(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetra­aza­cyclo­tetra­deca-4,11-diene)nickel(II) dibromide dihydrate

He, X.L.; Shi, F.; Lu, Y.

doi:10.1107/S1600536810033714

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1339

doi:10.1107/S1600536810033714

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(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene)nickel(II) dibromide dihydrate

XiuLi He,^a Feifei Shi ^a ^* and Yonghong Lu ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 28 July 2010; accepted 20 August 2010; online 30 September 2010)

The asymmetric unit of the title compound, [Ni(C₁₆H₃₂N₄)]Br₂·2H₂O, consists of one half [Ni(C₁₆H₃₂N₄)]²⁺ cation, one Br⁻ anion and one water molecule of crystallization. The Ni^II ion lies on an inversion centre in a square-planar environment formed by the four macrocyclic ligand N atoms. In the crystal structure, the cations, anions and water molecules are linked via intermolecular N—H⋯Br and O—H⋯Br hydrogen bonds, forming discrete chains with set-graph motif D(2)D₂²(7)D₂¹(3)D₃²(8). The water molecules and Br⁻ ions are linked with set-graph motif R₄²(8).

Related literature

For related structures, see: Ballester et al. (2000 ); Heinlein & Tebbe (1985 ); Shen et al. (1999 ); Szalda et al. (1989 ); Wang et al. (2007 ); Whimp et al. (1970 ); Yang (2005 ). For the preparation of the precursor complex C₁₆H₃₂N₄·2HBr·2H₂O, see: Hay et al. (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

[Ni(C₁₆H₃₂N₄)]Br₂·2H₂O
M_r = 535.02
Monoclinic, P 2₁ /c
a = 8.0349 (16) Å
b = 15.619 (3) Å
c = 8.9355 (18) Å
β = 99.72 (3)°
V = 1105.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 4.51 mm⁻¹
T = 293 K
0.27 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.831, T_max = 0.862
11266 measured reflections
2531 independent reflections
1995 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.099
S = 1.05
2531 reflections
116 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1ⁱ	0.91	2.53	3.413 (3)	164
O1—H1E⋯Br1ⁱⁱ	0.85	2.53	3.374 (3)	169
O1—H1F⋯Br1ⁱⁱⁱ	0.85	2.55	3.388 (5)	170
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y+1, z; (iii) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033714/bx2296sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810033714/bx2296Isup2.hkl

checkCIF report

Comment top

The structures of several related macrocyclic complexes have been reported (Whimp et al.,1970; Yang, 2005; Heinlein et al., 1985) for many times in the past years. The nickel(II) tetraazamacrocyclic complex cation, [Ni(C₁₆H₃₂N₄)]²⁺ has both meso and enantiomeric forms and can combine with different anions to form many kinds of structures (Shen et al., 1999; Ballester et al., 2000; Wang et al., 2007). We herein report the crystal structure of a new compound synthesized by reaction of Ni(CH₃COO)₂.4H₂O and the complex C₁₆H₃₂N₄.2HBr.2H₂O in methanol solution. As shown in Fig.1, the Ni^IIatom is coordinated by four N atoms from the tetraazamacrocycle in a square-planar geometry. The metal atom and the four N atoms are coplanar. The Ni—N(amine) and N(imine) bond distances are 1.934 (3) Å and 1.916 (3)Å and are similar to those in previously report (Szalda et al.,1989). In the crystal structure, the cations, anions and water molecules are linked via intermolecular N—H···Br and O— H···Br hydrogen bonds forming discrete chains with set-graph motif D₁¹(2), D₂²(7), D₂¹(3) and D₃²(8). The water molecules and Br^– ions are linked forming R₄²(8) set-graph motif (Bernstein et al., 1995), Fig 2.

Related literature top

For related structures, see: Ballester et al. (2000); Heinlein & Tebbe (1985); Shen et al. (1999); Szalda et al. (1989); Wang et al. (2007); Whimp et al. (1970); Yang (2005). For the preparation of the precursor complex C₁₆H₃₂N₄.2HBr.2H₂O, see: Hay et al. (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

All chemicals were of reagent grade and were used as received without further purification. The precursor complex C₁₆H₃₂N₄.2HBr.2H₂O was prepared by described in the literature method (Hay et al., 1975). To a 10 ml methanol solution of Ni(CH₃COO)₂.4H₂O (0.2 mmol, 0.049 g), a 5 ml methanol solution of C₁₆H₃₂N₄.2HBr.2H₂O (0.2 mmol, 0.0957 g) was added dropwise with stirring. The resulting solution was continuously stirred for about 30 min. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation at room temperature over several days.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Unlabeled atoms are related to labeled atoms by the symmetry code (1-x,1-y,1-z)
	Fig. 2. View of (I) along b, showing chains of organic cations running parallel to the (001) direction, with Br^- anions and water molecules lying between them.

(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradeca-4,11- diene)nickel(II) dibromide dihydrate top

Crystal data top

[Ni(C₁₆H₃₂N₄)]Br₂·2H₂O	F(000) = 548
M_r = 535.02	D_x = 1.608 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3476 reflections
a = 8.0349 (16) Å	θ = 2.3–27.5°
b = 15.619 (3) Å	µ = 4.51 mm⁻¹
c = 8.9355 (18) Å	T = 293 K
β = 99.72 (3)°	Prism, brown
V = 1105.3 (4) Å³	0.27 × 0.20 × 0.20 mm
Z = 2

Data collection top

Rigaku SCXmini diffractometer	2531 independent reflections
Radiation source: fine-focus sealed tube	1995 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
thin–slice ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
T_min = 0.831, T_max = 0.862	l = −11→11
11266 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0317P)² + 1.6713P] where P = (F_o² + 2F_c²)/3
2531 reflections	(Δ/σ)_max < 0.001
116 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

[Ni(C₁₆H₃₂N₄)]Br₂·2H₂O	V = 1105.3 (4) Å³
M_r = 535.02	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0349 (16) Å	µ = 4.51 mm⁻¹
b = 15.619 (3) Å	T = 293 K
c = 8.9355 (18) Å	0.27 × 0.20 × 0.20 mm
β = 99.72 (3)°

Data collection top

Rigaku SCXmini diffractometer	2531 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1995 reflections with I > 2σ(I)
T_min = 0.831, T_max = 0.862	R_int = 0.048
11266 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.05	Δρ_max = 0.74 e Å⁻³
2531 reflections	Δρ_min = −0.74 e Å⁻³
116 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
Ni1	0.5000	0.5000	0.5000	0.02894 (16)
Br1	0.69586 (6)	0.10330 (3)	0.63849 (6)	0.06334 (18)
C1	0.8076 (5)	0.5280 (2)	0.7876 (4)	0.0410 (8)
H1B	0.9228	0.5334	0.8406	0.061*
H1C	0.7344	0.5312	0.8633	0.061*
C2	0.7698 (4)	0.6042 (2)	0.6830 (4)	0.0362 (8)
C3	0.5246 (5)	0.6761 (2)	0.5232 (5)	0.0546 (11)
H3A	0.5877	0.6831	0.4405	0.065*
H3B	0.5384	0.7273	0.5854	0.065*
C4	0.3413 (5)	0.6610 (2)	0.4621 (5)	0.0536 (11)
H4A	0.2748	0.6656	0.5429	0.064*
H4B	0.3003	0.7030	0.3846	0.064*
C5	0.2117 (4)	0.5591 (2)	0.2827 (4)	0.0343 (7)
C6	0.8765 (5)	0.6034 (3)	0.5571 (5)	0.0503 (10)
H6A	0.8525	0.5525	0.4972	0.075*
H6B	0.9941	0.6044	0.6013	0.075*
H6C	0.8503	0.6528	0.4937	0.075*
C7	0.8061 (5)	0.6849 (3)	0.7812 (5)	0.0561 (11)
H7A	0.7833	0.7348	0.7184	0.084*
H7B	0.9225	0.6851	0.8290	0.084*
H7C	0.7353	0.6853	0.8576	0.084*
C8	0.0896 (5)	0.6244 (3)	0.2077 (5)	0.0528 (10)
H8A	0.0147	0.5984	0.1252	0.079*
H8B	0.1504	0.6702	0.1695	0.079*
H8C	0.0252	0.6468	0.2802	0.079*
N1	0.5857 (3)	0.60021 (16)	0.6151 (3)	0.0332 (6)
H1A	0.5300	0.6015	0.6957	0.040*
N2	0.3276 (3)	0.57404 (17)	0.3970 (3)	0.0333 (6)
O1	0.6240 (6)	0.8913 (2)	0.6616 (5)	0.0923 (12)
H1E	0.6525	0.9438	0.6665	0.111*
H1F	0.5421	0.8854	0.5885	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0263 (3)	0.0225 (3)	0.0368 (3)	0.0004 (2)	0.0016 (2)	0.0001 (3)
Br1	0.0521 (3)	0.0655 (3)	0.0752 (4)	−0.0076 (2)	0.0189 (2)	−0.0112 (2)
C1	0.041 (2)	0.046 (2)	0.0338 (19)	0.0010 (16)	−0.0019 (16)	−0.0021 (16)
C2	0.0299 (17)	0.0349 (19)	0.042 (2)	−0.0014 (14)	0.0011 (15)	−0.0035 (15)
C3	0.057 (3)	0.0238 (17)	0.075 (3)	−0.0031 (17)	−0.012 (2)	0.0055 (19)
C4	0.050 (2)	0.0277 (19)	0.074 (3)	0.0112 (17)	−0.013 (2)	−0.0055 (19)
C5	0.0321 (17)	0.0398 (19)	0.0319 (18)	0.0022 (14)	0.0079 (14)	0.0059 (15)
C6	0.043 (2)	0.051 (2)	0.061 (3)	−0.0022 (18)	0.021 (2)	0.008 (2)
C7	0.051 (2)	0.041 (2)	0.071 (3)	−0.0062 (18)	−0.004 (2)	−0.012 (2)
C8	0.048 (2)	0.057 (3)	0.048 (2)	0.019 (2)	−0.0043 (19)	0.003 (2)
N1	0.0299 (14)	0.0264 (14)	0.0430 (17)	−0.0001 (11)	0.0051 (12)	−0.0013 (12)
N2	0.0321 (15)	0.0257 (14)	0.0407 (16)	0.0040 (11)	0.0025 (13)	0.0021 (12)
O1	0.103 (3)	0.070 (2)	0.097 (3)	0.013 (2)	−0.001 (2)	0.019 (2)

Geometric parameters (Å, º) top

Ni1—N2	1.916 (3)	C4—H4B	0.9700
Ni1—N2ⁱ	1.916 (3)	C5—N2	1.282 (4)
Ni1—N1	1.934 (3)	C5—C8	1.494 (5)
Ni1—N1ⁱ	1.934 (3)	C5—C1ⁱ	1.494 (5)
C1—C5ⁱ	1.494 (5)	C6—H6A	0.9600
C1—C2	1.513 (5)	C6—H6B	0.9600
C1—H1B	0.9700	C6—H6C	0.9600
C1—H1C	0.9700	C7—H7A	0.9600
C2—N1	1.503 (4)	C7—H7B	0.9600
C2—C6	1.525 (5)	C7—H7C	0.9600
C2—C7	1.535 (5)	C8—H8A	0.9600
C3—N1	1.477 (4)	C8—H8B	0.9600
C3—C4	1.501 (5)	C8—H8C	0.9600
C3—H3A	0.9700	N1—H1A	0.9100
C3—H3B	0.9700	O1—H1E	0.8500
C4—N2	1.475 (5)	O1—H1F	0.8500
C4—H4A	0.9700

N2—Ni1—N2ⁱ	180.000 (1)	N2—C5—C1ⁱ	120.7 (3)
N2—Ni1—N1	86.01 (12)	C8—C5—C1ⁱ	114.8 (3)
N2ⁱ—Ni1—N1	93.99 (12)	C2—C6—H6A	109.5
N2—Ni1—N1ⁱ	93.99 (12)	C2—C6—H6B	109.5
N2ⁱ—Ni1—N1ⁱ	86.01 (12)	H6A—C6—H6B	109.5
N1—Ni1—N1ⁱ	180.0	C2—C6—H6C	109.5
C5ⁱ—C1—C2	117.5 (3)	H6A—C6—H6C	109.5
C5ⁱ—C1—H1B	107.9	H6B—C6—H6C	109.5
C2—C1—H1B	107.9	C2—C7—H7A	109.5
C5ⁱ—C1—H1C	107.9	C2—C7—H7B	109.5
C2—C1—H1C	107.9	H7A—C7—H7B	109.5
H1B—C1—H1C	107.2	C2—C7—H7C	109.5
N1—C2—C1	107.3 (3)	H7A—C7—H7C	109.5
N1—C2—C6	109.9 (3)	H7B—C7—H7C	109.5
C1—C2—C6	111.7 (3)	C5—C8—H8A	109.5
N1—C2—C7	110.1 (3)	C5—C8—H8B	109.5
C1—C2—C7	107.1 (3)	H8A—C8—H8B	109.5
C6—C2—C7	110.6 (3)	C5—C8—H8C	109.5
N1—C3—C4	106.8 (3)	H8A—C8—H8C	109.5
N1—C3—H3A	110.4	H8B—C8—H8C	109.5
C4—C3—H3A	110.4	C3—N1—C2	113.8 (3)
N1—C3—H3B	110.4	C3—N1—Ni1	107.4 (2)
C4—C3—H3B	110.4	C2—N1—Ni1	119.1 (2)
H3A—C3—H3B	108.6	C3—N1—H1A	105.1
N2—C4—C3	106.9 (3)	C2—N1—H1A	105.1
N2—C4—H4A	110.3	Ni1—N1—H1A	105.1
C3—C4—H4A	110.3	C5—N2—C4	118.5 (3)
N2—C4—H4B	110.3	C5—N2—Ni1	129.9 (2)
C3—C4—H4B	110.3	C4—N2—Ni1	111.5 (2)
H4A—C4—H4B	108.6	H1E—O1—H1F	108.1
N2—C5—C8	124.5 (3)

C5ⁱ—C1—C2—N1	64.1 (4)	N2—Ni1—N1—C2	−154.2 (3)
C5ⁱ—C1—C2—C6	−56.4 (4)	N2ⁱ—Ni1—N1—C2	25.8 (3)
C5ⁱ—C1—C2—C7	−177.6 (3)	N1ⁱ—Ni1—N1—C2	79 (100)
N1—C3—C4—N2	−48.4 (5)	C8—C5—N2—C4	1.2 (5)
C4—C3—N1—C2	179.0 (3)	C1ⁱ—C5—N2—C4	180.0 (3)
C4—C3—N1—Ni1	45.0 (4)	C8—C5—N2—Ni1	−176.6 (3)
C1—C2—N1—C3	173.5 (3)	C1ⁱ—C5—N2—Ni1	2.2 (5)
C6—C2—N1—C3	−64.9 (4)	C3—C4—N2—C5	−148.4 (4)
C7—C2—N1—C3	57.2 (4)	C3—C4—N2—Ni1	29.8 (4)
C1—C2—N1—Ni1	−58.4 (3)	N2ⁱ—Ni1—N2—C5	−65 (100)
C6—C2—N1—Ni1	63.2 (3)	N1—Ni1—N2—C5	173.9 (3)
C7—C2—N1—Ni1	−174.7 (3)	N1ⁱ—Ni1—N2—C5	−6.1 (3)
N2—Ni1—N1—C3	−23.2 (3)	N2ⁱ—Ni1—N2—C4	117 (100)
N2ⁱ—Ni1—N1—C3	156.8 (3)	N1—Ni1—N2—C4	−4.0 (3)
N1ⁱ—Ni1—N1—C3	−150 (100)	N1ⁱ—Ni1—N2—C4	176.0 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1ⁱⁱ	0.91	2.53	3.413 (3)	164
O1—H1E···Br1ⁱⁱⁱ	0.85	2.53	3.374 (3)	169
O1—H1F···Br1ⁱ	0.85	2.55	3.388 (5)	170

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₆H₃₂N₄)]Br₂·2H₂O
M_r	535.02
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.0349 (16), 15.619 (3), 8.9355 (18)
β (°)	99.72 (3)
V (Å³)	1105.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.51
Crystal size (mm)	0.27 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.831, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	11266, 2531, 1995
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.099, 1.05
No. of reflections	2531
No. of parameters	116
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.74

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1ⁱ	0.91	2.53	3.413 (3)	164
O1—H1E···Br1ⁱⁱ	0.85	2.53	3.374 (3)	169
O1—H1F···Br1ⁱⁱⁱ	0.85	2.55	3.388 (5)	170

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

References

Ballester, L., Gil, A. M., Gutiérrez, A., Perpiñán, M. F., Azcondo, M. T., Sánchez, A. E., Coronado, E. & Gómez-García, C. J. (2000). Inorg. Chem. 39, 2837–2842. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Hay, R. W., Lawrance, A. G. & Curtis, N. F. (1975). J. Chem. Soc. Perkin Trans. pp. 591–593. CrossRef Web of Science Google Scholar
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Volume 66| Part 10| October 2010| Page m1339

doi:10.1107/S1600536810033714

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

(meso-5,7,7,12,14,14-Hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­deca-4,11-diene)nickel(II) dibromide dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene)nickel(II) dibromide dihydrate