A second monoclinic polymorph of bis­(2,2′-bipyridine-κ2N,N′)diiodido­manganese(II)

Ha, K.

doi:10.1107/S1600536811036051

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1351

https://doi.org/10.1107/S1600536811036051

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A second monoclinic polymorph of bis(2,2′-bipyridine-κ²N,N′)diiodidomanganese(II)

Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 4 September 2011; accepted 4 September 2011; online 14 September 2011)

The Mn^II ion in the title complex, [MnI₂(C₁₀H₈N₂)₂], is six-coordinated in a distorted cis-N₄I₂Mn octahedral environment by four N atoms of the two chelating 2,2′-bipyridine ligands and two iodide anions. As a result of the different trans effects of the N and I atoms, the Mn—N bonds trans to the I atom are slightly longer than the Mn—N bonds trans to the N atom. The dihedral angle between the approximately planar ligands [maximum deviation = 0.064 (7) Å] is 75.0 (1)°. Numerous inter- and intramolecular π–π interactions between the pyridyl rings are present, the shortest centroid–centroid distance being 3.905 (5) Å. The structure reported herein represents a new monoclinic polymorph of the previously reported monoclinic (P2₁/c) form [Ha (2011 ). Z. Kristallogr. New Cryst. Struct. 226, 187–188].

Related literature

For the P2₁/c polymorph, see: Ha (2011).

Experimental

Crystal data

[MnI₂(C₁₀H₈N₂)₂]
M_r = 621.11
Monoclinic, C 2/c
a = 16.491 (4) Å
b = 15.403 (4) Å
c = 17.719 (4) Å
β = 110.187 (5)°
V = 4224.6 (18) Å³
Z = 8
Mo Kα radiation
μ = 3.56 mm⁻¹
T = 200 K
0.16 × 0.13 × 0.06 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.804, T_max = 1.000
15547 measured reflections
5222 independent reflections
2330 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.101
S = 0.89
5222 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 1.21 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036051/ng5226sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036051/ng5226Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title complex, [MnI₂(bipy)₂] (bipy = 2,2'-bipyridine, C₁₀H₈N₂), was previously reported in the monoclinic space group P2₁/c (Ha, 2011). The structure presented herein is essentially the same as the published structure and represents a new monoclinic polymorph with the space group C2/c.

The Mn^II ion in the complex is six-coordinated in a considerably distorted octahedral environment by four N atoms of the two chelating bipy ligands and two iodide anions in a cis-N₄I₂ coordination geometry (Fig. 1). The tight N—Mn—N chelating angles and the I—I repelling (Table 1) contribute the distortion of the ocataheron, which results in non-linear trans axes [<I1—Mn1—N1 = 169.67 (14)°, <I2—Mn1—N3 = 166.94 (15)° and <N2—Mn1—N4 = 153.33 (19)°]. The Mn—I bond lengths are nearly equal, but the Mn—N bond distances occur in two distinct sets, because of the different trans effects of the N and I atoms (Table 1). The Mn—N bonds trans to the I atom are slightly longer than the Mn—N bonds trans to the N atom. The dihedral angle between the nearly planar bipy ligands [maximum deviation = 0.064 (7) Å] is 75.0 (1)°. The dihedral angles between the pyridyl rings containing N1 and N2 as well as N3 and N4 are 4.5 (5)° and 4.1 (5)°, respectively. In the crystal structure, the complex displays numerous inter- and intramolecular π-π interactions between the pyridyl rings, the shortest ring centroid-centroid distance being 3.905 (5) Å (Fig. 2).

Related literature top

For the P2₁/c polymorph, see: Ha (2011).

Experimental top

To a solution of MnI₂ (0.3078 g, 0.997 mmol) in EtOH (30 ml) was added 2,2'-bipyridine (0.3131 g, 2.005 mmol) and stirred for 3 h at room temperature. The precipitate was separated by filtration, washed with acetone and dried at 50 °C, to give a yellow powder (0.0854 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from a methanol solution.

Structure description top

For the P2₁/c polymorph, see: Ha (2011).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title complex, with displacement ellipsoids drawn at the 40% probability level for non-H atoms.
	Fig. 2. View of the unit-cell contents of the title complex.

Bis(2,2'-bipyridine-κ²N,N')diiodidomanganese(II) top

Crystal data top

[MnI₂(C₁₀H₈N₂)₂]	F(000) = 2360
M_r = 621.11	D_x = 1.953 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2551 reflections
a = 16.491 (4) Å	θ = 2.5–25.9°
b = 15.403 (4) Å	µ = 3.56 mm⁻¹
c = 17.719 (4) Å	T = 200 K
β = 110.187 (5)°	Block, yellow
V = 4224.6 (18) Å³	0.16 × 0.13 × 0.06 mm
Z = 8

Data collection top

Bruker SMART 1000 CCD diffractometer	5222 independent reflections
Radiation source: fine-focus sealed tube	2330 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
φ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −21→22
T_min = 0.804, T_max = 1.000	k = −20→14
15547 measured reflections	l = −23→19

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.023P)²] where P = (F_o² + 2F_c²)/3
5222 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 1.21 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[MnI₂(C₁₀H₈N₂)₂]	V = 4224.6 (18) Å³
M_r = 621.11	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 16.491 (4) Å	µ = 3.56 mm⁻¹
b = 15.403 (4) Å	T = 200 K
c = 17.719 (4) Å	0.16 × 0.13 × 0.06 mm
β = 110.187 (5)°

Data collection top

Bruker SMART 1000 CCD diffractometer	5222 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2330 reflections with I > 2σ(I)
T_min = 0.804, T_max = 1.000	R_int = 0.089
15547 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 0.89	Δρ_max = 1.21 e Å⁻³
5222 reflections	Δρ_min = −0.83 e Å⁻³
244 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
I1	0.12615 (3)	−0.15566 (3)	0.39194 (3)	0.03965 (16)
I2	0.37597 (3)	−0.15176 (3)	0.36880 (3)	0.04233 (17)
Mn1	0.24841 (7)	−0.03413 (6)	0.37953 (6)	0.0274 (3)
N1	0.3267 (4)	0.0774 (3)	0.3538 (3)	0.0293 (14)
N2	0.1883 (4)	0.0017 (3)	0.2492 (3)	0.0290 (16)
N3	0.1705 (4)	0.0801 (3)	0.4074 (4)	0.0318 (15)
N4	0.3034 (4)	−0.0032 (3)	0.5106 (3)	0.0300 (15)
C1	0.3998 (5)	0.1097 (4)	0.4070 (5)	0.039 (2)
H1	0.4223	0.0838	0.4587	0.047*
C2	0.4434 (5)	0.1786 (4)	0.3898 (5)	0.040 (2)
H2	0.4945	0.2001	0.4293	0.048*
C3	0.4128 (5)	0.2159 (4)	0.3154 (5)	0.042 (2)
H3	0.4420	0.2634	0.3020	0.051*
C4	0.3378 (5)	0.1823 (5)	0.2600 (5)	0.044 (2)
H4	0.3144	0.2075	0.2080	0.053*
C5	0.2973 (4)	0.1128 (4)	0.2799 (4)	0.0311 (18)
C6	0.2205 (4)	0.0702 (4)	0.2211 (4)	0.0313 (18)
C7	0.1840 (5)	0.0976 (5)	0.1429 (4)	0.043 (2)
H7	0.2069	0.1465	0.1246	0.052*
C8	0.1139 (5)	0.0538 (6)	0.0911 (5)	0.057 (3)
H8	0.0887	0.0714	0.0366	0.069*
C9	0.0816 (7)	−0.0153 (6)	0.1198 (5)	0.060 (3)
H9	0.0332	−0.0466	0.0855	0.072*
C10	0.1194 (5)	−0.0384 (5)	0.1975 (5)	0.039 (2)
H10	0.0956	−0.0861	0.2168	0.046*
C11	0.1033 (5)	0.1199 (5)	0.3543 (4)	0.045 (2)
H11	0.0846	0.0985	0.3008	0.054*
C12	0.0594 (5)	0.1872 (5)	0.3691 (5)	0.052 (2)
H12	0.0100	0.2103	0.3285	0.063*
C13	0.0888 (6)	0.2208 (5)	0.4448 (5)	0.058 (3)
H13	0.0607	0.2692	0.4582	0.070*
C14	0.1609 (6)	0.1833 (5)	0.5026 (5)	0.058 (3)
H14	0.1829	0.2061	0.5556	0.069*
C15	0.1993 (4)	0.1125 (4)	0.4812 (4)	0.0303 (18)
C16	0.2741 (4)	0.0669 (4)	0.5397 (4)	0.0304 (17)
C17	0.3099 (5)	0.0904 (5)	0.6189 (4)	0.043 (2)
H17	0.2878	0.1388	0.6388	0.052*
C18	0.3771 (5)	0.0440 (5)	0.6689 (5)	0.047 (2)
H18	0.4038	0.0620	0.7232	0.057*
C19	0.4071 (5)	−0.0288 (6)	0.6417 (5)	0.052 (2)
H19	0.4531	−0.0628	0.6762	0.063*
C20	0.3669 (5)	−0.0496 (5)	0.5623 (4)	0.043 (2)
H20	0.3854	−0.1004	0.5426	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0403 (3)	0.0408 (3)	0.0426 (3)	−0.0101 (2)	0.0204 (3)	−0.0079 (3)
I2	0.0444 (3)	0.0424 (3)	0.0452 (4)	0.0141 (3)	0.0218 (3)	0.0070 (3)
Mn1	0.0275 (6)	0.0282 (6)	0.0252 (6)	0.0012 (5)	0.0073 (5)	−0.0008 (5)
N1	0.026 (4)	0.031 (3)	0.030 (4)	0.001 (3)	0.008 (3)	0.000 (3)
N2	0.030 (4)	0.028 (4)	0.026 (4)	−0.003 (2)	0.006 (3)	−0.005 (3)
N3	0.029 (4)	0.031 (3)	0.037 (4)	0.006 (3)	0.013 (3)	−0.001 (3)
N4	0.038 (4)	0.031 (4)	0.020 (3)	0.004 (3)	0.010 (3)	0.003 (3)
C1	0.044 (5)	0.027 (4)	0.043 (5)	0.007 (4)	0.010 (4)	0.002 (4)
C2	0.033 (5)	0.033 (5)	0.049 (6)	−0.001 (4)	0.008 (4)	−0.005 (4)
C3	0.032 (5)	0.030 (4)	0.059 (6)	−0.010 (4)	0.008 (4)	−0.002 (4)
C4	0.034 (5)	0.045 (5)	0.051 (6)	−0.002 (4)	0.013 (4)	0.015 (4)
C5	0.027 (4)	0.031 (4)	0.035 (5)	0.001 (3)	0.011 (4)	0.000 (4)
C6	0.026 (4)	0.032 (4)	0.038 (5)	−0.002 (3)	0.014 (4)	0.005 (3)
C7	0.047 (5)	0.053 (5)	0.024 (5)	0.000 (4)	0.005 (4)	0.016 (4)
C8	0.040 (5)	0.091 (7)	0.023 (5)	−0.009 (5)	−0.011 (4)	0.015 (5)
C9	0.080 (8)	0.071 (6)	0.027 (5)	−0.027 (5)	0.017 (5)	0.002 (4)
C10	0.038 (5)	0.038 (5)	0.044 (5)	−0.009 (4)	0.019 (4)	−0.002 (4)
C11	0.036 (5)	0.075 (6)	0.024 (5)	0.028 (4)	0.009 (4)	0.003 (4)
C12	0.041 (5)	0.066 (6)	0.040 (6)	0.033 (4)	0.002 (4)	0.004 (4)
C13	0.056 (6)	0.065 (6)	0.054 (6)	0.021 (5)	0.019 (5)	−0.013 (5)
C14	0.060 (6)	0.067 (6)	0.037 (5)	0.027 (5)	0.007 (5)	−0.013 (4)
C15	0.029 (4)	0.033 (4)	0.025 (4)	−0.005 (3)	0.006 (4)	−0.008 (3)
C16	0.022 (4)	0.037 (4)	0.031 (5)	−0.003 (3)	0.008 (3)	−0.001 (3)
C17	0.044 (5)	0.054 (5)	0.034 (5)	0.008 (4)	0.018 (4)	−0.004 (4)
C18	0.039 (5)	0.065 (6)	0.029 (5)	0.004 (4)	0.000 (4)	−0.015 (4)
C19	0.045 (6)	0.077 (6)	0.028 (5)	0.025 (5)	0.003 (4)	0.004 (5)
C20	0.048 (5)	0.054 (5)	0.022 (5)	0.018 (4)	0.007 (4)	−0.002 (4)

Geometric parameters (Å, º) top

I1—Mn1	2.8149 (13)	C7—C8	1.378 (10)
I2—Mn1	2.8322 (13)	C7—H7	0.9500
Mn1—N4	2.233 (6)	C8—C9	1.365 (10)
Mn1—N2	2.245 (6)	C8—H8	0.9500
Mn1—N1	2.288 (6)	C9—C10	1.349 (10)
Mn1—N3	2.330 (5)	C9—H9	0.9500
N1—C1	1.343 (8)	C10—H10	0.9500
N1—C5	1.345 (8)	C11—C12	1.340 (10)
N2—C10	1.339 (8)	C11—H11	0.9500
N2—C6	1.350 (8)	C12—C13	1.362 (10)
N3—C15	1.325 (8)	C12—H12	0.9500
N3—C11	1.330 (8)	C13—C14	1.399 (10)
N4—C20	1.336 (8)	C13—H13	0.9500
N4—C16	1.354 (8)	C14—C15	1.378 (9)
C1—C2	1.375 (10)	C14—H14	0.9500
C1—H1	0.9500	C15—C16	1.486 (9)
C2—C3	1.364 (10)	C16—C17	1.371 (9)
C2—H2	0.9500	C17—C18	1.358 (9)
C3—C4	1.387 (9)	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.378 (10)
C4—C5	1.370 (9)	C18—H18	0.9500
C4—H4	0.9500	C19—C20	1.371 (10)
C5—C6	1.487 (9)	C19—H19	0.9500
C6—C7	1.373 (9)	C20—H20	0.9500

N4—Mn1—N2	153.33 (19)	C7—C6—C5	122.8 (7)
N4—Mn1—N1	89.6 (2)	C6—C7—C8	119.8 (7)
N2—Mn1—N1	71.9 (2)	C6—C7—H7	120.1
N4—Mn1—N3	71.0 (2)	C8—C7—H7	120.1
N2—Mn1—N3	87.3 (2)	C9—C8—C7	118.7 (8)
N1—Mn1—N3	82.28 (19)	C9—C8—H8	120.7
N4—Mn1—I1	96.05 (16)	C7—C8—H8	120.7
N2—Mn1—I1	99.78 (15)	C10—C9—C8	118.9 (8)
N1—Mn1—I1	169.67 (14)	C10—C9—H9	120.6
N3—Mn1—I1	91.33 (15)	C8—C9—H9	120.6
N4—Mn1—I2	99.33 (16)	N2—C10—C9	124.1 (7)
N2—Mn1—I2	99.38 (15)	N2—C10—H10	117.9
N1—Mn1—I2	89.07 (14)	C9—C10—H10	117.9
N3—Mn1—I2	166.94 (15)	N3—C11—C12	126.4 (7)
I1—Mn1—I2	98.54 (4)	N3—C11—H11	116.8
C1—N1—C5	117.9 (6)	C12—C11—H11	116.8
C1—N1—Mn1	124.8 (5)	C11—C12—C13	116.9 (7)
C5—N1—Mn1	117.4 (4)	C11—C12—H12	121.5
C10—N2—C6	117.2 (6)	C13—C12—H12	121.5
C10—N2—Mn1	124.0 (5)	C12—C13—C14	119.2 (8)
C6—N2—Mn1	118.7 (5)	C12—C13—H13	120.4
C15—N3—C11	116.8 (6)	C14—C13—H13	120.4
C15—N3—Mn1	117.2 (5)	C15—C14—C13	118.7 (8)
C11—N3—Mn1	125.7 (5)	C15—C14—H14	120.6
C20—N4—C16	117.6 (6)	C13—C14—H14	120.6
C20—N4—Mn1	122.7 (5)	N3—C15—C14	121.8 (7)
C16—N4—Mn1	119.7 (5)	N3—C15—C16	116.0 (6)
N1—C1—C2	122.8 (7)	C14—C15—C16	122.1 (7)
N1—C1—H1	118.6	N4—C16—C17	121.1 (7)
C2—C1—H1	118.6	N4—C16—C15	115.5 (6)
C3—C2—C1	119.4 (7)	C17—C16—C15	123.4 (7)
C3—C2—H2	120.3	C18—C17—C16	119.7 (7)
C1—C2—H2	120.3	C18—C17—H17	120.2
C2—C3—C4	118.0 (7)	C16—C17—H17	120.2
C2—C3—H3	121.0	C17—C18—C19	120.7 (7)
C4—C3—H3	121.0	C17—C18—H18	119.7
C5—C4—C3	120.3 (8)	C19—C18—H18	119.7
C5—C4—H4	119.9	C20—C19—C18	116.4 (7)
C3—C4—H4	119.9	C20—C19—H19	121.8
N1—C5—C4	121.5 (7)	C18—C19—H19	121.8
N1—C5—C6	115.9 (6)	N4—C20—C19	124.5 (7)
C4—C5—C6	122.5 (7)	N4—C20—H20	117.8
N2—C6—C7	121.4 (7)	C19—C20—H20	117.8
N2—C6—C5	115.8 (6)

N4—Mn1—N1—C1	24.5 (6)	Mn1—N1—C5—C4	177.2 (6)
N2—Mn1—N1—C1	−175.1 (6)	C1—N1—C5—C6	175.0 (6)
N3—Mn1—N1—C1	95.3 (6)	Mn1—N1—C5—C6	−4.8 (8)
I1—Mn1—N1—C1	147.5 (7)	C3—C4—C5—N1	2.4 (12)
I2—Mn1—N1—C1	−74.9 (5)	C3—C4—C5—C6	−175.4 (7)
N4—Mn1—N1—C5	−155.7 (5)	C10—N2—C6—C7	0.1 (11)
N2—Mn1—N1—C5	4.7 (5)	Mn1—N2—C6—C7	−177.1 (6)
N3—Mn1—N1—C5	−84.9 (5)	C10—N2—C6—C5	−179.6 (6)
I1—Mn1—N1—C5	−32.7 (12)	Mn1—N2—C6—C5	3.2 (8)
I2—Mn1—N1—C5	104.9 (5)	N1—C5—C6—N2	1.1 (10)
N4—Mn1—N2—C10	−133.0 (6)	C4—C5—C6—N2	179.1 (7)
N1—Mn1—N2—C10	178.9 (6)	N1—C5—C6—C7	−178.6 (7)
N3—Mn1—N2—C10	−98.4 (6)	C4—C5—C6—C7	−0.6 (12)
I1—Mn1—N2—C10	−7.5 (6)	N2—C6—C7—C8	−1.1 (13)
I2—Mn1—N2—C10	93.0 (6)	C5—C6—C7—C8	178.6 (7)
N4—Mn1—N2—C6	43.9 (9)	C6—C7—C8—C9	1.2 (14)
N1—Mn1—N2—C6	−4.2 (5)	C7—C8—C9—C10	−0.2 (15)
N3—Mn1—N2—C6	78.6 (5)	C6—N2—C10—C9	0.9 (12)
I1—Mn1—N2—C6	169.5 (5)	Mn1—N2—C10—C9	177.9 (7)
I2—Mn1—N2—C6	−90.1 (5)	C8—C9—C10—N2	−0.9 (15)
N4—Mn1—N3—C15	6.2 (5)	C15—N3—C11—C12	−3.3 (13)
N2—Mn1—N3—C15	−158.2 (5)	Mn1—N3—C11—C12	−178.0 (7)
N1—Mn1—N3—C15	−86.0 (5)	N3—C11—C12—C13	3.3 (14)
I1—Mn1—N3—C15	102.1 (5)	C11—C12—C13—C14	−1.1 (14)
I2—Mn1—N3—C15	−37.1 (11)	C12—C13—C14—C15	−0.7 (14)
N4—Mn1—N3—C11	−179.2 (7)	C11—N3—C15—C14	1.1 (11)
N2—Mn1—N3—C11	16.5 (6)	Mn1—N3—C15—C14	176.2 (6)
N1—Mn1—N3—C11	88.6 (6)	C11—N3—C15—C16	179.7 (7)
I1—Mn1—N3—C11	−83.2 (6)	Mn1—N3—C15—C16	−5.1 (8)
I2—Mn1—N3—C11	137.6 (7)	C13—C14—C15—N3	0.8 (13)
N2—Mn1—N4—C20	−147.4 (6)	C13—C14—C15—C16	−177.7 (8)
N1—Mn1—N4—C20	−102.3 (6)	C20—N4—C16—C17	1.5 (11)
N3—Mn1—N4—C20	175.7 (6)	Mn1—N4—C16—C17	−176.3 (6)
I1—Mn1—N4—C20	86.4 (6)	C20—N4—C16—C15	−175.8 (7)
I2—Mn1—N4—C20	−13.3 (6)	Mn1—N4—C16—C15	6.4 (8)
N2—Mn1—N4—C16	30.4 (9)	N3—C15—C16—N4	−0.6 (10)
N1—Mn1—N4—C16	75.4 (5)	C14—C15—C16—N4	178.0 (7)
N3—Mn1—N4—C16	−6.6 (5)	N3—C15—C16—C17	−177.8 (7)
I1—Mn1—N4—C16	−95.9 (5)	C14—C15—C16—C17	0.8 (12)
I2—Mn1—N4—C16	164.4 (5)	N4—C16—C17—C18	1.5 (12)
C5—N1—C1—C2	2.2 (11)	C15—C16—C17—C18	178.6 (7)
Mn1—N1—C1—C2	−178.0 (5)	C16—C17—C18—C19	−3.1 (13)
N1—C1—C2—C3	−0.9 (12)	C17—C18—C19—C20	1.6 (14)
C1—C2—C3—C4	0.3 (12)	C16—N4—C20—C19	−3.2 (12)
C2—C3—C4—C5	−1.0 (12)	Mn1—N4—C20—C19	174.5 (7)
C1—N1—C5—C4	−3.0 (11)	C18—C19—C20—N4	1.7 (14)

Experimental details

Crystal data
Chemical formula	[MnI₂(C₁₀H₈N₂)₂]
M_r	621.11
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	200
a, b, c (Å)	16.491 (4), 15.403 (4), 17.719 (4)
β (°)	110.187 (5)
V (Å³)	4224.6 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.56
Crystal size (mm)	0.16 × 0.13 × 0.06

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.804, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15547, 5222, 2330
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.101, 0.89
No. of reflections	5222
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.21, −0.83

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Acknowledgements

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2010–0029626).

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ha, K. (2011). Z. Kristallogr. New Cryst. Struct. 226, 187–188. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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