{2,2'-[5-Bromo-pyridine-2,3-diylbis(nitrilo-methyl-idyne)]diphenolato}chlorido(dimethyl-formamide)manganese(III).

In the title complex, [Mn(C(19)H(12)BrN(3)O(2))Cl(C(3)H(7)NO)], the Mn(III) ion is coordinated by two N and two O atoms from the tetra-dentate Schiff base ligand, one O atom from the dimethyl-formamide ligand and a Cl anion in a distorted octa-hedral geometry. In the crystal structure, weak inter-molecular C-H⋯Cl hydrogen bonds link the mol-ecules 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 = 557.71

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.06

3945 reflections

291 parameters

H-atom parameters constrained

Δρmax = 1.30 e Å−3

Δρmin = −0.52 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C19H12BrN3O2)Cl(C3H7NO)]	F(000) = 1120
Mr = 557.71	Dx = 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

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

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(Fo2) + (0.0643P)2 + 1.7733P] where P = (Fo2 + 2Fc2)/3
3945 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 1.30 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .