4-[(4'-Chloro-methyl-[1,1'-biphen-yl]-4-yl)meth-yl]bis-(dimethyl-glyoximato-κN,N')(pyridine-κN)cobalt(III).

The title compound, [Co(C(14)H(14)Cl)(C(4)H(6)N(2)O(2))(2)(C(5)H(5)N)], is a model compound for the more complex cobalamines like vitamins B(12). The Co(III) atom is coordinated by a (4'-chloro-methyl-[1,1'-biphen-yl]-4-yl)methyl group, an N-bonded pyridine and two N,N'-bidentate dimethyl-glyoximate ligands in a distorted octa-hedral geometry. The glyoximate ligands exhibit intra-molecular O-H⋯O hydrogen bonds, which is very common in cobaloxime derivatives.

Related literature

For general background, see: Bresciani-Pahor et al. (1985 ▶); Revathi et al. (2009 ▶); Brown (2006 ▶); Randaccio (1999 ▶); For structure–property relationships, see: Gupta et al. (2004 ▶); Dutta et al. (2009 ▶). For a related structure, see: Kumar & Gupta (2011 ▶).

Experimental

Crystal data

[Co(C14H14Cl)(C4H6N2O2)2(C5H5N)]

M = 583.95

Triclinic,

a = 9.1208 (15) Å

b = 11.3999 (19) Å

c = 13.661 (2) Å

α = 72.869 (3)°

β = 77.504 (3)°

γ = 87.276 (3)°

V = 1325.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.79 mm−1

T = 100 K

0.32 × 0.28 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.786, T max = 0.821

7047 measured reflections

4789 independent reflections

3996 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 1.04

4789 reflections

349 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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: DIAMOND (Brandenburg, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001092/fk2049sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001092/fk2049Isup2.hkl

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

[Co(C14H14Cl)(C4H6N2O2)2(C5H5N)]	Z = 2
Mr = 583.95	F(000) = 608
Triclinic, P1	Dx = 1.464 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1208 (15) Å	Cell parameters from 2484 reflections
b = 11.3999 (19) Å	θ = 2.8–27.6°
c = 13.661 (2) Å	µ = 0.79 mm−1
α = 72.869 (3)°	T = 100 K
β = 77.504 (3)°	Prism, orange
γ = 87.276 (3)°	0.32 × 0.28 × 0.26 mm
V = 1325.1 (4) Å3

Bruker SMART CCD area-detector diffractometer	4789 independent reflections
Radiation source: fine-focus sealed tube	3996 reflections with I > 2σ(I)
graphite	Rint = 0.022
phi and ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.786, Tmax = 0.821	k = −13→13
7047 measured reflections	l = −9→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0624P)2 + 0.7675P] where P = (Fo2 + 2Fc2)/3
4789 reflections	(Δ/σ)max = 0.014
349 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.5467 (3)	0.4296 (3)	0.8689 (2)	0.0244 (6)
C2	0.4200 (3)	0.5114 (2)	0.8484 (2)	0.0236 (6)
C3	0.6928 (3)	0.4741 (3)	0.8776 (2)	0.0328 (7)
H3A	0.7613	0.4051	0.8907	0.049*
H3B	0.6763	0.5104	0.9358	0.049*
H3C	0.7369	0.5362	0.8122	0.049*
C4	0.4242 (4)	0.6451 (3)	0.8370 (3)	0.0353 (7)
H4A	0.3245	0.6793	0.8322	0.053*
H4B	0.4972	0.6864	0.7733	0.053*
H4C	0.4537	0.6578	0.8980	0.053*
C5	0.2347 (3)	0.0577 (3)	0.8636 (2)	0.0267 (6)
C6	0.1069 (3)	0.1387 (3)	0.8459 (2)	0.0259 (6)
C7	0.2347 (4)	−0.0776 (3)	0.8776 (3)	0.0405 (8)
H7A	0.3159	−0.0966	0.8249	0.061*
H7B	0.1381	−0.1030	0.8691	0.061*
H7C	0.2500	−0.1216	0.9478	0.061*
C8	−0.0405 (4)	0.0952 (3)	0.8371 (3)	0.0361 (7)
H8A	−0.1123	0.1623	0.8330	0.054*
H8B	−0.0790	0.0261	0.8987	0.054*
H8C	−0.0268	0.0687	0.7737	0.054*
C9	0.1205 (3)	0.2947 (2)	1.0542 (2)	0.0236 (6)
H9	0.0680	0.3500	1.0074	0.028*
C10	0.0644 (3)	0.2700 (2)	1.1611 (2)	0.0252 (6)
H10	−0.0247	0.3078	1.1869	0.030*
C11	0.1406 (3)	0.1892 (2)	1.2298 (2)	0.0261 (6)
H11	0.1055	0.1713	1.3035	0.031*
C12	0.2681 (3)	0.1354 (2)	1.1890 (2)	0.0249 (6)
H12	0.3219	0.0790	1.2342	0.030*
C13	0.3172 (3)	0.1641 (2)	1.0815 (2)	0.0216 (6)
H13	0.4051	0.1260	1.0542	0.026*
C14	0.4029 (3)	0.3241 (3)	0.6945 (2)	0.0280 (6)
H14A	0.4287	0.2461	0.6773	0.034*
H14B	0.3195	0.3607	0.6603	0.034*
C15	0.5346 (4)	0.4084 (3)	0.6493 (2)	0.0300 (7)
C16	0.5165 (3)	0.5349 (3)	0.6105 (2)	0.0301 (7)
H16	0.4186	0.5656	0.6066	0.036*
C17	0.6360 (3)	0.6165 (3)	0.5778 (2)	0.0311 (7)
H17	0.6188	0.7019	0.5526	0.037*
C18	0.7833 (3)	0.5753 (3)	0.5810 (2)	0.0297 (7)
C19	0.8023 (4)	0.4479 (3)	0.6162 (2)	0.0322 (7)
H19	0.9004	0.4166	0.6178	0.039*
C20	0.6826 (4)	0.3678 (3)	0.6480 (2)	0.0313 (7)
H20	0.7000	0.2821	0.6700	0.038*
C21	0.9099 (3)	0.6632 (3)	0.5546 (2)	0.0299 (7)
C22	0.9150 (4)	0.7773 (3)	0.4799 (2)	0.0335 (7)
H22	0.8370	0.7989	0.4420	0.040*
C23	1.0328 (4)	0.8605 (3)	0.4598 (2)	0.0372 (8)
H23	1.0331	0.9384	0.4094	0.045*
C24	1.1498 (4)	0.8307 (3)	0.5128 (2)	0.0361 (7)
C25	1.1457 (3)	0.7166 (3)	0.5874 (2)	0.0346 (7)
H25	1.2244	0.6946	0.6246	0.041*
C26	1.0279 (3)	0.6349 (3)	0.6076 (2)	0.0331 (7)
H26	1.0271	0.5575	0.6589	0.040*
C27	1.2793 (4)	0.9190 (4)	0.4875 (3)	0.0467 (9)
H27A	1.2576	0.9971	0.4376	0.056*
H27B	1.3707	0.8846	0.4528	0.056*
N1	0.1383 (3)	0.2514 (2)	0.83606 (18)	0.0246 (5)
N2	0.3515 (3)	0.1170 (2)	0.86675 (18)	0.0229 (5)
N3	0.3069 (3)	0.4537 (2)	0.83950 (17)	0.0223 (5)
N4	0.5175 (2)	0.3177 (2)	0.87419 (17)	0.0216 (5)
N5	0.2458 (2)	0.24374 (19)	1.01403 (18)	0.0204 (5)
O1	0.1808 (2)	0.51432 (17)	0.81945 (16)	0.0291 (5)
O2	0.6233 (2)	0.23031 (18)	0.89279 (16)	0.0277 (5)
H2	0.5929	0.1641	0.8882	0.042*
O3	0.0329 (2)	0.33869 (18)	0.81727 (17)	0.0313 (5)
H3	0.0696	0.4077	0.8099	0.047*
O4	0.4805 (2)	0.05861 (17)	0.87842 (16)	0.0289 (5)
Cl1	1.31444 (11)	0.94962 (9)	0.60281 (7)	0.0528 (3)
Co1	0.32783 (4)	0.28473 (3)	0.85516 (3)	0.02023 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0278 (15)	0.0268 (15)	0.0186 (13)	−0.0066 (12)	−0.0018 (11)	−0.0077 (11)
C2	0.0338 (16)	0.0185 (14)	0.0185 (13)	−0.0031 (12)	−0.0044 (12)	−0.0056 (11)
C3	0.0286 (16)	0.0409 (19)	0.0311 (16)	−0.0104 (14)	−0.0057 (13)	−0.0129 (14)
C4	0.050 (2)	0.0193 (15)	0.0385 (18)	−0.0059 (14)	−0.0092 (15)	−0.0105 (13)
C5	0.0354 (17)	0.0206 (14)	0.0276 (15)	−0.0019 (12)	−0.0099 (13)	−0.0099 (12)
C6	0.0293 (15)	0.0261 (15)	0.0269 (15)	−0.0042 (12)	−0.0109 (12)	−0.0104 (12)
C7	0.061 (2)	0.0227 (16)	0.045 (2)	−0.0017 (15)	−0.0239 (17)	−0.0126 (14)
C8	0.0325 (17)	0.0388 (18)	0.0441 (19)	−0.0069 (14)	−0.0158 (15)	−0.0160 (15)
C9	0.0239 (14)	0.0170 (13)	0.0333 (16)	0.0013 (11)	−0.0123 (12)	−0.0082 (12)
C10	0.0214 (14)	0.0198 (14)	0.0369 (16)	0.0003 (11)	−0.0059 (12)	−0.0122 (12)
C11	0.0282 (15)	0.0213 (14)	0.0283 (15)	−0.0026 (12)	−0.0049 (12)	−0.0066 (12)
C12	0.0292 (15)	0.0180 (14)	0.0286 (15)	−0.0005 (11)	−0.0118 (12)	−0.0041 (11)
C13	0.0201 (14)	0.0161 (13)	0.0301 (15)	0.0026 (10)	−0.0079 (11)	−0.0074 (11)
C14	0.0381 (17)	0.0275 (15)	0.0229 (14)	0.0062 (13)	−0.0121 (13)	−0.0110 (12)
C15	0.0409 (18)	0.0292 (16)	0.0218 (14)	0.0044 (13)	−0.0090 (13)	−0.0094 (12)
C16	0.0333 (17)	0.0332 (17)	0.0239 (15)	0.0115 (13)	−0.0091 (13)	−0.0082 (13)
C17	0.0385 (18)	0.0296 (16)	0.0238 (15)	0.0063 (13)	−0.0092 (13)	−0.0046 (13)
C18	0.0379 (17)	0.0299 (16)	0.0197 (14)	0.0083 (13)	−0.0060 (12)	−0.0061 (12)
C19	0.0357 (17)	0.0350 (17)	0.0246 (15)	0.0092 (14)	−0.0042 (13)	−0.0097 (13)
C20	0.0412 (18)	0.0260 (16)	0.0251 (15)	0.0071 (13)	−0.0039 (13)	−0.0083 (12)
C21	0.0308 (16)	0.0323 (16)	0.0246 (15)	0.0082 (13)	−0.0032 (12)	−0.0087 (13)
C22	0.0360 (17)	0.0364 (18)	0.0255 (15)	0.0075 (14)	−0.0072 (13)	−0.0059 (13)
C23	0.0402 (19)	0.0395 (19)	0.0266 (16)	0.0009 (15)	−0.0056 (14)	−0.0029 (14)
C24	0.0327 (17)	0.046 (2)	0.0271 (16)	0.0041 (14)	−0.0009 (13)	−0.0116 (14)
C25	0.0304 (17)	0.0438 (19)	0.0275 (16)	0.0110 (14)	−0.0037 (13)	−0.0107 (14)
C26	0.0346 (17)	0.0366 (18)	0.0248 (15)	0.0117 (14)	−0.0027 (13)	−0.0080 (13)
C27	0.042 (2)	0.060 (2)	0.0338 (18)	−0.0021 (17)	−0.0076 (15)	−0.0055 (17)
N1	0.0252 (12)	0.0218 (12)	0.0305 (13)	0.0056 (10)	−0.0133 (10)	−0.0086 (10)
N2	0.0261 (12)	0.0210 (12)	0.0255 (12)	0.0051 (10)	−0.0117 (10)	−0.0091 (10)
N3	0.0279 (12)	0.0188 (12)	0.0216 (12)	0.0014 (9)	−0.0089 (10)	−0.0057 (9)
N4	0.0217 (12)	0.0220 (12)	0.0214 (12)	0.0012 (9)	−0.0070 (9)	−0.0054 (9)
N5	0.0186 (11)	0.0154 (11)	0.0287 (12)	0.0000 (9)	−0.0082 (9)	−0.0062 (9)
O1	0.0333 (11)	0.0208 (10)	0.0357 (11)	0.0122 (8)	−0.0167 (9)	−0.0071 (9)
O2	0.0221 (10)	0.0277 (11)	0.0356 (11)	0.0059 (8)	−0.0124 (9)	−0.0091 (9)
O3	0.0299 (11)	0.0264 (11)	0.0437 (13)	0.0090 (9)	−0.0201 (10)	−0.0120 (10)
O4	0.0310 (11)	0.0223 (10)	0.0386 (12)	0.0131 (8)	−0.0161 (9)	−0.0121 (9)
Cl1	0.0548 (6)	0.0574 (6)	0.0447 (5)	−0.0059 (5)	−0.0189 (4)	−0.0054 (4)
Co1	0.0228 (2)	0.0156 (2)	0.0257 (2)	0.00326 (15)	−0.01128 (16)	−0.00724 (15)

C1—N4	1.294 (4)	C15—C16	1.398 (4)
C1—C2	1.472 (4)	C15—C20	1.404 (4)
C1—C3	1.489 (4)	C16—C17	1.376 (4)
C2—N3	1.295 (4)	C16—H16	0.9500
C2—C4	1.487 (4)	C17—C18	1.408 (4)
C3—H3A	0.9800	C17—H17	0.9500
C3—H3B	0.9800	C18—C19	1.404 (4)
C3—H3C	0.9800	C18—C21	1.477 (4)
C4—H4A	0.9800	C19—C20	1.367 (4)
C4—H4B	0.9800	C19—H19	0.9500
C4—H4C	0.9800	C20—H20	0.9500
C5—N2	1.304 (4)	C21—C22	1.393 (4)
C5—C6	1.469 (4)	C21—C26	1.398 (4)
C5—C7	1.497 (4)	C22—C23	1.395 (5)
C6—N1	1.291 (4)	C22—H22	0.9500
C6—C8	1.495 (4)	C23—C24	1.390 (4)
C7—H7A	0.9800	C23—H23	0.9500
C7—H7B	0.9800	C24—C25	1.392 (4)
C7—H7C	0.9800	C24—C27	1.503 (5)
C8—H8A	0.9800	C25—C26	1.383 (5)
C8—H8B	0.9800	C25—H25	0.9500
C8—H8C	0.9800	C26—H26	0.9500
C9—N5	1.341 (4)	C27—Cl1	1.805 (4)
C9—C10	1.387 (4)	C27—H27A	0.9900
C9—H9	0.9500	C27—H27B	0.9900
C10—C11	1.387 (4)	N1—O3	1.359 (3)
C10—H10	0.9500	N1—Co1	1.875 (2)
C11—C12	1.376 (4)	N2—O4	1.340 (3)
C11—H11	0.9500	N2—Co1	1.877 (2)
C12—C13	1.382 (4)	N3—O1	1.351 (3)
C12—H12	0.9500	N3—Co1	1.879 (2)
C13—N5	1.345 (3)	N4—O2	1.362 (3)
C13—H13	0.9500	N4—Co1	1.875 (2)
C14—C15	1.479 (4)	N5—Co1	2.055 (2)
C14—Co1	2.071 (3)	O2—H2	0.8400
C14—H14A	0.9900	O3—H3	0.8400
C14—H14B	0.9900
N4—C1—C2	112.3 (2)	C19—C18—C17	116.9 (3)
N4—C1—C3	124.9 (3)	C19—C18—C21	122.0 (3)
C2—C1—C3	122.8 (3)	C17—C18—C21	121.0 (3)
N3—C2—C1	112.0 (2)	C20—C19—C18	121.5 (3)
N3—C2—C4	124.5 (3)	C20—C19—H19	119.3
C1—C2—C4	123.5 (3)	C18—C19—H19	119.3
C1—C3—H3A	109.5	C19—C20—C15	122.0 (3)
C1—C3—H3B	109.5	C19—C20—H20	119.0
H3A—C3—H3B	109.5	C15—C20—H20	119.0
C1—C3—H3C	109.5	C22—C21—C26	117.5 (3)
H3A—C3—H3C	109.5	C22—C21—C18	122.4 (3)
H3B—C3—H3C	109.5	C26—C21—C18	120.1 (3)
C2—C4—H4A	109.5	C21—C22—C23	121.1 (3)
C2—C4—H4B	109.5	C21—C22—H22	119.5
H4A—C4—H4B	109.5	C23—C22—H22	119.5
C2—C4—H4C	109.5	C24—C23—C22	120.7 (3)
H4A—C4—H4C	109.5	C24—C23—H23	119.6
H4B—C4—H4C	109.5	C22—C23—H23	119.6
N2—C5—C6	112.2 (2)	C23—C24—C25	118.5 (3)
N2—C5—C7	122.5 (3)	C23—C24—C27	120.3 (3)
C6—C5—C7	125.3 (3)	C25—C24—C27	121.2 (3)
N1—C6—C5	112.2 (2)	C26—C25—C24	120.5 (3)
N1—C6—C8	124.3 (3)	C26—C25—H25	119.8
C5—C6—C8	123.5 (3)	C24—C25—H25	119.8
C5—C7—H7A	109.5	C25—C26—C21	121.7 (3)
C5—C7—H7B	109.5	C25—C26—H26	119.2
H7A—C7—H7B	109.5	C21—C26—H26	119.2
C5—C7—H7C	109.5	C24—C27—Cl1	112.3 (2)
H7A—C7—H7C	109.5	C24—C27—H27A	109.1
H7B—C7—H7C	109.5	Cl1—C27—H27A	109.1
C6—C8—H8A	109.5	C24—C27—H27B	109.1
C6—C8—H8B	109.5	Cl1—C27—H27B	109.1
H8A—C8—H8B	109.5	H27A—C27—H27B	107.9
C6—C8—H8C	109.5	C6—N1—O3	119.7 (2)
H8A—C8—H8C	109.5	C6—N1—Co1	117.25 (19)
H8B—C8—H8C	109.5	O3—N1—Co1	123.03 (17)
N5—C9—C10	122.7 (2)	C5—N2—O4	120.5 (2)
N5—C9—H9	118.6	C5—N2—Co1	116.67 (19)
C10—C9—H9	118.6	O4—N2—Co1	122.87 (17)
C11—C10—C9	118.9 (3)	C2—N3—O1	120.4 (2)
C11—C10—H10	120.5	C2—N3—Co1	117.09 (19)
C9—C10—H10	120.5	O1—N3—Co1	122.48 (17)
C12—C11—C10	118.6 (3)	C1—N4—O2	119.6 (2)
C12—C11—H11	120.7	C1—N4—Co1	117.2 (2)
C10—C11—H11	120.7	O2—N4—Co1	123.19 (17)
C11—C12—C13	119.4 (3)	C9—N5—C13	117.7 (2)
C11—C12—H12	120.3	C9—N5—Co1	121.72 (18)
C13—C12—H12	120.3	C13—N5—Co1	120.57 (19)
N5—C13—C12	122.7 (3)	N4—O2—H2	109.5
N5—C13—H13	118.6	N1—O3—H3	109.5
C12—C13—H13	118.6	N4—Co1—N1	179.86 (10)
C15—C14—Co1	115.2 (2)	N4—Co1—N2	98.40 (10)
C15—C14—H14A	108.5	N1—Co1—N2	81.46 (10)
Co1—C14—H14A	108.5	N4—Co1—N3	81.41 (10)
C15—C14—H14B	108.5	N1—Co1—N3	98.72 (10)
Co1—C14—H14B	108.5	N2—Co1—N3	178.36 (10)
H14A—C14—H14B	107.5	N4—Co1—N5	89.74 (9)
C16—C15—C20	116.5 (3)	N1—Co1—N5	90.30 (10)
C16—C15—C14	120.9 (3)	N2—Co1—N5	90.44 (9)
C20—C15—C14	122.6 (3)	N3—Co1—N5	91.19 (9)
C17—C16—C15	122.1 (3)	N4—Co1—C14	92.37 (11)
C17—C16—H16	119.0	N1—Co1—C14	87.59 (11)
C15—C16—H16	119.0	N2—Co1—C14	89.08 (11)
C16—C17—C18	121.0 (3)	N3—Co1—C14	89.30 (11)
C16—C17—H17	119.5	N5—Co1—C14	177.89 (10)
C18—C17—H17	119.5
N4—C1—C2—N3	−0.4 (3)	C12—C13—N5—C9	−1.2 (4)
C3—C1—C2—N3	177.2 (2)	C12—C13—N5—Co1	178.7 (2)
N4—C1—C2—C4	−179.1 (2)	C1—N4—Co1—N1	162 (100)
C3—C1—C2—C4	−1.4 (4)	O2—N4—Co1—N1	−17 (50)
N2—C5—C6—N1	0.8 (4)	C1—N4—Co1—N2	178.4 (2)
C7—C5—C6—N1	−179.7 (3)	O2—N4—Co1—N2	−1.4 (2)
N2—C5—C6—C8	178.9 (3)	C1—N4—Co1—N3	0.1 (2)
C7—C5—C6—C8	−1.5 (5)	O2—N4—Co1—N3	−179.8 (2)
N5—C9—C10—C11	−0.1 (4)	C1—N4—Co1—N5	−91.2 (2)
C9—C10—C11—C12	−0.8 (4)	O2—N4—Co1—N5	89.0 (2)
C10—C11—C12—C13	0.7 (4)	C1—N4—Co1—C14	89.0 (2)
C11—C12—C13—N5	0.4 (4)	O2—N4—Co1—C14	−90.9 (2)
Co1—C14—C15—C16	−92.7 (3)	C6—N1—Co1—N4	21 (50)
Co1—C14—C15—C20	83.7 (3)	O3—N1—Co1—N4	−162 (100)
C20—C15—C16—C17	−3.3 (4)	C6—N1—Co1—N2	4.5 (2)
C14—C15—C16—C17	173.3 (3)	O3—N1—Co1—N2	−178.4 (2)
C15—C16—C17—C18	0.7 (5)	C6—N1—Co1—N3	−177.1 (2)
C16—C17—C18—C19	1.7 (4)	O3—N1—Co1—N3	−0.1 (2)
C16—C17—C18—C21	−174.7 (3)	C6—N1—Co1—N5	−85.9 (2)
C17—C18—C19—C20	−1.5 (4)	O3—N1—Co1—N5	91.2 (2)
C21—C18—C19—C20	174.9 (3)	C6—N1—Co1—C14	93.9 (2)
C18—C19—C20—C15	−1.2 (5)	O3—N1—Co1—C14	−89.0 (2)
C16—C15—C20—C19	3.5 (4)	C5—N2—Co1—N4	176.0 (2)
C14—C15—C20—C19	−173.0 (3)	O4—N2—Co1—N4	−3.5 (2)
C19—C18—C21—C22	150.8 (3)	C5—N2—Co1—N1	−4.0 (2)
C17—C18—C21—C22	−33.0 (4)	O4—N2—Co1—N1	176.4 (2)
C19—C18—C21—C26	−31.4 (4)	C5—N2—Co1—N3	−101 (3)
C17—C18—C21—C26	144.9 (3)	O4—N2—Co1—N3	80 (3)
C26—C21—C22—C23	−0.7 (5)	C5—N2—Co1—N5	86.2 (2)
C18—C21—C22—C23	177.2 (3)	O4—N2—Co1—N5	−93.3 (2)
C21—C22—C23—C24	1.1 (5)	C5—N2—Co1—C14	−91.7 (2)
C22—C23—C24—C25	−0.8 (5)	O4—N2—Co1—C14	88.7 (2)
C22—C23—C24—C27	177.6 (3)	C2—N3—Co1—N4	−0.3 (2)
C23—C24—C25—C26	0.2 (5)	O1—N3—Co1—N4	179.4 (2)
C27—C24—C25—C26	−178.1 (3)	C2—N3—Co1—N1	179.7 (2)
C24—C25—C26—C21	0.1 (5)	O1—N3—Co1—N1	−0.5 (2)
C22—C21—C26—C25	0.1 (4)	C2—N3—Co1—N2	−84 (3)
C18—C21—C26—C25	−177.9 (3)	O1—N3—Co1—N2	96 (3)
C23—C24—C27—Cl1	127.7 (3)	C2—N3—Co1—N5	89.2 (2)
C25—C24—C27—Cl1	−53.9 (4)	O1—N3—Co1—N5	−91.0 (2)
C5—C6—N1—O3	178.8 (2)	C2—N3—Co1—C14	−92.8 (2)
C8—C6—N1—O3	0.6 (4)	O1—N3—Co1—C14	86.9 (2)
C5—C6—N1—Co1	−4.1 (3)	C9—N5—Co1—N4	129.1 (2)
C8—C6—N1—Co1	177.8 (2)	C13—N5—Co1—N4	−50.9 (2)
C6—C5—N2—O4	−177.5 (2)	C9—N5—Co1—N1	−51.0 (2)
C7—C5—N2—O4	2.9 (4)	C13—N5—Co1—N1	129.0 (2)
C6—C5—N2—Co1	2.9 (3)	C9—N5—Co1—N2	−132.5 (2)
C7—C5—N2—Co1	−176.7 (2)	C13—N5—Co1—N2	47.5 (2)
C1—C2—N3—O1	−179.3 (2)	C9—N5—Co1—N3	47.7 (2)
C4—C2—N3—O1	−0.6 (4)	C13—N5—Co1—N3	−132.3 (2)
C1—C2—N3—Co1	0.5 (3)	C9—N5—Co1—C14	−56 (3)
C4—C2—N3—Co1	179.1 (2)	C13—N5—Co1—C14	124 (3)
C2—C1—N4—O2	−180.0 (2)	C15—C14—Co1—N4	−25.2 (2)
C3—C1—N4—O2	2.4 (4)	C15—C14—Co1—N1	155.0 (2)
C2—C1—N4—Co1	0.2 (3)	C15—C14—Co1—N2	−123.5 (2)
C3—C1—N4—Co1	−177.4 (2)	C15—C14—Co1—N3	56.2 (2)
C10—C9—N5—C13	1.1 (4)	C15—C14—Co1—N5	160 (3)
C10—C9—N5—Co1	−178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.84	1.67	2.479 (3)	161.
O3—H3···O1	0.84	1.67	2.478 (3)	160.

Table 1

Selected bond lengths (Å)

Co1—N1	1.875 (2)
Co1—N2	1.877 (2)
Co1—N3	1.879 (2)
Co1—N4	1.875 (2)
Co1—N5	2.055 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4	0.84	1.67	2.479 (3)	161
O3—H3⋯O1	0.84	1.67	2.478 (3)	160