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

The asymmetric unit of the title compound, [MnCl(2)(C(11)H(17)N(3))], contains two crystallographically independent mol-ecules with slightly different geometries. In each mol-ecule, the Mn(II) ion is five coordinated by the N,N',N''-tridentate Schiff base and two Cl atoms in a distorted square-pyramidal geometry. In the crystal, C-H⋯Cl hydrogen bonds link adjacent mol-ecules into a three-dimensional network.

Related literature

For the structure of a CuCl2 complex of the same Schiff base, see: Saleh Salga et al. (2010) ▶. For structures of similar MnII complexes, see: Gibson et al. (2003 ▶); Reardon et al. (2002 ▶).

Experimental

Crystal data

[MnCl2(C11H17N3)]

M = 317.12

Monoclinic,

a = 17.6157 (8) Å

b = 9.9269 (4) Å

c = 20.4710 (8) Å

β = 124.592 (3)°

V = 2946.9 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.24 mm−1

T = 100 K

0.19 × 0.13 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.798, T max = 0.897

26611 measured reflections

6426 independent reflections

5326 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.063

S = 1.02

6426 reflections

313 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.32 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002030/is2666sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002030/is2666Isup2.hkl

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

[MnCl2(C11H17N3)]	F(000) = 1304
Mr = 317.12	Dx = 1.430 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7274 reflections
a = 17.6157 (8) Å	θ = 2.4–29.6°
b = 9.9269 (4) Å	µ = 1.24 mm−1
c = 20.4710 (8) Å	T = 100 K
β = 124.592 (3)°	Block, brown
V = 2946.9 (2) Å3	0.19 × 0.13 × 0.09 mm
Z = 8

Bruker APEXII CCD diffractometer	6426 independent reflections
Radiation source: fine-focus sealed tube	5326 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.798, Tmax = 0.897	k = −12→12
26611 measured reflections	l = −26→24

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0284P)2 + 0.699P] where P = (Fo2 + 2Fc2)/3
6426 reflections	(Δ/σ)max = 0.004
313 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.32 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	1.124031 (16)	0.97384 (3)	0.858429 (14)	0.01582 (7)
Cl1	1.23612 (3)	0.80041 (5)	0.91747 (2)	0.02316 (10)
Cl2	1.15773 (3)	1.20051 (5)	0.90329 (2)	0.02196 (10)
N1	1.04215 (9)	0.90231 (15)	0.90492 (8)	0.0168 (3)
N2	0.97678 (9)	0.99030 (14)	0.76157 (8)	0.0160 (3)
N3	1.12012 (10)	0.99132 (15)	0.74495 (9)	0.0197 (3)
C1	1.07802 (12)	0.85447 (19)	0.97795 (10)	0.0216 (4)
H1	1.1430	0.8435	1.0125	0.026*
C2	1.02463 (13)	0.8203 (2)	1.00538 (10)	0.0242 (4)
H2	1.0526	0.7877	1.0579	0.029*
C3	0.93044 (12)	0.83419 (19)	0.95525 (10)	0.0234 (4)
H3	0.8922	0.8111	0.9726	0.028*
C4	0.89186 (12)	0.88283 (19)	0.87851 (10)	0.0200 (4)
H4	0.8270	0.8929	0.8427	0.024*
C5	0.94953 (11)	0.91610 (18)	0.85543 (9)	0.0156 (3)
C6	0.91493 (11)	0.96556 (17)	0.77415 (9)	0.0153 (3)
C7	0.81348 (11)	0.98027 (19)	0.71441 (10)	0.0213 (4)
H7A	0.8021	1.0261	0.6672	0.032*
H7B	0.7871	1.0334	0.7373	0.032*
H7C	0.7847	0.8910	0.6995	0.032*
C8	0.95400 (11)	1.03545 (19)	0.68423 (10)	0.0188 (4)
H8A	0.9082	1.1093	0.6636	0.023*
H8B	0.9274	0.9602	0.6457	0.023*
C9	1.04255 (12)	1.08444 (19)	0.69561 (10)	0.0199 (4)
H9A	1.0325	1.0940	0.6431	0.024*
H9B	1.0585	1.1743	0.7211	0.024*
C10	1.20578 (13)	1.0510 (2)	0.76109 (12)	0.0322 (5)
H10A	1.1994	1.0662	0.7109	0.048*
H10B	1.2574	0.9895	0.7944	0.048*
H10C	1.2175	1.1371	0.7888	0.048*
C11	1.10379 (13)	0.8605 (2)	0.70528 (11)	0.0289 (4)
H11A	1.0482	0.8191	0.6965	0.043*
H11B	1.1568	0.8013	0.7387	0.043*
H11C	1.0955	0.8740	0.6542	0.043*
Mn2	0.399031 (16)	0.52217 (3)	0.750325 (14)	0.01472 (7)
Cl3	0.27334 (3)	0.67387 (4)	0.68459 (2)	0.01975 (9)
Cl4	0.35006 (3)	0.30314 (4)	0.75588 (2)	0.01934 (9)
N4	0.46738 (9)	0.59908 (15)	0.87463 (8)	0.0169 (3)
N5	0.55015 (9)	0.51120 (14)	0.80993 (8)	0.0169 (3)
N6	0.41710 (9)	0.49145 (14)	0.65054 (8)	0.0168 (3)
C12	0.42304 (12)	0.65017 (19)	0.90427 (10)	0.0207 (4)
H12	0.3578	0.6583	0.8703	0.025*
C13	0.46790 (13)	0.6921 (2)	0.98259 (10)	0.0257 (4)
H13	0.4340	0.7269	1.0020	0.031*
C14	0.56266 (13)	0.6821 (2)	1.03155 (10)	0.0272 (4)
H14	0.5952	0.7099	1.0854	0.033*
C15	0.60977 (12)	0.6307 (2)	1.00105 (10)	0.0238 (4)
H15	0.6751	0.6240	1.0337	0.029*
C16	0.56054 (11)	0.58944 (18)	0.92261 (10)	0.0178 (4)
C17	0.60500 (11)	0.53567 (18)	0.88397 (10)	0.0182 (4)
C18	0.70730 (12)	0.5158 (2)	0.93333 (11)	0.0286 (4)
H18A	0.7239	0.4444	0.9723	0.043*
H18B	0.7378	0.5999	0.9610	0.043*
H18C	0.7272	0.4901	0.8990	0.043*
C19	0.58162 (11)	0.46412 (18)	0.76133 (10)	0.0190 (4)
H19A	0.6300	0.3947	0.7904	0.023*
H19B	0.6079	0.5401	0.7490	0.023*
C20	0.49955 (11)	0.40536 (19)	0.68527 (10)	0.0198 (4)
H20A	0.5155	0.3942	0.6464	0.024*
H20B	0.4855	0.3151	0.6964	0.024*
C21	0.33693 (12)	0.4222 (2)	0.58233 (10)	0.0240 (4)
H21A	0.2820	0.4788	0.5603	0.036*
H21B	0.3270	0.3361	0.5998	0.036*
H21C	0.3485	0.4059	0.5415	0.036*
C22	0.43085 (12)	0.62049 (19)	0.62313 (10)	0.0235 (4)
H22A	0.4458	0.6033	0.5845	0.035*
H22B	0.4817	0.6699	0.6685	0.035*
H22C	0.3743	0.6742	0.5982	0.035*

	U11	U22	U33	U12	U13	U23
Mn1	0.01282 (12)	0.01482 (15)	0.01788 (13)	−0.00021 (10)	0.00756 (10)	−0.00039 (10)
Cl1	0.0172 (2)	0.0201 (3)	0.0250 (2)	0.00366 (17)	0.00763 (17)	−0.00099 (18)
Cl2	0.0208 (2)	0.0159 (2)	0.0226 (2)	−0.00041 (17)	0.00844 (17)	−0.00178 (17)
N1	0.0158 (7)	0.0151 (9)	0.0162 (7)	0.0004 (6)	0.0071 (6)	0.0001 (6)
N2	0.0165 (7)	0.0143 (8)	0.0165 (7)	−0.0002 (6)	0.0090 (6)	0.0007 (6)
N3	0.0177 (7)	0.0193 (9)	0.0244 (8)	−0.0016 (6)	0.0133 (6)	−0.0015 (6)
C1	0.0190 (8)	0.0213 (11)	0.0185 (8)	0.0008 (7)	0.0071 (7)	0.0017 (7)
C2	0.0292 (9)	0.0224 (11)	0.0187 (9)	−0.0008 (8)	0.0122 (8)	0.0030 (8)
C3	0.0296 (9)	0.0216 (11)	0.0263 (9)	−0.0020 (8)	0.0202 (8)	0.0005 (8)
C4	0.0187 (8)	0.0192 (11)	0.0217 (9)	−0.0001 (7)	0.0113 (7)	−0.0018 (7)
C5	0.0166 (8)	0.0115 (9)	0.0170 (8)	0.0003 (6)	0.0085 (7)	−0.0011 (7)
C6	0.0151 (8)	0.0116 (9)	0.0185 (8)	0.0006 (6)	0.0092 (7)	−0.0011 (7)
C7	0.0152 (8)	0.0259 (11)	0.0199 (9)	0.0009 (7)	0.0083 (7)	0.0019 (7)
C8	0.0194 (8)	0.0202 (11)	0.0165 (8)	0.0016 (7)	0.0099 (7)	0.0023 (7)
C9	0.0253 (9)	0.0161 (10)	0.0215 (9)	−0.0013 (7)	0.0152 (7)	0.0013 (7)
C10	0.0257 (10)	0.0407 (14)	0.0371 (11)	−0.0042 (9)	0.0221 (9)	0.0018 (9)
C11	0.0342 (11)	0.0244 (12)	0.0302 (10)	0.0037 (8)	0.0195 (9)	−0.0055 (8)
Mn2	0.01270 (12)	0.01534 (15)	0.01475 (13)	−0.00070 (10)	0.00696 (10)	−0.00102 (10)
Cl3	0.01567 (18)	0.0178 (2)	0.0222 (2)	0.00130 (16)	0.00860 (16)	0.00015 (17)
Cl4	0.01727 (19)	0.0164 (2)	0.0241 (2)	0.00004 (16)	0.01153 (17)	0.00154 (17)
N4	0.0164 (7)	0.0160 (9)	0.0176 (7)	−0.0028 (6)	0.0092 (6)	−0.0010 (6)
N5	0.0157 (7)	0.0154 (9)	0.0195 (7)	0.0004 (6)	0.0099 (6)	0.0007 (6)
N6	0.0171 (7)	0.0153 (9)	0.0166 (7)	−0.0017 (6)	0.0087 (6)	−0.0009 (6)
C12	0.0203 (8)	0.0191 (11)	0.0250 (9)	−0.0040 (7)	0.0143 (7)	−0.0020 (7)
C13	0.0324 (10)	0.0259 (12)	0.0254 (9)	−0.0054 (8)	0.0204 (8)	−0.0064 (8)
C14	0.0340 (10)	0.0276 (12)	0.0173 (9)	−0.0093 (8)	0.0129 (8)	−0.0057 (8)
C15	0.0210 (9)	0.0251 (12)	0.0182 (9)	−0.0038 (8)	0.0069 (7)	−0.0002 (7)
C16	0.0180 (8)	0.0148 (10)	0.0176 (8)	−0.0013 (7)	0.0083 (7)	0.0026 (7)
C17	0.0159 (8)	0.0141 (10)	0.0209 (8)	−0.0006 (7)	0.0082 (7)	0.0023 (7)
C18	0.0160 (9)	0.0335 (13)	0.0261 (10)	0.0028 (8)	0.0059 (8)	−0.0031 (8)
C19	0.0176 (8)	0.0182 (10)	0.0236 (9)	0.0024 (7)	0.0131 (7)	0.0008 (7)
C20	0.0242 (9)	0.0167 (10)	0.0233 (9)	0.0013 (7)	0.0163 (8)	−0.0011 (7)
C21	0.0228 (9)	0.0267 (12)	0.0187 (9)	−0.0051 (8)	0.0095 (7)	−0.0049 (8)
C22	0.0246 (9)	0.0217 (11)	0.0238 (9)	−0.0004 (8)	0.0135 (8)	0.0043 (8)

Mn1—N2	2.2015 (14)	Mn2—N5	2.2134 (13)
Mn1—N1	2.2470 (14)	Mn2—N4	2.2426 (13)
Mn1—N3	2.2911 (14)	Mn2—N6	2.2596 (14)
Mn1—Cl1	2.3694 (5)	Mn2—Cl4	2.3656 (5)
Mn1—Cl2	2.3748 (5)	Mn2—Cl3	2.3659 (5)
N1—C1	1.337 (2)	N4—C12	1.332 (2)
N1—C5	1.353 (2)	N4—C16	1.355 (2)
N2—C6	1.278 (2)	N5—C17	1.275 (2)
N2—C8	1.465 (2)	N5—C19	1.464 (2)
N3—C11	1.471 (2)	N6—C22	1.473 (2)
N3—C10	1.474 (2)	N6—C20	1.474 (2)
N3—C9	1.475 (2)	N6—C21	1.475 (2)
C1—C2	1.384 (2)	C12—C13	1.389 (2)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.375 (3)	C13—C14	1.379 (3)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.397 (2)	C14—C15	1.388 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.382 (2)	C15—C16	1.385 (2)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.493 (2)	C16—C17	1.493 (2)
C6—C7	1.493 (2)	C17—C18	1.497 (2)
C7—H7A	0.9800	C18—H18A	0.9800
C7—H7B	0.9800	C18—H18B	0.9800
C7—H7C	0.9800	C18—H18C	0.9800
C8—C9	1.520 (2)	C19—C20	1.516 (2)
C8—H8A	0.9900	C19—H19A	0.9900
C8—H8B	0.9900	C19—H19B	0.9900
C9—H9A	0.9900	C20—H20A	0.9900
C9—H9B	0.9900	C20—H20B	0.9900
C10—H10A	0.9800	C21—H21A	0.9800
C10—H10B	0.9800	C21—H21B	0.9800
C10—H10C	0.9800	C21—H21C	0.9800
C11—H11A	0.9800	C22—H22A	0.9800
C11—H11B	0.9800	C22—H22B	0.9800
C11—H11C	0.9800	C22—H22C	0.9800
N2—Mn1—N1	72.15 (5)	N5—Mn2—N4	71.84 (5)
N2—Mn1—N3	74.89 (5)	N5—Mn2—N6	75.47 (5)
N1—Mn1—N3	142.78 (5)	N4—Mn2—N6	144.23 (5)
N2—Mn1—Cl1	136.71 (4)	N5—Mn2—Cl4	106.59 (4)
N1—Mn1—Cl1	95.96 (4)	N4—Mn2—Cl4	103.53 (4)
N3—Mn1—Cl1	96.25 (4)	N6—Mn2—Cl4	99.31 (4)
N2—Mn1—Cl2	100.72 (4)	N5—Mn2—Cl3	142.11 (4)
N1—Mn1—Cl2	102.43 (4)	N4—Mn2—Cl3	98.91 (4)
N3—Mn1—Cl2	100.22 (4)	N6—Mn2—Cl3	97.95 (4)
Cl1—Mn1—Cl2	122.565 (18)	Cl4—Mn2—Cl3	111.302 (17)
C1—N1—C5	118.48 (14)	C12—N4—C16	118.60 (14)
C1—N1—Mn1	125.20 (11)	C12—N4—Mn2	124.80 (11)
C5—N1—Mn1	116.24 (11)	C16—N4—Mn2	116.58 (11)
C6—N2—C8	122.33 (14)	C17—N5—C19	123.01 (14)
C6—N2—Mn1	120.52 (11)	C17—N5—Mn2	120.56 (11)
C8—N2—Mn1	117.11 (10)	C19—N5—Mn2	116.24 (10)
C11—N3—C10	109.47 (15)	C22—N6—C20	110.98 (13)
C11—N3—C9	111.13 (14)	C22—N6—C21	108.69 (13)
C10—N3—C9	109.52 (14)	C20—N6—C21	109.77 (14)
C11—N3—Mn1	112.15 (11)	C22—N6—Mn2	111.41 (10)
C10—N3—Mn1	111.44 (11)	C20—N6—Mn2	104.36 (9)
C9—N3—Mn1	102.98 (10)	C21—N6—Mn2	111.59 (10)
N1—C1—C2	122.84 (16)	N4—C12—C13	122.92 (16)
N1—C1—H1	118.6	N4—C12—H12	118.5
C2—C1—H1	118.6	C13—C12—H12	118.5
C3—C2—C1	118.86 (16)	C14—C13—C12	118.55 (17)
C3—C2—H2	120.6	C14—C13—H13	120.7
C1—C2—H2	120.6	C12—C13—H13	120.7
C2—C3—C4	118.98 (16)	C13—C14—C15	119.07 (16)
C2—C3—H3	120.5	C13—C14—H14	120.5
C4—C3—H3	120.5	C15—C14—H14	120.5
C5—C4—C3	118.98 (15)	C16—C15—C14	119.31 (16)
C5—C4—H4	120.5	C16—C15—H15	120.3
C3—C4—H4	120.5	C14—C15—H15	120.3
N1—C5—C4	121.86 (15)	N4—C16—C15	121.54 (16)
N1—C5—C6	115.07 (14)	N4—C16—C17	115.15 (14)
C4—C5—C6	123.05 (14)	C15—C16—C17	123.29 (15)
N2—C6—C7	125.25 (15)	N5—C17—C16	115.24 (14)
N2—C6—C5	115.62 (14)	N5—C17—C18	125.93 (16)
C7—C6—C5	119.12 (14)	C16—C17—C18	118.83 (15)
C6—C7—H7A	109.5	C17—C18—H18A	109.5
C6—C7—H7B	109.5	C17—C18—H18B	109.5
H7A—C7—H7B	109.5	H18A—C18—H18B	109.5
C6—C7—H7C	109.5	C17—C18—H18C	109.5
H7A—C7—H7C	109.5	H18A—C18—H18C	109.5
H7B—C7—H7C	109.5	H18B—C18—H18C	109.5
N2—C8—C9	107.72 (13)	N5—C19—C20	108.22 (13)
N2—C8—H8A	110.2	N5—C19—H19A	110.1
C9—C8—H8A	110.2	C20—C19—H19A	110.1
N2—C8—H8B	110.2	N5—C19—H19B	110.1
C9—C8—H8B	110.2	C20—C19—H19B	110.1
H8A—C8—H8B	108.5	H19A—C19—H19B	108.4
N3—C9—C8	112.06 (14)	N6—C20—C19	112.10 (14)
N3—C9—H9A	109.2	N6—C20—H20A	109.2
C8—C9—H9A	109.2	C19—C20—H20A	109.2
N3—C9—H9B	109.2	N6—C20—H20B	109.2
C8—C9—H9B	109.2	C19—C20—H20B	109.2
H9A—C9—H9B	107.9	H20A—C20—H20B	107.9
N3—C10—H10A	109.5	N6—C21—H21A	109.5
N3—C10—H10B	109.5	N6—C21—H21B	109.5
H10A—C10—H10B	109.5	H21A—C21—H21B	109.5
N3—C10—H10C	109.5	N6—C21—H21C	109.5
H10A—C10—H10C	109.5	H21A—C21—H21C	109.5
H10B—C10—H10C	109.5	H21B—C21—H21C	109.5
N3—C11—H11A	109.5	N6—C22—H22A	109.5
N3—C11—H11B	109.5	N6—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
N3—C11—H11C	109.5	N6—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl4i	0.95	2.73	3.6115 (18)	155
C7—H7B···Cl3i	0.98	2.75	3.7280 (18)	175
C14—H14···Cl4ii	0.95	2.82	3.7048 (18)	156
C19—H19A···Cl3iii	0.99	2.64	3.5839 (18)	159
C19—H19B···Cl4i	0.99	2.73	3.6579 (19)	156
C22—H22B···Cl4i	0.98	2.78	3.6693 (19)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cl4i	0.95	2.73	3.6115 (18)	155
C7—H7B⋯Cl3i	0.98	2.75	3.7280 (18)	175
C14—H14⋯Cl4ii	0.95	2.82	3.7048 (18)	156
C19—H19A⋯Cl3iii	0.99	2.64	3.5839 (18)	159
C19—H19B⋯Cl4i	0.99	2.73	3.6579 (19)	156
C22—H22B⋯Cl4i	0.98	2.78	3.6693 (19)	151

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