(Benzyl-amine)chloridobis(ethane-1,2-diamine)cobalt(III) dichloride hemihydrate.

In the title compound, [CoCl(C(2)H(8)N(2))(2)(C(7)H(9)N)]Cl(2)·0.5H(2)O, there are two crystallographically independent cations and anions and one water mol-ecule in the asymmetric unit. Both Co(III) ions are bonded to two chelating ethylenediamine ligands, one benzylamine molecule and one chloride ion. The crystal packing is through N-H⋯O, N-H⋯Cl and O-H⋯Cl inter-actions.

Related literature

For the importance of metal complexes in the fields of bio­logical catalysis and functions, see: Gray (2003 ▶); Wohrle & Pomogailo (2003 ▶). For the biomedical applications of cobalt complexes, see: Osinsky (2004 ▶); Roth et al. (2002 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For related structures, see: Lee et al. (2007 ▶); Ramesh et al. (2008 ▶). cis-[CoIII(en)2(BzNH2)Cl]Cl2·0.5H2O was synthesized (Bailer & Clapp, 1945 ▶) by substituting the chloride ligand with benzyl amine in trans-[Co(en)2Cl2]Cl (Bailer & Rollinson, 1946 ▶).

Experimental

Crystal data

[CoCl(C2H8N2)2(C7H9N)]Cl2·0.5H2O

M = 401.65

Monoclinic,

a = 20.9361 (9) Å

b = 7.2447 (3) Å

c = 24.4340 (9) Å

β = 106.440 (2)°

V = 3554.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.42 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.718, T max = 0.765

40140 measured reflections

8911 independent reflections

6475 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.06

8911 reflections

458 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034849/bt5046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034849/bt5046Isup2.hkl

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

[CoCl(C2H8N2)2(C7H9N)]Cl2·0.5H2O	F(000) = 1672
Mr = 401.65	Dx = 1.501 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4562 reflections
a = 20.9361 (9) Å	θ = 1.0–28.4°
b = 7.2447 (3) Å	µ = 1.42 mm−1
c = 24.4340 (9) Å	T = 293 K
β = 106.440 (2)°	Block, pink
V = 3554.5 (3) Å3	0.25 × 0.20 × 0.20 mm
Z = 8

Bruker Kappa APEXII area-detector diffractometer	8911 independent reflections
Radiation source: fine-focus sealed tube	6475 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω and φ scans	θmax = 28.4°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −28→27
Tmin = 0.718, Tmax = 0.765	k = −9→9
40140 measured reflections	l = −32→32

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0439P)2 + 1.0235P] where P = (Fo2 + 2Fc2)/3
8911 reflections	(Δ/σ)max = 0.003
458 parameters	Δρmax = 0.61 e Å−3
2 restraints	Δρmin = −0.41 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
Co1	0.086901 (14)	0.76169 (4)	0.397792 (12)	0.02243 (8)
Co1'	0.378670 (14)	0.24118 (4)	0.376673 (12)	0.02283 (8)
Cl1	0.18662 (3)	0.89958 (10)	0.40924 (3)	0.04223 (16)
Cl1'	0.28589 (3)	0.41206 (9)	0.36007 (3)	0.04156 (16)
Cl2	0.03854 (4)	1.27863 (9)	0.47345 (3)	0.04187 (16)
Cl2'	0.44225 (3)	−0.22621 (9)	0.47024 (3)	0.03979 (16)
Cl3	0.07194 (4)	1.07730 (10)	0.24584 (3)	0.04584 (17)
Cl3'	0.40208 (4)	0.54666 (10)	0.23461 (3)	0.04853 (18)
O1	0.46177 (15)	−0.0796 (4)	0.28551 (13)	0.0771 (8)
H1W	0.4962 (16)	−0.050 (6)	0.2760 (17)	0.091 (15)*
H2W	0.453 (2)	−0.189 (3)	0.2743 (17)	0.090 (14)*
N1	0.04245 (11)	0.9940 (3)	0.37372 (10)	0.0301 (5)
H1A	0.0583 (14)	1.045 (4)	0.3509 (12)	0.040 (8)*
H1B	0.0506 (12)	1.073 (4)	0.4018 (11)	0.030 (7)*
N1'	0.42817 (10)	0.4624 (3)	0.36963 (10)	0.0285 (4)
H1C	0.4186 (17)	0.486 (5)	0.3355 (15)	0.066 (11)*
H1D	0.4160 (13)	0.558 (4)	0.3874 (11)	0.033 (7)*
C2	−0.02989 (13)	0.9642 (4)	0.34926 (11)	0.0372 (6)
H2A	−0.0396	0.9255	0.3097	0.045*
H2B	−0.0541	1.0774	0.3508	0.045*
C2'	0.50016 (12)	0.4304 (4)	0.39128 (12)	0.0399 (6)
H2C	0.5148	0.4459	0.4324	0.048*
H2D	0.5241	0.5175	0.3743	0.048*
C3	−0.04994 (12)	0.8175 (4)	0.38393 (11)	0.0385 (6)
H3A	−0.0485	0.8648	0.4214	0.046*
H3B	−0.0949	0.7759	0.3653	0.046*
C3'	0.51319 (13)	0.2377 (4)	0.37573 (13)	0.0402 (6)
H3C	0.5089	0.2299	0.3352	0.048*
H3D	0.5580	0.2007	0.3966	0.048*
N4	−0.00203 (10)	0.6626 (3)	0.38910 (10)	0.0293 (4)
H4A	−0.0026 (13)	0.589 (4)	0.4168 (12)	0.039 (8)*
H4B	−0.0154 (14)	0.589 (4)	0.3567 (13)	0.044 (8)*
N4'	0.46398 (10)	0.1153 (3)	0.39043 (10)	0.0300 (5)
H4C	0.4779 (15)	0.075 (4)	0.4248 (13)	0.049 (9)*
H4D	0.4624 (13)	0.019 (4)	0.3731 (11)	0.032 (8)*
N5	0.12897 (11)	0.5183 (3)	0.41295 (9)	0.0296 (4)
H5A	0.1141 (13)	0.451 (4)	0.4369 (11)	0.037 (8)*
H5B	0.1737 (15)	0.547 (4)	0.4276 (11)	0.040 (8)*
N5'	0.32999 (11)	0.0116 (3)	0.37956 (9)	0.0287 (4)
H5C	0.2923 (14)	0.045 (4)	0.3883 (11)	0.036 (7)*
H5D	0.3548 (15)	−0.055 (4)	0.4060 (13)	0.044 (9)*
C6	0.11746 (13)	0.4154 (3)	0.35841 (11)	0.0329 (5)
H6A	0.0732	0.3620	0.3474	0.039*
H6B	0.1498	0.3169	0.3623	0.039*
C6'	0.31418 (14)	−0.0861 (4)	0.32408 (11)	0.0398 (6)
H6C	0.2753	−0.1641	0.3195	0.048*
H6D	0.3514	−0.1631	0.3220	0.048*
C7	0.12481 (13)	0.5530 (3)	0.31469 (11)	0.0333 (5)
H7A	0.1707	0.5940	0.3229	0.040*
H7B	0.1116	0.4987	0.2769	0.040*
C7'	0.30080 (14)	0.0588 (4)	0.27837 (11)	0.0431 (7)
H7C	0.2975	0.0036	0.2415	0.052*
H7D	0.2596	0.1232	0.2763	0.052*
N8	0.08093 (11)	0.7084 (3)	0.31812 (9)	0.0278 (4)
H8A	0.0920 (15)	0.810 (5)	0.3010 (13)	0.055 (9)*
H8B	0.0437 (14)	0.683 (4)	0.3021 (12)	0.037 (8)*
N8'	0.35805 (12)	0.1872 (3)	0.29494 (9)	0.0331 (5)
H8C	0.3901 (16)	0.134 (4)	0.2844 (13)	0.051 (9)*
H8D	0.3526 (15)	0.293 (4)	0.2772 (13)	0.051 (9)*
N9	0.09587 (11)	0.8161 (3)	0.47994 (8)	0.0305 (5)
H9A	0.0589 (18)	0.808 (5)	0.4869 (14)	0.068 (11)*
H9B	0.1073 (15)	0.934 (4)	0.4830 (12)	0.048 (9)*
N9'	0.39414 (11)	0.2930 (3)	0.45935 (9)	0.0301 (5)
H9C	0.4328 (15)	0.255 (4)	0.4767 (12)	0.038 (8)*
H9D	0.3938 (12)	0.410 (4)	0.4623 (10)	0.024 (7)*
C10	0.14694 (15)	0.7113 (4)	0.52328 (11)	0.0466 (7)
H10A	0.1869	0.7033	0.5107	0.056*
H10B	0.1307	0.5866	0.5250	0.056*
C10'	0.34564 (14)	0.2178 (4)	0.48815 (11)	0.0390 (6)
H10C	0.3585	0.0928	0.5008	0.047*
H10D	0.3018	0.2127	0.4609	0.047*
C11	0.16542 (13)	0.7919 (4)	0.58258 (11)	0.0370 (6)
C11'	0.34216 (12)	0.3326 (4)	0.53849 (11)	0.0350 (6)
C12	0.15612 (14)	0.6896 (5)	0.62752 (12)	0.0482 (7)
H12	0.1346	0.5760	0.6204	0.058*
C12'	0.35761 (15)	0.2587 (4)	0.59266 (12)	0.0464 (7)
H12'	0.3706	0.1358	0.5986	0.056*
C13	0.17863 (16)	0.7549 (6)	0.68334 (13)	0.0595 (10)
H13	0.1722	0.6855	0.7134	0.071*
C13'	0.35379 (18)	0.3676 (6)	0.63837 (13)	0.0624 (10)
H13'	0.3640	0.3167	0.6748	0.075*
C14	0.20967 (15)	0.9192 (6)	0.69345 (14)	0.0643 (10)
H14	0.2252	0.9620	0.7307	0.077*
C14'	0.33530 (17)	0.5479 (6)	0.63053 (15)	0.0631 (10)
H14'	0.3332	0.6201	0.6615	0.076*
C15	0.21876 (15)	1.0241 (5)	0.64982 (15)	0.0619 (9)
H15	0.2400	1.1378	0.6575	0.074*
C15'	0.31972 (14)	0.6229 (5)	0.57686 (15)	0.0548 (8)
H15'	0.3071	0.7462	0.5714	0.066*
C16	0.19618 (15)	0.9606 (4)	0.59400 (13)	0.0487 (7)
H16	0.2019	1.0326	0.5642	0.058*
C16'	0.32269 (13)	0.5152 (4)	0.53083 (13)	0.0436 (7)
H16'	0.3115	0.5662	0.4944	0.052*

	U11	U22	U33	U12	U13	U23
Co1	0.01975 (15)	0.02389 (16)	0.02415 (16)	0.00014 (12)	0.00701 (12)	0.00230 (12)
Co1'	0.01926 (15)	0.02633 (16)	0.02270 (16)	−0.00031 (12)	0.00564 (12)	0.00163 (12)
Cl1	0.0292 (3)	0.0464 (4)	0.0532 (4)	−0.0123 (3)	0.0149 (3)	−0.0018 (3)
Cl1'	0.0254 (3)	0.0454 (4)	0.0503 (4)	0.0103 (3)	0.0049 (3)	0.0065 (3)
Cl2	0.0563 (4)	0.0368 (4)	0.0404 (4)	−0.0037 (3)	0.0264 (3)	−0.0006 (3)
Cl2'	0.0416 (4)	0.0367 (3)	0.0360 (3)	0.0009 (3)	0.0028 (3)	0.0037 (3)
Cl3	0.0526 (4)	0.0451 (4)	0.0382 (4)	0.0053 (3)	0.0102 (3)	0.0142 (3)
Cl3'	0.0563 (5)	0.0478 (4)	0.0434 (4)	−0.0077 (3)	0.0172 (3)	0.0094 (3)
O1	0.0703 (18)	0.0750 (19)	0.103 (2)	−0.0202 (15)	0.0519 (17)	−0.0476 (16)
N1	0.0357 (12)	0.0265 (11)	0.0293 (11)	0.0034 (9)	0.0111 (10)	0.0015 (9)
N1'	0.0266 (11)	0.0296 (11)	0.0286 (11)	−0.0022 (8)	0.0065 (9)	0.0016 (9)
C2	0.0335 (14)	0.0399 (15)	0.0340 (14)	0.0148 (11)	0.0028 (11)	−0.0009 (11)
C2'	0.0282 (13)	0.0447 (16)	0.0457 (16)	−0.0104 (12)	0.0085 (12)	−0.0029 (12)
C3	0.0234 (13)	0.0556 (17)	0.0379 (14)	0.0086 (12)	0.0109 (11)	−0.0016 (12)
C3'	0.0272 (13)	0.0449 (16)	0.0527 (17)	−0.0045 (11)	0.0182 (12)	−0.0063 (13)
N4	0.0244 (11)	0.0349 (12)	0.0288 (11)	−0.0010 (9)	0.0082 (9)	0.0050 (9)
N4'	0.0290 (11)	0.0306 (12)	0.0322 (12)	0.0022 (9)	0.0116 (10)	0.0026 (10)
N5	0.0286 (12)	0.0294 (11)	0.0319 (11)	0.0025 (9)	0.0105 (10)	0.0044 (9)
N5'	0.0257 (11)	0.0331 (11)	0.0286 (11)	−0.0027 (9)	0.0096 (9)	0.0020 (9)
C6	0.0326 (13)	0.0277 (12)	0.0387 (14)	0.0045 (10)	0.0105 (11)	−0.0014 (10)
C6'	0.0463 (16)	0.0359 (14)	0.0395 (15)	−0.0155 (12)	0.0159 (12)	−0.0071 (11)
C7	0.0343 (14)	0.0347 (14)	0.0335 (13)	0.0060 (11)	0.0136 (11)	−0.0016 (10)
C7'	0.0444 (16)	0.0530 (18)	0.0294 (14)	−0.0202 (14)	0.0064 (12)	−0.0079 (12)
N8	0.0260 (12)	0.0305 (11)	0.0279 (11)	0.0013 (9)	0.0093 (9)	0.0028 (8)
N8'	0.0373 (13)	0.0347 (12)	0.0274 (11)	−0.0104 (10)	0.0090 (10)	0.0000 (9)
N9	0.0266 (12)	0.0394 (13)	0.0243 (10)	0.0015 (9)	0.0053 (9)	0.0020 (9)
N9'	0.0251 (11)	0.0382 (13)	0.0276 (11)	0.0001 (9)	0.0084 (9)	−0.0004 (9)
C10	0.0485 (18)	0.0532 (18)	0.0299 (14)	0.0133 (14)	−0.0026 (13)	−0.0027 (12)
C10'	0.0430 (16)	0.0448 (16)	0.0352 (14)	−0.0079 (12)	0.0210 (12)	−0.0057 (12)
C11	0.0265 (13)	0.0515 (17)	0.0286 (13)	0.0064 (11)	0.0007 (10)	−0.0020 (11)
C11'	0.0297 (13)	0.0461 (15)	0.0329 (13)	−0.0057 (11)	0.0149 (11)	−0.0035 (11)
C12	0.0353 (16)	0.0614 (19)	0.0449 (17)	0.0061 (14)	0.0062 (13)	0.0066 (14)
C12'	0.0500 (18)	0.0554 (18)	0.0387 (15)	−0.0091 (14)	0.0206 (14)	0.0021 (13)
C13	0.0387 (17)	0.106 (3)	0.0333 (16)	0.0176 (19)	0.0089 (13)	0.0153 (17)
C13'	0.069 (2)	0.090 (3)	0.0370 (17)	−0.026 (2)	0.0282 (16)	−0.0092 (17)
C14	0.0352 (17)	0.117 (3)	0.0351 (17)	0.0052 (19)	0.0018 (14)	−0.0164 (19)
C14'	0.055 (2)	0.090 (3)	0.058 (2)	−0.0272 (19)	0.0379 (18)	−0.0359 (19)
C15	0.0395 (18)	0.080 (3)	0.062 (2)	−0.0099 (16)	0.0085 (16)	−0.0290 (19)
C15'	0.0350 (16)	0.059 (2)	0.077 (2)	−0.0031 (14)	0.0271 (16)	−0.0213 (17)
C16	0.0410 (17)	0.061 (2)	0.0433 (17)	0.0004 (14)	0.0109 (13)	−0.0036 (14)
C16'	0.0290 (14)	0.0562 (18)	0.0456 (16)	0.0028 (12)	0.0105 (12)	−0.0015 (13)

Co1—N1	1.933 (2)	C6'—H6C	0.9700
Co1—N4	1.950 (2)	C6'—H6D	0.9700
Co1—N8	1.954 (2)	C7—N8	1.471 (3)
Co1—N5	1.959 (2)	C7—H7A	0.9700
Co1—N9	2.001 (2)	C7—H7B	0.9700
Co1—Cl1	2.2592 (7)	C7'—N8'	1.480 (3)
Co1'—N1'	1.942 (2)	C7'—H7C	0.9700
Co1'—N4'	1.948 (2)	C7'—H7D	0.9700
Co1'—N8'	1.959 (2)	N8—H8A	0.91 (3)
Co1'—N5'	1.962 (2)	N8—H8B	0.79 (3)
Co1'—N9'	1.989 (2)	N8'—H8C	0.87 (3)
Co1'—Cl1'	2.2415 (7)	N8'—H8D	0.87 (3)
O1—H1W	0.84 (3)	N9—C10	1.483 (3)
O1—H2W	0.842 (17)	N9—H9A	0.84 (4)
N1—C2	1.478 (3)	N9—H9B	0.89 (3)
N1—H1A	0.81 (3)	N9'—C10'	1.492 (3)
N1—H1B	0.87 (3)	N9'—H9C	0.85 (3)
N1'—C2'	1.468 (3)	N9'—H9D	0.85 (3)
N1'—H1C	0.82 (3)	C10—C11	1.507 (4)
N1'—H1D	0.89 (3)	C10—H10A	0.9700
C2—C3	1.491 (4)	C10—H10B	0.9700
C2—H2A	0.9700	C10'—C11'	1.503 (3)
C2—H2B	0.9700	C10'—H10C	0.9700
C2'—C3'	1.492 (4)	C10'—H10D	0.9700
C2'—H2C	0.9700	C11—C16	1.373 (4)
C2'—H2D	0.9700	C11—C12	1.384 (4)
C3—N4	1.487 (3)	C11'—C12'	1.379 (4)
C3—H3A	0.9700	C11'—C16'	1.381 (4)
C3—H3B	0.9700	C12—C13	1.394 (4)
C3'—N4'	1.479 (3)	C12—H12	0.9300
C3'—H3C	0.9700	C12'—C13'	1.388 (4)
C3'—H3D	0.9700	C12'—H12'	0.9300
N4—H4A	0.87 (3)	C13—C14	1.345 (5)
N4—H4B	0.93 (3)	C13—H13	0.9300
N4'—H4C	0.86 (3)	C13'—C14'	1.361 (5)
N4'—H4D	0.81 (3)	C13'—H13'	0.9300
N5—C6	1.486 (3)	C14—C15	1.366 (5)
N5—H5A	0.88 (3)	C14—H14	0.9300
N5—H5B	0.93 (3)	C14'—C15'	1.371 (5)
N5'—C6'	1.481 (3)	C14'—H14'	0.9300
N5'—H5C	0.91 (3)	C15—C16	1.389 (4)
N5'—H5D	0.85 (3)	C15—H15	0.9300
C6—C7	1.500 (3)	C15'—C16'	1.385 (4)
C6—H6A	0.9700	C15'—H15'	0.9300
C6—H6B	0.9700	C16—H16	0.9300
C6'—C7'	1.500 (4)	C16'—H16'	0.9300
N1—Co1—N4	85.69 (9)	N5—C6—H6B	110.4
N1—Co1—N8	88.81 (9)	C7—C6—H6B	110.4
N4—Co1—N8	91.65 (10)	H6A—C6—H6B	108.6
N1—Co1—N5	173.44 (9)	N5'—C6'—C7'	107.0 (2)
N4—Co1—N5	93.07 (9)	N5'—C6'—H6C	110.3
N8—Co1—N5	84.78 (9)	C7'—C6'—H6C	110.3
N1—Co1—N9	91.95 (10)	N5'—C6'—H6D	110.3
N4—Co1—N9	89.85 (10)	C7'—C6'—H6D	110.3
N8—Co1—N9	178.36 (9)	H6C—C6'—H6D	108.6
N5—Co1—N9	94.48 (9)	N8—C7—C6	106.04 (19)
N1—Co1—Cl1	90.06 (7)	N8—C7—H7A	110.5
N4—Co1—Cl1	175.24 (7)	C6—C7—H7A	110.5
N8—Co1—Cl1	90.41 (7)	N8—C7—H7B	110.5
N5—Co1—Cl1	91.40 (7)	C6—C7—H7B	110.5
N9—Co1—Cl1	88.14 (7)	H7A—C7—H7B	108.7
N1'—Co1'—N4'	85.16 (9)	N8'—C7'—C6'	105.7 (2)
N1'—Co1'—N8'	92.50 (9)	N8'—C7'—H7C	110.6
N4'—Co1'—N8'	90.53 (11)	C6'—C7'—H7C	110.6
N1'—Co1'—N5'	176.43 (9)	N8'—C7'—H7D	110.6
N4'—Co1'—N5'	93.27 (9)	C6'—C7'—H7D	110.6
N8'—Co1'—N5'	84.30 (9)	H7C—C7'—H7D	108.7
N1'—Co1'—N9'	89.81 (10)	C7—N8—Co1	110.07 (15)
N4'—Co1'—N9'	92.02 (10)	C7—N8—H8A	110 (2)
N8'—Co1'—N9'	176.70 (9)	Co1—N8—H8A	110 (2)
N5'—Co1'—N9'	93.45 (9)	C7—N8—H8B	110 (2)
N1'—Co1'—Cl1'	89.14 (7)	Co1—N8—H8B	108 (2)
N4'—Co1'—Cl1'	174.30 (7)	H8A—N8—H8B	108 (3)
N8'—Co1'—Cl1'	89.78 (8)	C7'—N8'—Co1'	109.39 (16)
N5'—Co1'—Cl1'	92.42 (7)	C7'—N8'—H8C	106 (2)
N9'—Co1'—Cl1'	87.90 (7)	Co1'—N8'—H8C	115 (2)
H1W—O1—H2W	106 (4)	C7'—N8'—H8D	116 (2)
C2—N1—Co1	110.22 (16)	Co1'—N8'—H8D	107 (2)
C2—N1—H1A	111 (2)	H8C—N8'—H8D	104 (3)
Co1—N1—H1A	111 (2)	C10—N9—Co1	117.35 (17)
C2—N1—H1B	111.4 (17)	C10—N9—H9A	110 (2)
Co1—N1—H1B	111.2 (17)	Co1—N9—H9A	111 (2)
H1A—N1—H1B	102 (3)	C10—N9—H9B	108.2 (19)
C2'—N1'—Co1'	110.90 (16)	Co1—N9—H9B	102.8 (19)
C2'—N1'—H1C	109 (2)	H9A—N9—H9B	107 (3)
Co1'—N1'—H1C	106 (2)	C10'—N9'—Co1'	118.23 (17)
C2'—N1'—H1D	110.6 (17)	C10'—N9'—H9C	109.1 (19)
Co1'—N1'—H1D	111.5 (17)	Co1'—N9'—H9C	107.7 (19)
H1C—N1'—H1D	108 (3)	C10'—N9'—H9D	107.5 (16)
N1—C2—C3	107.2 (2)	Co1'—N9'—H9D	105.7 (16)
N1—C2—H2A	110.3	H9C—N9'—H9D	108 (2)
C3—C2—H2A	110.3	N9—C10—C11	115.2 (2)
N1—C2—H2B	110.3	N9—C10—H10A	108.5
C3—C2—H2B	110.3	C11—C10—H10A	108.5
H2A—C2—H2B	108.5	N9—C10—H10B	108.5
N1'—C2'—C3'	107.4 (2)	C11—C10—H10B	108.5
N1'—C2'—H2C	110.2	H10A—C10—H10B	107.5
C3'—C2'—H2C	110.2	N9'—C10'—C11'	112.4 (2)
N1'—C2'—H2D	110.2	N9'—C10'—H10C	109.1
C3'—C2'—H2D	110.2	C11'—C10'—H10C	109.1
H2C—C2'—H2D	108.5	N9'—C10'—H10D	109.1
N4—C3—C2	107.13 (19)	C11'—C10'—H10D	109.1
N4—C3—H3A	110.3	H10C—C10'—H10D	107.9
C2—C3—H3A	110.3	C16—C11—C12	118.6 (3)
N4—C3—H3B	110.3	C16—C11—C10	121.2 (3)
C2—C3—H3B	110.3	C12—C11—C10	120.0 (3)
H3A—C3—H3B	108.5	C12'—C11'—C16'	118.8 (3)
N4'—C3'—C2'	108.0 (2)	C12'—C11'—C10'	121.2 (3)
N4'—C3'—H3C	110.1	C16'—C11'—C10'	120.0 (2)
C2'—C3'—H3C	110.1	C11—C12—C13	120.7 (3)
N4'—C3'—H3D	110.1	C11—C12—H12	119.7
C2'—C3'—H3D	110.1	C13—C12—H12	119.7
H3C—C3'—H3D	108.4	C11'—C12'—C13'	120.0 (3)
C3—N4—Co1	109.37 (17)	C11'—C12'—H12'	120.0
C3—N4—H4A	112.0 (18)	C13'—C12'—H12'	120.0
Co1—N4—H4A	111.5 (18)	C14—C13—C12	119.5 (3)
C3—N4—H4B	109.0 (18)	C14—C13—H13	120.3
Co1—N4—H4B	110.7 (17)	C12—C13—H13	120.3
H4A—N4—H4B	104 (3)	C14'—C13'—C12'	120.8 (3)
C3'—N4'—Co1'	110.18 (16)	C14'—C13'—H13'	119.6
C3'—N4'—H4C	112 (2)	C12'—C13'—H13'	119.6
Co1'—N4'—H4C	112 (2)	C13—C14—C15	121.1 (3)
C3'—N4'—H4D	108.3 (19)	C13—C14—H14	119.5
Co1'—N4'—H4D	114.4 (19)	C15—C14—H14	119.5
H4C—N4'—H4D	100 (3)	C13'—C14'—C15'	119.7 (3)
C6—N5—Co1	109.37 (15)	C13'—C14'—H14'	120.1
C6—N5—H5A	108.6 (17)	C15'—C14'—H14'	120.1
Co1—N5—H5A	113.4 (17)	C14—C15—C16	119.9 (3)
C6—N5—H5B	110.4 (17)	C14—C15—H15	120.1
Co1—N5—H5B	102.9 (17)	C16—C15—H15	120.1
H5A—N5—H5B	112 (2)	C14'—C15'—C16'	120.0 (3)
C6'—N5'—Co1'	110.85 (15)	C14'—C15'—H15'	120.0
C6'—N5'—H5C	111.1 (17)	C16'—C15'—H15'	120.0
Co1'—N5'—H5C	106.0 (17)	C11—C16—C15	120.3 (3)
C6'—N5'—H5D	110.8 (19)	C11—C16—H16	119.9
Co1'—N5'—H5D	107.1 (19)	C15—C16—H16	119.9
H5C—N5'—H5D	111 (3)	C11'—C16'—C15'	120.6 (3)
N5—C6—C7	106.4 (2)	C11'—C16'—H16'	119.7
N5—C6—H6A	110.4	C15'—C16'—H16'	119.7
C7—C6—H6A	110.4
N4—Co1—N1—C2	−13.68 (17)	N4—Co1—N8—C7	−108.29 (17)
N8—Co1—N1—C2	78.07 (18)	N5—Co1—N8—C7	−15.35 (17)
N5—Co1—N1—C2	65.6 (9)	N9—Co1—N8—C7	48 (3)
N9—Co1—N1—C2	−103.38 (18)	Cl1—Co1—N8—C7	76.01 (16)
Cl1—Co1—N1—C2	168.47 (17)	C6'—C7'—N8'—Co1'	−44.3 (3)
N4'—Co1'—N1'—C2'	−13.81 (18)	N1'—Co1'—N8'—C7'	−161.0 (2)
N8'—Co1'—N1'—C2'	−104.13 (19)	N4'—Co1'—N8'—C7'	113.9 (2)
N5'—Co1'—N1'—C2'	−77.8 (16)	N5'—Co1'—N8'—C7'	20.6 (2)
N9'—Co1'—N1'—C2'	78.23 (19)	N9'—Co1'—N8'—C7'	−26.6 (19)
Cl1'—Co1'—N1'—C2'	166.13 (17)	Cl1'—Co1'—N8'—C7'	−71.82 (19)
Co1—N1—C2—C3	38.0 (2)	N1—Co1—N9—C10	−160.1 (2)
Co1'—N1'—C2'—C3'	36.6 (3)	N4—Co1—N9—C10	114.2 (2)
N1—C2—C3—N4	−48.9 (3)	N8—Co1—N9—C10	−42 (3)
N1'—C2'—C3'—N4'	−46.5 (3)	N5—Co1—N9—C10	21.1 (2)
C2—C3—N4—Co1	37.9 (2)	Cl1—Co1—N9—C10	−70.1 (2)
N1—Co1—N4—C3	−13.78 (17)	N1'—Co1'—N9'—C10'	154.6 (2)
N8—Co1—N4—C3	−102.47 (17)	N4'—Co1'—N9'—C10'	−120.3 (2)
N5—Co1—N4—C3	172.67 (17)	N8'—Co1'—N9'—C10'	20.1 (19)
N9—Co1—N4—C3	78.19 (17)	N5'—Co1'—N9'—C10'	−26.9 (2)
Cl1—Co1—N4—C3	13.1 (9)	Cl1'—Co1'—N9'—C10'	65.4 (2)
C2'—C3'—N4'—Co1'	35.6 (3)	Co1—N9—C10—C11	163.4 (2)
N1'—Co1'—N4'—C3'	−12.49 (19)	Co1'—N9'—C10'—C11'	−152.63 (19)
N8'—Co1'—N4'—C3'	79.97 (19)	N9—C10—C11—C16	−64.9 (4)
N5'—Co1'—N4'—C3'	164.29 (18)	N9—C10—C11—C12	120.1 (3)
N9'—Co1'—N4'—C3'	−102.13 (19)	N9'—C10'—C11'—C12'	−119.6 (3)
Cl1'—Co1'—N4'—C3'	−13.1 (9)	N9'—C10'—C11'—C16'	60.9 (3)
N1—Co1—N5—C6	−1.6 (9)	C16—C11—C12—C13	−1.2 (4)
N4—Co1—N5—C6	77.27 (17)	C10—C11—C12—C13	174.0 (3)
N8—Co1—N5—C6	−14.11 (17)	C16'—C11'—C12'—C13'	−0.3 (4)
N9—Co1—N5—C6	167.36 (17)	C10'—C11'—C12'—C13'	−179.8 (3)
Cl1—Co1—N5—C6	−104.39 (16)	C11—C12—C13—C14	0.0 (5)
N1'—Co1'—N5'—C6'	−18.2 (16)	C11'—C12'—C13'—C14'	−0.4 (5)
N4'—Co1'—N5'—C6'	−82.01 (19)	C12—C13—C14—C15	0.8 (5)
N8'—Co1'—N5'—C6'	8.20 (19)	C12'—C13'—C14'—C15'	0.5 (5)
N9'—Co1'—N5'—C6'	−174.23 (19)	C13—C14—C15—C16	−0.5 (5)
Cl1'—Co1'—N5'—C6'	97.73 (18)	C13'—C14'—C15'—C16'	0.1 (5)
Co1—N5—C6—C7	39.8 (2)	C12—C11—C16—C15	1.5 (4)
Co1'—N5'—C6'—C7'	−34.7 (3)	C10—C11—C16—C15	−173.6 (3)
N5—C6—C7—N8	−52.0 (3)	C14—C15—C16—C11	−0.7 (5)
N5'—C6'—C7'—N8'	50.7 (3)	C12'—C11'—C16'—C15'	1.0 (4)
C6—C7—N8—Co1	40.9 (2)	C10'—C11'—C16'—C15'	−179.5 (2)
N1—Co1—N8—C7	166.07 (18)	C14'—C15'—C16'—C11'	−0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl3	0.81 (3)	2.67 (3)	3.406 (2)	151 (3)
N1—H1B···Cl2	0.87 (3)	2.36 (3)	3.211 (2)	163 (2)
N8—H8A···Cl3	0.91 (3)	2.33 (3)	3.179 (2)	156 (3)
N4'—H4D···O1	0.81 (3)	2.25 (3)	2.915 (3)	139 (2)
N8'—H8C···O1	0.87 (3)	2.15 (3)	2.964 (4)	155 (3)
N1'—H1C···Cl3'	0.82 (3)	2.43 (4)	3.246 (2)	174 (3)
N4—H4A···Cl2i	0.87 (3)	2.65 (3)	3.423 (2)	149 (2)
N5'—H5D···Cl2'	0.85 (3)	2.39 (3)	3.233 (2)	168 (3)
N8'—H8D···Cl3'	0.87 (3)	2.48 (3)	3.252 (2)	148 (3)
N4—H4B···Cl3ii	0.93 (3)	2.45 (3)	3.265 (2)	147 (2)
N8—H8B···Cl3ii	0.79 (3)	2.49 (3)	3.280 (2)	176 (3)
N9—H9A···Cl2iii	0.84 (4)	2.57 (4)	3.391 (2)	166 (3)
N5'—H5C···Cl1i	0.91 (3)	2.63 (3)	3.380 (2)	141 (2)
N1'—H1D···Cl2'iv	0.89 (3)	2.49 (3)	3.288 (2)	149 (2)
N9'—H9D···Cl2'iv	0.85 (3)	2.81 (3)	3.615 (2)	158 (2)
N5—H5A···Cl2i	0.88 (3)	2.38 (3)	3.220 (2)	159 (2)
O1—H2W···Cl3'i	0.84 (2)	2.27 (2)	3.092 (3)	165 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl3	0.81 (3)	2.67 (3)	3.406 (2)	151 (3)
N1—H1B⋯Cl2	0.87 (3)	2.36 (3)	3.211 (2)	163 (2)
N8—H8A⋯Cl3	0.91 (3)	2.33 (3)	3.179 (2)	156 (3)
N4′—H4D⋯O1	0.81 (3)	2.25 (3)	2.915 (3)	139 (2)
N8′—H8C⋯O1	0.87 (3)	2.15 (3)	2.964 (4)	155 (3)
N1′—H1C⋯Cl3′	0.82 (3)	2.43 (4)	3.246 (2)	174 (3)
N4—H4A⋯Cl2i	0.87 (3)	2.65 (3)	3.423 (2)	149 (2)
N5′—H5D⋯Cl2′	0.85 (3)	2.39 (3)	3.233 (2)	168 (3)
N8′—H8D⋯Cl3′	0.87 (3)	2.48 (3)	3.252 (2)	148 (3)
N4—H4B⋯Cl3ii	0.93 (3)	2.45 (3)	3.265 (2)	147 (2)
N8—H8B⋯Cl3ii	0.79 (3)	2.49 (3)	3.280 (2)	176 (3)
N9—H9A⋯Cl2iii	0.84 (4)	2.57 (4)	3.391 (2)	166 (3)
N5′—H5C⋯Cl1i	0.91 (3)	2.63 (3)	3.380 (2)	141 (2)
N1′—H1D⋯Cl2′iv	0.89 (3)	2.49 (3)	3.288 (2)	149 (2)
N9′—H9D⋯Cl2′iv	0.85 (3)	2.81 (3)	3.615 (2)	158 (2)
N5—H5A⋯Cl2i	0.88 (3)	2.38 (3)	3.220 (2)	159 (2)
O1—H2W⋯Cl3′i	0.842 (17)	2.27 (2)	3.092 (3)	165 (4)

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