cis-Bis(2,2′-bipyrimidine-κ2N1,N1′)dibromidomanganese(II) nitro­methane monosolvate

Ha, K.

doi:10.1107/S1600536811010075

metal-organic compounds

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Volume 67| Part 4| April 2011| Page m474

doi:10.1107/S1600536811010075

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cis-Bis(2,2′-bipyrimidine-κ²N¹,N^1′)dibromidomanganese(II) nitromethane monosolvate

Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 16 March 2011; accepted 17 March 2011; online 23 March 2011)

The asymmetric unit of the title compound, [MnBr₂(C₈H₆N₄)₂]·CH₃NO₂, contains one half of a neutral Mn^II complex and one half of a nitromethane solvent molecule, the complete molecules being generated by the application of twofold symmetry. In the complex, the Mn^II ion has a distorted cis-Br₂N₄ octahedral coordination geometry defined by four N atoms of the two chelating 2,2′-bipyrimidine ligands and two Br⁻ ions. There are intra- and intermolecular C—H⋯Br and C—H⋯N contacts.

Related literature

For the crystal structures of mononuclear 2,2′-bipyrimidine Mn^II complexes, see: Hong et al. (1996 ); Smith et al. (2001 ).

Experimental

Crystal data

[MnBr₂(C₈H₆N₄)₂]·CH₃NO₂
M_r = 592.14
Orthorhombic, C 222₁
a = 8.3876 (4) Å
b = 12.1772 (6) Å
c = 20.7479 (11) Å
V = 2119.14 (18) Å³
Z = 4
Mo Kα radiation
μ = 4.43 mm⁻¹
T = 200 K
0.17 × 0.10 × 0.07 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.825, T_max = 1.000
7872 measured reflections
2608 independent reflections
1818 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.078
S = 1.02
2608 reflections
143 parameters
H-atom parameters constrained
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.86 e Å⁻³
Absolute structure: Flack (1983 ), 1121 Friedel pairs
Flack parameter: −0.003 (16)

Table 1
Selected geometric parameters (Å, °)

Mn1—Br1	2.6140 (9)
Mn1—N1	2.292 (5)
Mn1—N3	2.306 (5)

N1ⁱ—Mn1—N1	158.0 (2)
N3—Mn1—N3ⁱ	89.5 (2)
Br1—Mn1—Br1ⁱ	98.66 (5)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br1	0.95	2.87	3.542 (6)	129
C2—H2⋯Br1ⁱⁱ	0.95	2.91	3.802 (6)	156
C6—H6⋯Br1ⁱⁱⁱ	0.95	2.86	3.752 (5)	157
C9—H9C⋯N2^iv	0.98	2.57	3.430 (5)	147
Symmetry codes: (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010075/tk2729sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010075/tk2729Isup2.hkl

checkCIF report

Comment top

Mononuclear Mn^II complexes of 2,2'-bipyrimidine ligand have been investigated previously (Hong et al., 1996; Smith et al., 2001). The asymmetric unit of the title compound, [MnBr₂(bpym)₂].CH₃NO₂ (where bpym is 2,2'-bipyrimidine; C₈H₆N₄), contains half of a neutral Mn(II) complex and half of a nitromethane solvent molecule (Fig. 1). The complex is disposed about a twofold rotation axis running in the [010] direction passing through the Mn1 atom with the special position at (0, y, 1/4) (Wyckoff letter b). The solvent molecule is also located on a twofold rotation axis, but the axis is running along the [100] direction passing through the N5 and C9 atoms, which lie on the special positions of (x, 1/2, 0) (Wyckoff letter a). Because of the symmetry of the twofold rotation, the methyl group of the nitromethane molecule was modelled as disordered over two sites.

In the complex, the Mn^II ion is six-coordinated in a distorted octahedral environment defined by four N atoms of the two chelating 2,2'-bipyrimidine ligands and two Br^- anions, Table 1, which define a cis-Br₂N₄ donor set. The main contributions to the distortion are the tight N—Mn—N chelate angle and the Br—Br repulsion (N1—Mn1—N3^a = 71.1 (2) ° and Br1—Mn1—Br1^a = 98.66 (5) °; symmetry code a: -x, y, 1/2 - z), which result in non-linear trans axes (<N3—Mn1—Br1^a = 163.6 (1) ° and <N1—Mn1—N1^a = 158.0 (2) °). The Mn—N bond lengths are almost equivalent (Table 1) and the dihedral angle between the least-squares planes of the two bpym ligands is 73.05 (7) °.

In the crystal structure, the complexes are stacked in columns along the a axis. When viewed down the c axis, the successive complexes are stacked in the opposite direction. In the columns, several inter- and intramolecular π-π interactions between adjacent pyrimidine rings are present. The shortest distance between Cg1 (the centroid of ring N1—C4) and Cg2ⁱ (ring N3—C8, symmetry code i: 1/2 - x, 1/2 + y, 1/2 - z) is 4.411 (3) Å, and the dihedral angle between the ring planes is 4.7 (3) °. Moreover, there are intra- and inter-molecular C—H···Br and C—H···N contacts with d(C···Br) = 3.542 (6)–3.802 (6) Å, and d(C···N) = 3.430 (5) Å (Fig. 2, Table 2).

Related literature top

For the crystal structures of mononuclear 2,2'-bipyrimidine Mn^II complexes, see: Hong et al. (1996); Smith et al. (2001).

Experimental top

To a solution of MnBr₂.4H₂O (0.2867 g, 1.000 mmol) in EtOH (30 ml) was added 2,2'-bipyrimidine (0.1584 g, 1.002 mmol) followed by stirring for 3 h. The precipitate was separated by filtration, washed with EtOH and dried at 323 K to give a yellow powder (0.3441 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from a CH₃NO₂ solution.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level for non-H atoms [Symmetry codes: (a) -x, y, 1/2 - z, (b) x, 1 - y, -z]. H atoms are shown as small circles of arbitrary radius and the bonds of the disordered methyl group are shown with dashed lines.
	Fig. 2. View of the unit-cell contents of the title compound. Hydrogen-bond interactions are drawn with dashed lines.

Bis(2,2'-bipyrimidine-κ²N,N')dibromidomanganese(II) nitromethane monosolvate top

Crystal data top

[MnBr₂(C₈H₆N₄)₂]·CH₃NO₂	F(000) = 1164
M_r = 592.14	D_x = 1.856 Mg m⁻³
Orthorhombic, C222₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 2401 reflections
a = 8.3876 (4) Å	θ = 3.0–25.5°
b = 12.1772 (6) Å	µ = 4.43 mm⁻¹
c = 20.7479 (11) Å	T = 200 K
V = 2119.14 (18) Å³	Block, yellow
Z = 4	0.17 × 0.10 × 0.07 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	2608 independent reflections
Radiation source: fine-focus sealed tube	1818 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→11
T_min = 0.825, T_max = 1.000	k = −16→15
7872 measured reflections	l = −24→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.010P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2608 reflections	Δρ_max = 0.87 e Å⁻³
143 parameters	Δρ_min = −0.86 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1121 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.003 (16)

Crystal data top

[MnBr₂(C₈H₆N₄)₂]·CH₃NO₂	V = 2119.14 (18) Å³
M_r = 592.14	Z = 4
Orthorhombic, C222₁	Mo Kα radiation
a = 8.3876 (4) Å	µ = 4.43 mm⁻¹
b = 12.1772 (6) Å	T = 200 K
c = 20.7479 (11) Å	0.17 × 0.10 × 0.07 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	2608 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1818 reflections with I > 2σ(I)
T_min = 0.825, T_max = 1.000	R_int = 0.069
7872 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.87 e Å⁻³
S = 1.02	Δρ_min = −0.86 e Å⁻³
2608 reflections	Absolute structure: Flack (1983), 1121 Friedel pairs
143 parameters	Absolute structure parameter: −0.003 (16)
0 restraints

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	Occ. (<1)
Br1	0.17577 (6)	0.51358 (4)	0.18610 (3)	0.03361 (16)
Mn1	0.0000	0.37369 (10)	0.2500	0.0262 (3)
N1	0.1984 (5)	0.3378 (3)	0.3230 (2)	0.0258 (11)
N2	0.2612 (6)	0.2496 (4)	0.4234 (2)	0.0306 (12)
N3	0.0862 (5)	0.2392 (4)	0.1799 (3)	0.0261 (10)
N4	0.0382 (6)	0.1601 (4)	0.0767 (2)	0.0341 (13)
C1	0.3439 (6)	0.3827 (4)	0.3225 (3)	0.0288 (12)
H1	0.3728	0.4299	0.2880	0.035*
C2	0.4533 (6)	0.3625 (5)	0.3707 (3)	0.0323 (15)
H2	0.5572	0.3935	0.3694	0.039*
C3	0.4059 (7)	0.2952 (5)	0.4210 (3)	0.0331 (16)
H3	0.4789	0.2809	0.4550	0.040*
C4	0.1658 (7)	0.2722 (4)	0.3736 (3)	0.0246 (12)
C5	0.2306 (6)	0.1925 (4)	0.1809 (3)	0.0324 (14)
H5	0.2971	0.2028	0.2175	0.039*
C6	0.2853 (6)	0.1295 (5)	0.1300 (3)	0.0332 (15)
H6	0.3876	0.0960	0.1308	0.040*
C7	0.1849 (8)	0.1177 (5)	0.0783 (3)	0.0373 (14)
H7	0.2214	0.0775	0.0420	0.045*
C8	−0.0027 (7)	0.2208 (4)	0.1271 (3)	0.0255 (12)
O1	−0.0029 (7)	0.4220 (4)	0.0230 (2)	0.0712 (16)
N5	0.0678 (8)	0.5000	0.0000	0.0372 (18)
C9	0.2426 (8)	0.5000	0.0000	0.046 (3)
H9A	0.2815	0.4843	0.0436	0.069*	0.50
H9B	0.2815	0.5721	−0.0138	0.069*	0.50
H9C	0.2815	0.4435	−0.0297	0.069*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0310 (3)	0.0361 (3)	0.0337 (3)	−0.0004 (3)	0.0036 (3)	0.0056 (3)
Mn1	0.0250 (6)	0.0294 (7)	0.0240 (7)	0.000	−0.0007 (6)	0.000
N1	0.024 (2)	0.025 (2)	0.028 (3)	−0.002 (2)	−0.002 (2)	0.002 (2)
N2	0.028 (3)	0.036 (3)	0.028 (3)	0.003 (2)	−0.004 (2)	−0.007 (3)
N3	0.023 (2)	0.030 (2)	0.025 (3)	−0.0023 (19)	−0.004 (2)	0.002 (2)
N4	0.031 (3)	0.038 (3)	0.034 (3)	0.004 (2)	0.005 (2)	0.000 (3)
C1	0.030 (3)	0.032 (3)	0.025 (3)	0.000 (3)	0.002 (3)	−0.004 (3)
C2	0.024 (3)	0.035 (4)	0.038 (4)	−0.009 (3)	−0.001 (3)	−0.002 (3)
C3	0.030 (4)	0.041 (4)	0.028 (4)	0.004 (3)	−0.007 (3)	−0.005 (3)
C4	0.025 (3)	0.025 (3)	0.024 (3)	0.009 (3)	−0.002 (3)	−0.008 (2)
C5	0.034 (3)	0.030 (3)	0.033 (4)	−0.003 (3)	−0.003 (3)	0.004 (3)
C6	0.027 (3)	0.031 (3)	0.042 (4)	0.011 (3)	0.006 (3)	0.004 (3)
C7	0.037 (4)	0.039 (4)	0.036 (4)	0.006 (4)	0.003 (3)	−0.009 (3)
C8	0.033 (3)	0.021 (3)	0.022 (3)	−0.004 (3)	0.002 (3)	0.006 (2)
O1	0.070 (3)	0.066 (4)	0.077 (4)	−0.027 (3)	0.007 (3)	0.002 (3)
N5	0.046 (5)	0.033 (5)	0.032 (5)	0.000	0.000	−0.003 (4)
C9	0.032 (4)	0.065 (7)	0.040 (6)	0.000	0.000	−0.017 (6)

Geometric parameters (Å, º) top

Mn1—Br1	2.6140 (9)	C2—C3	1.386 (8)
Mn1—N1ⁱ	2.292 (5)	C2—H2	0.9500
Mn1—N1	2.292 (5)	C3—H3	0.9500
Mn1—N3	2.306 (5)	C4—C8ⁱ	1.505 (8)
Mn1—N3ⁱ	2.306 (5)	C5—C6	1.385 (8)
Mn1—Br1ⁱ	2.6140 (9)	C5—H5	0.9500
N1—C1	1.338 (6)	C6—C7	1.370 (8)
N1—C4	1.347 (7)	C6—H6	0.9500
N2—C3	1.336 (6)	C7—H7	0.9500
N2—C4	1.336 (7)	C8—C4ⁱ	1.505 (8)
N3—C5	1.338 (6)	O1—N5	1.217 (5)
N3—C8	1.344 (7)	N5—O1ⁱⁱ	1.217 (5)
N4—C8	1.326 (7)	N5—C9	1.466 (9)
N4—C7	1.334 (7)	C9—H9A	0.9800
C1—C2	1.379 (7)	C9—H9B	0.9800
C1—H1	0.9500	C9—H9C	0.9800

N1ⁱ—Mn1—N1	158.0 (2)	C3—C2—H2	121.3
N1ⁱ—Mn1—N3	71.06 (16)	N2—C3—C2	122.3 (6)
N1—Mn1—N3	93.09 (15)	N2—C3—H3	118.8
N1ⁱ—Mn1—N3ⁱ	93.09 (15)	C2—C3—H3	118.8
N1—Mn1—N3ⁱ	71.06 (16)	N2—C4—N1	127.2 (5)
N3—Mn1—N3ⁱ	89.5 (2)	N2—C4—C8ⁱ	117.8 (5)
N1ⁱ—Mn1—Br1	101.45 (11)	N1—C4—C8ⁱ	115.1 (5)
N1—Mn1—Br1	92.87 (11)	N3—C5—C6	121.6 (6)
N3—Mn1—Br1	88.07 (11)	N3—C5—H5	119.2
N3ⁱ—Mn1—Br1	163.59 (10)	C6—C5—H5	119.2
N1ⁱ—Mn1—Br1ⁱ	92.87 (11)	C7—C6—C5	116.8 (5)
N1—Mn1—Br1ⁱ	101.45 (11)	C7—C6—H6	121.6
N3—Mn1—Br1ⁱ	163.59 (10)	C5—C6—H6	121.6
N3ⁱ—Mn1—Br1ⁱ	88.07 (11)	N4—C7—C6	123.1 (6)
Br1—Mn1—Br1ⁱ	98.66 (5)	N4—C7—H7	118.4
C1—N1—C4	115.6 (5)	C6—C7—H7	118.4
C1—N1—Mn1	125.4 (4)	N4—C8—N3	126.3 (6)
C4—N1—Mn1	118.7 (4)	N4—C8—C4ⁱ	117.4 (5)
C3—N2—C4	115.4 (5)	N3—C8—C4ⁱ	116.2 (5)
C5—N3—C8	116.3 (5)	O1—N5—O1ⁱⁱ	121.6 (8)
C5—N3—Mn1	125.1 (4)	O1—N5—C9	119.2 (4)
C8—N3—Mn1	117.3 (4)	O1ⁱⁱ—N5—C9	119.2 (4)
C8—N4—C7	115.7 (5)	N5—C9—H9A	109.5
N1—C1—C2	122.0 (5)	N5—C9—H9B	109.5
N1—C1—H1	119.0	H9A—C9—H9B	109.5
C2—C1—H1	119.0	N5—C9—H9C	109.5
C1—C2—C3	117.4 (5)	H9A—C9—H9C	109.5
C1—C2—H2	121.3	H9B—C9—H9C	109.5

N1ⁱ—Mn1—N1—C1	130.5 (4)	Mn1—N1—C1—C2	175.5 (4)
N3—Mn1—N1—C1	87.8 (4)	N1—C1—C2—C3	−1.4 (8)
N3ⁱ—Mn1—N1—C1	176.2 (4)	C4—N2—C3—C2	0.8 (8)
Br1—Mn1—N1—C1	−0.4 (4)	C1—C2—C3—N2	0.8 (9)
Br1ⁱ—Mn1—N1—C1	−99.9 (4)	C3—N2—C4—N1	−2.1 (8)
N1ⁱ—Mn1—N1—C4	−54.4 (4)	C3—N2—C4—C8ⁱ	178.5 (5)
N3—Mn1—N1—C4	−97.1 (4)	C1—N1—C4—N2	1.6 (8)
N3ⁱ—Mn1—N1—C4	−8.7 (4)	Mn1—N1—C4—N2	−174.0 (4)
Br1—Mn1—N1—C4	174.7 (4)	C1—N1—C4—C8ⁱ	−179.0 (4)
Br1ⁱ—Mn1—N1—C4	75.3 (4)	Mn1—N1—C4—C8ⁱ	5.4 (6)
N1ⁱ—Mn1—N3—C5	178.2 (5)	C8—N3—C5—C6	0.5 (7)
N1—Mn1—N3—C5	−17.4 (4)	Mn1—N3—C5—C6	−166.5 (4)
N3ⁱ—Mn1—N3—C5	−88.4 (5)	N3—C5—C6—C7	0.3 (8)
Br1—Mn1—N3—C5	75.4 (4)	C8—N4—C7—C6	3.8 (9)
Br1ⁱ—Mn1—N3—C5	−169.8 (3)	C5—C6—C7—N4	−2.6 (9)
N1ⁱ—Mn1—N3—C8	11.3 (4)	C7—N4—C8—N3	−3.0 (9)
N1—Mn1—N3—C8	175.7 (4)	C7—N4—C8—C4ⁱ	178.6 (5)
N3ⁱ—Mn1—N3—C8	104.7 (4)	C5—N3—C8—N4	0.9 (8)
Br1—Mn1—N3—C8	−91.5 (4)	Mn1—N3—C8—N4	168.9 (4)
Br1ⁱ—Mn1—N3—C8	23.3 (7)	C5—N3—C8—C4ⁱ	179.3 (4)
C4—N1—C1—C2	0.3 (7)	Mn1—N3—C8—C4ⁱ	−12.7 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1	0.95	2.87	3.542 (6)	129
C2—H2···Br1ⁱⁱⁱ	0.95	2.91	3.802 (6)	156
C6—H6···Br1^iv	0.95	2.86	3.752 (5)	157
C9—H9C···N2^v	0.98	2.57	3.430 (5)	147

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

Experimental details

Crystal data
Chemical formula	[MnBr₂(C₈H₆N₄)₂]·CH₃NO₂
M_r	592.14
Crystal system, space group	Orthorhombic, C222₁
Temperature (K)	200
a, b, c (Å)	8.3876 (4), 12.1772 (6), 20.7479 (11)
V (Å³)	2119.14 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.43
Crystal size (mm)	0.17 × 0.10 × 0.07

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.825, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7872, 2608, 1818
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.078, 1.02
No. of reflections	2608
No. of parameters	143
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.86
Absolute structure	Flack (1983), 1121 Friedel pairs
Absolute structure parameter	−0.003 (16)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

Mn1—Br1	2.6140 (9)	Mn1—N3	2.306 (5)
Mn1—N1	2.292 (5)

N1ⁱ—Mn1—N1	158.0 (2)	Br1—Mn1—Br1ⁱ	98.66 (5)
N3—Mn1—N3ⁱ	89.5 (2)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1	0.95	2.87	3.542 (6)	129
C2—H2···Br1ⁱⁱ	0.95	2.91	3.802 (6)	156
C6—H6···Br1ⁱⁱⁱ	0.95	2.86	3.752 (5)	157
C9—H9C···N2^iv	0.98	2.57	3.430 (5)	147

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

Acknowledgements

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2010–0029626). The author thanks the KBSI, Jeonju Center, for the X-ray data collection.

References

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