{6,6'-Dimeth-oxy-2,2'-[naphthalene-2,3-diylbis(nitrilo-methyl-idyne)]diphenolato}thio-cyanato-cobalt(III) diethyl ether dichloro-methane solvate.

In the title complex, [Co(C(26)H(20)N(2)O(4))(NCS)]·C(4)H(10)O·CH(2)Cl(2), the penta-coordinated Co(III) atom exhibits a distorted square-pyramidal geometry with an N,N',O,O' tetra-dentate Schiff base ligand in the basal plane and one thio-cyanate ligand at the apical site. The diethyl ether mol-ecule is located in a cavity provided by four O atoms of the ligand with weak C-H⋯O inter-actions, generating two short O⋯O contact distances [2.766 (3) and 2.745 (3) Å] between the diethyl ether mol-ecule and the ligand. The crystal structure is stabilized by the weak C-H⋯O and C-H⋯N inter-actions and π-π inter-actions between the naphthyl ring system and the benzene ring [centroid-centroid distance = 3.657 (5) Å] and between the two naphthyl ring systems [centroid-centroid distance = 4.305 (2) Å].

Related literature

For the properties of Co(III) complexes with Schiff base ligands, see: Ito & Katsuki (1999 ▶); Wezenberg & Kleij (2008 ▶); Di Bella et al. (1995 ▶). For related structures, see: Kennedy et al. (1984 ▶); Marzilli et al. (1985 ▶); Álvarez et al. (2002 ▶). For hydrogen-bond length data, see: Desiraju & Steiner (1999 ▶). For non-bonded contact distances, see: Rowland & Taylor (1996 ▶); De Angelis et al. (1996 ▶). For the preparation of bis­(o-vanillin)-2,3-naphthalene­diimine, see: Nabei et al. (2008 ▶).

Experimental

Crystal data

[Co(C26H20N2O4)(NCS)]·C4H10O·CH2Cl2

M = 700.52

Monoclinic,

a = 9.1935 (9) Å

b = 13.3640 (11) Å

c = 25.910 (3) Å

β = 92.462 (6)°

V = 3180.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.82 mm−1

T = 120 (1) K

0.40 × 0.10 × 0.10 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.799, T max = 0.921

24340 measured reflections

7241 independent reflections

6234 reflections with I 2 > 2σ(I 2)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.136

S = 1.21

7241 reflections

397 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.60 e Å−3

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000841/is2372sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000841/is2372Isup2.hkl

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

[Co(C26H20N2O4)(NCS)]·C4H10O·CH2Cl2	F(000) = 1448.00
Mr = 700.52	Dx = 1.463 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 8164 reflections
a = 9.1935 (9) Å	θ = 3.0–27.5°
b = 13.3640 (11) Å	µ = 0.82 mm−1
c = 25.910 (3) Å	T = 120 K
β = 92.462 (6)°	Block, brown
V = 3180.4 (5) Å3	0.40 × 0.10 × 0.10 mm
Z = 4

Rigaku Mercury diffractometer	6234 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1	Rint = 0.051
ω scans	θmax = 27.5°
Absorption correction: multi-scan (Jacobson, 1998)	h = −11→11
Tmin = 0.799, Tmax = 0.921	k = −17→16
24340 measured reflections	l = −33→33
7241 independent reflections

Refinement on F2	0 restraints
R[F2 > 2σ(F2)] = 0.075	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0406P)2 + 5.4074P] where P = (Fo2 + 2Fc2)/3
S = 1.21	(Δ/σ)max < 0.001
7241 reflections	Δρmax = 0.69 e Å−3
397 parameters	Δρmin = −0.60 e Å−3

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Co1	0.86917 (5)	0.14242 (3)	0.104634 (16)	0.01291 (12)
Cl1	0.94249 (14)	−0.01789 (9)	0.26072 (5)	0.0457 (3)
Cl2	1.08816 (13)	0.13888 (10)	0.32166 (4)	0.0432 (2)
S1	1.23023 (10)	−0.10089 (7)	0.16110 (3)	0.0209 (2)
O1	0.9600 (2)	0.26531 (17)	0.07695 (9)	0.0169 (5)
O2	0.8278 (2)	0.20652 (17)	0.17258 (9)	0.0169 (5)
O3	1.1184 (2)	0.42651 (18)	0.06792 (9)	0.0208 (5)
O4	0.8313 (2)	0.30348 (19)	0.25937 (9)	0.0227 (5)
O5	0.9766 (3)	0.3836 (2)	0.16464 (11)	0.0342 (7)
N1	0.8470 (3)	0.0896 (2)	0.02833 (10)	0.0136 (5)
N2	0.6785 (3)	0.0629 (2)	0.10650 (10)	0.0125 (5)
N3	1.0299 (3)	0.0455 (2)	0.12721 (11)	0.0200 (6)
C1	0.7473 (3)	−0.0599 (2)	−0.01750 (12)	0.0143 (6)
C2	0.7520 (3)	0.0062 (2)	0.02329 (13)	0.0135 (6)
C3	0.6577 (3)	−0.0073 (2)	0.06516 (12)	0.0136 (6)
C4	0.5599 (3)	−0.0851 (2)	0.06453 (13)	0.0152 (6)
C5	0.4501 (3)	−0.2336 (2)	0.02066 (14)	0.0212 (7)
C6	0.4441 (4)	−0.2974 (2)	−0.02095 (14)	0.0231 (8)
C7	0.5377 (4)	−0.2840 (2)	−0.06230 (15)	0.0237 (8)
C8	0.6372 (3)	−0.2082 (2)	−0.06120 (13)	0.0188 (7)
C9	0.6461 (3)	−0.1400 (2)	−0.01923 (13)	0.0159 (6)
C10	0.5509 (3)	−0.1530 (2)	0.02226 (13)	0.0155 (6)
C11	0.8959 (3)	0.1312 (2)	−0.01225 (12)	0.0151 (6)
C12	0.9881 (3)	0.2190 (2)	−0.01257 (13)	0.0151 (6)
C13	1.0523 (3)	0.2418 (2)	−0.05992 (13)	0.0185 (7)
C14	1.1415 (4)	0.3229 (2)	−0.06411 (14)	0.0224 (8)
C15	1.1658 (4)	0.3869 (2)	−0.02166 (14)	0.0202 (7)
C16	1.1014 (3)	0.3677 (2)	0.02430 (13)	0.0175 (7)
C17	1.0133 (3)	0.2812 (2)	0.03134 (13)	0.0156 (7)
C18	1.2007 (4)	0.5168 (2)	0.06299 (15)	0.0267 (8)
C19	0.5787 (3)	0.0745 (2)	0.14003 (13)	0.0140 (6)
C20	0.5903 (3)	0.1340 (2)	0.18630 (12)	0.0144 (6)
C21	0.4719 (3)	0.1279 (2)	0.21954 (13)	0.0176 (7)
C22	0.4720 (4)	0.1784 (2)	0.26559 (13)	0.0207 (7)
C23	0.5933 (4)	0.2381 (2)	0.28035 (13)	0.0193 (7)
C24	0.7092 (3)	0.2458 (2)	0.24873 (13)	0.0165 (7)
C25	0.7134 (3)	0.1936 (2)	0.20060 (12)	0.0141 (6)
C26	0.8445 (4)	0.3472 (3)	0.30996 (14)	0.0286 (9)
C27	1.1133 (3)	−0.0151 (2)	0.14180 (13)	0.0163 (7)
C28	1.0497 (4)	0.0897 (3)	0.25913 (15)	0.0294 (9)
C29	1.1140 (4)	0.4060 (2)	0.19570 (14)	0.0223 (7)
C30	1.2196 (4)	0.3211 (3)	0.19249 (17)	0.0334 (9)
C31	0.8751 (4)	0.4713 (2)	0.16089 (15)	0.0229 (8)
C32	0.7414 (4)	0.4437 (3)	0.12821 (15)	0.0258 (8)
H1	0.8123	−0.0517	−0.0447	0.017*
H4	0.4977	−0.0935	0.0926	0.018*
H5	0.3870	−0.2434	0.0483	0.025*
H6	0.3763	−0.3511	−0.0220	0.028*
H7	0.5312	−0.3281	−0.0911	0.028*
H8	0.7011	−0.2010	−0.0888	0.023*
H11	0.8691	0.1019	−0.0447	0.018*
H13	1.0330	0.2002	−0.0891	0.022*
H14	1.1870	0.3358	−0.0957	0.027*
H15	1.2269	0.4438	−0.0247	0.024*
H18A	1.2052	0.5524	0.0961	0.032*
H18B	1.1536	0.5595	0.0364	0.032*
H18C	1.2996	0.5003	0.0531	0.032*
H19	0.4893	0.0403	0.1333	0.017*
H21	0.3902	0.0877	0.2096	0.021*
H22	0.3916	0.1732	0.2873	0.025*
H23	0.5950	0.2731	0.3123	0.023*
H26A	0.9345	0.3864	0.3132	0.034*
H26B	0.8471	0.2941	0.3361	0.034*
H26C	0.7609	0.3910	0.3152	0.034*
H28A	0.9985	0.1411	0.2377	0.035*
H28B	1.1423	0.0737	0.2428	0.035*
H29A	1.1586	0.4679	0.1825	0.027*
H29B	1.0910	0.4173	0.2322	0.027*
H30A	1.3087	0.3372	0.2130	0.040*
H30B	1.2433	0.3106	0.1564	0.040*
H30C	1.1760	0.2602	0.2061	0.040*
H31A	0.9247	0.5289	0.1452	0.027*
H31B	0.8466	0.4911	0.1959	0.027*
H32A	0.6753	0.5012	0.1257	0.031*
H32B	0.6920	0.3874	0.1441	0.031*
H32C	0.7700	0.4247	0.0936	0.031*

	U11	U22	U33	U12	U13	U23
Co1	0.0163 (2)	0.0129 (2)	0.0096 (2)	−0.00135 (19)	0.00109 (17)	0.00003 (18)
Cl1	0.0561 (7)	0.0395 (6)	0.0431 (6)	−0.0178 (5)	0.0187 (5)	−0.0048 (5)
Cl2	0.0424 (6)	0.0508 (7)	0.0355 (6)	0.0001 (5)	−0.0067 (5)	−0.0069 (5)
S1	0.0193 (4)	0.0229 (4)	0.0203 (4)	0.0029 (3)	−0.0010 (3)	0.0034 (3)
O1	0.0238 (13)	0.0165 (12)	0.0107 (11)	−0.0038 (10)	0.0018 (9)	−0.0011 (9)
O2	0.0203 (12)	0.0179 (12)	0.0128 (11)	−0.0037 (10)	0.0036 (9)	−0.0025 (9)
O3	0.0301 (14)	0.0181 (12)	0.0142 (12)	−0.0102 (11)	−0.0006 (10)	−0.0005 (9)
O4	0.0307 (14)	0.0230 (13)	0.0145 (12)	−0.0071 (11)	0.0018 (10)	−0.0085 (10)
O5	0.0363 (17)	0.0322 (16)	0.0337 (16)	−0.0014 (13)	−0.0025 (13)	−0.0020 (12)
N1	0.0176 (14)	0.0122 (13)	0.0109 (13)	0.0019 (11)	0.0002 (11)	0.0002 (10)
N2	0.0181 (14)	0.0104 (12)	0.0089 (12)	0.0011 (11)	−0.0013 (11)	0.0010 (10)
N3	0.0247 (16)	0.0222 (16)	0.0132 (14)	0.0026 (13)	0.0005 (12)	−0.0002 (12)
C1	0.0149 (16)	0.0161 (16)	0.0119 (15)	0.0025 (13)	0.0015 (13)	0.0024 (12)
C2	0.0141 (16)	0.0124 (15)	0.0137 (15)	0.0031 (13)	−0.0031 (13)	0.0012 (12)
C3	0.0164 (16)	0.0138 (16)	0.0102 (15)	0.0023 (13)	−0.0043 (13)	−0.0014 (12)
C4	0.0161 (16)	0.0165 (16)	0.0130 (15)	0.0026 (13)	−0.0001 (13)	0.0002 (12)
C5	0.0193 (18)	0.0216 (18)	0.0228 (18)	−0.0006 (15)	0.0002 (15)	0.0013 (14)
C6	0.0213 (18)	0.0219 (19)	0.0257 (19)	−0.0073 (15)	−0.0045 (15)	−0.0028 (15)
C7	0.028 (2)	0.0192 (18)	0.0233 (19)	0.0012 (16)	−0.0072 (16)	−0.0064 (14)
C8	0.0209 (18)	0.0200 (17)	0.0151 (16)	0.0053 (14)	−0.0040 (14)	−0.0003 (13)
C9	0.0171 (16)	0.0146 (16)	0.0155 (16)	0.0040 (14)	−0.0040 (13)	−0.0005 (13)
C10	0.0164 (16)	0.0134 (16)	0.0164 (16)	0.0011 (13)	−0.0043 (13)	0.0010 (13)
C11	0.0193 (17)	0.0142 (16)	0.0118 (15)	0.0027 (13)	−0.0011 (13)	0.0008 (12)
C12	0.0185 (17)	0.0139 (16)	0.0129 (16)	0.0017 (13)	−0.0005 (13)	0.0035 (12)
C13	0.0262 (19)	0.0163 (17)	0.0133 (16)	−0.0008 (14)	0.0037 (14)	0.0011 (13)
C14	0.029 (2)	0.0248 (19)	0.0141 (16)	0.0014 (16)	0.0080 (15)	0.0073 (14)
C15	0.0218 (18)	0.0183 (17)	0.0202 (17)	−0.0032 (14)	−0.0012 (15)	0.0053 (14)
C16	0.0196 (17)	0.0172 (17)	0.0153 (16)	−0.0011 (14)	−0.0048 (13)	0.0011 (13)
C17	0.0167 (17)	0.0160 (16)	0.0140 (16)	0.0026 (13)	−0.0019 (13)	0.0030 (13)
C18	0.032 (2)	0.0218 (19)	0.026 (2)	−0.0113 (16)	0.0010 (17)	0.0001 (15)
C19	0.0142 (16)	0.0115 (15)	0.0162 (16)	0.0029 (12)	−0.0013 (13)	0.0014 (12)
C20	0.0197 (17)	0.0105 (15)	0.0131 (15)	0.0050 (13)	0.0012 (13)	0.0027 (12)
C21	0.0170 (16)	0.0168 (17)	0.0193 (17)	0.0009 (14)	0.0019 (13)	0.0003 (13)
C22	0.0238 (19)	0.0217 (18)	0.0173 (17)	0.0043 (15)	0.0102 (15)	0.0019 (14)
C23	0.030 (2)	0.0138 (16)	0.0140 (16)	0.0032 (14)	0.0037 (14)	−0.0026 (13)
C24	0.0226 (18)	0.0139 (16)	0.0129 (16)	0.0005 (14)	−0.0004 (14)	−0.0015 (12)
C25	0.0217 (17)	0.0103 (15)	0.0102 (15)	0.0029 (13)	0.0010 (13)	0.0021 (12)
C26	0.035 (2)	0.034 (2)	0.0175 (18)	−0.0041 (18)	0.0019 (16)	−0.0138 (16)
C27	0.0176 (17)	0.0192 (17)	0.0119 (15)	−0.0047 (14)	0.0012 (13)	−0.0020 (13)
C28	0.027 (2)	0.035 (2)	0.026 (2)	−0.0033 (18)	−0.0015 (17)	−0.0021 (17)
C29	0.0241 (19)	0.0248 (19)	0.0176 (17)	−0.0020 (15)	−0.0053 (15)	−0.0033 (14)
C30	0.031 (2)	0.031 (2)	0.037 (2)	0.0029 (18)	−0.0063 (19)	−0.0046 (18)
C31	0.0255 (19)	0.0165 (17)	0.026 (2)	−0.0014 (15)	−0.0012 (16)	0.0001 (14)
C32	0.026 (2)	0.025 (2)	0.026 (2)	0.0010 (16)	−0.0039 (16)	0.0008 (16)

Co1—O1	1.990 (2)	C20—C21	1.419 (4)
Co1—O2	2.009 (2)	C20—C25	1.420 (4)
Co1—N1	2.101 (2)	C21—C22	1.371 (4)
Co1—N2	2.053 (2)	C22—C23	1.411 (5)
Co1—N3	2.033 (3)	C23—C24	1.376 (5)
Cl1—C28	1.745 (4)	C24—C25	1.430 (4)
Cl2—C28	1.770 (4)	C29—C30	1.498 (5)
S1—C27	1.635 (3)	C31—C32	1.508 (5)
O1—C17	1.316 (4)	C1—H1	0.950
O2—C25	1.315 (4)	C4—H4	0.950
O3—C16	1.380 (4)	C5—H5	0.950
O3—C18	1.433 (4)	C6—H6	0.950
O4—C24	1.380 (4)	C7—H7	0.950
O4—C26	1.436 (4)	C8—H8	0.950
O5—C29	1.499 (4)	C11—H11	0.950
O5—C31	1.499 (4)	C13—H13	0.950
N1—C2	1.419 (4)	C14—H14	0.950
N1—C11	1.287 (4)	C15—H15	0.950
N2—C3	1.430 (4)	C18—H18A	0.980
N2—C19	1.299 (4)	C18—H18B	0.980
N3—C27	1.166 (4)	C18—H18C	0.980
C1—C2	1.376 (4)	C19—H19	0.950
C1—C9	1.418 (4)	C21—H21	0.950
C2—C3	1.428 (4)	C22—H22	0.950
C3—C4	1.375 (4)	C23—H23	0.950
C4—C10	1.422 (4)	C26—H26A	0.980
C5—C6	1.374 (5)	C26—H26B	0.980
C5—C10	1.420 (4)	C26—H26C	0.980
C6—C7	1.414 (5)	C28—H28A	0.990
C7—C8	1.364 (5)	C28—H28B	0.990
C8—C9	1.419 (4)	C29—H29A	0.990
C9—C10	1.426 (4)	C29—H29B	0.990
C11—C12	1.448 (4)	C30—H30A	0.980
C12—C13	1.417 (4)	C30—H30B	0.980
C12—C17	1.420 (4)	C30—H30C	0.980
C13—C14	1.366 (5)	C31—H31A	0.990
C14—C15	1.404 (5)	C31—H31B	0.990
C15—C16	1.377 (5)	C32—H32A	0.980
C16—C17	1.428 (4)	C32—H32B	0.980
C19—C20	1.439 (4)	C32—H32C	0.980
O1···O5	2.766 (3)	O1···H30B	3.305
O1···C32	3.423 (4)	O1···H32B	3.483
O2···O5	2.745 (3)	O1···H32C	2.799
O2···C28	3.352 (4)	O2···H28A	2.417
O2···C31	3.580 (4)	O2···H30C	3.358
O2···C32	3.453 (4)	O2···H32B	2.804
O3···O5	2.931 (3)	O2···H32C	3.589
O3···C29	3.324 (4)	O3···H29A	3.028
O3···C31	3.410 (4)	O3···H30B	2.957
O4···O5	3.039 (3)	O3···H31A	3.059
O4···C29	3.424 (4)	O3···H32C	3.299
O4···C31	3.434 (4)	O4···H28A	2.732
O5···O1	2.766 (3)	O4···H29B	2.942
O5···O2	2.745 (3)	O4···H30C	3.558
O5···O3	2.931 (3)	O4···H31B	3.006
O5···O4	3.039 (3)	O4···H32B	3.389
O5···C30	2.464 (5)	H1···N3i	2.636
O5···C32	2.457 (4)	H28A···O2	2.417
C1···N3i	3.579 (4)	H29A···O3	3.028
C28···O2	3.352 (4)	H29B···O4	2.942
C29···O3	3.324 (4)	H30B···O1	3.305
C29···O4	3.424 (4)	H30B···O3	2.957
C30···O5	2.464 (5)	H31A···O3	3.059
C31···O2	3.580 (4)	H31B···O4	3.006
C31···O3	3.410 (4)	H32B···O1	3.483
C31···O4	3.434 (4)	H32B···O2	2.804
C32···Cl1ii	3.438 (4)	H32B···O4	3.389
C32···O1	3.423 (4)	H32C···O1	2.799
C32···O2	3.453 (4)	H32C···O2	3.589
C32···O5	2.457 (4)	H32C···O3	3.299
O1—Co1—O2	93.56 (9)	O5—C31—C32	109.6 (2)
O1—Co1—N1	87.90 (10)	C2—C1—H1	119.7
O1—Co1—N2	143.89 (10)	C9—C1—H1	119.8
O1—Co1—N3	108.59 (11)	C3—C4—H4	119.7
O2—Co1—N1	162.48 (10)	C10—C4—H4	119.7
O2—Co1—N2	90.36 (10)	C6—C5—H5	120.1
O2—Co1—N3	100.51 (10)	C10—C5—H5	120.1
N1—Co1—N2	78.44 (10)	C5—C6—H6	119.7
N1—Co1—N3	95.54 (11)	C7—C6—H6	119.7
N2—Co1—N3	105.92 (11)	C6—C7—H7	119.7
Co1—O1—C17	129.4 (2)	C8—C7—H7	119.7
Co1—O2—C25	127.9 (2)	C7—C8—H8	119.7
C16—O3—C18	116.6 (2)	C9—C8—H8	119.7
C24—O4—C26	116.5 (2)	N1—C11—H11	117.3
C29—O5—C31	112.7 (2)	C12—C11—H11	117.3
Co1—N1—C2	112.7 (2)	C12—C13—H13	119.6
Co1—N1—C11	126.9 (2)	C14—C13—H13	119.5
C2—N1—C11	119.9 (2)	C13—C14—H14	120.1
Co1—N2—C3	114.1 (2)	C15—C14—H14	120.1
Co1—N2—C19	125.6 (2)	C14—C15—H15	119.9
C3—N2—C19	120.3 (2)	C16—C15—H15	119.9
Co1—N3—C27	174.4 (2)	O3—C18—H18A	109.5
C2—C1—C9	120.5 (3)	O3—C18—H18B	109.5
N1—C2—C1	125.0 (3)	O3—C18—H18C	109.5
N1—C2—C3	114.8 (2)	H18A—C18—H18B	109.5
C1—C2—C3	120.2 (2)	H18A—C18—H18C	109.5
N2—C3—C2	114.9 (2)	H18B—C18—H18C	109.5
N2—C3—C4	124.8 (2)	N2—C19—H19	116.8
C2—C3—C4	120.3 (2)	C20—C19—H19	116.8
C3—C4—C10	120.6 (3)	C20—C21—H21	119.1
C6—C5—C10	119.9 (3)	C22—C21—H21	119.1
C5—C6—C7	120.7 (3)	C21—C22—H22	120.5
C6—C7—C8	120.5 (3)	C23—C22—H22	120.5
C7—C8—C9	120.6 (3)	C22—C23—H23	119.9
C1—C9—C8	121.7 (3)	C24—C23—H23	119.9
C1—C9—C10	119.5 (3)	O4—C26—H26A	109.5
C8—C9—C10	118.8 (3)	O4—C26—H26B	109.5
C4—C10—C5	121.5 (3)	O4—C26—H26C	109.5
C4—C10—C9	119.0 (3)	H26A—C26—H26B	109.5
C5—C10—C9	119.4 (3)	H26A—C26—H26C	109.5
N1—C11—C12	125.4 (2)	H26B—C26—H26C	109.5
C11—C12—C13	116.4 (2)	Cl1—C28—H28A	109.2
C11—C12—C17	123.0 (3)	Cl1—C28—H28B	109.2
C13—C12—C17	120.5 (3)	Cl2—C28—H28A	109.2
C12—C13—C14	120.9 (3)	Cl2—C28—H28B	109.2
C13—C14—C15	119.8 (3)	H28A—C28—H28B	107.9
C14—C15—C16	120.2 (3)	O5—C29—H29A	109.5
O3—C16—C15	124.3 (3)	O5—C29—H29B	109.5
O3—C16—C17	113.7 (2)	C30—C29—H29A	109.5
C15—C16—C17	122.0 (3)	C30—C29—H29B	109.5
O1—C17—C12	124.8 (3)	H29A—C29—H29B	108.1
O1—C17—C16	118.7 (2)	C29—C30—H30A	109.5
C12—C17—C16	116.5 (3)	C29—C30—H30B	109.5
N2—C19—C20	126.4 (3)	C29—C30—H30C	109.5
C19—C20—C21	116.3 (2)	H30A—C30—H30B	109.5
C19—C20—C25	123.9 (3)	H30A—C30—H30C	109.5
C21—C20—C25	119.8 (2)	H30B—C30—H30C	109.5
C20—C21—C22	121.9 (3)	O5—C31—H31A	109.8
C21—C22—C23	119.1 (3)	O5—C31—H31B	109.8
C22—C23—C24	120.3 (3)	C32—C31—H31A	109.8
O4—C24—C23	124.5 (3)	C32—C31—H31B	109.8
O4—C24—C25	113.2 (2)	H31A—C31—H31B	108.2
C23—C24—C25	122.2 (3)	C31—C32—H32A	109.5
O2—C25—C20	125.2 (2)	C31—C32—H32B	109.5
O2—C25—C24	118.0 (2)	C31—C32—H32C	109.5
C20—C25—C24	116.7 (3)	H32A—C32—H32B	109.5
S1—C27—N3	178.9 (3)	H32A—C32—H32C	109.5
Cl1—C28—Cl2	112.0 (2)	H32B—C32—H32C	109.5
O5—C29—C30	110.6 (3)
O1—Co1—O2—C25	142.7 (2)	N1—C2—C3—N2	−2.6 (4)
O2—Co1—O1—C17	−178.3 (2)	N1—C2—C3—C4	179.5 (2)
O1—Co1—N1—C2	−166.2 (2)	C1—C2—C3—N2	176.7 (2)
O1—Co1—N1—C11	5.6 (2)	C1—C2—C3—C4	−1.2 (4)
N1—Co1—O1—C17	−15.8 (2)	N2—C3—C4—C10	−177.8 (3)
O1—Co1—N2—C3	88.5 (2)	C2—C3—C4—C10	−0.1 (3)
O1—Co1—N2—C19	−89.0 (3)	C3—C4—C10—C5	−179.7 (3)
N2—Co1—O1—C17	−82.8 (3)	C3—C4—C10—C9	0.7 (4)
N3—Co1—O1—C17	79.3 (2)	C6—C5—C10—C4	179.7 (3)
O2—Co1—N1—C2	−71.0 (4)	C6—C5—C10—C9	−0.7 (5)
O2—Co1—N1—C11	100.8 (4)	C10—C5—C6—C7	0.2 (5)
N1—Co1—O2—C25	48.4 (4)	C5—C6—C7—C8	1.0 (5)
O2—Co1—N2—C3	−175.0 (2)	C6—C7—C8—C9	−1.6 (5)
O2—Co1—N2—C19	7.6 (2)	C7—C8—C9—C1	−179.2 (3)
N2—Co1—O2—C25	−1.3 (2)	C7—C8—C9—C10	1.1 (5)
N3—Co1—O2—C25	−107.6 (2)	C1—C9—C10—C4	0.0 (4)
N1—Co1—N2—C3	18.6 (2)	C1—C9—C10—C5	−179.6 (3)
N1—Co1—N2—C19	−158.9 (2)	C8—C9—C10—C4	179.7 (3)
N2—Co1—N1—C2	−19.8 (2)	C8—C9—C10—C5	0.1 (3)
N2—Co1—N1—C11	152.0 (3)	N1—C11—C12—C13	168.5 (3)
N3—Co1—N1—C2	85.4 (2)	N1—C11—C12—C17	−12.5 (5)
N3—Co1—N1—C11	−102.9 (2)	C11—C12—C13—C14	−179.7 (3)
N3—Co1—N2—C3	−74.0 (2)	C11—C12—C17—O1	1.8 (5)
N3—Co1—N2—C19	108.6 (2)	C11—C12—C17—C16	−177.1 (3)
Co1—O1—C17—C12	14.8 (4)	C13—C12—C17—O1	−179.1 (3)
Co1—O1—C17—C16	−166.3 (2)	C13—C12—C17—C16	1.9 (4)
Co1—O2—C25—C20	−3.5 (4)	C17—C12—C13—C14	1.2 (5)
Co1—O2—C25—C24	178.4 (2)	C12—C13—C14—C15	−2.6 (5)
C18—O3—C16—C15	4.5 (4)	C13—C14—C15—C16	0.8 (5)
C18—O3—C16—C17	−177.5 (2)	C14—C15—C16—O3	−179.7 (3)
C26—O4—C24—C23	8.5 (4)	C14—C15—C16—C17	2.5 (5)
C26—O4—C24—C25	−171.8 (2)	O3—C16—C17—O1	−0.8 (4)
C29—O5—C31—C32	178.8 (2)	O3—C16—C17—C12	178.3 (2)
C31—O5—C29—C30	−172.5 (3)	C15—C16—C17—O1	177.2 (3)
Co1—N1—C2—C1	−161.2 (2)	C15—C16—C17—C12	−3.7 (5)
Co1—N1—C2—C3	18.0 (3)	N2—C19—C20—C21	−174.3 (3)
Co1—N1—C11—C12	6.0 (4)	N2—C19—C20—C25	3.3 (5)
C2—N1—C11—C12	177.2 (3)	C19—C20—C21—C22	177.8 (3)
C11—N1—C2—C1	26.4 (4)	C19—C20—C25—O2	3.9 (5)
C11—N1—C2—C3	−154.4 (3)	C19—C20—C25—C24	−178.0 (3)
Co1—N2—C3—C2	−14.6 (3)	C21—C20—C25—O2	−178.6 (3)
Co1—N2—C3—C4	163.2 (2)	C21—C20—C25—C24	−0.5 (4)
Co1—N2—C19—C20	−9.6 (4)	C25—C20—C21—C22	0.1 (3)
C3—N2—C19—C20	173.2 (3)	C21—C22—C23—C24	0.4 (5)
C19—N2—C3—C2	163.0 (2)	C22—C23—C24—O4	178.8 (3)
C19—N2—C3—C4	−19.2 (4)	C22—C23—C24—C25	−0.8 (5)
C2—C1—C9—C8	178.9 (3)	O4—C24—C25—O2	−0.6 (4)
C2—C1—C9—C10	−1.4 (4)	O4—C24—C25—C20	−178.8 (2)
C9—C1—C2—N1	−178.8 (3)	C23—C24—C25—O2	179.1 (3)
C9—C1—C2—C3	2.0 (4)	C23—C24—C25—C20	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N3i	0.95	2.64	3.579 (4)	172
C28—H28A···O2	0.99	2.42	3.352 (4)	157
C29—H29B···O4	0.99	2.94	3.424 (4)	111
C30—H30B···O3	0.98	2.96	3.607 (5)	125
C32—H32B···O2	0.98	2.80	3.453 (4)	124
C32—H32C···O1	0.98	2.80	3.423 (4)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N3i	0.95	2.64	3.579 (4)	172
C28—H28A⋯O2	0.99	2.42	3.352 (4)	157
C29—H29B⋯O4	0.99	2.94	3.424 (4)	111
C30—H30B⋯O3	0.98	2.96	3.607 (5)	125
C32—H32B⋯O2	0.98	2.80	3.453 (4)	124
C32—H32C⋯O1	0.98	2.80	3.423 (4)	122

Symmetry code: (i) .