Bis(N,N-dimethyl­formamide-κO)bis­(1-methyl­imidazole-2-carbaldehyde oximato-κ2N,O)manganese(III) perchlorate

Wang, F.; Zhang, J.; Wang, Q.; Huang, S.

doi:10.1107/S1600536808034016

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1462

doi:10.1107/S1600536808034016

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Bis(N,N-dimethylformamide-κO)bis(1-methylimidazole-2-carbaldehyde oximato-κ²N,O)manganese(III) perchlorate

Feng Wang,^a Jianming Zhang,^a ^* Qirong Wang ^b and Shiying Huang ^c

^aCollege of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People's Republic of China, ^bSchool of Chemistry and Materials Science, Xiaogan University, Xiaogan, Hubei 432000, People's Republic of China, and ^cHubei Polytechnic Institute, Xiaogan, Hubei 432000, People's Republic of China
^*Correspondence e-mail: wangfeng9802@126.com

(Received 16 October 2008; accepted 17 October 2008; online 25 October 2008)

In the title compound, [Mn(C₅H₆N₃O)₂(C₃H₇NO)]ClO₄, the Mn^III atom lies on the inversion centre of the centrosymmetric complex cation and has a distorted octahedral coordination geometry, formed by two N atoms and two O atoms from two 1-methylimidazole-2-carbaldehyde oximate ligands and two O atoms from two dimethylformamide ligands. Perchlorate acts as a counterion to balance the charge. The crystal structure of the title compound is stabilized by C—H⋯O hydrogen-bonding interactions.

Related literature

For related literature, see: Miyasaka et al. (2005 ); Saitoh et al. (2007 ).

Experimental

Crystal data

[Mn(C₅H₆N₃O)₂(C₃H₇NO)]ClO₄
M_r = 548.84
Triclinic, $[P \overline 1]$
a = 7.6158 (11) Å
b = 12.324 (2) Å
c = 12.8600 (16) Å
α = 82.841 (10)°
β = 85.273 (11)°
γ = 80.471 (16)°
V = 1178.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 298 (2) K
0.23 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.850, T_max = 0.930
9397 measured reflections
4101 independent reflections
3191 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.158
S = 1.08
4101 reflections
313 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—O1	1.886 (3)
Mn1—O2	1.893 (3)
Mn1—N4	1.997 (3)
Mn1—N2	2.002 (3)
Mn1—O4	2.204 (3)
Mn1—O3	2.443 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O7ⁱ	0.93	2.54	3.433 (6)	161
C5—H5⋯O7ⁱⁱ	0.93	2.60	3.402 (6)	145
C12—H12A⋯O8ⁱⁱ	0.96	2.49	3.399 (6)	157
C13—H13C⋯O5ⁱⁱⁱ	0.96	2.40	3.261 (7)	150
C14—H14⋯O6	0.93	2.59	3.477 (6)	161
Symmetry codes: (i) x-1, y+1, z; (ii) x, y+1, z; (iii) -x+2, -y+1, -z+2.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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 I, global. DOI: 10.1107/S1600536808034016/at2654sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034016/at2654Isup2.hkl

checkCIF report

Comment top

The metal complexes with the 2-((hydroxyimino)methyl)-1-methylimidazole and 2-((hydroxyimino)methyl)-1-ethylimidazole had some good activities (Miyasaka et al., 2005; Saitoh et al., 2007). Herein, we report the crystal structure of such a novel compound, [Mn(C₅H₆N₃O)₂(C₃H₇NO)](ClO₄), (I).

The molecular structure of (I) is shown in Fig.1. The Mn atom lying on the inversion center of the centrosymmetric cation has a distorted octahedral geometry and is coordinated by two N atoms and two O atoms (O3,O4) from two 2-((hydroxyimino)methyl)-1-methylimidazole ligands, which lie in the equatorial plane, with the torsional angle O1—N2—O2—N4 = -2.19°, and two O atoms from two N',N-dimthylformamide molecules occupy the axial sites, which is nearly linear [O3—Mn—O4 = 176.62 (10)°] (Table 1). The distance from Mn to the equatorial plane is 0.0828 (15) Å. O3 and O4 are far away from the equatorial plane, with the mean distance 2.32 Å. As shown in Fig. 2, an organic cation layer is linked to an inorganic anionic layer through a series of C—H···O hydrogen bonding interactions (Table 2). In the structure, there are not π-π interactions.

Related literature top

For related literature, see: Miyasaka et al. (2005); Saitoh et al. (2007).

Experimental top

[Mn(C₅H₆N₃O)₂(C₃H₇NO)](ClO₄) was prepared as followings: to a solution of 2-((Hydroxyimino)methyl)-1-methylimidazole 0.50 g(4 mmol) in DMF(25 mL) and triethylamine (0.05 mL) was added Mn(ClO₄)₂(0.724 g, 2.0 mmol). After the mixture was stirred for a one hour, the solution was filtered. The filtrate was kept for several days at ambient temperature, and brown block crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. The molecular structure of (I), showing ellipsoids at the 50% probability level.
	Fig. 2. The hydrogen-bonding structure of the molecular packing diagram of (I).

Bis(N,N-dimethylformamide-κO)bis(1-methylimidazole-2- carbaldehyde oximato-κ²N,O)manganese(III) perchlorate top

Crystal data top

[Mn(C₅H₆N₃O)₂(C₃H₇NO)]ClO₄	Z = 2
M_r = 548.84	F(000) = 568
Triclinic, P1	D_x = 1.546 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6158 (11) Å	Cell parameters from 2239 reflections
b = 12.324 (2) Å	θ = 2.5–22.4°
c = 12.8600 (16) Å	µ = 0.73 mm⁻¹
α = 82.841 (10)°	T = 298 K
β = 85.273 (11)°	Block, brown
γ = 80.471 (16)°	0.23 × 0.20 × 0.10 mm
V = 1178.7 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4101 independent reflections
Radiation source: fine-focus sealed tube	3191 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
T_min = 0.850, T_max = 0.930	k = −14→12
9397 measured reflections	l = −15→15

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0845P)² + 0.2454P] where P = (F_o² + 2F_c²)/3
4101 reflections	(Δ/σ)_max = 0.002
313 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Mn(C₅H₆N₃O)₂(C₃H₇NO)]ClO₄	γ = 80.471 (16)°
M_r = 548.84	V = 1178.7 (3) Å³
Triclinic, P1	Z = 2
a = 7.6158 (11) Å	Mo Kα radiation
b = 12.324 (2) Å	µ = 0.73 mm⁻¹
c = 12.8600 (16) Å	T = 298 K
α = 82.841 (10)°	0.23 × 0.20 × 0.10 mm
β = 85.273 (11)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4101 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3191 reflections with I > 2σ(I)
T_min = 0.850, T_max = 0.930	R_int = 0.039
9397 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.08	Δρ_max = 0.40 e Å⁻³
4101 reflections	Δρ_min = −0.29 e Å⁻³
313 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
Mn1	0.67156 (7)	0.67997 (4)	0.75744 (4)	0.0366 (2)
C1	0.3414 (5)	0.8512 (4)	0.7017 (3)	0.0513 (11)
H1	0.2579	0.8049	0.7250	0.062*
C2	0.3042 (6)	0.9582 (4)	0.6627 (3)	0.0579 (12)
H2	0.1912	0.9989	0.6537	0.070*
C3	0.5955 (6)	0.9116 (3)	0.6626 (3)	0.0446 (10)
C4	0.4845 (7)	1.1121 (3)	0.5958 (4)	0.0667 (14)
H4A	0.5257	1.1481	0.6491	0.100*
H4B	0.3719	1.1521	0.5742	0.100*
H4C	0.5699	1.1104	0.5366	0.100*
C5	0.7840 (6)	0.9159 (4)	0.6449 (3)	0.0529 (11)
H5	0.8146	0.9804	0.6076	0.063*
C6	0.9974 (5)	0.5219 (3)	0.8403 (3)	0.0389 (9)
H6	1.0818	0.5646	0.8096	0.047*
C7	1.0311 (5)	0.4261 (3)	0.9042 (3)	0.0415 (9)
H7	1.1425	0.3912	0.9251	0.050*
C8	0.7428 (5)	0.4639 (3)	0.8846 (3)	0.0358 (9)
C9	0.8461 (6)	0.2892 (3)	1.0015 (3)	0.0533 (11)
H9A	0.7266	0.2973	1.0330	0.080*
H9B	0.9294	0.2769	1.0555	0.080*
H9C	0.8660	0.2272	0.9612	0.080*
C10	0.5576 (5)	0.4523 (3)	0.8923 (3)	0.0462 (10)
H10	0.5274	0.3893	0.9328	0.055*
C11	0.6945 (5)	0.8367 (3)	0.9405 (3)	0.0431 (10)
H11	0.7584	0.8692	0.8836	0.052*
C12	0.7615 (6)	0.9785 (4)	1.0387 (3)	0.0573 (12)
H12A	0.8234	1.0007	0.9734	0.086*
H12B	0.8445	0.9599	1.0928	0.086*
H12C	0.6711	1.0384	1.0570	0.086*
C13	0.5781 (6)	0.8394 (4)	1.1206 (3)	0.0624 (13)
H13A	0.5095	0.7868	1.1020	0.094*
H13B	0.4993	0.8994	1.1488	0.094*
H13C	0.6591	0.8038	1.1724	0.094*
C14	0.7324 (5)	0.5286 (4)	0.5742 (3)	0.0497 (11)
H14	0.7438	0.4704	0.6278	0.060*
C15	0.7250 (11)	0.5901 (4)	0.3915 (4)	0.109 (3)
H15A	0.6469	0.6535	0.4141	0.164*
H15B	0.6748	0.5641	0.3350	0.164*
H15C	0.8393	0.6104	0.3680	0.164*
C16	0.7802 (8)	0.3905 (4)	0.4514 (4)	0.0720 (15)
H16A	0.7721	0.3403	0.5143	0.108*
H16B	0.8976	0.3759	0.4177	0.108*
H16C	0.6935	0.3805	0.4047	0.108*
N1	0.4629 (5)	0.9964 (3)	0.6388 (3)	0.0507 (9)
N2	0.5233 (4)	0.8215 (3)	0.7014 (2)	0.0416 (8)
N3	0.9150 (5)	0.8411 (3)	0.6746 (3)	0.0547 (9)
N4	0.8164 (4)	0.5454 (2)	0.8285 (2)	0.0355 (7)
N5	0.8711 (4)	0.3896 (3)	0.9328 (2)	0.0382 (7)
N6	0.4281 (4)	0.5195 (3)	0.8494 (3)	0.0487 (8)
N7	0.6785 (4)	0.8821 (3)	1.0277 (2)	0.0429 (8)
N8	0.7459 (5)	0.5038 (3)	0.4778 (2)	0.0471 (8)
O1	0.8785 (3)	0.7471 (2)	0.7320 (2)	0.0478 (7)
O2	0.4629 (3)	0.6147 (2)	0.7914 (2)	0.0508 (7)
O3	0.6303 (4)	0.7528 (2)	0.9275 (2)	0.0523 (7)
O4	0.7056 (4)	0.6244 (2)	0.5996 (2)	0.0528 (7)
Cl1	0.90018 (14)	0.19042 (8)	0.72382 (8)	0.0490 (3)
O5	1.0504 (6)	0.2250 (4)	0.7606 (4)	0.1166 (16)
O6	0.7487 (5)	0.2738 (3)	0.7265 (3)	0.0903 (12)
O7	0.9418 (5)	0.1610 (3)	0.6206 (2)	0.0731 (10)
O8	0.8620 (5)	0.0947 (3)	0.7917 (3)	0.0839 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0330 (3)	0.0354 (4)	0.0413 (3)	−0.0012 (2)	−0.0041 (2)	−0.0077 (3)
C1	0.038 (2)	0.058 (3)	0.055 (2)	0.004 (2)	−0.0040 (18)	−0.010 (2)
C2	0.048 (3)	0.065 (3)	0.053 (2)	0.019 (2)	−0.007 (2)	−0.009 (2)
C3	0.053 (2)	0.041 (2)	0.042 (2)	0.002 (2)	−0.0120 (18)	−0.0156 (18)
C4	0.101 (4)	0.037 (3)	0.058 (3)	0.010 (2)	−0.026 (3)	−0.006 (2)
C5	0.060 (3)	0.038 (2)	0.063 (3)	−0.015 (2)	−0.010 (2)	0.000 (2)
C6	0.032 (2)	0.040 (2)	0.045 (2)	−0.0012 (17)	−0.0015 (16)	−0.0104 (18)
C7	0.030 (2)	0.044 (2)	0.050 (2)	−0.0010 (18)	−0.0050 (17)	−0.0114 (19)
C8	0.033 (2)	0.032 (2)	0.0417 (19)	0.0022 (16)	−0.0043 (15)	−0.0125 (17)
C9	0.052 (3)	0.041 (2)	0.061 (3)	−0.002 (2)	0.000 (2)	0.006 (2)
C10	0.041 (2)	0.039 (2)	0.061 (2)	−0.0122 (19)	−0.0018 (19)	−0.008 (2)
C11	0.040 (2)	0.046 (3)	0.043 (2)	0.0006 (19)	−0.0045 (16)	−0.0091 (19)
C12	0.066 (3)	0.053 (3)	0.054 (2)	−0.015 (2)	−0.007 (2)	−0.006 (2)
C13	0.071 (3)	0.075 (3)	0.046 (2)	−0.026 (3)	0.008 (2)	−0.014 (2)
C14	0.051 (2)	0.055 (3)	0.042 (2)	−0.003 (2)	−0.0034 (18)	−0.008 (2)
C15	0.214 (8)	0.056 (4)	0.049 (3)	−0.001 (4)	0.007 (4)	−0.009 (3)
C16	0.108 (4)	0.045 (3)	0.059 (3)	0.011 (3)	−0.011 (3)	−0.016 (2)
N1	0.062 (2)	0.042 (2)	0.0467 (19)	0.0087 (18)	−0.0146 (16)	−0.0158 (16)
N2	0.0407 (19)	0.040 (2)	0.0439 (17)	0.0022 (15)	−0.0072 (14)	−0.0124 (15)
N3	0.050 (2)	0.051 (2)	0.065 (2)	−0.0155 (19)	−0.0046 (17)	−0.0029 (19)
N4	0.0321 (16)	0.0362 (18)	0.0394 (16)	−0.0043 (14)	−0.0039 (13)	−0.0098 (14)
N5	0.0349 (17)	0.0350 (18)	0.0441 (17)	−0.0014 (14)	−0.0020 (13)	−0.0080 (14)
N6	0.0378 (19)	0.047 (2)	0.063 (2)	−0.0114 (17)	−0.0043 (16)	−0.0048 (18)
N7	0.0455 (19)	0.047 (2)	0.0383 (17)	−0.0110 (16)	−0.0037 (14)	−0.0052 (15)
N8	0.063 (2)	0.039 (2)	0.0374 (17)	−0.0003 (17)	−0.0038 (15)	−0.0041 (15)
O1	0.0418 (16)	0.0430 (17)	0.0573 (16)	−0.0054 (13)	−0.0033 (12)	−0.0020 (14)
O2	0.0359 (15)	0.0536 (19)	0.0620 (17)	−0.0066 (13)	−0.0089 (13)	0.0001 (15)
O3	0.0614 (19)	0.0491 (18)	0.0478 (16)	−0.0076 (15)	−0.0047 (13)	−0.0112 (14)
O4	0.071 (2)	0.0438 (17)	0.0434 (15)	−0.0033 (15)	−0.0003 (13)	−0.0156 (13)
Cl1	0.0570 (7)	0.0428 (6)	0.0473 (5)	−0.0056 (5)	−0.0017 (4)	−0.0092 (5)
O5	0.098 (3)	0.150 (4)	0.124 (3)	−0.060 (3)	−0.011 (3)	−0.046 (3)
O6	0.101 (3)	0.067 (2)	0.088 (2)	0.027 (2)	0.002 (2)	−0.008 (2)
O7	0.102 (3)	0.062 (2)	0.0477 (17)	0.0068 (19)	0.0013 (17)	−0.0089 (15)
O8	0.113 (3)	0.067 (2)	0.064 (2)	−0.015 (2)	0.0083 (19)	0.0157 (18)

Geometric parameters (Å, º) top

Mn1—O1	1.886 (3)	C9—H9C	0.9600
Mn1—O2	1.893 (3)	C10—N6	1.292 (5)
Mn1—N4	1.997 (3)	C10—H10	0.9300
Mn1—N2	2.002 (3)	C11—O3	1.249 (5)
Mn1—O4	2.204 (3)	C11—N7	1.304 (5)
Mn1—O3	2.443 (3)	C11—H11	0.9300
C1—C2	1.344 (6)	C12—N7	1.461 (5)
C1—N2	1.372 (5)	C12—H12A	0.9600
C1—H1	0.9300	C12—H12B	0.9600
C2—N1	1.367 (6)	C12—H12C	0.9600
C2—H2	0.9300	C13—N7	1.455 (5)
C3—N2	1.343 (5)	C13—H13A	0.9600
C3—N1	1.352 (5)	C13—H13B	0.9600
C3—C5	1.443 (6)	C13—H13C	0.9600
C4—N1	1.493 (5)	C14—O4	1.244 (5)
C4—H4A	0.9600	C14—N8	1.306 (5)
C4—H4B	0.9600	C14—H14	0.9300
C4—H4C	0.9600	C15—N8	1.437 (6)
C5—N3	1.289 (5)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.351 (5)	C15—H15C	0.9600
C6—N4	1.377 (5)	C16—N8	1.455 (5)
C6—H6	0.9300	C16—H16A	0.9600
C7—N5	1.375 (5)	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600
C8—N4	1.335 (5)	N3—O1	1.350 (4)
C8—N5	1.356 (4)	N6—O2	1.362 (4)
C8—C10	1.436 (5)	Cl1—O6	1.413 (3)
C9—N5	1.458 (5)	Cl1—O7	1.416 (3)
C9—H9A	0.9600	Cl1—O5	1.420 (4)
C9—H9B	0.9600	Cl1—O8	1.433 (3)

O1—Mn1—O2	176.56 (11)	H12A—C12—H12B	109.5
O1—Mn1—N4	89.45 (12)	N7—C12—H12C	109.5
O2—Mn1—N4	89.88 (12)	H12A—C12—H12C	109.5
O1—Mn1—N2	90.13 (13)	H12B—C12—H12C	109.5
O2—Mn1—N2	90.18 (13)	N7—C13—H13A	109.5
N4—Mn1—N2	173.75 (11)	N7—C13—H13B	109.5
O1—Mn1—O4	91.23 (11)	H13A—C13—H13B	109.5
O2—Mn1—O4	92.20 (12)	N7—C13—H13C	109.5
N4—Mn1—O4	95.89 (11)	H13A—C13—H13C	109.5
N2—Mn1—O4	90.35 (11)	H13B—C13—H13C	109.5
O1—Mn1—O3	87.46 (11)	O4—C14—N8	124.9 (4)
O2—Mn1—O3	89.13 (11)	O4—C14—H14	117.6
N4—Mn1—O3	87.21 (10)	N8—C14—H14	117.6
N2—Mn1—O3	86.54 (10)	N8—C15—H15A	109.5
O4—Mn1—O3	176.62 (10)	N8—C15—H15B	109.5
C2—C1—N2	108.6 (4)	H15A—C15—H15B	109.5
C2—C1—H1	125.7	N8—C15—H15C	109.5
N2—C1—H1	125.7	H15A—C15—H15C	109.5
C1—C2—N1	107.5 (4)	H15B—C15—H15C	109.5
C1—C2—H2	126.3	N8—C16—H16A	109.5
N1—C2—H2	126.3	N8—C16—H16B	109.5
N2—C3—N1	108.9 (4)	H16A—C16—H16B	109.5
N2—C3—C5	125.5 (4)	N8—C16—H16C	109.5
N1—C3—C5	125.5 (4)	H16A—C16—H16C	109.5
N1—C4—H4A	109.5	H16B—C16—H16C	109.5
N1—C4—H4B	109.5	C3—N1—C2	107.8 (4)
H4A—C4—H4B	109.5	C3—N1—C4	126.4 (4)
N1—C4—H4C	109.5	C2—N1—C4	125.7 (4)
H4A—C4—H4C	109.5	C3—N2—C1	107.2 (4)
H4B—C4—H4C	109.5	C3—N2—Mn1	122.2 (3)
N3—C5—C3	127.9 (4)	C1—N2—Mn1	130.4 (3)
N3—C5—H5	116.1	C5—N3—O1	118.6 (3)
C3—C5—H5	116.1	C8—N4—C6	107.2 (3)
C7—C6—N4	108.3 (3)	C8—N4—Mn1	122.6 (2)
C7—C6—H6	125.9	C6—N4—Mn1	129.8 (3)
N4—C6—H6	125.9	C8—N5—C7	107.1 (3)
C6—C7—N5	107.7 (3)	C8—N5—C9	127.0 (3)
C6—C7—H7	126.2	C7—N5—C9	125.9 (3)
N5—C7—H7	126.2	C10—N6—O2	119.1 (3)
N4—C8—N5	109.7 (3)	C11—N7—C13	122.0 (4)
N4—C8—C10	126.5 (3)	C11—N7—C12	122.2 (3)
N5—C8—C10	123.7 (4)	C13—N7—C12	115.8 (3)
N5—C9—H9A	109.5	C14—N8—C15	120.2 (4)
N5—C9—H9B	109.5	C14—N8—C16	123.1 (4)
H9A—C9—H9B	109.5	C15—N8—C16	116.7 (3)
N5—C9—H9C	109.5	N3—O1—Mn1	133.5 (2)
H9A—C9—H9C	109.5	N6—O2—Mn1	134.0 (2)
H9B—C9—H9C	109.5	C11—O3—Mn1	120.4 (2)
N6—C10—C8	127.3 (4)	C14—O4—Mn1	129.3 (3)
N6—C10—H10	116.3	O6—Cl1—O7	110.6 (2)
C8—C10—H10	116.3	O6—Cl1—O5	111.4 (3)
O3—C11—N7	124.9 (4)	O7—Cl1—O5	109.5 (2)
O3—C11—H11	117.6	O6—Cl1—O8	108.6 (2)
N7—C11—H11	117.6	O7—Cl1—O8	108.9 (2)
N7—C12—H12A	109.5	O5—Cl1—O8	107.7 (3)
N7—C12—H12B	109.5

N2—C1—C2—N1	−0.6 (4)	O3—Mn1—N4—C8	81.1 (3)
N2—C3—C5—N3	−9.7 (7)	O1—Mn1—N4—C6	−3.9 (3)
N1—C3—C5—N3	173.1 (4)	O2—Mn1—N4—C6	179.5 (3)
N4—C6—C7—N5	−0.2 (4)	O4—Mn1—N4—C6	87.3 (3)
N4—C8—C10—N6	−2.3 (6)	O3—Mn1—N4—C6	−91.4 (3)
N5—C8—C10—N6	179.7 (4)	N4—C8—N5—C7	−0.6 (4)
N2—C3—N1—C2	−0.3 (4)	C10—C8—N5—C7	177.7 (3)
C5—C3—N1—C2	177.2 (4)	N4—C8—N5—C9	179.7 (3)
N2—C3—N1—C4	178.6 (3)	C10—C8—N5—C9	−1.9 (5)
C5—C3—N1—C4	−3.8 (6)	C6—C7—N5—C8	0.5 (4)
C1—C2—N1—C3	0.6 (4)	C6—C7—N5—C9	−179.9 (3)
C1—C2—N1—C4	−178.4 (3)	C8—C10—N6—O2	−1.7 (6)
N1—C3—N2—C1	0.0 (4)	O3—C11—N7—C13	−1.3 (6)
C5—C3—N2—C1	−177.6 (3)	O3—C11—N7—C12	178.2 (4)
N1—C3—N2—Mn1	−175.1 (2)	O4—C14—N8—C15	−1.6 (7)
C5—C3—N2—Mn1	7.4 (5)	O4—C14—N8—C16	179.0 (4)
C2—C1—N2—C3	0.4 (4)	C5—N3—O1—Mn1	16.5 (5)
C2—C1—N2—Mn1	174.9 (3)	N4—Mn1—O1—N3	171.2 (3)
O1—Mn1—N2—C3	2.4 (3)	N2—Mn1—O1—N3	−15.0 (3)
O2—Mn1—N2—C3	178.9 (3)	O3—Mn1—O1—N3	−101.5 (3)
O4—Mn1—N2—C3	−88.9 (3)	C10—N6—O2—Mn1	−1.6 (5)
O3—Mn1—N2—C3	89.8 (3)	N4—Mn1—O2—N6	5.5 (3)
O1—Mn1—N2—C1	−171.4 (3)	N2—Mn1—O2—N6	−168.3 (3)
O2—Mn1—N2—C1	5.1 (3)	O4—Mn1—O2—N6	101.4 (3)
O4—Mn1—N2—C1	97.3 (3)	O3—Mn1—O2—N6	−81.7 (3)
O3—Mn1—N2—C1	−84.0 (3)	N7—C11—O3—Mn1	179.5 (3)
C3—C5—N3—O1	−2.1 (6)	O1—Mn1—O3—C11	25.0 (3)
N5—C8—N4—C6	0.5 (4)	O2—Mn1—O3—C11	−155.5 (3)
C10—C8—N4—C6	−177.8 (3)	N4—Mn1—O3—C11	114.6 (3)
N5—C8—N4—Mn1	−173.4 (2)	N2—Mn1—O3—C11	−65.2 (3)
C10—C8—N4—Mn1	8.3 (5)	N8—C14—O4—Mn1	177.9 (3)
C7—C6—N4—C8	−0.2 (4)	O1—Mn1—O4—C14	117.2 (4)
C7—C6—N4—Mn1	173.1 (2)	O2—Mn1—O4—C14	−62.5 (4)
O1—Mn1—N4—C8	168.6 (3)	N4—Mn1—O4—C14	27.6 (4)
O2—Mn1—N4—C8	−8.1 (3)	N2—Mn1—O4—C14	−152.7 (4)
O4—Mn1—N4—C8	−100.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O7ⁱ	0.93	2.54	3.433 (6)	161
C5—H5···O7ⁱⁱ	0.93	2.60	3.402 (6)	145
C12—H12A···O8ⁱⁱ	0.96	2.49	3.399 (6)	157
C13—H13A···O3	0.96	2.41	2.797 (5)	103
C13—H13C···O5ⁱⁱⁱ	0.96	2.40	3.261 (7)	150
C14—H14···O6	0.93	2.59	3.477 (6)	161

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

Experimental details

Crystal data
Chemical formula	[Mn(C₅H₆N₃O)₂(C₃H₇NO)]ClO₄
M_r	548.84
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.6158 (11), 12.324 (2), 12.8600 (16)
α, β, γ (°)	82.841 (10), 85.273 (11), 80.471 (16)
V (Å³)	1178.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.23 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.850, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	9397, 4101, 3191
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.158, 1.08
No. of reflections	4101
No. of parameters	313
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.29

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Mn1—O1	1.886 (3)	Mn1—N2	2.002 (3)
Mn1—O2	1.893 (3)	Mn1—O4	2.204 (3)
Mn1—N4	1.997 (3)	Mn1—O3	2.443 (3)

O1—Mn1—O2	176.56 (11)	N4—Mn1—O4	95.89 (11)
O1—Mn1—N4	89.45 (12)	N2—Mn1—O4	90.35 (11)
O2—Mn1—N4	89.88 (12)	O1—Mn1—O3	87.46 (11)
O1—Mn1—N2	90.13 (13)	O2—Mn1—O3	89.13 (11)
O2—Mn1—N2	90.18 (13)	N4—Mn1—O3	87.21 (10)
N4—Mn1—N2	173.75 (11)	N2—Mn1—O3	86.54 (10)
O1—Mn1—O4	91.23 (11)	O4—Mn1—O3	176.62 (10)
O2—Mn1—O4	92.20 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O7ⁱ	0.93	2.54	3.433 (6)	161
C5—H5···O7ⁱⁱ	0.93	2.60	3.402 (6)	145
C12—H12A···O8ⁱⁱ	0.96	2.49	3.399 (6)	157
C13—H13A···O3	0.96	2.41	2.797 (5)	103
C13—H13C···O5ⁱⁱⁱ	0.96	2.40	3.261 (7)	150
C14—H14···O6	0.93	2.59	3.477 (6)	161

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

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Miyasaka, H., Saitoh, A., Yanagida, S., Kachi-Terajima, C., Sugiura, K. & Yamashita, M. (2005). Inorg. Chim. Acta, 358, 3525–3535. Web of Science CSD CrossRef CAS Google Scholar
Saitoh, A., Miyasaka, H., Yamashita, M. & Clerac, R. (2007). J. Mater. Chem. 17, 2002–2012. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 11| November 2008| Page m1462

doi:10.1107/S1600536808034016

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