{2,2′-[5-Bromo­pyridine-2,3-diylbis(nitrilo­methyl­idyne)]diphenolato}chlorido(dimethyl­formamide)manganese(III)

Xie, H.; Meng, S.; Zhu, Y.; Bai, P.

doi:10.1107/S1600536809049484

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1671

doi:10.1107/S1600536809049484

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{2,2′-[5-Bromopyridine-2,3-diylbis(nitrilomethylidyne)]diphenolato}chlorido(dimethylformamide)manganese(III)

Hai Xie,^a ^* Shuangming Meng,^a Yongjun Zhu ^a and Peiwan Bai ^a

^aCollege of Chemistry & Chemical Engineering, Shanxi Datong University, Shanxi 037009, People's Republic of China
^*Correspondence e-mail: haixiedt@126.com

(Received 13 November 2009; accepted 19 November 2009; online 25 November 2009)

In the title complex, [Mn(C₁₉H₁₂BrN₃O₂)Cl(C₃H₇NO)], the Mn^III ion is coordinated by two N and two O atoms from the tetradentate Schiff base ligand, one O atom from the dimethylformamide ligand and a Cl anion in a distorted octahedral geometry. In the crystal structure, weak intermolecular C—H⋯Cl hydrogen bonds link the molecules into centrosymmetric dimers with a short distance of 3.878 (3) Å between the centroids of the aromatic rings.

Related literature

For related structures, see: Li et al. (2008 ); Eltayeb et al. (2008a ,b ); Fei & Fang (2008 ).

Experimental

Crystal data

[Mn(C₁₉H₁₂BrN₃O₂)Cl(C₃H₇NO)]
M_r = 557.71
Monoclinic, P 2₁ /c
a = 13.2834 (11) Å
b = 15.4971 (13) Å
c = 12.2314 (11) Å
β = 117.143 (1)°
V = 2240.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.52 mm⁻¹
T = 293 K
0.31 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.508, T_max = 0.646
10906 measured reflections
3945 independent reflections
3238 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.116
S = 1.06
3945 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 1.30 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯Cl1ⁱ	0.93	2.81	3.691 (2)	159
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049484/cv2658sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049484/cv2658Isup2.hkl

checkCIF report

Comment top

Because of their interesting structures and wide potential applications, the synthesis and structural investigation of Schiff base complexes have been given much attention. Furthermore, these types of complexes play an important part in the development of coordination chemistry as well as inorganic biochemistry, catalysis, optical materials and so on (Li et al., 2008; Fei & Fang, 2008).

The crystal structure of the title compound is shown in Fig. 1. The coordination sphere of the Mn^III ion is a slightly distorted octahedron, in which the four equatorial positions are occupied by two N atoms and two O atoms coming from the tetradentate Schiff base ligand, and the two axial ones with a trans conformation are occupied by one Cl ion and one O atom of the coordinated dimethylamine-methoxyl, respectively. The Mn—N, Mn—O and Mn—Cl bond lengths are basically consistant with those corresponding distances in other Mn-Schiff base complexes (Li et al., 2008; Eltayeb et al., 2008a, b). It is worth noting that centrosymmetric dimers with the short distance of 3.878 (3) Å between the centroids of aromatic rings are formed under the help of the weak intermolecular C—H···Cl hydrogen bond interaction (Table 1).

Related literature top

For related structures, see: Li et al. (2008); Eltayeb et al. (2008a,b); Fei & Fang (2008).

Experimental top

The Schiff base ligand was synthesized by condensation of 5-bromo-2,3-diaminopyridine and 2-hydroxy-benzaldehyde with the ratio 1:2 in ethanol. The synthesis of the title complex was carried out by reacting Mn(ClO₄)₂.6H₂O, and the schiff-base ligand (1:1, molar ratio) in methanol. After the stirring process was continued for about one hour at room temperature, the mixture was filtered. The insoluble dark-brown solid was filtered out, dissolved in DMF and layered with ether. After one month, the block dark-brown crystals suitable for X-ray diffraction were obtained with a yield about 50%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. All H-atoms are omitted for clarity.

{2,2'-[5-Bromopyridine-2,3-diylbis(nitrilomethylidyne)]diphenolato} chlorido(dimethylformamide)manganese(III) top

Crystal data top

[Mn(C₁₉H₁₂BrN₃O₂)Cl(C₃H₇NO)]	F(000) = 1120
M_r = 557.71	D_x = 1.653 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2012 reflections
a = 13.2834 (11) Å	θ = 2.1–26.7°
b = 15.4971 (13) Å	µ = 2.52 mm⁻¹
c = 12.2314 (11) Å	T = 293 K
β = 117.143 (1)°	Block, dark-brown
V = 2240.6 (3) Å³	0.31 × 0.21 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3945 independent reflections
Radiation source: fine-focus sealed tube	3238 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −15→15
T_min = 0.508, T_max = 0.646	k = −13→18
10906 measured reflections	l = −14→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0643P)² + 1.7733P] where P = (F_o² + 2F_c²)/3
3945 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 1.30 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Mn(C₁₉H₁₂BrN₃O₂)Cl(C₃H₇NO)]	V = 2240.6 (3) Å³
M_r = 557.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2834 (11) Å	µ = 2.52 mm⁻¹
b = 15.4971 (13) Å	T = 293 K
c = 12.2314 (11) Å	0.31 × 0.21 × 0.19 mm
β = 117.143 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3945 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	3238 reflections with I > 2σ(I)
T_min = 0.508, T_max = 0.646	R_int = 0.022
10906 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.06	Δρ_max = 1.30 e Å⁻³
3945 reflections	Δρ_min = −0.52 e Å⁻³
291 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	0.45611 (4)	0.63147 (3)	0.36373 (4)	0.06441 (17)
Mn1	0.81172 (4)	0.45734 (3)	0.12690 (5)	0.03870 (16)
Cl1	0.68097 (8)	0.34011 (7)	0.05359 (10)	0.0587 (3)
O1	0.9460 (2)	0.38529 (17)	0.1822 (2)	0.0521 (6)
O2	0.7824 (2)	0.49890 (18)	−0.0267 (2)	0.0518 (6)
O3	0.9317 (2)	0.56444 (18)	0.2006 (3)	0.0567 (7)
N1	0.8278 (2)	0.45131 (18)	0.3010 (3)	0.0423 (7)
N2	0.6755 (2)	0.54058 (18)	0.1157 (3)	0.0418 (7)
N3	0.7332 (3)	0.4802 (2)	0.4180 (3)	0.0516 (8)
N4	1.0806 (3)	0.6366 (2)	0.1995 (3)	0.0503 (8)
C1	0.7383 (3)	0.4907 (2)	0.3157 (3)	0.0418 (8)
C2	0.6585 (3)	0.5396 (2)	0.2180 (3)	0.0401 (8)
C3	0.5713 (3)	0.5821 (2)	0.2312 (3)	0.0459 (8)
H3	0.5175	0.6151	0.1681	0.055*
C4	0.5694 (3)	0.5727 (2)	0.3378 (4)	0.0482 (9)
C5	0.6486 (3)	0.5208 (3)	0.4285 (4)	0.0530 (9)
H5	0.6428	0.5135	0.5009	0.064*
C6	1.0097 (3)	0.3730 (2)	0.3939 (4)	0.0455 (9)
C7	1.0197 (3)	0.3568 (2)	0.2899 (4)	0.0455 (9)
C8	1.1146 (3)	0.3060 (3)	0.3007 (4)	0.0550 (10)
H8	1.1228	0.2951	0.2304	0.066*
C9	1.1925 (3)	0.2733 (3)	0.4095 (5)	0.0618 (11)
H9	1.2519	0.2399	0.4125	0.074*
C10	1.1839 (3)	0.2892 (3)	0.5137 (4)	0.0623 (11)
H10	1.2372	0.2675	0.5888	0.075*
C11	1.0937 (3)	0.3385 (3)	0.5056 (4)	0.0559 (10)
H11	1.0881	0.3496	0.5774	0.067*
C12	0.9159 (3)	0.4184 (2)	0.3953 (3)	0.0463 (8)
H12	0.9177	0.4252	0.4717	0.056*
C13	0.6144 (3)	0.5898 (2)	−0.0885 (3)	0.0432 (8)
C14	0.7045 (3)	0.5503 (2)	−0.1064 (3)	0.0450 (8)
C15	0.7093 (4)	0.5706 (3)	−0.2114 (4)	0.0555 (10)
H15	0.7676	0.5487	−0.2254	0.067*
C16	0.6292 (4)	0.6232 (3)	−0.2976 (4)	0.0620 (11)
H16	0.6349	0.6356	−0.3689	0.074*
C17	0.5388 (4)	0.6590 (3)	−0.2831 (4)	0.0605 (11)
H17	0.4853	0.6937	−0.3438	0.073*
C18	0.5322 (3)	0.6420 (3)	−0.1807 (4)	0.0528 (9)
H18	0.4728	0.6645	−0.1693	0.063*
C19	0.6052 (3)	0.5823 (2)	0.0182 (3)	0.0418 (8)
H19	0.5438	0.6091	0.0213	0.050*
C20	0.9824 (3)	0.5958 (3)	0.1477 (4)	0.0518 (9)
H20	0.9484	0.5902	0.0627	0.062*
C21	1.1408 (4)	0.6469 (4)	0.3284 (4)	0.0799 (14)
H21A	1.1098	0.6946	0.3532	0.120*
H21B	1.2191	0.6579	0.3515	0.120*
H21C	1.1344	0.5952	0.3680	0.120*
C22	1.1358 (4)	0.6716 (3)	0.1327 (4)	0.0620 (11)
H22A	1.0857	0.6687	0.0462	0.093*
H22B	1.2030	0.6390	0.1508	0.093*
H22C	1.1558	0.7307	0.1562	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0571 (3)	0.0792 (3)	0.0650 (3)	0.0171 (2)	0.0349 (2)	0.0026 (2)
Mn1	0.0317 (3)	0.0426 (3)	0.0388 (3)	0.0076 (2)	0.0134 (2)	0.0029 (2)
Cl1	0.0422 (5)	0.0516 (5)	0.0713 (7)	0.0020 (4)	0.0165 (5)	−0.0049 (5)
O1	0.0397 (14)	0.0642 (17)	0.0499 (15)	0.0126 (12)	0.0184 (12)	0.0036 (12)
O2	0.0499 (15)	0.0583 (16)	0.0463 (14)	0.0128 (13)	0.0212 (12)	0.0064 (12)
O3	0.0516 (15)	0.0600 (17)	0.0592 (17)	−0.0085 (13)	0.0259 (14)	−0.0013 (13)
N1	0.0373 (15)	0.0417 (16)	0.0448 (16)	0.0038 (12)	0.0161 (13)	0.0031 (13)
N2	0.0378 (15)	0.0421 (16)	0.0402 (16)	0.0030 (12)	0.0133 (13)	0.0013 (12)
N3	0.0526 (19)	0.061 (2)	0.0447 (18)	0.0090 (16)	0.0252 (15)	0.0067 (14)
N4	0.0459 (18)	0.0497 (18)	0.057 (2)	0.0010 (14)	0.0248 (16)	0.0029 (14)
C1	0.0361 (18)	0.0406 (19)	0.047 (2)	0.0007 (15)	0.0179 (16)	−0.0015 (15)
C2	0.0362 (18)	0.0412 (18)	0.0413 (19)	−0.0008 (14)	0.0163 (15)	−0.0027 (14)
C3	0.0387 (19)	0.045 (2)	0.047 (2)	0.0038 (16)	0.0134 (16)	0.0002 (16)
C4	0.042 (2)	0.051 (2)	0.055 (2)	0.0018 (16)	0.0245 (18)	−0.0021 (17)
C5	0.057 (2)	0.057 (2)	0.050 (2)	0.0087 (19)	0.0292 (19)	0.0052 (18)
C6	0.0330 (18)	0.045 (2)	0.052 (2)	0.0016 (14)	0.0131 (16)	0.0069 (16)
C7	0.0298 (17)	0.0419 (19)	0.058 (2)	0.0004 (14)	0.0142 (17)	0.0061 (16)
C8	0.044 (2)	0.049 (2)	0.073 (3)	0.0061 (17)	0.028 (2)	0.0050 (19)
C9	0.033 (2)	0.054 (2)	0.089 (3)	0.0102 (17)	0.020 (2)	0.014 (2)
C10	0.039 (2)	0.060 (3)	0.070 (3)	0.0065 (18)	0.009 (2)	0.019 (2)
C11	0.043 (2)	0.059 (2)	0.053 (2)	−0.0006 (18)	0.0110 (18)	0.0064 (19)
C12	0.042 (2)	0.049 (2)	0.044 (2)	0.0027 (16)	0.0164 (17)	0.0019 (16)
C13	0.0367 (18)	0.0402 (19)	0.0426 (19)	−0.0040 (15)	0.0094 (15)	0.0022 (15)
C14	0.0415 (19)	0.046 (2)	0.0420 (19)	−0.0066 (16)	0.0139 (16)	−0.0031 (15)
C15	0.056 (2)	0.063 (3)	0.051 (2)	−0.004 (2)	0.027 (2)	−0.0019 (19)
C16	0.064 (3)	0.071 (3)	0.045 (2)	−0.006 (2)	0.020 (2)	0.0082 (19)
C17	0.059 (3)	0.063 (3)	0.048 (2)	0.004 (2)	0.014 (2)	0.0117 (19)
C18	0.046 (2)	0.056 (2)	0.050 (2)	0.0023 (17)	0.0159 (18)	0.0049 (18)
C19	0.0339 (17)	0.0390 (18)	0.049 (2)	0.0023 (15)	0.0159 (16)	0.0002 (15)
C20	0.049 (2)	0.053 (2)	0.050 (2)	0.0000 (18)	0.0201 (19)	0.0005 (18)
C21	0.067 (3)	0.105 (4)	0.062 (3)	−0.029 (3)	0.024 (2)	−0.006 (3)
C22	0.060 (3)	0.063 (3)	0.077 (3)	0.002 (2)	0.043 (2)	0.008 (2)

Geometric parameters (Å, º) top

Br1—C4	1.906 (4)	C7—C8	1.441 (5)
Mn1—O2	1.851 (3)	C8—C9	1.357 (6)
Mn1—O1	1.945 (2)	C8—H8	0.9300
Mn1—N1	2.043 (3)	C9—C10	1.352 (6)
Mn1—N2	2.175 (3)	C9—H9	0.9300
Mn1—O3	2.190 (3)	C10—C11	1.387 (6)
Mn1—Cl1	2.3875 (11)	C10—H10	0.9300
O1—C7	1.308 (4)	C11—H11	0.9300
O2—C14	1.317 (4)	C12—H12	0.9300
O3—C20	1.227 (5)	C13—C19	1.371 (5)
N1—C12	1.315 (4)	C13—C18	1.412 (5)
N1—C1	1.419 (4)	C13—C14	1.447 (5)
N2—C19	1.302 (4)	C14—C15	1.352 (5)
N2—C2	1.369 (4)	C15—C16	1.372 (6)
N3—C1	1.294 (5)	C15—H15	0.9300
N3—C5	1.344 (5)	C16—C17	1.404 (6)
N4—C20	1.323 (5)	C16—H16	0.9300
N4—C21	1.414 (6)	C17—C18	1.322 (6)
N4—C22	1.431 (5)	C17—H17	0.9300
C1—C2	1.404 (5)	C18—H18	0.9300
C2—C3	1.404 (5)	C19—H19	0.9300
C3—C4	1.324 (5)	C20—H20	0.9300
C3—H3	0.9300	C21—H21A	0.9600
C4—C5	1.385 (5)	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.362 (5)	C22—H22A	0.9600
C6—C11	1.416 (5)	C22—H22B	0.9600
C6—C12	1.438 (5)	C22—H22C	0.9600

O2—Mn1—O1	106.71 (11)	C9—C8—H8	118.8
O2—Mn1—N1	161.27 (12)	C7—C8—H8	118.8
O1—Mn1—N1	88.18 (11)	C10—C9—C8	120.2 (4)
O2—Mn1—N2	86.90 (11)	C10—C9—H9	119.9
O1—Mn1—N2	165.18 (11)	C8—C9—H9	119.9
N1—Mn1—N2	77.35 (11)	C9—C10—C11	118.3 (4)
O2—Mn1—O3	86.03 (11)	C9—C10—H10	120.8
O1—Mn1—O3	84.97 (11)	C11—C10—H10	120.8
N1—Mn1—O3	83.99 (11)	C10—C11—C6	123.5 (4)
N2—Mn1—O3	90.27 (11)	C10—C11—H11	118.3
O2—Mn1—Cl1	95.93 (9)	C6—C11—H11	118.3
O1—Mn1—Cl1	95.06 (9)	N1—C12—C6	127.6 (3)
N1—Mn1—Cl1	93.95 (9)	N1—C12—H12	116.2
N2—Mn1—Cl1	89.19 (8)	C6—C12—H12	116.2
O3—Mn1—Cl1	177.93 (8)	C19—C13—C18	115.9 (3)
C7—O1—Mn1	133.6 (2)	C19—C13—C14	123.2 (3)
C14—O2—Mn1	133.8 (2)	C18—C13—C14	120.8 (3)
C20—O3—Mn1	123.7 (3)	O2—C14—C15	118.8 (4)
C12—N1—C1	121.2 (3)	O2—C14—C13	124.6 (3)
C12—N1—Mn1	124.0 (2)	C15—C14—C13	116.5 (3)
C1—N1—Mn1	114.7 (2)	C14—C15—C16	120.8 (4)
C19—N2—C2	119.6 (3)	C14—C15—H15	119.6
C19—N2—Mn1	125.5 (2)	C16—C15—H15	119.6
C2—N2—Mn1	114.5 (2)	C15—C16—C17	123.1 (4)
C1—N3—C5	116.6 (3)	C15—C16—H16	118.4
C20—N4—C21	121.4 (4)	C17—C16—H16	118.4
C20—N4—C22	123.9 (4)	C18—C17—C16	118.0 (4)
C21—N4—C22	114.7 (4)	C18—C17—H17	121.0
N3—C1—C2	122.6 (3)	C16—C17—H17	121.0
N3—C1—N1	119.0 (3)	C17—C18—C13	120.7 (4)
C2—C1—N1	118.4 (3)	C17—C18—H18	119.7
N2—C2—C1	114.1 (3)	C13—C18—H18	119.7
N2—C2—C3	126.0 (3)	N2—C19—C13	125.1 (3)
C1—C2—C3	119.9 (3)	N2—C19—H19	117.4
C4—C3—C2	116.7 (3)	C13—C19—H19	117.4
C4—C3—H3	121.7	O3—C20—N4	126.5 (4)
C2—C3—H3	121.7	O3—C20—H20	116.7
C3—C4—C5	120.3 (3)	N4—C20—H20	116.7
C3—C4—Br1	118.9 (3)	N4—C21—H21A	109.5
C5—C4—Br1	120.9 (3)	N4—C21—H21B	109.5
N3—C5—C4	123.9 (4)	H21A—C21—H21B	109.5
N3—C5—H5	118.1	N4—C21—H21C	109.5
C4—C5—H5	118.1	H21A—C21—H21C	109.5
C7—C6—C11	117.6 (3)	H21B—C21—H21C	109.5
C7—C6—C12	123.7 (3)	N4—C22—H22A	109.5
C11—C6—C12	118.6 (4)	N4—C22—H22B	109.5
O1—C7—C6	122.2 (3)	H22A—C22—H22B	109.5
O1—C7—C8	119.9 (4)	N4—C22—H22C	109.5
C6—C7—C8	118.0 (3)	H22A—C22—H22C	109.5
C9—C8—C7	122.5 (4)	H22B—C22—H22C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Cl1ⁱ	0.93	2.81	3.691 (2)	159

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₉H₁₂BrN₃O₂)Cl(C₃H₇NO)]
M_r	557.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.2834 (11), 15.4971 (13), 12.2314 (11)
β (°)	117.143 (1)
V (Å³)	2240.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.52
Crystal size (mm)	0.31 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.508, 0.646
No. of measured, independent and observed [I > 2σ(I)] reflections	10906, 3945, 3238
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.116, 1.06
No. of reflections	3945
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.30, −0.52

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Cl1ⁱ	0.93	2.81	3.691 (2)	158.87

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

This work was funded by a research grant from the Shanxi Datong University Foundation of Shanxi Province of the People's Republic of China (grant No. 2008 K1). We also thank Huazhong Normal University for supporting this study.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008a). Acta Cryst. E64, m124–m125. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008b). Acta Cryst. E64, m670–m671. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fei, L. & Fang, Z. (2008). Acta Cryst. E64, m406. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, C. H., Huang, K. L., Dou, J. M., Chi, Y. N., Xu, Y. Q., Shen, L., Wang, D. Q. & Hu, C. W. (2008). CrystEngComm, 8, 3141–3143. CAS Google Scholar
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Page m1671

doi:10.1107/S1600536809049484

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

{2,2′-[5-Bromo­pyridine-2,3-diylbis(nitrilo­methyl­­idyne)]diphenolato}chlorido(di­methyl­formamide)manganese(III)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{2,2′-[5-Bromopyridine-2,3-diylbis(nitrilomethylidyne)]diphenolato}chlorido(dimethylformamide)manganese(III)