Dichlorido(dipyrido[3,2-a:2′,3′-c]phenazine)manganese(II)

Xu, M.-L.; Sun, S.-B.; Li, X.-Y.; Che, G.-B.

doi:10.1107/S1600536808043468

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m136

doi:10.1107/S1600536808043468

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Dichlorido(dipyrido[3,2-a:2′,3′-c]phenazine)manganese(II)

Mao-Liang Xu,^a Shu-Bo Sun,^b Xiu-Ying Li ^c and Guang-Bo Che ^c ^*

^aXi'an Modern Chemistry Research Institute, Xi'an 710065, People's Republic of China, ^bDepartment of Base, Shenyang Polytechnic College, Shenyang 110045, People's Republic of China, and ^cDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
^*Correspondence e-mail: guangbochejl@yahoo.com

(Received 18 December 2008; accepted 20 December 2008; online 8 January 2009)

The complete molecule of the title compound, [MnCl₂(C₁₈H₁₀N₄)₂], is generated by crystallographic twofold symmetry with the Mn atom lying on the rotation axis. The Mn coordination geometry is a distorted cis-MnCl₂N₄ octahedron, arising from two N,N′-bidentate dipyrido[3,2-a:2′,3′-c]phenazine (DPPZ) ligands and two chloride ions. In the crystal structure, neighbouring mononuclear units pack together through π–π contacts between the DPPZ rings [shortest centroid–centroid distance = 3.480 (2) Å], leading to a chain-like structure along [001]. C—H⋯Cl hydrogen bonds complete the structure.

Related literature

For background, see: Che et al. (2006 , 2008 ); Xu et al. (2008 ).

Experimental

Crystal data

[MnCl₂(C₁₈H₁₀N₄)₂]
M_r = 690.44
Monoclinic, C 2/c
a = 8.4017 (17) Å
b = 12.256 (3) Å
c = 28.226 (6) Å
β = 95.09 (3)°
V = 2895.0 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 292 (2) K
0.38 × 0.24 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.821, T_max = 0.864
11873 measured reflections
2866 independent reflections
1748 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.120
S = 1.00
2866 reflections
243 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn—N1	2.283 (3)
Mn—N2	2.316 (3)
Mn—Cl	2.4644 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Clⁱ	1.09 (3)	2.67 (3)	3.737 (4)	168 (2)
C15—H15⋯Clⁱⁱ	1.04 (3)	2.64 (3)	3.648 (4)	163 (3)
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043468/hb2884sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043468/hb2884Isup2.hkl

checkCIF report

Comment top

1,10-Phenanthroline (phen) and its derivatives, as chelating N-containing aromatic ligands, has been extensively studied in the chemistry of coordination polymers (Che et al., 2008). Here, we report the crystal structure of the title compound, [Mn(DPPZ)₂Cl₂] or [Mn(C₁₈H₁₀N₄)₂Cl₂] (I), based on the dipyrido[3,2 - a:2',3'-c]-phenazine (DPPZ) ligand (Xu et al., 2008).

In compound (I), the Mn atom (site symmetry 2) is coordinated in a distorted octahedral fashion (Fig. 1) by four N atoms from two DPPZ ligands and two Cl ions (Table 1). The DPPZ ring systems is almost planar and the dihedral angle between the two symmetry-related DPPZ planes is 70.66°.

π-π stacking interactions between the DPPZ ligands assemble mononuclear complex molecules into one-dimensional chains along (001) [centroid-centroid distances = 3.480 (2) Å] (Fig. 2). Finally, C—H···Cl hydrogen bonds involving the hydrogen of aromatic rings and the Cl ions further stabilize the crystal structure (Table 2).

Related literature top

For background, see: Che et al. (2006, 2008); Xu et al. (2008).

Experimental top

The DPPZ ligand was synthesized according to the literature method of Che et al. (2006). A mixture of DPPZ, MnCl₂ and water in a molar ratio of 2:1:5000 was sealed in a Teflon-lined autoclave and heated to 423 K for 3 d. Upon cooling and opening the bomb, yellow blocks of (I) were obtained (81% yield based on Mn).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of (I). Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for the H atoms). [Symmetry code: (i) -x + 2, y, -z + 1/2.]
	Fig. 2. View of the supramolecular chain structure of (I) arising from π-π stacking. H atoms have been omitted. [Symmetry code: (A) -x + 2, y, -z + 1/2; (B) x, -y + 1, -z; (C) x, y, -z - 1; (BA) x, -y + 1, -z - 1.]

Dichlorido(dipyrido[3,2-a:2',3'-c]phenazine)manganese(II) top

Crystal data top

[MnCl₂(C₁₈H₁₀N₄)₂]	F(000) = 1404
M_r = 690.44	D_x = 1.584 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2001 reflections
a = 8.4017 (17) Å	θ = 2.9–26.1°
b = 12.256 (3) Å	µ = 0.69 mm⁻¹
c = 28.226 (6) Å	T = 292 K
β = 95.09 (3)°	Block, yellow
V = 2895.0 (10) Å³	0.38 × 0.24 × 0.21 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2866 independent reflections
Radiation source: fine-focus sealed tube	1748 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ω scans	θ_max = 26.1°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
T_min = 0.821, T_max = 0.864	k = −15→15
11873 measured reflections	l = −34→34

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0518P)²] where P = (F_o² + 2F_c²)/3
2866 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[MnCl₂(C₁₈H₁₀N₄)₂]	V = 2895.0 (10) Å³
M_r = 690.44	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 8.4017 (17) Å	µ = 0.69 mm⁻¹
b = 12.256 (3) Å	T = 292 K
c = 28.226 (6) Å	0.38 × 0.24 × 0.21 mm
β = 95.09 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2866 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1748 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.864	R_int = 0.078
11873 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.32 e Å⁻³
2866 reflections	Δρ_min = −0.43 e Å⁻³
243 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
C1	0.6671 (4)	0.3405 (3)	0.29912 (12)	0.0408 (9)
C2	0.5622 (4)	0.3550 (3)	0.33399 (12)	0.0459 (10)
C3	0.6118 (4)	0.4167 (3)	0.37276 (13)	0.0461 (10)
C4	0.7619 (4)	0.4666 (3)	0.37635 (11)	0.0343 (8)
C5	0.8223 (4)	0.5307 (3)	0.41737 (11)	0.0367 (9)
C7	0.7118 (5)	0.6056 (3)	0.53324 (14)	0.0508 (11)
C8	0.7738 (5)	0.6604 (3)	0.57158 (13)	0.0521 (11)
C9	0.9253 (5)	0.7097 (3)	0.57276 (13)	0.0501 (11)
C10	1.0139 (5)	0.7010 (3)	0.53419 (13)	0.0508 (11)
C11	0.9520 (4)	0.6445 (3)	0.49315 (12)	0.0424 (9)
C12	0.9766 (4)	0.5811 (3)	0.41822 (12)	0.0373 (9)
C13	1.0710 (4)	0.5678 (3)	0.37731 (11)	0.0364 (9)
C14	1.2220 (4)	0.6152 (3)	0.37604 (13)	0.0448 (10)
C15	1.3054 (4)	0.5992 (3)	0.33699 (13)	0.0472 (10)
C16	1.2389 (4)	0.5345 (3)	0.30016 (13)	0.0419 (9)
C17	1.0135 (4)	0.5042 (3)	0.33907 (11)	0.0345 (8)
C18	0.8568 (4)	0.4510 (3)	0.33849 (11)	0.0333 (8)
C6	0.7985 (4)	0.5942 (3)	0.49265 (12)	0.0404 (9)
N1	0.8113 (3)	0.3861 (2)	0.30102 (9)	0.0377 (7)
N2	1.0963 (3)	0.4861 (2)	0.30080 (9)	0.0380 (7)
N3	0.7343 (3)	0.5382 (2)	0.45415 (9)	0.0409 (8)
N4	1.0403 (3)	0.6370 (2)	0.45531 (10)	0.0427 (8)
Mn	1.0000	0.34811 (7)	0.2500	0.0383 (3)
Cl	0.82991 (11)	0.22033 (8)	0.20077 (3)	0.0501 (3)
H1	0.634 (4)	0.289 (3)	0.2722 (13)	0.060*
H2	0.448 (4)	0.313 (3)	0.3296 (12)	0.060*
H3	0.550 (4)	0.427 (3)	0.3977 (13)	0.060*
H7	0.613 (4)	0.566 (3)	0.5315 (12)	0.060*
H8	0.720 (4)	0.663 (3)	0.5996 (13)	0.060*
H9	0.973 (4)	0.751 (3)	0.6018 (14)	0.060*
H10	1.116 (4)	0.738 (3)	0.5341 (13)	0.060*
H14	1.264 (4)	0.661 (3)	0.3997 (13)	0.060*
H15	1.417 (4)	0.634 (3)	0.3341 (12)	0.060*
H16	1.299 (4)	0.524 (3)	0.2703 (12)	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (2)	0.056 (3)	0.031 (2)	−0.0009 (19)	0.0073 (16)	−0.0062 (19)
C2	0.036 (2)	0.068 (3)	0.035 (2)	−0.003 (2)	0.0089 (17)	−0.006 (2)
C3	0.037 (2)	0.069 (3)	0.035 (2)	0.003 (2)	0.0195 (18)	0.000 (2)
C4	0.0330 (19)	0.043 (2)	0.0278 (19)	0.0012 (17)	0.0080 (15)	0.0006 (16)
C5	0.037 (2)	0.045 (2)	0.0288 (19)	0.0031 (18)	0.0086 (16)	0.0008 (17)
C7	0.058 (3)	0.061 (3)	0.036 (2)	0.005 (2)	0.019 (2)	−0.003 (2)
C8	0.061 (3)	0.069 (3)	0.029 (2)	0.004 (2)	0.0175 (19)	−0.008 (2)
C9	0.060 (3)	0.058 (3)	0.032 (2)	0.012 (2)	0.002 (2)	−0.008 (2)
C10	0.054 (3)	0.061 (3)	0.037 (2)	−0.002 (2)	0.007 (2)	−0.009 (2)
C11	0.049 (2)	0.050 (2)	0.029 (2)	0.005 (2)	0.0079 (17)	−0.0027 (18)
C12	0.041 (2)	0.042 (2)	0.030 (2)	0.0025 (18)	0.0095 (16)	−0.0019 (18)
C13	0.039 (2)	0.042 (2)	0.030 (2)	0.0012 (17)	0.0075 (16)	−0.0004 (17)
C14	0.045 (2)	0.051 (3)	0.039 (2)	−0.010 (2)	0.0098 (18)	−0.0088 (19)
C15	0.038 (2)	0.056 (3)	0.049 (2)	−0.009 (2)	0.0158 (19)	−0.002 (2)
C16	0.044 (2)	0.051 (2)	0.032 (2)	−0.0016 (19)	0.0128 (17)	0.0011 (19)
C17	0.0339 (19)	0.044 (2)	0.0269 (19)	0.0051 (17)	0.0078 (15)	0.0047 (17)
C18	0.0342 (19)	0.041 (2)	0.0257 (19)	0.0034 (17)	0.0065 (15)	0.0021 (17)
C6	0.047 (2)	0.050 (2)	0.025 (2)	0.0076 (19)	0.0090 (16)	−0.0031 (18)
N1	0.0344 (16)	0.049 (2)	0.0300 (17)	−0.0013 (15)	0.0053 (13)	−0.0018 (15)
N2	0.0379 (17)	0.050 (2)	0.0283 (16)	0.0001 (15)	0.0129 (13)	0.0004 (14)
N3	0.0396 (17)	0.054 (2)	0.0307 (17)	0.0027 (15)	0.0128 (14)	−0.0028 (15)
N4	0.0452 (18)	0.052 (2)	0.0317 (17)	0.0017 (15)	0.0091 (14)	−0.0061 (15)
Mn	0.0351 (4)	0.0540 (6)	0.0273 (4)	0.000	0.0113 (3)	0.000
Cl	0.0432 (6)	0.0631 (7)	0.0448 (6)	0.0003 (5)	0.0081 (4)	−0.0096 (5)

Geometric parameters (Å, º) top

C1—N1	1.330 (4)	C11—C6	1.429 (5)
C1—C2	1.390 (5)	C12—N4	1.323 (4)
C1—H1	1.01 (4)	C12—C13	1.467 (4)
C2—C3	1.365 (5)	C13—C17	1.383 (4)
C2—H2	1.08 (4)	C13—C14	1.399 (5)
C3—C4	1.397 (5)	C14—C15	1.372 (5)
C3—H3	0.92 (4)	C14—H14	0.92 (4)
C4—C18	1.402 (4)	C15—C16	1.385 (5)
C4—C5	1.453 (4)	C15—H15	1.04 (4)
C5—N3	1.330 (4)	C16—N2	1.339 (4)
C5—C12	1.434 (4)	C16—H16	1.03 (3)
C7—C8	1.339 (5)	C17—N2	1.354 (4)
C7—C6	1.418 (5)	C17—C18	1.468 (4)
C7—H7	0.96 (3)	C18—N1	1.351 (4)
C8—C9	1.406 (5)	C6—N3	1.356 (4)
C8—H8	0.95 (4)	Mn—N1	2.283 (3)
C9—C10	1.377 (5)	Mn—N2	2.316 (3)
C9—H9	1.02 (4)	Mn—Cl	2.4644 (12)
C10—C11	1.409 (5)	Mn—N1ⁱ	2.283 (3)
C10—H10	0.97 (4)	Mn—N2ⁱ	2.316 (3)
C11—N4	1.357 (4)	Mn—Clⁱ	2.4644 (12)

N1—C1—C2	123.4 (4)	C14—C15—C16	119.0 (3)
N1—C1—H1	119 (2)	C14—C15—H15	122 (2)
C2—C1—H1	118 (2)	C16—C15—H15	118.7 (19)
C3—C2—C1	118.1 (4)	N2—C16—C15	123.1 (3)
C3—C2—H2	123.9 (19)	N2—C16—H16	117.5 (19)
C1—C2—H2	118.0 (19)	C15—C16—H16	119 (2)
C2—C3—C4	120.7 (3)	N2—C17—C13	123.1 (3)
C2—C3—H3	123 (2)	N2—C17—C18	116.2 (3)
C4—C3—H3	117 (2)	C13—C17—C18	120.6 (3)
C3—C4—C18	117.1 (3)	N1—C18—C4	122.4 (3)
C3—C4—C5	122.9 (3)	N1—C18—C17	117.5 (3)
C18—C4—C5	119.9 (3)	C4—C18—C17	120.1 (3)
N3—C5—C12	121.5 (3)	N3—C6—C7	120.1 (3)
N3—C5—C4	118.7 (3)	N3—C6—C11	121.4 (3)
C12—C5—C4	119.8 (3)	C7—C6—C11	118.5 (3)
C8—C7—C6	120.8 (4)	C1—N1—C18	118.2 (3)
C8—C7—H7	125 (2)	C1—N1—Mn	124.7 (2)
C6—C7—H7	114 (2)	C18—N1—Mn	116.7 (2)
C7—C8—C9	121.4 (4)	C16—N2—C17	117.5 (3)
C7—C8—H8	121 (2)	C16—N2—Mn	125.4 (2)
C9—C8—H8	118 (2)	C17—N2—Mn	116.0 (2)
C10—C9—C8	120.0 (4)	C5—N3—C6	116.8 (3)
C10—C9—H9	118 (2)	C12—N4—C11	116.6 (3)
C8—C9—H9	122 (2)	N1ⁱ—Mn—N1	156.48 (15)
C9—C10—C11	120.1 (4)	N1ⁱ—Mn—N2	91.01 (10)
C9—C10—H10	120 (2)	N1—Mn—N2	71.63 (10)
C11—C10—H10	119 (2)	N1ⁱ—Mn—N2ⁱ	71.63 (10)
N4—C11—C10	119.5 (3)	N1—Mn—N2ⁱ	91.01 (10)
N4—C11—C6	121.3 (3)	N2—Mn—N2ⁱ	86.22 (14)
C10—C11—C6	119.2 (3)	N1ⁱ—Mn—Cl	100.04 (7)
N4—C12—C5	122.5 (3)	N1—Mn—Cl	94.86 (8)
N4—C12—C13	118.1 (3)	N2—Mn—Cl	165.09 (7)
C5—C12—C13	119.3 (3)	N2ⁱ—Mn—Cl	87.79 (8)
C17—C13—C14	118.0 (3)	N1ⁱ—Mn—Clⁱ	94.86 (8)
C17—C13—C12	120.1 (3)	N1—Mn—Clⁱ	100.04 (7)
C14—C13—C12	121.9 (3)	N2—Mn—Clⁱ	87.79 (8)
C15—C14—C13	119.4 (4)	N2ⁱ—Mn—Clⁱ	165.09 (7)
C15—C14—H14	119 (2)	Cl—Mn—Clⁱ	101.09 (6)
C13—C14—H14	122 (2)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Clⁱⁱ	1.09 (3)	2.67 (3)	3.737 (4)	168 (2)
C15—H15···Clⁱⁱⁱ	1.04 (3)	2.64 (3)	3.648 (4)	163 (3)

Symmetry codes: (ii) −x+1, y, −z+1/2; (iii) −x+5/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[MnCl₂(C₁₈H₁₀N₄)₂]
M_r	690.44
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	292
a, b, c (Å)	8.4017 (17), 12.256 (3), 28.226 (6)
β (°)	95.09 (3)
V (Å³)	2895.0 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.38 × 0.24 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.821, 0.864
No. of measured, independent and observed [I > 2σ(I)] reflections	11873, 2866, 1748
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.120, 1.00
No. of reflections	2866
No. of parameters	243
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.43

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Mn—N1	2.283 (3)	Mn—Cl	2.4644 (12)
Mn—N2	2.316 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Clⁱ	1.09 (3)	2.67 (3)	3.737 (4)	168 (2)
C15—H15···Clⁱⁱ	1.04 (3)	2.64 (3)	3.648 (4)	163 (3)

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2.

Acknowledgements

The authors thank the Doctoral Foundation of Jilin Normal University (grant Nos. 2006006 and 2007009) and the Subject and Base Construction Foundation of Jilin Normal University (grant No. 2006041).

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