Bromido(1,4,7,10,13-penta­aza­cyclo­hexa­deca­ne)cobalt(III) dibromide dihydrate

Kurisaki, T.; Hamano, M.; Wakita, H.

doi:10.1107/S1600536813004947

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages m179-m180

doi:10.1107/S1600536813004947

Open

access

Bromido(1,4,7,10,13-pentaazacyclohexadecane)cobalt(III) dibromide dihydrate

Tsutomu Kurisaki,^a ^* Makoto Hamano ^a and Hisanobu Wakita ^a

^aDepartment of Chemistry, Faculty of Science, Fukuoka University, Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan
^*Correspondence e-mail: kurisaki@fukuoka-u.ac.jp

(Received 28 January 2013; accepted 20 February 2013; online 2 March 2013)

The title salt, [CoBr(C₁₁H₂₇N₅)]Br₂·2H₂O, contains a complex cation with mirror symmetry and two Br⁻ counter-anions that are likewise located on the mirror plane. The central Co^III atom of the complex cation has one Br⁻ ion in an axial position, one N atom of the pentadentate macrocyclic ligand in the other axial position and four N atoms of the ligand in equatorial positions, defining a distorted octahedral coordination geometry. The macrocyclic ligand is coordinated to the Co^III atom within a 5, 6, 5 arrangement of chelate rings in the equatorial plane of the four N atoms. Due to symmetry, the configuration of the chiral N atoms is 1RS, 4SR, 10RS, 13SR. In the crystal, N—H⋯Br, O—H⋯Br and N—H⋯O hydrogen bonds between the complex cation, anions and lattice water molecules generate a three-dimensional network.

Related literature

For background to metal complexes with azamacrocycles, see: Mewis & Archida (2010 ). For related structures, see: Curtis et al. (1987a ,b ); Eigenbrot et al. (1988 ); Tahirov et al. (1993 ); Bombieri et al. (1982 ). For the synthesis of the macrocyclic ligand, see: Richman & Atkins (1974 ).

Experimental

Crystal data

[CoBr(C₁₁H₂₇N₅)]Br₂·2H₂O
M_r = 564.07
Orthorhombic, P n m a
a = 13.139 (3) Å
b = 9.6674 (18) Å
c = 15.393 (3) Å
V = 1955.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 7.02 mm⁻¹
T = 296 K
0.40 × 0.22 × 0.14 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999 ) T_min = 0.189, T_max = 0.501
28744 measured reflections
2370 independent reflections
1964 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.076
S = 1.02
2370 reflections
109 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Br2	0.91	2.5	3.303 (3)	147
N2—H2⋯Br3	0.91	2.57	3.415 (2)	155
N3—H3⋯OWⁱ	0.91	2.24	3.060 (4)	150
OW—HW2⋯Br2	0.87	2.64	3.491 (3)	168
OW—HW1⋯Br3ⁱⁱ	0.82	2.67	3.489 (3)	170
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2008 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813004947/wm2723sup1.cif

Supporting information file. DOI: 10.1107/S1600536813004947/wm2723Isup2.tif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004947/wm2723Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536813004947/wm2723Isup4.cdx

checkCIF report

Comment top

Azamacrocycles are popular ligands for the preparation of metal complexes because of their stability and defined geometry. These ligands often possess enough conformational freedom for their intended functionalities (Mewis & Archida, 2010). The coordination of pentaaza macrocycles to the cobalt(III) ion can result in a number of isomeric forms. The complexes formed between cobalt(III) and a series of eight pentaaza macrocycles with ring sizes varying from 15- to 20-membered rings have been investigated (Curtis et al., 1987a,b). These cobalt(III) complexes may exist as three diastereoisomers, i.e. meso-syn, meso-anti, and the racemic isomer. For the cobalt(III) complex of 1,4,7,11,14-pentaazacycloheptadecane ([17]aneN₅) it has been reported that two isomeric forms could be isolated. The crystal structures of these two isomers, [CoBr([17]aneN₅)][ZnBr₄] (Eigenbrot et al., 1988) and [CoCl([17]aneN₅)]Cl(ClO₄) (Tahirov et al., 1993), have been determined as the racemic and the meso-anti isomer, respectively. Furthermore, the cobalt(III) complex of 1,4,7,11,14-pentaazacyclohexadecane ([16]aneN₅), [CoCl([16]aneN₅)](ClO₄)₂, crystallized as the meso-syn isomer (Bombieri et al., 1982).

In the title complex, [CoBr(C₁₁H₂₇N₅)]Br₂^.2H₂O, the Co^III atom is surrounded by one Br^- anion and N atoms of the macrocyclic ligand to form a distorted octahedral environment (Fig.1). The Co—N(axial) bond in the complex is longer than the Co—N(equatorial) bonds, presumably caused by the trans effect of the Br atom. The average Co—N(equatorial) distance of 1.967 Å is shorter than that in cobalt(III) complexes of 1,4,7,11,14-pentaazacycloheptadecane (Eigenbrot et al., 1988) and 1,4,7,11,15-pentaazacyclooctadecane (Curtis et al., 1987a). The macrocyclic ligand adopts a stable conformation with the one six-membered chelate ring in chair form and four five-membered chelate rings in gauche forms. The macrocyclic ligand is coordinated in a configuration with five-, six-, and five-membered chelate rings in the equatorial plane. The deviation of the Co^III atom from the equatorial plane is 0.03 A. The N3 and N3* atoms have opposite chirality giving the meso-syn diastereoisomer. The macrocyclic ligand coordinates in the meso-syn configuration with hydrogen atoms on N2, N2*, N3, and N3* on the same side of the equatorial plane relative to the axially coordinating bromide anion. Due to mirror symmetry of the entire complec cation, the configurations of the four chiral amine N atoms are 1RS, 4SR, 10RS, and 13SR. Hydrogen bonds between N atoms of the macrocyclic ligand, water molecules and bromide counter anions exists (Fig. 2; Table 1), stabilizing the crystal packing within a three-dimensional network.

Related literature top

For background to metal complexes with azamacrocycles, see: Mewis & Archida (2010). For related structures, see: Curtis et al. (1987a,b); Eigenbrot et al. (1988); Tahirov et al. (1993); Bombieri et al. (1982). For the synthesis of the macrocyclic ligand, see: Richman & Atkins (1974).

Experimental top

The ligand 1,4,7,10,13-pentaazacyclohexadecane pentahydrobromide was prepared according to the literature method (Richman & Atkins, 1974). The ligand (1.26 g, 2 mmol) was dissolved in water and treated with freshly prepared Na₃[Co(CO₃)₃]^.3H₂O (0.72 g, 2 mmol). The mixture was refluxed for 1 h and filtered. To the filtrate was added NH₄Br in excess and the solution allowed to stand for several days whereupon dark violet crystals of the title compound were formed.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Crystal Structure of the title compound with view along the b axis. Intermolecular hydrogen bonding is shown as dashed lines.

Bromido(1,4,7,10,13-pentaazacyclohexadecane)cobalt(III) dibromide dihydrate top

Crystal data top

[CoBr(C₁₁H₂₇N₅)]Br₂·2H₂O	F(000) = 1120
M_r = 564.07	D_x = 1.916 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 4654 reflections
a = 13.139 (3) Å	θ = 3.1–27.5°
b = 9.6674 (18) Å	µ = 7.02 mm⁻¹
c = 15.393 (3) Å	T = 296 K
V = 1955.2 (7) Å³	Prism, dark violet
Z = 4	0.40 × 0.22 × 0.14 mm

Data collection top

Rigaku Saturn724+ diffractometer	2370 independent reflections
Radiation source: rotating anode	1964 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
dtprofit.ref scans	h = −17→17
Absorption correction: numerical (NUMABS; Rigaku, 1999)	k = −12→12
T_min = 0.189, T_max = 0.501	l = −19→19
28744 measured reflections

Refinement top

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0392P)²] where P = (F_o² + 2F_c²)/3
2370 reflections	(Δ/σ)_max = 0.001
109 parameters	Δρ_max = 0.89 e Å⁻³
4 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

[CoBr(C₁₁H₂₇N₅)]Br₂·2H₂O	V = 1955.2 (7) Å³
M_r = 564.07	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 13.139 (3) Å	µ = 7.02 mm⁻¹
b = 9.6674 (18) Å	T = 296 K
c = 15.393 (3) Å	0.40 × 0.22 × 0.14 mm

Data collection top

Rigaku Saturn724+ diffractometer	2370 independent reflections
Absorption correction: numerical (NUMABS; Rigaku, 1999)	1964 reflections with I > 2σ(I)
T_min = 0.189, T_max = 0.501	R_int = 0.075
28744 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	4 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	Δρ_max = 0.89 e Å⁻³
2370 reflections	Δρ_min = −0.88 e Å⁻³
109 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.97038 (3)	0.25	0.51348 (3)	0.04287 (14)
Br2	0.44795 (3)	0.25	0.38291 (3)	0.04299 (14)
Br3	0.89341 (4)	0.25	0.77417 (3)	0.04833 (15)
Co	0.78735 (4)	0.25	0.50953 (3)	0.02053 (13)
OW	0.4692 (2)	0.0362 (3)	0.20106 (17)	0.0743 (9)
HW1	0.5085	−0.0263	0.2156	0.111*
HW2	0.4701	0.0986	0.2416	0.111*
N1	0.6374 (2)	0.25	0.5240 (2)	0.0227 (7)
H1	0.6083	0.25	0.4703	0.027*
N2	0.78844 (16)	0.0990 (2)	0.59473 (15)	0.0272 (5)
H2	0.8333	0.1219	0.6374	0.033*
N3	0.79176 (17)	0.1035 (2)	0.42054 (15)	0.0298 (5)
H3	0.8556	0.1076	0.3977	0.036*
C1	0.60554 (19)	0.1226 (3)	0.57002 (19)	0.0309 (6)
H1A	0.5957	0.0482	0.5286	0.037*
H1B	0.5416	0.1385	0.5998	0.037*
C2	0.6869 (2)	0.0825 (3)	0.63512 (19)	0.0344 (7)
H2A	0.6818	0.1408	0.6862	0.041*
H2B	0.6773	−0.0129	0.653	0.041*
C3	0.8268 (2)	−0.0279 (3)	0.5511 (2)	0.0395 (7)
H3A	0.8063	−0.109	0.5838	0.047*
H3B	0.9006	−0.0258	0.5488	0.047*
C4	0.7838 (2)	−0.0351 (3)	0.4602 (2)	0.0396 (7)
H4A	0.8217	−0.1018	0.4259	0.047*
H4B	0.7132	−0.0641	0.4621	0.047*
C5	0.7214 (2)	0.1176 (3)	0.34490 (19)	0.0369 (7)
H5A	0.6517	0.1154	0.3656	0.044*
H5B	0.7309	0.0392	0.3064	0.044*
C6	0.7384 (4)	0.25	0.2943 (3)	0.0452 (12)
H6A	0.6932	0.25	0.2445	0.054*
H6B	0.8076	0.25	0.2724	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0225 (2)	0.0483 (3)	0.0578 (3)	0	0.00093 (19)	0
Br2	0.0392 (3)	0.0353 (3)	0.0546 (3)	0	−0.0198 (2)	0
Br3	0.0605 (3)	0.0443 (3)	0.0402 (3)	0	−0.0220 (2)	0
Co	0.0186 (3)	0.0205 (3)	0.0225 (3)	0	0.00025 (19)	0
OW	0.082 (2)	0.087 (2)	0.0533 (17)	0.0336 (16)	−0.0023 (14)	0.0002 (15)
N1	0.0247 (16)	0.0235 (16)	0.0198 (16)	0	0.0005 (13)	0
N2	0.0270 (12)	0.0243 (12)	0.0301 (13)	−0.0013 (9)	−0.0066 (10)	0.0031 (10)
N3	0.0284 (12)	0.0313 (13)	0.0297 (13)	0.0026 (10)	0.0031 (10)	−0.0055 (11)
C1	0.0261 (14)	0.0318 (16)	0.0349 (16)	−0.0057 (11)	0.0035 (12)	0.0017 (12)
C2	0.0421 (17)	0.0318 (16)	0.0293 (16)	−0.0035 (13)	0.0006 (13)	0.0094 (13)
C3	0.0450 (18)	0.0248 (15)	0.049 (2)	0.0108 (13)	−0.0048 (15)	0.0010 (14)
C4	0.0480 (19)	0.0256 (16)	0.0451 (18)	0.0056 (13)	0.0024 (16)	−0.0090 (14)
C5	0.0392 (17)	0.0436 (18)	0.0280 (15)	0.0022 (14)	0.0001 (13)	−0.0145 (14)
C6	0.049 (3)	0.062 (3)	0.025 (2)	0	0.000 (2)	0

Geometric parameters (Å, º) top

Br1—Co	2.4056 (8)	C1—C2	1.516 (4)
Co—N2ⁱ	1.962 (2)	C1—H1A	0.97
Co—N2	1.962 (2)	C1—H1B	0.97
Co—N3	1.971 (2)	C2—H2A	0.97
Co—N3ⁱ	1.971 (2)	C2—H2B	0.97
Co—N1	1.982 (3)	C3—C4	1.512 (4)
OW—HW1	0.8249	C3—H3A	0.97
OW—HW2	0.8682	C3—H3B	0.97
N1—C1ⁱ	1.482 (3)	C4—H4A	0.97
N1—C1	1.482 (3)	C4—H4B	0.97
N1—H1	0.91	C5—C6	1.516 (4)
N2—C2	1.481 (3)	C5—H5A	0.97
N2—C3	1.486 (3)	C5—H5B	0.97
N2—H2	0.91	C6—C5ⁱ	1.516 (4)
N3—C4	1.476 (4)	C6—H6A	0.97
N3—C5	1.493 (4)	C6—H6B	0.97
N3—H3	0.91

N2ⁱ—Co—N2	96.11 (14)	N1—C1—H1A	109.8
N2ⁱ—Co—N3	177.03 (10)	C2—C1—H1A	109.8
N2—Co—N3	85.97 (10)	N1—C1—H1B	109.8
N2ⁱ—Co—N3ⁱ	85.97 (10)	C2—C1—H1B	109.8
N2—Co—N3ⁱ	177.03 (10)	H1A—C1—H1B	108.3
N3—Co—N3ⁱ	91.87 (14)	N2—C2—C1	109.3 (2)
N2ⁱ—Co—N1	86.12 (9)	N2—C2—H2A	109.8
N2—Co—N1	86.12 (9)	C1—C2—H2A	109.8
N3—Co—N1	96.15 (9)	N2—C2—H2B	109.8
N3ⁱ—Co—N1	96.15 (9)	C1—C2—H2B	109.8
N2ⁱ—Co—Br1	88.61 (6)	H2A—C2—H2B	108.3
N2—Co—Br1	88.61 (6)	N2—C3—C4	109.3 (2)
N3—Co—Br1	89.32 (7)	N2—C3—H3A	109.8
N3ⁱ—Co—Br1	89.32 (7)	C4—C3—H3A	109.8
N1—Co—Br1	172.11 (9)	N2—C3—H3B	109.8
HW1—OW—HW2	107.8	C4—C3—H3B	109.8
C1ⁱ—N1—C1	112.5 (3)	H3A—C3—H3B	108.3
C1ⁱ—N1—Co	109.54 (16)	N3—C4—C3	108.3 (2)
C1—N1—Co	109.54 (16)	N3—C4—H4A	110
C1ⁱ—N1—H1	108.4	C3—C4—H4A	110
C1—N1—H1	108.4	N3—C4—H4B	110
Co—N1—H1	108.4	C3—C4—H4B	110
C2—N2—C3	113.9 (2)	H4A—C4—H4B	108.4
C2—N2—Co	110.77 (16)	N3—C5—C6	112.8 (3)
C3—N2—Co	108.34 (18)	N3—C5—H5A	109
C2—N2—H2	107.9	C6—C5—H5A	109
C3—N2—H2	107.9	N3—C5—H5B	109
Co—N2—H2	107.9	C6—C5—H5B	109
C4—N3—C5	111.2 (2)	H5A—C5—H5B	107.8
C4—N3—Co	111.29 (18)	C5—C6—C5ⁱ	115.3 (4)
C5—N3—Co	117.28 (17)	C5—C6—H6A	108.4
C4—N3—H3	105.3	C5ⁱ—C6—H6A	108.4
C5—N3—H3	105.3	C5—C6—H6B	108.4
Co—N3—H3	105.3	C5ⁱ—C6—H6B	108.4
N1—C1—C2	109.2 (2)	H6A—C6—H6B	107.5

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br2	0.91	2.5	3.303 (3)	147
N2—H2···Br3	0.91	2.57	3.415 (2)	155
N3—H3···OWⁱⁱ	0.91	2.24	3.060 (4)	150
OW—HW2···Br2	0.87	2.64	3.491 (3)	168
OW—HW1···Br3ⁱⁱⁱ	0.82	2.67	3.489 (3)	170

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

Experimental details

Crystal data
Chemical formula	[CoBr(C₁₁H₂₇N₅)]Br₂·2H₂O
M_r	564.07
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	296
a, b, c (Å)	13.139 (3), 9.6674 (18), 15.393 (3)
V (Å³)	1955.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.02
Crystal size (mm)	0.40 × 0.22 × 0.14

Data collection
Diffractometer	Rigaku Saturn724+ diffractometer
Absorption correction	Numerical (NUMABS; Rigaku, 1999)
T_min, T_max	0.189, 0.501
No. of measured, independent and observed [I > 2σ(I)] reflections	28744, 2370, 1964
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.076, 1.02
No. of reflections	2370
No. of parameters	109
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.89, −0.88

Computer programs: CrystalClear (Rigaku, 2008), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br2	0.91	2.5	3.303 (3)	147.4
N2—H2···Br3	0.91	2.57	3.415 (2)	155.3
N3—H3···OWⁱ	0.91	2.24	3.060 (4)	149.7
OW—HW2···Br2	0.87	2.64	3.491 (3)	167.7
OW—HW1···Br3ⁱⁱ	0.82	2.67	3.489 (3)	169.9

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x+3/2, −y, z−1/2.

Acknowledgements

This work was partially supported by Grants-in-Aid for Scientific Research (C) 22550088 and (B) 23300319 from the Japan Society for the Promotion of Science.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bombieri, G., Forsellini, E., Delpra, A., Cooksey, C. J., Humanes, M. & Tobe, M. L. (1982). Inorg. Chim. Acta, 61, 43–49. CSD CrossRef CAS Web of Science Google Scholar
Curtis, N. F., Gainsford, G. J., Osvath, P. & Weatherburn, D. C. (1987b). Aust. J. Chem. 40, 829–839. CSD CrossRef Google Scholar
Curtis, N. F., Osvath, P. & Weatherburn, D. C. (1987a). Aust. J. Chem. 40, 811–827. CrossRef CAS Google Scholar
Eigenbrot, C., Osvath, P., Lappin, A. G., Curtis, N. F. & Weatherburn, D. C. (1988). Acta Cryst. C44, 2085–2087. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mewis, R. E. & Archida, S. J. (2010). Coord. Chem. Rev. 254, 1686–1712. Web of Science CrossRef CAS Google Scholar
Richman, J. E. & Atkins, T. J. (1974). J. Am. Chem. Soc. 96, 2268–2270. CrossRef CAS Web of Science Google Scholar
Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tahirov, T. H., Lu, T.-H., Chen, B.-H., Lai, C.-Y. & Chung, C.-S. (1993). Acta Cryst. C49, 1910–1912. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages m179-m180

doi:10.1107/S1600536813004947

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bromido(1,4,7,10,13-penta­aza­cyclo­hexa­deca­ne)cobalt(III) dibromide dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bromido(1,4,7,10,13-pentaazacyclohexadecane)cobalt(III) dibromide dihydrate