Bis[N-(8-quinol­yl)pyridine-2-carbox­amidato-κ3N,N′,N′′]manganese(III) perchlorate monohydrate

Meng, Q.; Wang, L.; Liu, Y.; Pang, Y.

doi:10.1107/S1600536808000287

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m332

doi:10.1107/S1600536808000287

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: Bis[N-(8-quinolyl)pyridine-2-carboxamidato-κ³N,N′,N′′]manganese(III) perchlorate monohydrate

Qingguo Meng,^a ^* Lintong Wang,^a Yanzhen Liu ^a and Yan Pang ^a

^aCollege of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: qgmeng_weifang@yahoo.cn

(Received 6 November 2007; accepted 4 January 2008; online 11 January 2008)

The Mn^III ion in the title complex, [Mn(C₁₅H₁₀N₃O)₂]ClO₄·H₂O, is coordinated meridionally by six N atoms from two tridentate N-(8-quinolyl)pyridine-2-carboxamidate ligands, yielding a distorted octahedral coordination geometry. The two ligands are nearly planar and their mean planes are almost perpendicular, with a dihedral angle of 86.7 (2)°.

Related literature

For related literature, see: Dutta et al. (2000 ); Ni et al. (2006 ); Ni (2007 ); Zhang et al. (2001 ).

Experimental

Crystal data

[Mn(C₁₅H₁₀N₃O)₂]ClO₄·H₂O
M_r = 668.93
Triclinic, $[P \overline 1]$
a = 9.2314 (5) Å
b = 12.9987 (10) Å
c = 12.0126 (5) Å
α = 95.786 (1)°
β = 91.592 (2)°
γ = 90.486 (1)°
V = 1433.48 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 293 (2) K
0.28 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.847, T_max = 0.898
5004 measured reflections
4920 independent reflections
3731 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.189
S = 1.00
4920 reflections
406 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000287/cf2173sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000287/cf2173Isup2.hkl

checkCIF report

Comment top

To date, many symmetrical pyridinecarboxamide ligands and their coordination complexes have been synthesized (Ni et al., 2006). However, unsymetrical pyridinecarboxamide ligands are limited (Zhang et al., 2001). Here we report a new Mn^III complex, [Mn(C₁₅H₁₀N₃O)₂]ClO₄.H₂O, (I), containing two unsymmetrical pyridinecarboxamide tridentate ligands, 8-(pyridine-2-carboxamido)quinoline.

The structure and labeling scheme for the title complex are shown in Figure 1. The title compound comprises a [Mn^III(pcq)₂]⁺ (Hpcq = 8-(pyridine-2-carboxamido)quinoline) cation and a ClO₄^- anion as well as an uncoordinated water molecule. The Mn^III ion in the cation is coordinated by six nitrogen atoms from two mer pcq^- ligands, giving a distorted octahedral coordination environment. The C—O, C_pyridine—N, and C_carboxy—N bond distances in the title complex agree well with those reported for other complexes containing pyridinecarboxamide ligands (Dutta et al., 2000; Ni, 2007) and with the ligand precursor Hpcq (Zhang et al., 2001). The average Mn—N_pyridine bond distance is 1.914 Å and the average Mn—N_amide bond length is 2.028 Å. The two pcq^- ligands in (I) are both nearly planar, and the two mean planes are almost perpendicular, with a dihedral angle of 86.7 (2)°. There is probably a hydrogen bond between water and perchlorate, but the H atoms of the water molecule could not be located.

Related literature top

For related literature, see: Dutta et al. (2000); Ni et al. (2006); Ni (2007); Zhang et al. (2001).

Experimental top

The material Hpcq was synthesized according to the literature (Zhang et al., 2001). Solid Hpcq (500 mg, 2 mmol) was added to a methanol/water solution (20 ml, MeOH/H₂O = 4:1 v/v) of Mn^III acetate (326 mg, 1 mmol) containing 0.5 ml pyridine The mixture was stirred for about 0.5 h. The mixture was then filtered and the resulting solution was kept at room temperature for about one week, giving rise to pink block crystals. Yield: 50%. Elemental analysis [found (calculated)] for C₃₀H₂₂ClMnN₆O₇: C 53.65 (53.79), H 3.35 (3.31), N 12.39% (12.55%).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

Fig. 1. A view of (I) with the unique atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Bis[N-(8-quinolyl)pyridine-2-carboxamidato-κ³N,N',N'']manganate(III) perchlorate monohydrate top

Crystal data top

[Mn(C₁₅H₁₀N₃O)₂]ClO₄·H₂O	Z = 2
M_r = 668.93	F(000) = 684
Triclinic, P1	D_x = 1.550 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2314 (5) Å	Cell parameters from 4924 reflections
b = 12.9987 (10) Å	θ = 3.1–25.0°
c = 12.0126 (5) Å	µ = 0.61 mm⁻¹
α = 95.786 (1)°	T = 293 K
β = 91.592 (2)°	Block, pink
γ = 90.486 (1)°	0.28 × 0.22 × 0.18 mm
V = 1433.48 (15) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4920 independent reflections
Radiation source: fine-focus sealed tube	3731 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.847, T_max = 0.898	k = −15→15
5004 measured reflections	l = −14→14

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1288P)² + 0.5125P] where P = (F_o² + 2F_c²)/3
4920 reflections	(Δ/σ)_max < 0.001
406 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Mn(C₁₅H₁₀N₃O)₂]ClO₄·H₂O	γ = 90.486 (1)°
M_r = 668.93	V = 1433.48 (15) Å³
Triclinic, P1	Z = 2
a = 9.2314 (5) Å	Mo Kα radiation
b = 12.9987 (10) Å	µ = 0.61 mm⁻¹
c = 12.0126 (5) Å	T = 293 K
α = 95.786 (1)°	0.28 × 0.22 × 0.18 mm
β = 91.592 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4920 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3731 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.898	R_int = 0.029
5004 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.00	Δρ_max = 0.59 e Å⁻³
4920 reflections	Δρ_min = −0.67 e Å⁻³
406 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	1.01973 (6)	0.24180 (4)	0.24794 (4)	0.0384 (2)
Cl1	0.51979 (17)	0.11333 (15)	0.74568 (15)	0.0909 (5)
N2	0.9935 (4)	0.3931 (3)	0.3109 (3)	0.0518 (9)
N6	0.9288 (4)	0.1667 (3)	0.3589 (3)	0.0475 (8)
N5	1.0500 (4)	0.0939 (3)	0.1904 (3)	0.0495 (8)
N4	1.1108 (4)	0.2804 (3)	0.1203 (3)	0.0527 (9)
N1	0.8270 (4)	0.2620 (3)	0.1907 (3)	0.0531 (9)
C21	1.1198 (5)	0.0783 (4)	0.0992 (4)	0.0574 (12)
C8	0.8606 (5)	0.4385 (4)	0.2926 (4)	0.0551 (11)
C30	0.9270 (5)	0.0526 (3)	0.3384 (3)	0.0490 (10)
C22	0.9966 (5)	0.0084 (3)	0.2476 (3)	0.0493 (10)
O1	1.1111 (5)	0.5442 (3)	0.4079 (4)	0.0856 (12)
O2	1.1503 (5)	−0.0117 (3)	0.0524 (3)	0.0824 (11)
N3	1.2070 (4)	0.2650 (3)	0.3217 (3)	0.0475 (8)
C20	1.1555 (5)	0.1885 (4)	0.0605 (3)	0.0564 (12)
C29	0.8639 (5)	0.2116 (4)	0.4435 (3)	0.0538 (11)
H29A	0.8655	0.2831	0.4598	0.065*
C10	1.1042 (5)	0.4462 (4)	0.3671 (4)	0.0581 (11)
C26	0.8586 (5)	−0.0202 (4)	0.4046 (4)	0.0599 (12)
C9	0.7712 (5)	0.3641 (4)	0.2238 (4)	0.0542 (11)
C19	1.2233 (6)	0.1982 (6)	−0.0317 (4)	0.0755 (16)
H19A	1.2555	0.1408	−0.0763	0.091*
C16	1.1330 (6)	0.3830 (5)	0.0897 (4)	0.0669 (14)
H16A	1.0992	0.4398	0.1346	0.080*
C3	0.5529 (7)	0.3131 (6)	0.1275 (5)	0.0885 (19)
H3A	0.4579	0.3260	0.1054	0.106*
C4	0.6317 (6)	0.3950 (5)	0.1946 (4)	0.0683 (14)
C27	0.7876 (5)	0.0330 (5)	0.4904 (4)	0.0675 (14)
H27A	0.7353	−0.0039	0.5385	0.081*
C25	0.8682 (6)	−0.1357 (4)	0.3793 (5)	0.0711 (15)
H25A	0.8232	−0.1787	0.4255	0.085*
C1	0.7488 (6)	0.1890 (5)	0.1282 (4)	0.0686 (14)
H1A	0.7861	0.1235	0.1091	0.082*
C7	0.8077 (6)	0.5402 (4)	0.3300 (4)	0.0646 (13)
H7A	0.8676	0.5861	0.3748	0.078*
C15	1.3127 (5)	0.1909 (4)	0.3235 (4)	0.0577 (11)
H15A	1.2969	0.1248	0.2878	0.069*
C28	0.7912 (6)	0.1470 (5)	0.5094 (4)	0.0690 (14)
H28A	0.7411	0.1780	0.5698	0.083*
C24	0.9389 (7)	−0.1761 (4)	0.2934 (6)	0.0758 (16)
H24A	0.9466	−0.2473	0.2773	0.091*
C11	1.2259 (5)	0.3692 (4)	0.3732 (4)	0.0572 (11)
C12	1.3534 (6)	0.3970 (5)	0.4287 (5)	0.0775 (16)
H12A	1.3695	0.4635	0.4636	0.093*
C17	1.2026 (7)	0.3964 (6)	−0.0036 (5)	0.0810 (17)
H17A	1.2204	0.4610	−0.0277	0.097*
C23	1.0035 (6)	−0.1057 (4)	0.2258 (4)	0.0623 (12)
H23A	1.0534	−0.1331	0.1636	0.075*
C2	0.6104 (7)	0.2143 (6)	0.0929 (5)	0.094 (2)
H2A	0.5552	0.1666	0.0465	0.112*
C18	1.2466 (7)	0.3029 (7)	−0.0623 (5)	0.091 (2)
H18A	1.2960	0.3086	−0.1278	0.109*
C14	1.4402 (6)	0.2164 (5)	0.3784 (5)	0.0732 (15)
H14A	1.5138	0.1684	0.3824	0.088*
C13	1.4573 (7)	0.3211 (6)	0.4304 (6)	0.0904 (19)
H13A	1.5449	0.3388	0.4679	0.108*
C5	0.5839 (7)	0.5006 (6)	0.2351 (5)	0.0828 (18)
H5A	0.4908	0.5198	0.2149	0.099*
C6	0.6675 (7)	0.5712 (5)	0.3000 (5)	0.0816 (17)
H6A	0.6336	0.6368	0.3233	0.098*
O3	0.4151 (9)	0.0401 (7)	0.7756 (7)	0.182 (3)
O6	0.6578 (6)	0.0767 (6)	0.7331 (6)	0.142 (2)
O5	0.4784 (9)	0.1497 (12)	0.6457 (8)	0.258 (7)
O4	0.5174 (12)	0.2145 (7)	0.8072 (9)	0.220 (4)
O1W	0.7670 (12)	0.3638 (8)	0.8063 (11)	0.254 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0473 (4)	0.0421 (4)	0.0250 (3)	0.0047 (2)	0.0057 (2)	−0.0016 (2)
Cl1	0.0727 (9)	0.1085 (13)	0.0909 (11)	0.0234 (9)	0.0159 (8)	0.0013 (9)
N2	0.067 (2)	0.0450 (19)	0.0427 (19)	0.0049 (17)	0.0095 (17)	−0.0011 (16)
N6	0.052 (2)	0.056 (2)	0.0325 (17)	0.0015 (16)	0.0008 (14)	−0.0011 (15)
N5	0.052 (2)	0.062 (2)	0.0333 (17)	0.0084 (17)	0.0005 (14)	−0.0034 (16)
N4	0.053 (2)	0.076 (3)	0.0299 (17)	0.0037 (18)	0.0016 (14)	0.0087 (17)
N1	0.058 (2)	0.069 (2)	0.0309 (17)	0.0032 (18)	0.0042 (15)	0.0008 (16)
C21	0.062 (3)	0.068 (3)	0.038 (2)	0.019 (2)	−0.0008 (19)	−0.013 (2)
C8	0.068 (3)	0.058 (3)	0.041 (2)	0.008 (2)	0.011 (2)	0.011 (2)
C30	0.049 (2)	0.058 (3)	0.040 (2)	−0.0046 (19)	−0.0094 (17)	0.0057 (19)
C22	0.050 (2)	0.051 (2)	0.044 (2)	0.0004 (19)	−0.0096 (18)	−0.0038 (19)
O1	0.106 (3)	0.055 (2)	0.090 (3)	0.000 (2)	−0.003 (2)	−0.0202 (19)
O2	0.107 (3)	0.089 (3)	0.0469 (19)	0.027 (2)	0.0061 (19)	−0.0160 (18)
N3	0.050 (2)	0.059 (2)	0.0334 (17)	−0.0011 (16)	0.0063 (14)	0.0023 (15)
C20	0.048 (2)	0.091 (4)	0.029 (2)	0.007 (2)	−0.0020 (16)	−0.004 (2)
C29	0.058 (3)	0.068 (3)	0.035 (2)	0.006 (2)	0.0039 (18)	0.003 (2)
C10	0.068 (3)	0.054 (3)	0.051 (3)	−0.003 (2)	0.007 (2)	−0.006 (2)
C26	0.057 (3)	0.074 (3)	0.050 (3)	−0.015 (2)	−0.012 (2)	0.018 (2)
C9	0.064 (3)	0.063 (3)	0.037 (2)	0.013 (2)	0.0147 (19)	0.0106 (19)
C19	0.067 (3)	0.127 (5)	0.031 (2)	0.003 (3)	0.010 (2)	0.000 (3)
C16	0.068 (3)	0.093 (4)	0.042 (3)	0.005 (3)	0.003 (2)	0.020 (3)
C3	0.065 (4)	0.130 (6)	0.071 (4)	0.024 (4)	−0.006 (3)	0.015 (4)
C4	0.066 (3)	0.093 (4)	0.051 (3)	0.023 (3)	0.009 (2)	0.023 (3)
C27	0.056 (3)	0.101 (4)	0.049 (3)	−0.011 (3)	0.001 (2)	0.026 (3)
C25	0.075 (4)	0.068 (3)	0.073 (4)	−0.014 (3)	−0.007 (3)	0.026 (3)
C1	0.065 (3)	0.083 (4)	0.054 (3)	0.014 (3)	−0.008 (2)	−0.009 (3)
C7	0.087 (4)	0.053 (3)	0.056 (3)	0.014 (2)	0.017 (2)	0.010 (2)
C15	0.068 (3)	0.063 (3)	0.043 (2)	0.008 (2)	0.003 (2)	0.008 (2)
C28	0.063 (3)	0.106 (4)	0.041 (2)	0.004 (3)	0.012 (2)	0.014 (3)
C24	0.087 (4)	0.051 (3)	0.089 (4)	−0.005 (3)	−0.013 (3)	0.009 (3)
C11	0.067 (3)	0.058 (3)	0.045 (2)	−0.009 (2)	0.006 (2)	−0.002 (2)
C12	0.073 (4)	0.083 (4)	0.071 (3)	−0.018 (3)	−0.006 (3)	−0.015 (3)
C17	0.082 (4)	0.114 (5)	0.051 (3)	−0.006 (3)	0.003 (3)	0.027 (3)
C23	0.073 (3)	0.055 (3)	0.056 (3)	0.005 (2)	−0.006 (2)	−0.005 (2)
C2	0.078 (4)	0.133 (6)	0.064 (4)	0.009 (4)	−0.021 (3)	−0.013 (4)
C18	0.077 (4)	0.154 (7)	0.042 (3)	0.002 (4)	0.014 (3)	0.014 (4)
C14	0.052 (3)	0.099 (4)	0.067 (3)	0.008 (3)	−0.011 (2)	0.005 (3)
C13	0.069 (4)	0.108 (5)	0.091 (4)	0.000 (3)	−0.015 (3)	−0.003 (4)
C5	0.077 (4)	0.109 (5)	0.068 (4)	0.032 (4)	0.011 (3)	0.030 (3)
C6	0.096 (4)	0.082 (4)	0.072 (4)	0.026 (3)	0.026 (3)	0.021 (3)
O3	0.164 (7)	0.217 (8)	0.172 (7)	−0.050 (6)	0.047 (5)	0.050 (6)
O6	0.109 (4)	0.176 (6)	0.146 (5)	0.063 (4)	0.029 (4)	0.034 (5)
O5	0.138 (7)	0.51 (2)	0.150 (7)	0.019 (9)	0.001 (5)	0.155 (10)
O4	0.280 (11)	0.141 (6)	0.231 (10)	0.035 (7)	0.097 (8)	−0.047 (6)
O1W	0.240 (11)	0.150 (7)	0.350 (16)	−0.003 (7)	0.052 (10)	−0.088 (9)

Geometric parameters (Å, º) top

Mn1—N4	1.878 (3)	C9—C4	1.398 (7)
Mn1—N1	1.919 (4)	C19—C18	1.461 (10)
Mn1—N3	1.928 (4)	C19—H19A	0.930
Mn1—N6	1.935 (4)	C16—C17	1.334 (7)
Mn1—N5	2.000 (4)	C16—H16A	0.930
Mn1—N2	2.054 (4)	C3—C2	1.421 (10)
Cl1—O6	1.371 (5)	C3—C4	1.447 (9)
Cl1—O5	1.380 (8)	C3—H3A	0.930
Cl1—O3	1.429 (7)	C4—C5	1.485 (9)
Cl1—O4	1.442 (8)	C27—C28	1.477 (8)
N2—C10	1.353 (6)	C27—H27A	0.930
N2—C8	1.388 (6)	C25—C24	1.303 (9)
N6—C29	1.286 (6)	C25—H25A	0.930
N6—C30	1.478 (6)	C1—C2	1.388 (8)
N5—C21	1.286 (6)	C1—H1A	0.930
N5—C22	1.454 (6)	C7—C6	1.406 (9)
N4—C20	1.402 (6)	C7—H7A	0.930
N4—C16	1.433 (7)	C15—C14	1.355 (7)
N1—C1	1.342 (6)	C15—H15A	0.930
N1—C9	1.450 (6)	C28—H28A	0.930
C21—O2	1.283 (6)	C24—C23	1.422 (8)
C21—C20	1.585 (8)	C24—H24A	0.930
C8—C9	1.445 (7)	C11—C12	1.364 (7)
C8—C7	1.446 (7)	C12—C13	1.384 (9)
C30—C22	1.360 (6)	C12—H12A	0.930
C30—C26	1.449 (6)	C17—C18	1.411 (10)
C22—C23	1.481 (6)	C17—H17A	0.930
O1—C10	1.318 (6)	C23—H23A	0.930
N3—C15	1.378 (6)	C2—H2A	0.930
N3—C11	1.438 (6)	C18—H18A	0.930
C20—C19	1.304 (6)	C14—C13	1.444 (9)
C29—C28	1.391 (7)	C14—H14A	0.930
C29—H29A	0.930	C13—H13A	0.930
C10—C11	1.516 (7)	C5—C6	1.362 (9)
C26—C27	1.369 (8)	C5—H5A	0.930
C26—C25	1.505 (8)	C6—H6A	0.930

N4—Mn1—N1	94.61 (15)	C8—C9—N1	119.6 (4)
N4—Mn1—N3	85.35 (14)	C20—C19—C18	117.4 (6)
N1—Mn1—N3	162.60 (16)	C20—C19—H19A	121.3
N4—Mn1—N6	165.15 (17)	C18—C19—H19A	121.3
N1—Mn1—N6	86.06 (15)	C17—C16—N4	119.4 (6)
N3—Mn1—N6	98.42 (14)	C17—C16—H16A	120.3
N4—Mn1—N5	88.36 (16)	N4—C16—H16A	120.3
N1—Mn1—N5	100.50 (16)	C2—C3—C4	124.5 (5)
N3—Mn1—N5	96.89 (15)	C2—C3—H3A	117.7
N6—Mn1—N5	76.95 (15)	C4—C3—H3A	117.7
N4—Mn1—N2	92.24 (16)	C9—C4—C3	111.5 (5)
N1—Mn1—N2	81.17 (16)	C9—C4—C5	119.0 (6)
N3—Mn1—N2	81.45 (16)	C3—C4—C5	129.4 (5)
N6—Mn1—N2	102.51 (15)	C26—C27—C28	122.3 (5)
N5—Mn1—N2	178.18 (15)	C26—C27—H27A	118.8
O6—Cl1—O5	106.8 (5)	C28—C27—H27A	118.9
O6—Cl1—O3	115.4 (5)	C24—C25—C26	120.8 (5)
O5—Cl1—O3	110.0 (6)	C24—C25—H25A	119.6
O6—Cl1—O4	112.3 (6)	C26—C25—H25A	119.6
O5—Cl1—O4	93.5 (8)	N1—C1—C2	117.8 (6)
O3—Cl1—O4	116.3 (5)	N1—C1—H1A	121.1
C10—N2—C8	121.8 (4)	C2—C1—H1A	121.1
C10—N2—Mn1	120.3 (3)	C6—C7—C8	121.4 (5)
C8—N2—Mn1	117.9 (3)	C6—C7—H7A	119.3
C29—N6—C30	120.0 (4)	C8—C7—H7A	119.3
C29—N6—Mn1	123.0 (3)	C14—C15—N3	118.6 (5)
C30—N6—Mn1	116.8 (3)	C14—C15—H15A	120.7
C21—N5—C22	121.4 (4)	N3—C15—H15A	120.7
C21—N5—Mn1	116.1 (3)	C29—C28—C27	124.8 (5)
C22—N5—Mn1	122.5 (3)	C29—C28—H28A	117.6
C20—N4—C16	126.2 (4)	C27—C28—H28A	117.6
C20—N4—Mn1	106.4 (3)	C25—C24—C23	116.6 (5)
C16—N4—Mn1	127.4 (3)	C25—C24—H24A	121.7
C1—N1—C9	122.6 (4)	C23—C24—H24A	121.7
C1—N1—Mn1	124.1 (4)	C12—C11—N3	119.2 (5)
C9—N1—Mn1	113.4 (3)	C12—C11—C10	120.7 (5)
O2—C21—N5	123.9 (5)	N3—C11—C10	120.1 (4)
O2—C21—C20	129.2 (4)	C11—C12—C13	116.4 (5)
N5—C21—C20	106.9 (4)	C11—C12—H12A	121.8
N2—C8—C9	107.8 (4)	C13—C12—H12A	121.8
N2—C8—C7	130.8 (5)	C16—C17—C18	113.3 (6)
C9—C8—C7	121.4 (5)	C16—C17—H17A	123.3
C22—C30—C26	114.5 (4)	C18—C17—H17A	123.3
C22—C30—N6	118.1 (4)	C24—C23—C22	124.4 (5)
C26—C30—N6	127.4 (4)	C24—C23—H23A	117.8
C30—C22—N5	105.6 (4)	C22—C23—H23A	117.8
C30—C22—C23	120.3 (4)	C1—C2—C3	120.2 (6)
N5—C22—C23	134.1 (4)	C1—C2—H2A	119.9
C15—N3—C11	123.4 (4)	C3—C2—H2A	119.9
C15—N3—Mn1	124.0 (3)	C17—C18—C19	127.4 (5)
C11—N3—Mn1	112.6 (3)	C17—C18—H18A	116.3
C19—C20—N4	116.3 (5)	C19—C18—H18A	116.3
C19—C20—C21	121.5 (5)	C15—C14—C13	117.4 (5)
N4—C20—C21	122.1 (4)	C15—C14—H14A	121.3
N6—C29—C28	116.1 (5)	C13—C14—H14A	121.3
N6—C29—H29A	121.9	C12—C13—C14	125.0 (5)
C28—C29—H29A	121.9	C12—C13—H13A	117.5
O1—C10—N2	129.2 (5)	C14—C13—H13A	117.5
O1—C10—C11	125.3 (4)	C6—C5—C4	124.3 (6)
N2—C10—C11	105.5 (4)	C6—C5—H5A	117.9
C27—C26—C30	109.2 (5)	C4—C5—H5A	117.8
C27—C26—C25	127.4 (5)	C5—C6—C7	116.8 (6)
C30—C26—C25	123.4 (5)	C5—C6—H6A	121.6
C4—C9—C8	117.0 (5)	C7—C6—H6A	121.6
C4—C9—N1	123.3 (5)

Experimental details

Crystal data
Chemical formula	[Mn(C₁₅H₁₀N₃O)₂]ClO₄·H₂O
M_r	668.93
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.2314 (5), 12.9987 (10), 12.0126 (5)
α, β, γ (°)	95.786 (1), 91.592 (2), 90.486 (1)
V (Å³)	1433.48 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.847, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	5004, 4920, 3731
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.189, 1.00
No. of reflections	4920
No. of parameters	406
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.67

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 2001).

Acknowledgements

The authors thank the Education Department of Shandong Province for research and development projects (J06A55).

References

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