{Tris[2-(5-bromo-2-oxidobenzyl­idene­amino)eth­yl]amine}manganese(III)

Hwang, I.-C.; Ha, K.

doi:10.1107/S160053680804172X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m63

doi:10.1107/S160053680804172X

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{Tris[2-(5-bromo-2-oxidobenzylideneamino)ethyl]amine}manganese(III)

In-Chul Hwang ^a and Kwang Ha ^b ^*

^aDepartment of Chemistry, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea, and ^bSchool 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 24 November 2008; accepted 9 December 2008; online 13 December 2008)

In the title complex, [Mn(C₂₇H₂₄Br₃N₄O₃)], the Mn^III ion is six-coordinated in a distorted octahedral environment by three N atoms and three O atoms from the trianion of the hexadentate ligand tris[2-(5-bromo-2-oxidobenzylideneamino)ethyl]amine. All three N (and O) atoms are cis to each other. The three N and the three O atoms are in a fac conformation among each other.

Related literature

For related literature, see: Hwang & Ha (2007 ); Mitra et al. (2006 ).

Experimental

Crystal data

[Mn(C₂₇H₂₄Br₃N₄O₃)]
M_r = 747.17
Triclinic, $[P \overline 1]$
a = 9.5892 (15) Å
b = 11.7558 (18) Å
c = 13.417 (2) Å
α = 80.041 (3)°
β = 78.084 (3)°
γ = 89.069 (3)°
V = 1457.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 4.60 mm⁻¹
T = 293 (2) K
0.25 × 0.15 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.422, T_max = 0.631
9621 measured reflections
5820 independent reflections
3794 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.238
S = 1.04
5820 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 2.66 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn—O2	1.884 (5)
Mn—O1	1.905 (5)
Mn—N3	2.064 (6)
Mn—N2	2.073 (6)
Mn—O3	2.105 (5)
Mn—N1	2.369 (6)

O2—Mn—N3	169.7 (2)
O1—Mn—N2	171.2 (2)
O3—Mn—N1	169.35 (19)

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, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804172X/bt2817sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680804172X/bt2817Isup2.hkl

checkCIF report

Comment top

In the title complex, [Mn(C₂₇H₂₄Br₃N₄O₃)], the Mn³⁺ ion is six-coordinated in a distorted octahedral environment by three N atoms and three O atoms from the trianion of the hexadentate ligand N,N',N"-tris(5-bromosalicylidene)tris(2-aminoethyl)amine. All three N (and O) atoms are adjacent and lie in the facial position (Fig.1 and Fig.2). The apical O1—Mn—N2, O2—Mn—N3 and O3—Mn—N1 bond angles are 171.2 (2)°, 169.7 (2)° and 169.35 (19)°, respectively (Table 1). The Mn—N bonds are on average 0.204 Å longer than the Mn—O bonds (mean lengths: Mn—N 2.169 Å, Mn—O 1.965 Å).

Related literature top

For related literature, see: Hwang & Ha (2007); Mitra et al. (2006).

Experimental top

Mn(CH₃COO)₃.2H₂O (0.50 g, 1.86 mmol) and N,N',N"-tris(5-bromosalicylidene)tris(2-aminoethyl)amine (Brsaltren; 1.30 g, 1.87 mmol) in EtOH (70 ml) were stirred for 3 h at room temparature. The formed precipitate was separated by filtration and washed with acetone, and dried under vacuum, to give a dark green powder (1.16 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from an acetone/EtOH solution. MS (FAB): m/z 746, 748, 750, 752 (Mn(Brsaltren-H)⁺); IR (KBr): 3448 cm^-1 (broad).

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, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound with the numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. View of the unit-cell contents of the title complex.

{Tris[2-(5-bromo-2-oxidobenzylideneamino)ethyl]amine}manganese(III) top

Crystal data top

[Mn(C₂₇H₂₄Br₃N₄O₃)]	Z = 2
M_r = 747.17	F(000) = 736
Triclinic, P1	D_x = 1.703 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5892 (15) Å	Cell parameters from 2848 reflections
b = 11.7558 (18) Å	θ = 2.8–24.2°
c = 13.417 (2) Å	µ = 4.60 mm⁻¹
α = 80.041 (3)°	T = 293 K
β = 78.084 (3)°	Plate, black
γ = 89.069 (3)°	0.25 × 0.15 × 0.10 mm
V = 1457.3 (4) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	5820 independent reflections
Radiation source: fine-focus sealed tube	3794 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
T_min = 0.422, T_max = 0.631	k = −10→14
9621 measured reflections	l = −16→16

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.238	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1477P)²] where P = (F_o² + 2F_c²)/3
5820 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 2.66 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Mn(C₂₇H₂₄Br₃N₄O₃)]	γ = 89.069 (3)°
M_r = 747.17	V = 1457.3 (4) Å³
Triclinic, P1	Z = 2
a = 9.5892 (15) Å	Mo Kα radiation
b = 11.7558 (18) Å	µ = 4.60 mm⁻¹
c = 13.417 (2) Å	T = 293 K
α = 80.041 (3)°	0.25 × 0.15 × 0.10 mm
β = 78.084 (3)°

Data collection top

Bruker SMART 1000 CCD diffractometer	5820 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3794 reflections with I > 2σ(I)
T_min = 0.422, T_max = 0.631	R_int = 0.025
9621 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.238	H-atom parameters constrained
S = 1.04	Δρ_max = 2.66 e Å⁻³
5820 reflections	Δρ_min = −0.52 e Å⁻³
343 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
Mn	0.89446 (11)	0.29092 (8)	0.37296 (8)	0.0339 (3)
Br1	0.43752 (9)	0.63459 (7)	0.07601 (7)	0.0562 (3)
Br2	0.65915 (12)	−0.10364 (9)	0.06388 (9)	0.0773 (4)
Br3	0.92383 (12)	0.21717 (12)	0.94128 (7)	0.0817 (4)
O1	0.8231 (6)	0.4437 (4)	0.3637 (4)	0.0440 (13)
O2	0.7336 (5)	0.2435 (4)	0.3291 (4)	0.0390 (12)
O3	0.7913 (6)	0.2169 (4)	0.5240 (4)	0.0438 (12)
N1	0.9821 (6)	0.3512 (5)	0.1933 (4)	0.0379 (14)
N2	0.9811 (6)	0.1304 (5)	0.3586 (4)	0.0345 (13)
N3	1.0442 (6)	0.3553 (5)	0.4404 (5)	0.0371 (14)
N4	1.2302 (6)	0.2689 (5)	0.2753 (5)	0.0421 (14)
C1	0.7448 (8)	0.4866 (6)	0.2978 (6)	0.0386 (16)
C2	0.6213 (9)	0.5503 (7)	0.3293 (6)	0.0471 (19)
H2	0.5994	0.5618	0.3976	0.056*
C3	0.5340 (9)	0.5950 (7)	0.2667 (7)	0.055 (2)
H3	0.4540	0.6354	0.2917	0.066*
C4	0.5650 (8)	0.5800 (6)	0.1638 (6)	0.0423 (18)
C5	0.6844 (9)	0.5206 (7)	0.1259 (6)	0.0475 (19)
H5	0.7041	0.5118	0.0569	0.057*
C6	0.7768 (8)	0.4732 (6)	0.1912 (6)	0.0416 (17)
C7	0.8986 (8)	0.4149 (6)	0.1456 (6)	0.0434 (18)
H7	0.9195	0.4240	0.0738	0.052*
C8	1.0976 (8)	0.2977 (7)	0.1326 (6)	0.0445 (18)
H8A	1.1076	0.3320	0.0603	0.053*
H8B	1.0754	0.2161	0.1395	0.053*
C9	1.2362 (8)	0.3111 (7)	0.1653 (6)	0.0462 (19)
H9A	1.3090	0.2695	0.1251	0.055*
H9B	1.2643	0.3922	0.1495	0.055*
C10	0.7244 (7)	0.1687 (6)	0.2679 (5)	0.0332 (15)
C11	0.6176 (8)	0.1814 (7)	0.2102 (6)	0.0440 (18)
H11	0.5571	0.2439	0.2131	0.053*
C12	0.6016 (8)	0.1000 (7)	0.1481 (6)	0.0465 (19)
H12	0.5314	0.1092	0.1090	0.056*
C13	0.6884 (8)	0.0077 (7)	0.1451 (6)	0.0451 (19)
C14	0.7932 (8)	−0.0056 (6)	0.1990 (6)	0.0422 (18)
H14	0.8513	−0.0695	0.1953	0.051*
C15	0.8169 (7)	0.0738 (6)	0.2602 (5)	0.0350 (15)
C16	0.9320 (8)	0.0567 (6)	0.3142 (6)	0.0386 (16)
H16	0.9751	−0.0149	0.3172	0.046*
C17	1.1154 (7)	0.0991 (6)	0.3940 (6)	0.0381 (16)
H17A	1.1218	0.0157	0.4099	0.046*
H17B	1.1168	0.1301	0.4562	0.046*
C18	1.2411 (8)	0.1481 (6)	0.3092 (6)	0.0430 (18)
H18A	1.3284	0.1337	0.3348	0.052*
H18B	1.2466	0.1085	0.2509	0.052*
C19	0.8246 (8)	0.2186 (6)	0.6102 (6)	0.0398 (17)
C20	0.7371 (9)	0.1565 (7)	0.7023 (6)	0.0442 (18)
H20	0.6570	0.1161	0.6971	0.053*
C21	0.7678 (9)	0.1546 (7)	0.8001 (6)	0.050 (2)
H21	0.7097	0.1128	0.8588	0.060*
C22	0.8866 (9)	0.2160 (7)	0.8083 (6)	0.049 (2)
C23	0.9756 (9)	0.2779 (7)	0.7228 (6)	0.0463 (19)
H23	1.0542	0.3187	0.7299	0.056*
C24	0.9449 (8)	0.2781 (6)	0.6232 (6)	0.0382 (16)
C25	1.0426 (9)	0.3453 (6)	0.5379 (6)	0.0421 (18)
H25	1.1132	0.3866	0.5554	0.051*
C26	1.1647 (8)	0.4255 (6)	0.3728 (6)	0.0451 (18)
H26A	1.2006	0.4773	0.4111	0.054*
H26B	1.1332	0.4717	0.3146	0.054*
C27	1.2823 (8)	0.3454 (7)	0.3340 (6)	0.0460 (19)
H27A	1.3628	0.3909	0.2906	0.055*
H27B	1.3144	0.3002	0.3923	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn	0.0380 (6)	0.0287 (6)	0.0393 (6)	0.0037 (4)	−0.0134 (5)	−0.0116 (5)
Br1	0.0540 (5)	0.0463 (5)	0.0767 (6)	0.0125 (4)	−0.0318 (5)	−0.0126 (4)
Br2	0.0940 (8)	0.0649 (7)	0.0999 (9)	0.0106 (6)	−0.0553 (7)	−0.0468 (6)
Br3	0.0812 (8)	0.1293 (11)	0.0422 (6)	0.0090 (7)	−0.0231 (5)	−0.0234 (6)
O1	0.053 (3)	0.035 (3)	0.054 (3)	0.010 (2)	−0.025 (3)	−0.020 (2)
O2	0.037 (3)	0.038 (3)	0.048 (3)	0.008 (2)	−0.013 (2)	−0.017 (2)
O3	0.048 (3)	0.050 (3)	0.037 (3)	−0.005 (2)	−0.015 (2)	−0.012 (2)
N1	0.039 (3)	0.038 (3)	0.038 (3)	0.005 (3)	−0.008 (3)	−0.008 (3)
N2	0.031 (3)	0.034 (3)	0.041 (3)	0.002 (2)	−0.010 (3)	−0.010 (3)
N3	0.045 (4)	0.028 (3)	0.043 (4)	0.003 (3)	−0.014 (3)	−0.012 (3)
N4	0.039 (3)	0.039 (4)	0.048 (4)	0.000 (3)	−0.010 (3)	−0.006 (3)
C1	0.040 (4)	0.028 (4)	0.050 (4)	0.000 (3)	−0.012 (3)	−0.011 (3)
C2	0.057 (5)	0.044 (4)	0.044 (4)	0.008 (4)	−0.013 (4)	−0.017 (4)
C3	0.043 (5)	0.042 (5)	0.088 (7)	0.014 (4)	−0.022 (4)	−0.026 (4)
C4	0.044 (4)	0.029 (4)	0.059 (5)	0.008 (3)	−0.023 (4)	−0.008 (3)
C5	0.057 (5)	0.043 (5)	0.046 (5)	0.001 (4)	−0.020 (4)	−0.005 (4)
C6	0.042 (4)	0.032 (4)	0.052 (5)	0.004 (3)	−0.015 (4)	−0.004 (3)
C7	0.048 (5)	0.045 (4)	0.039 (4)	−0.001 (4)	−0.009 (4)	−0.014 (3)
C8	0.049 (5)	0.044 (4)	0.041 (4)	0.008 (4)	−0.007 (3)	−0.010 (3)
C9	0.039 (4)	0.045 (5)	0.052 (5)	0.004 (3)	−0.006 (4)	−0.007 (4)
C10	0.033 (4)	0.030 (4)	0.036 (4)	−0.008 (3)	−0.004 (3)	−0.006 (3)
C11	0.036 (4)	0.050 (5)	0.051 (5)	0.008 (3)	−0.011 (3)	−0.021 (4)
C12	0.039 (4)	0.048 (5)	0.059 (5)	0.001 (3)	−0.020 (4)	−0.017 (4)
C13	0.050 (5)	0.040 (4)	0.054 (5)	0.000 (4)	−0.021 (4)	−0.023 (4)
C14	0.043 (4)	0.037 (4)	0.050 (5)	0.004 (3)	−0.011 (4)	−0.016 (3)
C15	0.033 (4)	0.031 (4)	0.044 (4)	0.003 (3)	−0.010 (3)	−0.011 (3)
C16	0.040 (4)	0.031 (4)	0.048 (4)	0.008 (3)	−0.012 (3)	−0.015 (3)
C17	0.036 (4)	0.036 (4)	0.046 (4)	0.005 (3)	−0.016 (3)	−0.010 (3)
C18	0.040 (4)	0.041 (4)	0.050 (5)	0.005 (3)	−0.010 (3)	−0.014 (4)
C19	0.044 (4)	0.032 (4)	0.045 (4)	0.004 (3)	−0.010 (3)	−0.013 (3)
C20	0.050 (5)	0.042 (4)	0.044 (4)	0.006 (4)	−0.009 (4)	−0.017 (3)
C21	0.051 (5)	0.054 (5)	0.043 (5)	0.010 (4)	−0.003 (4)	−0.012 (4)
C22	0.058 (5)	0.061 (5)	0.035 (4)	0.016 (4)	−0.017 (4)	−0.024 (4)
C23	0.054 (5)	0.049 (5)	0.042 (4)	0.006 (4)	−0.020 (4)	−0.015 (4)
C24	0.046 (4)	0.030 (4)	0.042 (4)	0.003 (3)	−0.014 (3)	−0.012 (3)
C25	0.056 (5)	0.025 (4)	0.051 (5)	0.005 (3)	−0.019 (4)	−0.013 (3)
C26	0.053 (5)	0.035 (4)	0.047 (5)	−0.008 (4)	−0.009 (4)	−0.008 (3)
C27	0.037 (4)	0.041 (4)	0.059 (5)	−0.007 (3)	−0.005 (4)	−0.011 (4)

Geometric parameters (Å, º) top

Mn—O2	1.884 (5)	C9—H9A	0.9700
Mn—O1	1.905 (5)	C9—H9B	0.9700
Mn—N3	2.064 (6)	C10—C11	1.397 (10)
Mn—N2	2.073 (6)	C10—C15	1.418 (9)
Mn—O3	2.105 (5)	C11—C12	1.403 (10)
Mn—N1	2.369 (6)	C11—H11	0.9300
Br1—C4	1.898 (7)	C12—C13	1.357 (10)
Br2—C13	1.901 (7)	C12—H12	0.9300
Br3—C22	1.892 (7)	C13—C14	1.346 (10)
O1—C1	1.306 (8)	C14—C15	1.396 (9)
O2—C10	1.319 (8)	C14—H14	0.9300
O3—C19	1.265 (8)	C15—C16	1.433 (9)
N1—C7	1.280 (9)	C16—H16	0.9300
N1—C8	1.438 (9)	C17—C18	1.519 (10)
N2—C16	1.278 (9)	C17—H17A	0.9700
N2—C17	1.482 (8)	C17—H17B	0.9700
N3—C25	1.291 (9)	C18—H18A	0.9700
N3—C26	1.476 (10)	C18—H18B	0.9700
N4—C18	1.424 (9)	C19—C24	1.416 (10)
N4—C27	1.449 (9)	C19—C20	1.429 (11)
N4—C9	1.464 (10)	C20—C21	1.400 (10)
C1—C2	1.420 (10)	C20—H20	0.9300
C1—C6	1.435 (10)	C21—C22	1.392 (12)
C2—C3	1.343 (10)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.379 (12)
C3—C4	1.392 (12)	C23—C24	1.426 (10)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.382 (11)	C24—C25	1.442 (11)
C5—C6	1.414 (10)	C25—H25	0.9300
C5—H5	0.9300	C26—C27	1.523 (10)
C6—C7	1.426 (10)	C26—H26A	0.9700
C7—H7	0.9300	C26—H26B	0.9700
C8—C9	1.501 (10)	C27—H27A	0.9700
C8—H8A	0.9700	C27—H27B	0.9700
C8—H8B	0.9700

O2—Mn—O1	89.3 (2)	C11—C10—C15	118.6 (6)
O2—Mn—N3	169.7 (2)	C10—C11—C12	120.0 (7)
O1—Mn—N3	84.2 (2)	C10—C11—H11	120.0
O2—Mn—N2	88.6 (2)	C12—C11—H11	120.0
O1—Mn—N2	171.2 (2)	C13—C12—C11	120.1 (7)
N3—Mn—N2	98.9 (2)	C13—C12—H12	120.0
O2—Mn—O3	86.9 (2)	C11—C12—H12	120.0
O1—Mn—O3	101.1 (2)	C14—C13—C12	121.0 (7)
N3—Mn—O3	86.5 (2)	C14—C13—Br2	120.2 (6)
N2—Mn—O3	87.3 (2)	C12—C13—Br2	118.9 (6)
O2—Mn—N1	83.2 (2)	C13—C14—C15	121.8 (7)
O1—Mn—N1	82.7 (2)	C13—C14—H14	119.1
N3—Mn—N1	103.9 (2)	C15—C14—H14	119.1
N2—Mn—N1	88.5 (2)	C14—C15—C10	118.5 (6)
O3—Mn—N1	169.35 (19)	C14—C15—C16	119.5 (6)
C1—O1—Mn	123.1 (4)	C10—C15—C16	122.0 (6)
C10—O2—Mn	129.3 (4)	N2—C16—C15	126.4 (6)
C19—O3—Mn	130.7 (5)	N2—C16—H16	116.8
C7—N1—C8	117.9 (6)	C15—C16—H16	116.8
C7—N1—Mn	115.4 (5)	N2—C17—C18	109.2 (6)
C8—N1—Mn	124.4 (5)	N2—C17—H17A	109.8
C16—N2—C17	115.8 (6)	C18—C17—H17A	109.8
C16—N2—Mn	124.4 (5)	N2—C17—H17B	109.8
C17—N2—Mn	119.6 (4)	C18—C17—H17B	109.8
C25—N3—C26	114.3 (6)	H17A—C17—H17B	108.3
C25—N3—Mn	127.1 (5)	N4—C18—C17	112.4 (6)
C26—N3—Mn	118.5 (5)	N4—C18—H18A	109.1
C18—N4—C27	117.0 (6)	C17—C18—H18A	109.1
C18—N4—C9	118.5 (6)	N4—C18—H18B	109.1
C27—N4—C9	117.8 (6)	C17—C18—H18B	109.1
O1—C1—C2	120.7 (7)	H18A—C18—H18B	107.9
O1—C1—C6	123.1 (6)	O3—C19—C24	124.5 (7)
C2—C1—C6	116.2 (7)	O3—C19—C20	119.2 (7)
C3—C2—C1	124.2 (8)	C24—C19—C20	116.3 (7)
C3—C2—H2	117.9	C21—C20—C19	122.2 (7)
C1—C2—H2	117.9	C21—C20—H20	118.9
C2—C3—C4	119.1 (7)	C19—C20—H20	118.9
C2—C3—H3	120.4	C22—C21—C20	119.0 (8)
C4—C3—H3	120.4	C22—C21—H21	120.5
C5—C4—C3	120.7 (7)	C20—C21—H21	120.5
C5—C4—Br1	119.4 (6)	C23—C22—C21	121.9 (7)
C3—C4—Br1	119.8 (6)	C23—C22—Br3	119.3 (6)
C4—C5—C6	120.6 (8)	C21—C22—Br3	118.8 (7)
C4—C5—H5	119.7	C22—C23—C24	118.8 (7)
C6—C5—H5	119.7	C22—C23—H23	120.6
C5—C6—C7	117.0 (7)	C24—C23—H23	120.6
C5—C6—C1	119.2 (7)	C19—C24—C23	121.8 (7)
C7—C6—C1	123.8 (7)	C19—C24—C25	122.9 (6)
N1—C7—C6	126.7 (7)	C23—C24—C25	115.3 (7)
N1—C7—H7	116.7	N3—C25—C24	128.0 (7)
C6—C7—H7	116.7	N3—C25—H25	116.0
N1—C8—C9	112.1 (6)	C24—C25—H25	116.0
N1—C8—H8A	109.2	N3—C26—C27	109.1 (6)
C9—C8—H8A	109.2	N3—C26—H26A	109.9
N1—C8—H8B	109.2	C27—C26—H26A	109.9
C9—C8—H8B	109.2	N3—C26—H26B	109.9
H8A—C8—H8B	107.9	C27—C26—H26B	109.9
N4—C9—C8	113.7 (7)	H26A—C26—H26B	108.3
N4—C9—H9A	108.8	N4—C27—C26	110.2 (6)
C8—C9—H9A	108.8	N4—C27—H27A	109.6
N4—C9—H9B	108.8	C26—C27—H27A	109.6
C8—C9—H9B	108.8	N4—C27—H27B	109.6
H9A—C9—H9B	107.7	C26—C27—H27B	109.6
O2—C10—C11	119.0 (6)	H27A—C27—H27B	108.1
O2—C10—C15	122.4 (6)

O2—Mn—O1—C1	−30.1 (6)	C8—N1—C7—C6	178.5 (7)
N3—Mn—O1—C1	158.0 (6)	Mn—N1—C7—C6	15.1 (10)
O3—Mn—O1—C1	−116.8 (6)	C5—C6—C7—N1	−168.3 (7)
N1—Mn—O1—C1	53.1 (6)	C1—C6—C7—N1	12.2 (12)
O1—Mn—O2—C10	142.7 (6)	C7—N1—C8—C9	133.5 (7)
N3—Mn—O2—C10	−166.1 (11)	Mn—N1—C8—C9	−64.7 (8)
N2—Mn—O2—C10	−28.8 (6)	C18—N4—C9—C8	80.4 (8)
O3—Mn—O2—C10	−116.1 (6)	C27—N4—C9—C8	−129.2 (7)
N1—Mn—O2—C10	59.9 (6)	N1—C8—C9—N4	55.0 (9)
O2—Mn—O3—C19	−173.2 (6)	Mn—O2—C10—C11	−152.4 (6)
O1—Mn—O3—C19	−84.5 (6)	Mn—O2—C10—C15	29.2 (9)
N3—Mn—O3—C19	−1.1 (6)	O2—C10—C11—C12	−177.1 (7)
N2—Mn—O3—C19	98.0 (6)	C15—C10—C11—C12	1.3 (11)
N1—Mn—O3—C19	165.3 (9)	C10—C11—C12—C13	1.0 (12)
O2—Mn—N1—C7	51.5 (5)	C11—C12—C13—C14	−1.8 (13)
O1—Mn—N1—C7	−38.7 (5)	C11—C12—C13—Br2	177.8 (6)
N3—Mn—N1—C7	−120.9 (5)	C12—C13—C14—C15	0.3 (13)
N2—Mn—N1—C7	140.3 (5)	Br2—C13—C14—C15	−179.4 (6)
O3—Mn—N1—C7	73.1 (12)	C13—C14—C15—C10	2.1 (12)
O2—Mn—N1—C8	−110.7 (6)	C13—C14—C15—C16	−178.6 (8)
O1—Mn—N1—C8	159.1 (6)	O2—C10—C15—C14	175.6 (7)
N3—Mn—N1—C8	76.9 (6)	C11—C10—C15—C14	−2.8 (10)
N2—Mn—N1—C8	−21.9 (6)	O2—C10—C15—C16	−3.6 (11)
O3—Mn—N1—C8	−89.1 (12)	C11—C10—C15—C16	177.9 (7)
O2—Mn—N2—C16	11.6 (6)	C17—N2—C16—C15	−170.2 (7)
N3—Mn—N2—C16	−175.5 (6)	Mn—N2—C16—C15	5.0 (11)
O3—Mn—N2—C16	98.5 (6)	C14—C15—C16—N2	167.7 (7)
N1—Mn—N2—C16	−71.7 (6)	C10—C15—C16—N2	−13.1 (12)
O2—Mn—N2—C17	−173.4 (5)	C16—N2—C17—C18	92.1 (7)
N3—Mn—N2—C17	−0.5 (5)	Mn—N2—C17—C18	−83.4 (6)
O3—Mn—N2—C17	−86.5 (5)	C27—N4—C18—C17	85.2 (8)
N1—Mn—N2—C17	103.3 (5)	C9—N4—C18—C17	−124.2 (7)
O2—Mn—N3—C25	46.9 (15)	N2—C17—C18—N4	53.6 (8)
O1—Mn—N3—C25	98.5 (6)	Mn—O3—C19—C24	2.1 (11)
N2—Mn—N3—C25	−89.8 (6)	Mn—O3—C19—C20	−177.6 (5)
O3—Mn—N3—C25	−3.1 (6)	O3—C19—C20—C21	179.9 (7)
N1—Mn—N3—C25	179.5 (6)	C24—C19—C20—C21	0.1 (10)
O2—Mn—N3—C26	−130.0 (12)	C19—C20—C21—C22	0.7 (11)
O1—Mn—N3—C26	−78.4 (5)	C20—C21—C22—C23	−0.6 (12)
N2—Mn—N3—C26	93.3 (5)	C20—C21—C22—Br3	177.9 (6)
O3—Mn—N3—C26	−180.0 (5)	C21—C22—C23—C24	−0.3 (12)
N1—Mn—N3—C26	2.6 (5)	Br3—C22—C23—C24	−178.8 (5)
Mn—O1—C1—C2	135.6 (6)	O3—C19—C24—C23	179.2 (7)
Mn—O1—C1—C6	−44.6 (9)	C20—C19—C24—C23	−1.1 (10)
O1—C1—C2—C3	−178.6 (7)	O3—C19—C24—C25	0.8 (11)
C6—C1—C2—C3	1.5 (12)	C20—C19—C24—C25	−179.4 (6)
C1—C2—C3—C4	−0.6 (13)	C22—C23—C24—C19	1.2 (11)
C2—C3—C4—C5	−0.5 (13)	C22—C23—C24—C25	179.7 (7)
C2—C3—C4—Br1	176.4 (6)	C26—N3—C25—C24	−176.3 (7)
C3—C4—C5—C6	0.5 (12)	Mn—N3—C25—C24	6.7 (11)
Br1—C4—C5—C6	−176.3 (6)	C19—C24—C25—N3	−5.6 (12)
C4—C5—C6—C7	−179.1 (7)	C23—C24—C25—N3	176.0 (7)
C4—C5—C6—C1	0.5 (12)	C25—N3—C26—C27	97.6 (7)
O1—C1—C6—C5	178.8 (7)	Mn—N3—C26—C27	−85.1 (7)
C2—C1—C6—C5	−1.4 (11)	C18—N4—C27—C26	−123.4 (7)
O1—C1—C6—C7	−1.7 (12)	C9—N4—C27—C26	85.7 (8)
C2—C1—C6—C7	178.1 (7)	N3—C26—C27—N4	60.4 (8)

Experimental details

Crystal data
Chemical formula	[Mn(C₂₇H₂₄Br₃N₄O₃)]
M_r	747.17
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.5892 (15), 11.7558 (18), 13.417 (2)
α, β, γ (°)	80.041 (3), 78.084 (3), 89.069 (3)
V (Å³)	1457.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.60
Crystal size (mm)	0.25 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.422, 0.631
No. of measured, independent and observed [I > 2σ(I)] reflections	9621, 5820, 3794
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.238, 1.04
No. of reflections	5820
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.66, −0.52

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Mn—O2	1.884 (5)	Mn—N2	2.073 (6)
Mn—O1	1.905 (5)	Mn—O3	2.105 (5)
Mn—N3	2.064 (6)	Mn—N1	2.369 (6)

O2—Mn—N3	169.7 (2)	O3—Mn—N1	169.35 (19)
O1—Mn—N2	171.2 (2)

Acknowledgements

This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2007–412-J02001).

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hwang, I.-C. & Ha, K. (2007). Acta Cryst. E63, m2365. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar