2	90.63 (15)	C15—C16—C19	120.9 (5)
O10—Co1—O2	88.22 (15)	C17—C16—C19	119.1 (6)
O10i—Co1—O2	91.78 (15)	C8—C17—C16	121.6 (6)
O2i—Co1—O2	179.998 (1)	C8—C17—H17	119.2
C6—N1—C5	121.2 (4)	C16—C17—H17	119.2
C6—N1—C7	119.1 (4)	O3—C18—H18A	109.5
C5—N1—C7	119.6 (4)	O3—C18—H18B	109.5
C24—N2—C20	120.7 (5)	H18A—C18—H18B	109.5
C24—N2—C19	122.8 (4)	O3—C18—H18C	109.5
C20—N2—C19	116.5 (4)	H18A—C18—H18C	109.5
C1—O2—Co1	127.1 (4)	H18B—C18—H18C	109.5
C18—O3—C15	117.9 (6)	C16—C19—N2	115.7 (4)
O2—C1—O1	126.4 (5)	C16—C19—H19A	108.3
O2—C1—C2	116.4 (5)	N2—C19—H19A	108.3
O1—C1—C2	117.2 (5)	C16—C19—H19B	108.3
C6—C2—C3	118.9 (5)	N2—C19—H19B	108.3
C6—C2—C1	120.1 (5)	H19A—C19—H19B	107.4
C3—C2—C1	121.0 (5)	N2—C20—C21	120.3 (5)
C4—C3—C2	119.6 (5)	N2—C20—H20	119.8
C4—C3—H3	120.2	C21—C20—H20	119.8
C2—C3—H3	120.2	C20—C21—C22	119.6 (5)
C5—C4—C3	119.8 (5)	C20—C21—H21	120.2
C5—C4—H4	120.1	C22—C21—H21	120.2
C3—C4—H4	120.1	C21—C22—C23	119.7 (5)
N1—C5—C4	119.8 (5)	C21—C22—H22	120.1
N1—C5—H5	120.1	C23—C22—H22	120.1
C4—C5—H5	120.1	C24—C23—C22	118.2 (5)
N1—C6—C2	120.6 (5)	C24—C23—C25	119.7 (5)
N1—C6—H6	119.7	C22—C23—C25	122.1 (5)
C2—C6—H6	119.7	N2—C24—C23	121.4 (5)
N1—C7—C8	114.6 (4)	N2—C24—H24	119.3
N1—C7—H7A	108.6	C23—C24—H24	119.3
C8—C7—H7A	108.6	O5—C25—O4	129.2 (5)
N1—C7—H7B	108.6	O5—C25—C23	115.8 (5)
C8—C7—H7B	108.6	O4—C25—C23	115.0 (5)
H7A—C7—H7B	107.6	O8—Cl1—O7	109.3 (4)
C17—C8—C9	119.5 (5)	O8—Cl1—O6	110.4 (3)
C17—C8—C7	118.3 (5)	O7—Cl1—O6	109.7 (4)
C9—C8—C7	121.7 (5)	O8—Cl1—O9	109.5 (3)
C10—C9—C14	117.9 (5)	O7—Cl1—O9	109.0 (3)
C10—C9—C8	122.8 (5)	O6—Cl1—O9	108.9 (3)
C14—C9—C8	119.3 (5)	Co1—O10—H10A	116 (5)
C9—C10—C11	121.7 (5)	Co1—O10—H10B	96 (4)
C9—C10—H10	119.1	H10A—O10—H10B	109 (4)
C11—C10—H10	119.1	Co1—O11—H11A	116 (4)
C12—C11—C10	120.0 (6)	Co1—O11—H11B	124 (4)
C12—C11—H11	120.0	H11A—O11—H11B	105 (4)
C10—C11—H11	120.0	H12A—O12—H12B	107 (5)
C11—C12—C13	119.0 (6)	H13A—O13—H13B	105 (4)
C11—C12—H12	120.5	H14A—O14—H14B	105 (4)
O11—Co1—O2—C1	−107.3 (5)	C10—C9—C14—C15	−178.3 (5)
O11i—Co1—O2—C1	72.7 (5)	C8—C9—C14—C15	−0.2 (7)
O10—Co1—O2—C1	162.8 (5)	C12—C13—C14—C9	3.4 (8)
O10i—Co1—O2—C1	−17.2 (5)	C12—C13—C14—C15	−178.5 (5)
O2i—Co1—O2—C1	40 (29)	C18—O3—C15—C16	−84.6 (8)
Co1—O2—C1—O1	−4.0 (10)	C18—O3—C15—C14	101.7 (8)
Co1—O2—C1—C2	174.9 (4)	C9—C14—C15—C16	−0.8 (8)
O2—C1—C2—C6	173.3 (5)	C13—C14—C15—C16	−178.9 (5)
O1—C1—C2—C6	−7.7 (9)	C9—C14—C15—O3	173.1 (5)
O2—C1—C2—C3	−8.1 (9)	C13—C14—C15—O3	−5.0 (7)
O1—C1—C2—C3	171.0 (7)	O3—C15—C16—C17	−172.9 (5)
C6—C2—C3—C4	1.2 (9)	C14—C15—C16—C17	0.6 (8)
C1—C2—C3—C4	−177.5 (6)	O3—C15—C16—C19	−1.3 (8)
C2—C3—C4—C5	−0.4 (9)	C14—C15—C16—C19	172.2 (5)
C6—N1—C5—C4	1.7 (8)	C9—C8—C17—C16	−1.7 (8)
C7—N1—C5—C4	178.1 (5)	C7—C8—C17—C16	170.2 (5)
C3—C4—C5—N1	−1.1 (9)	C15—C16—C17—C8	0.7 (8)
C5—N1—C6—C2	−1.0 (8)	C19—C16—C17—C8	−171.1 (5)
C7—N1—C6—C2	−177.4 (5)	C15—C16—C19—N2	92.2 (7)
C3—C2—C6—N1	−0.5 (8)	C17—C16—C19—N2	−96.1 (6)
C1—C2—C6—N1	178.2 (5)	C24—N2—C19—C16	16.4 (8)
C6—N1—C7—C8	−61.4 (6)	C20—N2—C19—C16	−166.5 (5)
C5—N1—C7—C8	122.1 (5)	C24—N2—C20—C21	−2.2 (8)
N1—C7—C8—C17	114.7 (5)	C19—N2—C20—C21	−179.3 (5)
N1—C7—C8—C9	−73.6 (6)	N2—C20—C21—C22	−0.5 (9)
C17—C8—C9—C10	179.5 (5)	C20—C21—C22—C23	2.6 (9)
C7—C8—C9—C10	7.8 (8)	C21—C22—C23—C24	−2.2 (8)
C17—C8—C9—C14	1.5 (7)	C21—C22—C23—C25	178.1 (5)
C7—C8—C9—C14	−170.2 (5)	C20—N2—C24—C23	2.6 (8)
C14—C9—C10—C11	−4.3 (9)	C19—N2—C24—C23	179.6 (5)
C8—C9—C10—C11	177.6 (6)	C22—C23—C24—N2	−0.4 (8)
C9—C10—C11—C12	5.8 (10)	C25—C23—C24—N2	179.3 (5)
C10—C11—C12—C13	−2.5 (9)	C24—C23—C25—O5	−166.5 (5)
C11—C12—C13—C14	−2.0 (9)	C22—C23—C25—O5	13.3 (8)
C10—C9—C14—C13	−0.2 (8)	C24—C23—C25—O4	14.9 (8)
C8—C9—C14—C13	177.9 (5)	C22—C23—C25—O4	−165.4 (5)

Symmetry codes: (i) −x+3, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···O13ii	0.84 (4)	1.83 (4)	2.665 (5)	171 (6)
O10—H10B···O1i	0.85 (4)	1.84 (4)	2.668 (6)	166 (6)
O11—H11A···O12ii	0.87 (4)	1.83 (4)	2.690 (6)	174 (7)
O11—H11B···O14iii	0.86 (4)	1.85 (4)	2.701 (5)	173 (6)
O12—H12A···O1	0.83 (4)	1.84 (5)	2.654 (6)	164 (8)
O12—H12B···O4	0.87 (4)	1.91 (4)	2.772 (6)	173 (8)
O13—H13A···O5iv	0.86 (4)	1.94 (4)	2.787 (6)	172 (7)
O13—H13B···O9v	0.86 (4)	1.95 (4)	2.815 (6)	175 (7)
O13—H13B···Cl1v	0.86 (4)	2.69 (6)	3.451 (4)	147 (6)
O14—H14A···O4ii	0.86 (4)	1.88 (4)	2.724 (6)	165 (7)
O14—H14B···O5vi	0.86 (4)	1.98 (4)	2.811 (6)	160 (7)

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