Diaqua­bis­[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl-κN3)nicotinato-κN]manganese(II)

Gao, P.; Liu, J.-Z.; Zhang, Z.; Huang, Z.-J.

doi:10.1107/S1600536810048506

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1668

https://doi.org/10.1107/S1600536810048506

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Diaquabis[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl-κN³)nicotinato-κN]manganese(II)

Peng Gao,^a Ji-Zhong Liu,^a Zhong Zhang ^a and Zhong-Jing Huang ^a ^*

^aDepartment of Chemistry, Guangxi University for Nationalities, Nanning 530006, People's Republic of China
^*Correspondence e-mail: huangzhongjing1@yahoo.com.cn

(Received 11 November 2010; accepted 21 November 2010; online 27 November 2010)

In the title compound, [Mn(C₁₃H₁₄N₃O₃)₂(H₂O)₂], the Mn^II ion is coordinated by four N atoms from two (±)-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinate ligands and two water molecules in a distorted octahedral environment. Intermolecular O—H⋯O hydrogen bonds lead to a chain along [010]. Intramolecular N—H⋯O and O—H⋯O hydrogen bonds are observed.

Related literature

For coordination compounds with pyridinecarboxylic acids, see: Chatterjee et al. (1998 ); Nathan & Mai (2000 ); Park et al. (2007 ); Yang et al. (2002 ). For the synthesis of compounds containing imidazolidinone derivatives, see: Erre et al. (1998 ).

Experimental

Crystal data

[Mn(C₁₃H₁₄N₃O₃)₂(H₂O)₂]
M_r = 611.52
Orthorhombic, P b c a
a = 12.620 (3) Å
b = 19.753 (4) Å
c = 23.017 (5) Å
V = 5738 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 298 K
0.50 × 0.48 × 0.35 mm

Data collection

Bruker SMART 1000 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.782, T_max = 0.839
25491 measured reflections
5057 independent reflections
3208 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.179
S = 1.06
5057 reflections
376 parameters
5 restraints
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	1.74	2.524 (5)	151
N5—H5⋯O5	0.86	1.76	2.535 (6)	149
O7—H7A⋯O3	0.85	2.09	2.838 (5)	147
O7—H7B⋯O1ⁱ	0.85	1.80	2.638 (5)	170
O8—H8A⋯O6	0.85	2.06	2.791 (5)	143
O8—H8B⋯O4ⁱⁱ	0.85	1.77	2.609 (5)	171
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: SMART (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: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048506/hy2382sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048506/hy2382Isup2.hkl

checkCIF report

Comment top

(±)-2-(4-Isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl) nicotinic acid (imina) is a novel pyridylimidazolidinone ligand, which provides with efficient metal-chelating ability. The pyridine carboxylic acids have been extensively used in the design of coordination compounds, due to a variety of bonding modes and ability to form strong hydrogen bonds (Chatterjee et al., 1998; Nathan & Mai, 2000; Park et al., 2007; Yang et al., 2002). Imidazole group, which is one of the polydentate amine ligands, generally coordinates to metal ions using N atoms as donors. The synthesis of imina and its manganese(II) complex has been reported (Erre et al., 1998). Here we present the structure of a manganese(II) complex with 2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H- imidazol-2-yl)nicotinate (L) ligand.

The molecular structure of the title complex is shown in Fig. 1. The asymmetric unit contains one Mn^II atom, two L ligands and two coordinated water molecules. The Mn^II atom exhibits a distorted octahedral geometry, defined by four N atoms from two L ligands and two O atoms from two water molecules. The dihedral angle between the two L planes in the complex is 61.58 (9)°. Intramolecular N—H···O and O—H···O hydrogen bonds are observed (Table 1). The complex molecules are connected via intermolecular O—H···O hydrogen bonds, forming a one-dimensional chain (Fig. 2).

Related literature top

For coordination compounds with pyridinecarboxylic acids, see: Chatterjee et al. (1998); Nathan & Mai (2000); Park et al. (2007); Yang et al. (2002). For the synthesis of compounds containing imidazolidinone derivatives, see: Erre et al. (1998).

Experimental top

A mixture of Mn(CH₃CO₂)₂.4H₂O (0.122 g, 0.5 mmol), imina (0.392 g, 0.5 mmol), DMF (5 ml) and H₂O (15 ml) was heated in a Teflon-lined steel bomb at 423 K for 3 d. Yellow crystals were obtained by slow evaporation of the solution at room temperature (yield: 78% ). Analysis, calculated for C₂₆H₃₂MnN₆O₈: C 51.07, H 5.27, N 13.74%; found: C 51.02, H 5.23, N 13.70%.

Structure description top

For coordination compounds with pyridinecarboxylic acids, see: Chatterjee et al. (1998); Nathan & Mai (2000); Park et al. (2007); Yang et al. (2002). For the synthesis of compounds containing imidazolidinone derivatives, see: Erre et al. (1998).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. Part of the chain structure in the title compound. Dashed lines indicate hydrongen bonds.

Diaquabis[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H- imidazol-2-yl-κN³)nicotinato-κN]manganese(II) top

Crystal data top

[Mn(C₁₃H₁₄N₃O₃)₂(H₂O)₂]	F(000) = 2552
M_r = 611.52	D_x = 1.416 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5733 reflections
a = 12.620 (3) Å	θ = 2.4–27.9°
b = 19.753 (4) Å	µ = 0.52 mm⁻¹
c = 23.017 (5) Å	T = 298 K
V = 5738 (2) Å³	Block, yellow
Z = 8	0.50 × 0.48 × 0.35 mm

Data collection top

Bruker SMART 1000 diffractometer	5057 independent reflections
Radiation source: fine-focus sealed tube	3208 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→15
T_min = 0.782, T_max = 0.839	k = −23→23
25491 measured reflections	l = −14→27

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0592P)² + 17.1897P] where P = (F_o² + 2F_c²)/3
5057 reflections	(Δ/σ)_max < 0.001
376 parameters	Δρ_max = 1.08 e Å⁻³
5 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Mn(C₁₃H₁₄N₃O₃)₂(H₂O)₂]	V = 5738 (2) Å³
M_r = 611.52	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.620 (3) Å	µ = 0.52 mm⁻¹
b = 19.753 (4) Å	T = 298 K
c = 23.017 (5) Å	0.50 × 0.48 × 0.35 mm

Data collection top

Bruker SMART 1000 diffractometer	5057 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3208 reflections with I > 2σ(I)
T_min = 0.782, T_max = 0.839	R_int = 0.055
25491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	5 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0592P)² + 17.1897P] where P = (F_o² + 2F_c²)/3
5057 reflections	Δρ_max = 1.08 e Å⁻³
376 parameters	Δρ_min = −0.47 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Mn1	0.28498 (5)	0.10909 (3)	0.37476 (3)	0.0311 (2)
N1	0.1631 (3)	0.19583 (18)	0.39468 (16)	0.0367 (9)
N2	0.2232 (4)	0.2701 (2)	0.25716 (17)	0.0490 (11)
H2	0.1965	0.3100	0.2544	0.059*
N3	0.2672 (3)	0.17162 (18)	0.29797 (15)	0.0355 (9)
N4	0.1688 (3)	0.02058 (18)	0.35275 (16)	0.0365 (9)
N5	0.2283 (4)	−0.0537 (2)	0.49061 (18)	0.0664 (15)
H5	0.2023	−0.0939	0.4929	0.080*
N6	0.2631 (3)	0.04717 (18)	0.45175 (15)	0.0350 (9)
O1	0.0913 (3)	0.42772 (17)	0.36537 (17)	0.0651 (11)
O2	0.1213 (4)	0.37586 (18)	0.28288 (17)	0.0650 (12)
O3	0.3547 (3)	0.12123 (19)	0.22133 (16)	0.0646 (11)
O4	0.0995 (3)	−0.21079 (17)	0.38402 (18)	0.0673 (12)
O5	0.1178 (5)	−0.1567 (2)	0.46503 (19)	0.110 (2)
O6	0.3470 (3)	0.09912 (18)	0.52887 (15)	0.0637 (11)
O7	0.4045 (3)	0.05333 (16)	0.32650 (15)	0.0475 (9)
H7A	0.3963	0.0573	0.2900	0.057*
H7B	0.4022	0.0115	0.3351	0.057*
O8	0.3971 (2)	0.16651 (15)	0.42592 (14)	0.0440 (8)
H8A	0.3819	0.1647	0.4619	0.053*
H8B	0.3977	0.2080	0.4162	0.053*
C1	0.1092 (3)	0.3765 (2)	0.3365 (2)	0.0391 (11)
C2	0.1627 (3)	0.2491 (2)	0.35795 (19)	0.0308 (10)
C3	0.1138 (3)	0.3108 (2)	0.37203 (19)	0.0301 (10)
C4	0.0613 (4)	0.3130 (2)	0.4252 (2)	0.0468 (13)
H4	0.0279	0.3528	0.4366	0.056*
C5	0.0578 (5)	0.2576 (3)	0.4611 (2)	0.0643 (17)
H5A	0.0199	0.2587	0.4958	0.077*
C6	0.1118 (5)	0.2006 (3)	0.4444 (2)	0.0565 (15)
H6	0.1123	0.1635	0.4693	0.068*
C7	0.2186 (4)	0.2319 (2)	0.30315 (18)	0.0341 (10)
C8	0.3063 (4)	0.1685 (2)	0.2425 (2)	0.0461 (12)
C9	0.2812 (4)	0.2346 (3)	0.2106 (2)	0.0473 (12)
C10	0.3824 (5)	0.2715 (3)	0.1936 (3)	0.0673 (17)
H10A	0.3653	0.3162	0.1803	0.101*
H10B	0.4173	0.2470	0.1631	0.101*
H10C	0.4284	0.2744	0.2267	0.101*
C11	0.2073 (5)	0.2211 (3)	0.1594 (2)	0.0609 (15)
H11	0.2455	0.1906	0.1331	0.073*
C12	0.1066 (5)	0.1839 (3)	0.1777 (3)	0.0666 (17)
H12A	0.1252	0.1447	0.2002	0.100*
H12B	0.0682	0.1700	0.1437	0.100*
H12C	0.0632	0.2135	0.2006	0.100*
C13	0.1825 (7)	0.2845 (4)	0.1247 (3)	0.095 (2)
H13A	0.1352	0.2734	0.0935	0.142*
H13B	0.2469	0.3029	0.1091	0.142*
H13C	0.1497	0.3174	0.1497	0.142*
C14	0.1122 (4)	−0.1588 (2)	0.4119 (2)	0.0452 (12)
C15	0.1655 (3)	−0.0322 (2)	0.39010 (18)	0.0309 (10)
C16	0.1191 (3)	−0.0941 (2)	0.3754 (2)	0.0339 (10)
C17	0.0734 (4)	−0.0981 (2)	0.3206 (2)	0.0443 (12)
H17	0.0420	−0.1385	0.3088	0.053*
C18	0.0735 (5)	−0.0442 (3)	0.2836 (2)	0.0543 (14)
H18	0.0406	−0.0469	0.2475	0.065*
C19	0.1235 (4)	0.0142 (3)	0.3011 (2)	0.0518 (14)
H19	0.1256	0.0508	0.2756	0.062*
C20	0.2189 (4)	−0.0141 (2)	0.44567 (19)	0.0373 (11)
C21	0.3027 (5)	0.0501 (3)	0.5075 (2)	0.0505 (13)
C22	0.2893 (5)	−0.0204 (3)	0.5368 (2)	0.0533 (12)
C23	0.3975 (5)	−0.0538 (3)	0.5459 (3)	0.0712 (17)
H23A	0.3879	−0.0982	0.5620	0.107*
H23B	0.4390	−0.0269	0.5721	0.107*
H23C	0.4336	−0.0573	0.5093	0.107*
C24	0.2253 (5)	−0.0186 (4)	0.5912 (3)	0.0735 (16)
H24	0.2100	−0.0655	0.6021	0.088*
C25	0.2858 (7)	0.0140 (4)	0.6421 (3)	0.101 (3)
H25A	0.3512	−0.0097	0.6482	0.152*
H25B	0.2434	0.0115	0.6767	0.152*
H25C	0.3004	0.0606	0.6332	0.152*
C26	0.1188 (6)	0.0170 (4)	0.5812 (3)	0.100 (2)
H26A	0.1310	0.0639	0.5726	0.150*
H26B	0.0760	0.0132	0.6155	0.150*
H26C	0.0828	−0.0039	0.5491	0.150*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0387 (4)	0.0209 (3)	0.0337 (4)	−0.0009 (3)	−0.0012 (3)	0.0038 (3)
N1	0.047 (2)	0.029 (2)	0.034 (2)	0.0061 (17)	0.0065 (18)	0.0057 (17)
N2	0.078 (3)	0.031 (2)	0.037 (2)	0.015 (2)	0.004 (2)	0.0046 (19)
N3	0.049 (2)	0.0263 (19)	0.031 (2)	0.0067 (17)	0.0038 (17)	0.0039 (17)
N4	0.044 (2)	0.032 (2)	0.033 (2)	−0.0081 (17)	−0.0043 (18)	0.0033 (17)
N5	0.115 (4)	0.046 (3)	0.039 (2)	−0.034 (3)	−0.013 (3)	0.012 (2)
N6	0.047 (2)	0.0271 (19)	0.0307 (19)	−0.0084 (17)	−0.0055 (17)	0.0025 (17)
O1	0.097 (3)	0.0228 (18)	0.076 (3)	0.0018 (19)	0.020 (2)	−0.0028 (18)
O2	0.105 (3)	0.038 (2)	0.052 (2)	0.029 (2)	−0.003 (2)	0.0107 (18)
O3	0.097 (3)	0.051 (2)	0.046 (2)	0.028 (2)	0.019 (2)	0.0007 (18)
O4	0.090 (3)	0.0272 (19)	0.085 (3)	−0.0018 (19)	−0.016 (2)	0.003 (2)
O5	0.220 (6)	0.056 (3)	0.052 (3)	−0.075 (3)	−0.003 (3)	0.016 (2)
O6	0.099 (3)	0.050 (2)	0.042 (2)	−0.032 (2)	−0.020 (2)	0.0020 (18)
O7	0.056 (2)	0.0297 (17)	0.056 (2)	0.0084 (16)	0.0059 (18)	0.0029 (16)
O8	0.052 (2)	0.0286 (17)	0.052 (2)	−0.0086 (15)	−0.0028 (17)	0.0019 (16)
C1	0.031 (2)	0.027 (3)	0.059 (3)	0.0029 (19)	−0.002 (2)	−0.001 (2)
C2	0.030 (2)	0.028 (2)	0.034 (2)	0.0033 (18)	−0.0049 (19)	0.0007 (19)
C3	0.025 (2)	0.026 (2)	0.039 (2)	0.0009 (17)	−0.005 (2)	−0.001 (2)
C4	0.048 (3)	0.036 (3)	0.056 (3)	0.013 (2)	0.006 (3)	−0.006 (3)
C5	0.081 (4)	0.060 (4)	0.052 (3)	0.025 (3)	0.031 (3)	0.009 (3)
C6	0.075 (4)	0.045 (3)	0.049 (3)	0.018 (3)	0.024 (3)	0.016 (3)
C7	0.045 (3)	0.025 (2)	0.032 (2)	0.003 (2)	−0.003 (2)	0.004 (2)
C8	0.064 (3)	0.038 (3)	0.037 (3)	0.011 (3)	0.003 (2)	0.002 (2)
C9	0.056 (3)	0.046 (3)	0.040 (3)	0.006 (3)	0.004 (2)	0.003 (2)
C10	0.060 (4)	0.073 (4)	0.069 (4)	−0.018 (3)	0.014 (3)	0.013 (3)
C11	0.068 (4)	0.069 (4)	0.046 (3)	0.010 (3)	−0.005 (3)	−0.001 (3)
C12	0.060 (4)	0.072 (4)	0.068 (4)	−0.012 (3)	−0.016 (3)	−0.005 (3)
C13	0.109 (6)	0.103 (6)	0.073 (5)	0.009 (5)	−0.016 (4)	0.032 (4)
C14	0.047 (3)	0.033 (3)	0.056 (3)	−0.012 (2)	−0.005 (3)	0.005 (3)
C15	0.032 (2)	0.027 (2)	0.033 (2)	−0.0045 (18)	0.0043 (19)	0.0029 (19)
C16	0.032 (2)	0.028 (2)	0.042 (3)	−0.0045 (18)	0.004 (2)	−0.003 (2)
C17	0.047 (3)	0.033 (3)	0.053 (3)	−0.009 (2)	0.000 (2)	−0.007 (2)
C18	0.068 (4)	0.055 (3)	0.040 (3)	−0.021 (3)	−0.015 (3)	0.001 (3)
C19	0.067 (4)	0.050 (3)	0.039 (3)	−0.021 (3)	−0.012 (3)	0.010 (2)
C20	0.051 (3)	0.030 (2)	0.031 (2)	−0.009 (2)	0.000 (2)	0.003 (2)
C21	0.076 (4)	0.042 (3)	0.034 (3)	−0.013 (3)	−0.008 (3)	0.004 (2)
C22	0.064 (3)	0.051 (3)	0.045 (3)	−0.006 (2)	−0.005 (2)	−0.001 (3)
C23	0.081 (3)	0.066 (4)	0.066 (4)	0.016 (3)	−0.012 (3)	0.015 (3)
C24	0.085 (4)	0.084 (5)	0.052 (3)	−0.014 (3)	0.006 (3)	0.001 (3)
C25	0.164 (8)	0.097 (6)	0.043 (3)	−0.030 (6)	−0.006 (4)	−0.004 (4)
C26	0.077 (4)	0.148 (8)	0.075 (5)	0.003 (4)	0.018 (3)	−0.010 (5)

Geometric parameters (Å, º) top

Mn1—O8	2.163 (3)	C8—C9	1.533 (7)
Mn1—N3	2.168 (4)	C9—C10	1.520 (7)
Mn1—N6	2.171 (4)	C9—C11	1.525 (7)
Mn1—O7	2.173 (3)	C10—H10A	0.9600
Mn1—N4	2.337 (4)	C10—H10B	0.9600
Mn1—N1	2.348 (4)	C10—H10C	0.9600
N1—C6	1.318 (6)	C11—C13	1.519 (8)
N1—C2	1.350 (5)	C11—C12	1.527 (8)
N2—C7	1.301 (5)	C11—H11	0.9800
N2—C9	1.475 (6)	C12—H12A	0.9600
N2—H2	0.8600	C12—H12B	0.9600
N3—C7	1.345 (5)	C12—H12C	0.9600
N3—C8	1.369 (6)	C13—H13A	0.9600
N4—C19	1.325 (6)	C13—H13B	0.9600
N4—C15	1.351 (5)	C13—H13C	0.9600
N5—C20	1.303 (6)	C14—C16	1.531 (6)
N5—C22	1.468 (7)	C15—C16	1.398 (6)
N5—H5	0.8600	C15—C20	1.489 (6)
N6—C20	1.340 (5)	C16—C17	1.390 (7)
N6—C21	1.377 (6)	C17—C18	1.363 (7)
O1—C1	1.231 (6)	C17—H17	0.9300
O2—C1	1.243 (6)	C18—C19	1.376 (7)
O3—C8	1.218 (6)	C18—H18	0.9300
O4—C14	1.222 (6)	C19—H19	0.9300
O5—C14	1.225 (6)	C21—C22	1.556 (7)
O6—C21	1.222 (6)	C22—C24	1.492 (8)
O7—H7A	0.8499	C22—C23	1.531 (8)
O7—H7B	0.8500	C23—H23A	0.9600
O8—H8A	0.8500	C23—H23B	0.9600
O8—H8B	0.8500	C23—H23C	0.9600
C1—C3	1.536 (6)	C24—C26	1.534 (10)
C2—C3	1.403 (6)	C24—C25	1.539 (9)
C2—C7	1.485 (6)	C24—H24	0.9800
C3—C4	1.393 (7)	C25—H25A	0.9600
C4—C5	1.372 (7)	C25—H25B	0.9600
C4—H4	0.9300	C25—H25C	0.9600
C5—C6	1.372 (7)	C26—H26A	0.9600
C5—H5A	0.9300	C26—H26B	0.9600
C6—H6	0.9300	C26—H26C	0.9600

O8—Mn1—N3	102.29 (13)	H10B—C10—H10C	109.5
O8—Mn1—N6	86.22 (13)	C13—C11—C9	112.7 (5)
N3—Mn1—N6	166.75 (15)	C13—C11—C12	111.7 (5)
O8—Mn1—O7	95.15 (13)	C9—C11—C12	112.4 (5)
N3—Mn1—O7	86.80 (13)	C13—C11—H11	106.5
N6—Mn1—O7	102.69 (14)	C9—C11—H11	106.5
O8—Mn1—N4	157.06 (13)	C12—C11—H11	106.5
N3—Mn1—N4	100.64 (14)	C11—C12—H12A	109.5
N6—Mn1—N4	71.08 (13)	C11—C12—H12B	109.5
O7—Mn1—N4	86.87 (13)	H12A—C12—H12B	109.5
O8—Mn1—N1	86.55 (13)	C11—C12—H12C	109.5
N3—Mn1—N1	71.07 (13)	H12A—C12—H12C	109.5
N6—Mn1—N1	99.70 (14)	H12B—C12—H12C	109.5
O7—Mn1—N1	157.60 (13)	C11—C13—H13A	109.5
N4—Mn1—N1	100.21 (14)	C11—C13—H13B	109.5
C6—N1—C2	119.1 (4)	H13A—C13—H13B	109.5
C6—N1—Mn1	122.9 (3)	C11—C13—H13C	109.5
C2—N1—Mn1	116.7 (3)	H13A—C13—H13C	109.5
C7—N2—C9	109.8 (4)	H13B—C13—H13C	109.5
C7—N2—H2	125.1	O4—C14—O5	124.1 (5)
C9—N2—H2	125.1	O4—C14—C16	114.9 (5)
C7—N3—C8	106.7 (4)	O5—C14—C16	121.1 (5)
C7—N3—Mn1	118.7 (3)	N4—C15—C16	122.3 (4)
C8—N3—Mn1	134.2 (3)	N4—C15—C20	110.3 (4)
C19—N4—C15	118.9 (4)	C16—C15—C20	127.4 (4)
C19—N4—Mn1	122.4 (3)	C17—C16—C15	116.3 (4)
C15—N4—Mn1	117.3 (3)	C17—C16—C14	115.3 (4)
C20—N5—C22	110.7 (4)	C15—C16—C14	128.4 (4)
C20—N5—H5	124.7	C18—C17—C16	121.5 (4)
C22—N5—H5	124.7	C18—C17—H17	119.2
C20—N6—C21	106.6 (4)	C16—C17—H17	119.2
C20—N6—Mn1	118.5 (3)	C17—C18—C19	118.2 (5)
C21—N6—Mn1	133.7 (3)	C17—C18—H18	120.9
Mn1—O7—H7A	111.9	C19—C18—H18	120.9
Mn1—O7—H7B	110.5	N4—C19—C18	122.7 (5)
H7A—O7—H7B	108.4	N4—C19—H19	118.6
Mn1—O8—H8A	111.1	C18—C19—H19	118.6
Mn1—O8—H8B	111.5	N5—C20—N6	114.9 (4)
H8A—O8—H8B	107.4	N5—C20—C15	125.4 (4)
O1—C1—O2	124.6 (5)	N6—C20—C15	119.6 (4)
O1—C1—C3	114.4 (4)	O6—C21—N6	125.0 (5)
O2—C1—C3	121.0 (4)	O6—C21—C22	125.7 (4)
N1—C2—C3	122.3 (4)	N6—C21—C22	109.1 (4)
N1—C2—C7	110.6 (4)	N5—C22—C24	109.6 (5)
C3—C2—C7	127.2 (4)	N5—C22—C23	112.0 (5)
C4—C3—C2	116.1 (4)	C24—C22—C23	112.2 (5)
C4—C3—C1	115.1 (4)	N5—C22—C21	98.3 (4)
C2—C3—C1	128.9 (4)	C24—C22—C21	113.7 (5)
C5—C4—C3	121.3 (4)	C23—C22—C21	110.4 (5)
C5—C4—H4	119.3	C22—C23—H23A	109.5
C3—C4—H4	119.3	C22—C23—H23B	109.5
C4—C5—C6	118.0 (5)	H23A—C23—H23B	109.5
C4—C5—H5A	121.0	C22—C23—H23C	109.5
C6—C5—H5A	121.0	H23A—C23—H23C	109.5
N1—C6—C5	123.1 (5)	H23B—C23—H23C	109.5
N1—C6—H6	118.5	C22—C24—C26	111.0 (5)
C5—C6—H6	118.5	C22—C24—C25	112.4 (6)
N2—C7—N3	114.9 (4)	C26—C24—C25	111.0 (6)
N2—C7—C2	125.4 (4)	C22—C24—H24	107.4
N3—C7—C2	119.7 (4)	C26—C24—H24	107.4
O3—C8—N3	126.1 (4)	C25—C24—H24	107.4
O3—C8—C9	124.4 (4)	C24—C25—H25A	109.5
N3—C8—C9	109.6 (4)	C24—C25—H25B	109.5
N2—C9—C10	112.1 (4)	H25A—C25—H25B	109.5
N2—C9—C11	110.0 (4)	C24—C25—H25C	109.5
C10—C9—C11	113.6 (5)	H25A—C25—H25C	109.5
N2—C9—C8	99.1 (4)	H25B—C25—H25C	109.5
C10—C9—C8	110.9 (5)	C24—C26—H26A	109.5
C11—C9—C8	110.3 (4)	C24—C26—H26B	109.5
C9—C10—H10A	109.5	H26A—C26—H26B	109.5
C9—C10—H10B	109.5	C24—C26—H26C	109.5
H10A—C10—H10B	109.5	H26A—C26—H26C	109.5
C9—C10—H10C	109.5	H26B—C26—H26C	109.5
H10A—C10—H10C	109.5

O8—Mn1—N1—C6	−79.3 (4)	C3—C2—C7—N3	175.8 (4)
N3—Mn1—N1—C6	176.5 (5)	C7—N3—C8—O3	−179.3 (5)
N6—Mn1—N1—C6	6.3 (4)	Mn1—N3—C8—O3	9.4 (9)
O7—Mn1—N1—C6	−174.4 (4)	C7—N3—C8—C9	1.4 (6)
N4—Mn1—N1—C6	78.7 (4)	Mn1—N3—C8—C9	−169.9 (3)
O8—Mn1—N1—C2	87.5 (3)	C7—N2—C9—C10	−117.0 (5)
N3—Mn1—N1—C2	−16.8 (3)	C7—N2—C9—C11	115.7 (5)
N6—Mn1—N1—C2	173.1 (3)	C7—N2—C9—C8	0.1 (5)
O7—Mn1—N1—C2	−7.7 (6)	O3—C8—C9—N2	179.8 (5)
N4—Mn1—N1—C2	−114.6 (3)	N3—C8—C9—N2	−0.9 (5)
O8—Mn1—N3—C7	−68.3 (3)	O3—C8—C9—C10	−62.2 (7)
N6—Mn1—N3—C7	60.8 (8)	N3—C8—C9—C10	117.0 (5)
O7—Mn1—N3—C7	−162.9 (3)	O3—C8—C9—C11	64.5 (7)
N4—Mn1—N3—C7	110.9 (3)	N3—C8—C9—C11	−116.2 (5)
N1—Mn1—N3—C7	13.6 (3)	N2—C9—C11—C13	73.7 (6)
O8—Mn1—N3—C8	102.1 (5)	C10—C9—C11—C13	−52.8 (7)
N6—Mn1—N3—C8	−128.7 (6)	C8—C9—C11—C13	−178.1 (5)
O7—Mn1—N3—C8	7.5 (5)	N2—C9—C11—C12	−53.7 (6)
N4—Mn1—N3—C8	−78.7 (5)	C10—C9—C11—C12	179.8 (5)
N1—Mn1—N3—C8	−175.9 (5)	C8—C9—C11—C12	54.6 (6)
O8—Mn1—N4—C19	−173.7 (4)	C19—N4—C15—C16	2.4 (7)
N3—Mn1—N4—C19	8.3 (4)	Mn1—N4—C15—C16	−164.7 (3)
N6—Mn1—N4—C19	177.6 (4)	C19—N4—C15—C20	−178.9 (4)
O7—Mn1—N4—C19	−77.8 (4)	Mn1—N4—C15—C20	14.0 (5)
N1—Mn1—N4—C19	80.7 (4)	N4—C15—C16—C17	−2.0 (7)
O8—Mn1—N4—C15	−7.0 (6)	C20—C15—C16—C17	179.6 (4)
N3—Mn1—N4—C15	174.9 (3)	N4—C15—C16—C14	177.9 (4)
N6—Mn1—N4—C15	−15.8 (3)	C20—C15—C16—C14	−0.6 (8)
O7—Mn1—N4—C15	88.8 (3)	O4—C14—C16—C17	22.3 (6)
N1—Mn1—N4—C15	−112.6 (3)	O5—C14—C16—C17	−156.7 (6)
O8—Mn1—N6—C20	−162.1 (4)	O4—C14—C16—C15	−157.6 (5)
N3—Mn1—N6—C20	67.3 (7)	O5—C14—C16—C15	23.5 (8)
O7—Mn1—N6—C20	−67.6 (4)	C15—C16—C17—C18	−0.4 (7)
N4—Mn1—N6—C20	14.5 (3)	C14—C16—C17—C18	179.7 (5)
N1—Mn1—N6—C20	112.1 (4)	C16—C17—C18—C19	2.2 (8)
O8—Mn1—N6—C21	3.2 (5)	C15—N4—C19—C18	−0.5 (8)
N3—Mn1—N6—C21	−127.4 (6)	Mn1—N4—C19—C18	166.0 (4)
O7—Mn1—N6—C21	97.6 (5)	C17—C18—C19—N4	−1.8 (9)
N4—Mn1—N6—C21	179.8 (5)	C22—N5—C20—N6	−1.6 (7)
N1—Mn1—N6—C21	−82.7 (5)	C22—N5—C20—C15	177.6 (5)
C6—N1—C2—C3	3.1 (7)	C21—N6—C20—N5	−2.7 (6)
Mn1—N1—C2—C3	−164.1 (3)	Mn1—N6—C20—N5	166.2 (4)
C6—N1—C2—C7	−176.3 (4)	C21—N6—C20—C15	178.1 (4)
Mn1—N1—C2—C7	16.5 (5)	Mn1—N6—C20—C15	−13.0 (6)
N1—C2—C3—C4	−2.8 (6)	N4—C15—C20—N5	179.5 (5)
C7—C2—C3—C4	176.5 (4)	C16—C15—C20—N5	−1.9 (8)
N1—C2—C3—C1	177.9 (4)	N4—C15—C20—N6	−1.4 (6)
C7—C2—C3—C1	−2.8 (7)	C16—C15—C20—N6	177.2 (4)
O1—C1—C3—C4	22.3 (6)	C20—N6—C21—O6	−178.5 (6)
O2—C1—C3—C4	−156.6 (5)	Mn1—N6—C21—O6	15.0 (9)
O1—C1—C3—C2	−158.4 (5)	C20—N6—C21—C22	5.6 (6)
O2—C1—C3—C2	22.7 (7)	Mn1—N6—C21—C22	−160.9 (4)
C2—C3—C4—C5	−0.3 (7)	C20—N5—C22—C24	123.4 (6)
C1—C3—C4—C5	179.1 (5)	C20—N5—C22—C23	−111.5 (6)
C3—C4—C5—C6	2.9 (9)	C20—N5—C22—C21	4.5 (6)
C2—N1—C6—C5	−0.2 (9)	O6—C21—C22—N5	178.0 (6)
Mn1—N1—C6—C5	166.2 (5)	N6—C21—C22—N5	−6.1 (6)
C4—C5—C6—N1	−2.7 (10)	O6—C21—C22—C24	62.3 (8)
C9—N2—C7—N3	0.8 (6)	N6—C21—C22—C24	−121.8 (5)
C9—N2—C7—C2	−177.3 (4)	O6—C21—C22—C23	−64.8 (8)
C8—N3—C7—N2	−1.4 (6)	N6—C21—C22—C23	111.1 (5)
Mn1—N3—C7—N2	171.4 (3)	N5—C22—C24—C26	−56.6 (7)
C8—N3—C7—C2	176.8 (4)	C23—C22—C24—C26	178.3 (6)
Mn1—N3—C7—C2	−10.3 (5)	C21—C22—C24—C26	52.2 (7)
N1—C2—C7—N2	173.2 (5)	N5—C22—C24—C25	178.4 (5)
C3—C2—C7—N2	−6.2 (8)	C23—C22—C24—C25	53.4 (8)
N1—C2—C7—N3	−4.9 (6)	C21—C22—C24—C25	−72.8 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.74	2.524 (5)	151
N5—H5···O5	0.86	1.76	2.535 (6)	149
O7—H7A···O3	0.85	2.09	2.838 (5)	147
O7—H7B···O1ⁱ	0.85	1.80	2.638 (5)	170
O8—H8A···O6	0.85	2.06	2.791 (5)	143
O8—H8B···O4ⁱⁱ	0.85	1.77	2.609 (5)	171

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

Experimental details

Crystal data
Chemical formula	[Mn(C₁₃H₁₄N₃O₃)₂(H₂O)₂]
M_r	611.52
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	12.620 (3), 19.753 (4), 23.017 (5)
V (Å³)	5738 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.50 × 0.48 × 0.35

Data collection
Diffractometer	Bruker SMART 1000
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.782, 0.839
No. of measured, independent and observed [I > 2σ(I)] reflections	25491, 5057, 3208
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.179, 1.06
No. of reflections	5057
No. of parameters	376
No. of restraints	5
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0592P)² + 17.1897P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.08, −0.47

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.74	2.524 (5)	151
N5—H5···O5	0.86	1.76	2.535 (6)	149
O7—H7A···O3	0.85	2.09	2.838 (5)	147
O7—H7B···O1ⁱ	0.85	1.80	2.638 (5)	170
O8—H8A···O6	0.85	2.06	2.791 (5)	143
O8—H8B···O4ⁱⁱ	0.85	1.77	2.609 (5)	171

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

Acknowledgements

This work was supported by the Innovation Project of Guangxi University for Nationalities (gxun-chx2009080).

References

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