Dichlorido{2-morpholino-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine-κN,N',N''}manganese(II).

In the title compound, [MnCl(2)(C(13)H(19)N(3)O)], the Mn(II) ion is penta-coordinated in a distorted square-pyramidal geometry. The coordination environment is defined by the N,N',N''-tridentate Schiff base ligand and one Cl atom in the basal positions and one Cl atom in the apical position. In the crystal, inter-molecular C-H⋯Cl hydrogen bonds link the mol-ecules into a three-dimensional network. An intra-molecular C-H⋯Cl hydrogen bond is also observed.

Related literature

For the crystal structure of the analogous CdII complex, see: Ikmal Hisham et al. (2010 ▶). For the crystal structure of [MnCl2(C24H25N3)], a structurally similar MnII complex, see: Schmiege et al. (2007 ▶).

Experimental

Crystal data

[MnCl2(C13H19N3O)]

M = 359.15

Monoclinic,

a = 9.6117 (6) Å

b = 13.8507 (8) Å

c = 12.1330 (7) Å

β = 106.738 (1)°

V = 1546.82 (16) Å3

Z = 4

Mo Kα radiation

μ = 1.20 mm−1

T = 100 K

0.40 × 0.35 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.646, T max = 0.754

15613 measured reflections

3543 independent reflections

3370 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.053

S = 1.11

3543 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050221/is2637sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050221/is2637Isup2.hkl

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

[MnCl2(C13H19N3O)]	F(000) = 740
Mr = 359.15	Dx = 1.542 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9925 reflections
a = 9.6117 (6) Å	θ = 2.2–31.4°
b = 13.8507 (8) Å	µ = 1.20 mm−1
c = 12.1330 (7) Å	T = 100 K
β = 106.738 (1)°	Block, orange
V = 1546.82 (16) Å3	0.40 × 0.35 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	3543 independent reflections
Radiation source: fine-focus sealed tube	3370 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.646, Tmax = 0.754	k = −16→17
15613 measured reflections	l = −15→15

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.053	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0202P)2 + 0.8164P] where P = (Fo2 + 2Fc2)/3
3543 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 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
Mn1	0.227997 (19)	0.094201 (13)	0.662679 (15)	0.01293 (6)
Cl1	0.46326 (3)	0.14018 (2)	0.77456 (2)	0.01695 (7)
Cl2	0.04111 (3)	0.21023 (2)	0.63296 (3)	0.01823 (7)
O1	0.18363 (10)	0.06033 (8)	1.01401 (8)	0.0220 (2)
N1	0.26463 (11)	0.11770 (8)	0.48657 (9)	0.0147 (2)
N2	0.24422 (11)	−0.04625 (8)	0.58539 (9)	0.0152 (2)
N3	0.15480 (11)	−0.01520 (8)	0.78545 (8)	0.0144 (2)
C1	0.25654 (14)	0.20208 (9)	0.43212 (11)	0.0176 (2)
H1	0.2251	0.2573	0.4647	0.021*
C2	0.29241 (14)	0.21242 (10)	0.32937 (11)	0.0195 (3)
H2	0.2854	0.2735	0.2926	0.023*
C3	0.33834 (14)	0.13223 (10)	0.28210 (11)	0.0198 (3)
H3	0.3649	0.1375	0.2127	0.024*
C4	0.34524 (13)	0.04350 (10)	0.33739 (11)	0.0172 (2)
H4	0.3760	−0.0127	0.3061	0.021*
C5	0.30645 (12)	0.03845 (9)	0.43907 (10)	0.0141 (2)
C6	0.29694 (13)	−0.05409 (9)	0.50011 (10)	0.0143 (2)
C7	0.34077 (14)	−0.14781 (9)	0.45884 (11)	0.0178 (2)
H7A	0.3963	−0.1860	0.5249	0.027*
H7B	0.4010	−0.1352	0.4076	0.027*
H7C	0.2537	−0.1837	0.4169	0.027*
C8	0.21498 (15)	−0.13062 (9)	0.64771 (11)	0.0184 (3)
H8A	0.3055	−0.1530	0.7043	0.022*
H8B	0.1756	−0.1841	0.5935	0.022*
C9	0.10472 (15)	−0.09964 (9)	0.70858 (11)	0.0187 (3)
H9A	0.0123	−0.0831	0.6503	0.022*
H9B	0.0856	−0.1544	0.7547	0.022*
C10	0.02951 (13)	0.01896 (10)	0.82360 (11)	0.0182 (3)
H10A	−0.0132	−0.0362	0.8544	0.022*
H10B	−0.0461	0.0455	0.7568	0.022*
C11	0.07601 (15)	0.09582 (10)	0.91531 (11)	0.0209 (3)
H11A	0.1154	0.1519	0.8835	0.025*
H11B	−0.0096	0.1179	0.9382	0.025*
C12	0.30849 (14)	0.03123 (10)	0.98074 (11)	0.0201 (3)
H12A	0.3838	0.0067	1.0490	0.024*
H12B	0.3490	0.0878	0.9507	0.024*
C13	0.27076 (14)	−0.04662 (10)	0.88940 (11)	0.0182 (2)
H13A	0.3589	−0.0638	0.8670	0.022*
H13B	0.2380	−0.1051	0.9217	0.022*

	U11	U22	U33	U12	U13	U23
Mn1	0.01418 (10)	0.01214 (10)	0.01314 (9)	−0.00041 (7)	0.00499 (7)	−0.00097 (6)
Cl1	0.01485 (13)	0.01773 (15)	0.01853 (14)	−0.00194 (11)	0.00523 (11)	−0.00213 (11)
Cl2	0.01707 (14)	0.01822 (15)	0.01954 (14)	0.00326 (11)	0.00548 (11)	−0.00012 (11)
O1	0.0215 (5)	0.0319 (5)	0.0142 (4)	0.0012 (4)	0.0078 (4)	−0.0010 (4)
N1	0.0148 (5)	0.0144 (5)	0.0146 (5)	−0.0003 (4)	0.0039 (4)	−0.0008 (4)
N2	0.0172 (5)	0.0137 (5)	0.0144 (5)	−0.0015 (4)	0.0042 (4)	−0.0005 (4)
N3	0.0146 (5)	0.0154 (5)	0.0136 (5)	−0.0011 (4)	0.0045 (4)	−0.0010 (4)
C1	0.0190 (6)	0.0155 (6)	0.0177 (6)	0.0002 (5)	0.0043 (5)	−0.0003 (5)
C2	0.0216 (6)	0.0184 (6)	0.0172 (6)	−0.0021 (5)	0.0035 (5)	0.0030 (5)
C3	0.0205 (6)	0.0252 (7)	0.0139 (5)	−0.0032 (5)	0.0055 (5)	−0.0001 (5)
C4	0.0160 (6)	0.0193 (6)	0.0165 (6)	−0.0009 (5)	0.0049 (5)	−0.0031 (5)
C5	0.0116 (5)	0.0152 (6)	0.0141 (5)	−0.0004 (4)	0.0016 (4)	−0.0016 (4)
C6	0.0117 (5)	0.0148 (6)	0.0147 (5)	−0.0009 (4)	0.0011 (4)	−0.0023 (4)
C7	0.0185 (6)	0.0150 (6)	0.0206 (6)	0.0007 (5)	0.0067 (5)	−0.0030 (5)
C8	0.0265 (6)	0.0123 (6)	0.0172 (6)	−0.0025 (5)	0.0078 (5)	−0.0002 (5)
C9	0.0222 (6)	0.0161 (6)	0.0184 (6)	−0.0064 (5)	0.0068 (5)	−0.0016 (5)
C10	0.0143 (6)	0.0237 (7)	0.0179 (6)	−0.0007 (5)	0.0067 (5)	0.0016 (5)
C11	0.0215 (6)	0.0248 (7)	0.0185 (6)	0.0045 (5)	0.0090 (5)	0.0002 (5)
C12	0.0177 (6)	0.0277 (7)	0.0151 (6)	−0.0004 (5)	0.0050 (5)	−0.0006 (5)
C13	0.0185 (6)	0.0195 (6)	0.0159 (6)	0.0022 (5)	0.0039 (5)	0.0030 (5)

Mn1—N2	2.1845 (11)	C4—H4	0.9500
Mn1—N1	2.2867 (10)	C5—C6	1.4963 (17)
Mn1—Cl2	2.3593 (4)	C6—C7	1.4949 (17)
Mn1—Cl1	2.3651 (4)	C7—H7A	0.9800
Mn1—N3	2.3694 (10)	C7—H7B	0.9800
O1—C11	1.4255 (16)	C7—H7C	0.9800
O1—C12	1.4300 (15)	C8—C9	1.5178 (18)
N1—C1	1.3337 (17)	C8—H8A	0.9900
N1—C5	1.3535 (16)	C8—H8B	0.9900
N2—C6	1.2811 (16)	C9—H9A	0.9900
N2—C8	1.4624 (16)	C9—H9B	0.9900
N3—C10	1.4864 (15)	C10—C11	1.5116 (18)
N3—C9	1.4869 (16)	C10—H10A	0.9900
N3—C13	1.4875 (16)	C10—H10B	0.9900
C1—C2	1.3932 (17)	C11—H11A	0.9900
C1—H1	0.9500	C11—H11B	0.9900
C2—C3	1.3796 (19)	C12—C13	1.5135 (18)
C2—H2	0.9500	C12—H12A	0.9900
C3—C4	1.3925 (19)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.3896 (17)	C13—H13B	0.9900
N2—Mn1—N1	71.12 (4)	C6—C7—H7B	109.5
N2—Mn1—Cl2	133.34 (3)	H7A—C7—H7B	109.5
N1—Mn1—Cl2	94.33 (3)	C6—C7—H7C	109.5
N2—Mn1—Cl1	108.15 (3)	H7A—C7—H7C	109.5
N1—Mn1—Cl1	96.83 (3)	H7B—C7—H7C	109.5
Cl2—Mn1—Cl1	117.667 (13)	N2—C8—C9	106.90 (10)
N2—Mn1—N3	76.77 (4)	N2—C8—H8A	110.3
N1—Mn1—N3	146.31 (4)	C9—C8—H8A	110.3
Cl2—Mn1—N3	100.42 (3)	N2—C8—H8B	110.3
Cl1—Mn1—N3	102.67 (3)	C9—C8—H8B	110.3
C11—O1—C12	108.96 (9)	H8A—C8—H8B	108.6
C1—N1—C5	118.81 (11)	N3—C9—C8	112.48 (10)
C1—N1—Mn1	125.80 (8)	N3—C9—H9A	109.1
C5—N1—Mn1	115.27 (8)	C8—C9—H9A	109.1
C6—N2—C8	121.97 (11)	N3—C9—H9B	109.1
C6—N2—Mn1	121.06 (9)	C8—C9—H9B	109.1
C8—N2—Mn1	116.20 (8)	H9A—C9—H9B	107.8
C10—N3—C9	107.50 (10)	N3—C10—C11	111.04 (10)
C10—N3—C13	107.79 (9)	N3—C10—H10A	109.4
C9—N3—C13	109.27 (10)	C11—C10—H10A	109.4
C10—N3—Mn1	113.96 (8)	N3—C10—H10B	109.4
C9—N3—Mn1	102.11 (7)	C11—C10—H10B	109.4
C13—N3—Mn1	115.75 (7)	H10A—C10—H10B	108.0
N1—C1—C2	122.63 (12)	O1—C11—C10	111.39 (11)
N1—C1—H1	118.7	O1—C11—H11A	109.3
C2—C1—H1	118.7	C10—C11—H11A	109.3
C3—C2—C1	118.72 (12)	O1—C11—H11B	109.3
C3—C2—H2	120.6	C10—C11—H11B	109.3
C1—C2—H2	120.6	H11A—C11—H11B	108.0
C2—C3—C4	119.13 (12)	O1—C12—C13	111.34 (11)
C2—C3—H3	120.4	O1—C12—H12A	109.4
C4—C3—H3	120.4	C13—C12—H12A	109.4
C5—C4—C3	118.98 (12)	O1—C12—H12B	109.4
C5—C4—H4	120.5	C13—C12—H12B	109.4
C3—C4—H4	120.5	H12A—C12—H12B	108.0
N1—C5—C4	121.71 (11)	N3—C13—C12	112.05 (11)
N1—C5—C6	114.59 (10)	N3—C13—H13A	109.2
C4—C5—C6	123.57 (11)	C12—C13—H13A	109.2
N2—C6—C7	124.01 (12)	N3—C13—H13B	109.2
N2—C6—C5	114.95 (11)	C12—C13—H13B	109.2
C7—C6—C5	120.98 (11)	H13A—C13—H13B	107.9
C6—C7—H7A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl1i	0.95	2.71	3.6257 (13)	163.
C7—H7C···Cl2ii	0.98	2.75	3.6202 (13)	149.
C8—H8A···Cl2iii	0.99	2.83	3.7207 (14)	151.
C12—H12B···Cl1	0.99	2.77	3.5904 (14)	141.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cl1i	0.95	2.71	3.6257 (13)	163
C7—H7C⋯Cl2ii	0.98	2.75	3.6202 (13)	149
C8—H8A⋯Cl2iii	0.99	2.83	3.7207 (14)	151
C12—H12B⋯Cl1	0.99	2.77	3.5904 (14)	141

Symmetry codes: (i) ; (ii) ; (iii) .