Poly[di-μ-cis-cyclo­hexane-1,4-dicarboxyl­ato-μ-trans-cyclo­hexane-1,4-dicarboxyl­ato-bis­[dipyrido[3,2-a:2′,3′-c]phenazine]trimanganese(II)]

Zhang, W.-Z.; Yuan, X.-H.

doi:10.1107/S1600536808012737

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m781-m782

doi:10.1107/S1600536808012737

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Poly[di-μ-cis-cyclohexane-1,4-dicarboxylato-μ-trans-cyclohexane-1,4-dicarboxylato-bis[dipyrido[3,2-a:2′,3′-c]phenazine]trimanganese(II)]

Wen-Zhi Zhang ^a ^* and Xiao-Huan Yuan ^b

^aCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, Heilongjiang Province, People's Republic of China, and ^bHeilongjiang Key Laboratory of Fibrosis Biotherapy, Mudanjiang Medical College, Mudanjiang 157011, Heilongjiang Province, People's Republic of China
^*Correspondence e-mail: zhangwenzhi1968@yahoo.com.cn

(Received 26 April 2008; accepted 30 April 2008; online 7 May 2008)

In the title compound, [Mn₃(C₈H₁₀O₄)₃(C₁₈H₁₀N₄)₂], one Mn atom and one cyclohexane-1,4-dicarboxylate (chdc) ligand are located on centres of inversion. One of the two independent Mn atoms is seven-coordinate, binding to five carboxylate O atoms from different chdc ligands and two phenanthrene N atoms from a dipyrido[3,2-a:2′,3′-c]phenazine (L) ligand, while the second Mn atom is six-coordinate, binding to six carboxylate O atoms from different chdc ligands. The cis-chdc ligands bridge the trinuclear Mn^II clusters, forming chains, which are further linked into a three-dimensional network.

Related literature

For related structures, see: De (2007 ); Li (2007 ).

Experimental

Crystal data

[Mn₃(C₈H₁₀O₄)₃(C₁₈H₁₀N₄)₂]
M_r = 1239.90
Triclinic, $[P \overline 1]$
a = 8.5730 (17) Å
b = 10.614 (2) Å
c = 14.846 (3) Å
α = 77.34 (3)°
β = 81.99 (3)°
γ = 82.67 (3)°
V = 1298.6 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 293 (2) K
0.33 × 0.22 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.762, T_max = 0.863
12776 measured reflections
5830 independent reflections
3707 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.176
S = 1.05
5830 reflections
376 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012737/bt2704sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012737/bt2704Isup2.hkl

checkCIF report

Comment top

1,4-Cyclohexanedicarboxylic acid (H₂chdc), as a flexible multidentate ligand, has been extensively studied in the chemistry of coordination polymers (De, 2007; Li, 2007). Here, we report a new Mn^II coordination polymer with chdc ligand, namely [Mn₃(cis-chdc)₃(trans-chdc)(L)₂] (I), where L = dipyrido[3,2-a:2',3'-c]-phenazine.

In (I) the Mn1 atom is seven-coordinate binding to five carboxylate O atoms from different chdc ligands, and two phenanthrene N atoms from L ligand (Fig. 1 and Table 1). The Mn2 atom is six-coordinate binding to six carboxylate O atoms from different chdc ligands (Fig. 1 and Table 1). Interestingly, the chdc ligands bridge neighboring Mn^II atoms to give a trinuclear Mn^II cluster. The cis-chdc ligands bridge the trinuclear Mn^II clusters to form a chain structure, which are further linked into a 3D network structure (Fig. 2). One Mn atom and one 1,4-cyclohexanedicarboxylate molecule are located on a centre of inversion.

Related literature top

For related structures, see: De (2007); Li (2007).

Experimental top

A mixture of Mn(NO₃)₂^.2H₂O (1 mmol), H₂chdc (1 mmol) and L (1 mmol) was dissolved in 12 ml distilled water, followed by addition of triethylamine until the pH value of the system was approximately 5.5. The resulting solution was sealed in a 23-ml Teflon-lined stainless steel autoclave and heated at 175°C for 8 days under autogenous pressure. The reaction vessel was then slowly cooled to room temperature. Pale yellow block-like crystals of (I) suitable for single-crystal X-ray diffraction analysis were obtained from the resulting solution.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) x-1, y, z; (ii) 2-x, 1-y, -z; (iii) 3-x, 1-y, -z; (iv) 2-x, 2-y, -z.
	Fig. 2. Packing diagram of (I).

Poly[di-µ-cis-cyclohexane-1,4-dicarboxylato-µ-trans-cyclohexane-1,4- dicarboxylato-bis[dipyrido[3,2-a:2',3'-c]phenazine]trimanganese(II)] top

Crystal data top

[Mn₃(C₈H₁₀O₄)₃(C₁₈H₁₀N₄)₂]	Z = 1
M_r = 1239.90	F(000) = 637
Triclinic, P1	D_x = 1.585 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5730 (17) Å	Cell parameters from 8527 reflections
b = 10.614 (2) Å	θ = 3.0–27.5°
c = 14.846 (3) Å	µ = 0.80 mm⁻¹
α = 77.34 (3)°	T = 293 K
β = 81.99 (3)°	Block, pale yellow
γ = 82.67 (3)°	0.33 × 0.22 × 0.19 mm
V = 1298.6 (4) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	5830 independent reflections
Radiation source: rotating anode	3707 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
T_min = 0.762, T_max = 0.863	l = −16→19
12776 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0908P)²] where P = (F_o² + 2F_c²)/3
5830 reflections	(Δ/σ)_max < 0.001
376 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

[Mn₃(C₈H₁₀O₄)₃(C₁₈H₁₀N₄)₂]	γ = 82.67 (3)°
M_r = 1239.90	V = 1298.6 (4) Å³
Triclinic, P1	Z = 1
a = 8.5730 (17) Å	Mo Kα radiation
b = 10.614 (2) Å	µ = 0.80 mm⁻¹
c = 14.846 (3) Å	T = 293 K
α = 77.34 (3)°	0.33 × 0.22 × 0.19 mm
β = 81.99 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5830 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3707 reflections with I > 2σ(I)
T_min = 0.762, T_max = 0.863	R_int = 0.062
12776 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.05	Δρ_max = 0.64 e Å⁻³
5830 reflections	Δρ_min = −0.74 e Å⁻³
376 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.3154 (5)	0.6357 (5)	0.2263 (4)	0.0481 (12)
H1	1.3426	0.6017	0.1729	0.058*
C2	1.4234 (5)	0.7038 (5)	0.2518 (4)	0.0542 (13)
H2	1.5216	0.7137	0.2169	0.065*
C3	1.3834 (5)	0.7570 (5)	0.3297 (4)	0.0513 (13)
H3	1.4535	0.8044	0.3476	0.062*
C4	1.2354 (5)	0.7384 (4)	0.3817 (3)	0.0361 (9)
C5	1.1352 (4)	0.6662 (4)	0.3517 (3)	0.0322 (9)
C6	0.9812 (5)	0.6398 (4)	0.4043 (3)	0.0312 (8)
C7	0.7506 (5)	0.5439 (4)	0.4195 (3)	0.0428 (10)
H7	0.6873	0.4949	0.3977	0.051*
C8	0.6944 (5)	0.5891 (5)	0.5002 (3)	0.0448 (11)
H8	0.5957	0.5702	0.5314	0.054*
C9	0.7855 (5)	0.6617 (4)	0.5334 (3)	0.0405 (10)
H9	0.7504	0.6915	0.5879	0.049*
C10	0.9314 (5)	0.6901 (4)	0.4842 (3)	0.0334 (9)
C11	1.0314 (5)	0.7716 (4)	0.5137 (3)	0.0320 (9)
C12	1.1837 (5)	0.7951 (4)	0.4643 (3)	0.0361 (9)
C13	1.2187 (5)	0.9248 (4)	0.5624 (3)	0.0368 (9)
C14	1.3088 (5)	1.0088 (5)	0.5907 (4)	0.0467 (11)
H14	1.4085	1.0250	0.5597	0.056*
C15	1.2492 (5)	1.0660 (4)	0.6635 (3)	0.0455 (11)
H15	1.3096	1.1204	0.6821	0.055*
C16	1.0994 (6)	1.0448 (4)	0.7108 (3)	0.0451 (11)
H16	1.0602	1.0862	0.7596	0.054*
C17	1.0108 (6)	0.9640 (5)	0.6856 (3)	0.0459 (11)
H17	0.9116	0.9492	0.7178	0.055*
C18	1.0681 (5)	0.9021 (4)	0.6110 (3)	0.0372 (9)
C19	1.2088 (4)	0.3188 (4)	0.1441 (3)	0.0330 (9)
C20	1.3374 (4)	0.2042 (4)	0.1547 (3)	0.0329 (9)
H20	1.2888	0.1277	0.1496	0.039*
C21	1.4043 (5)	0.1721 (4)	0.2488 (3)	0.0371 (9)
H21A	1.3173	0.1678	0.2983	0.044*
H21B	1.4648	0.0875	0.2559	0.044*
C22	1.5100 (4)	0.2725 (4)	0.2577 (3)	0.0329 (9)
H22A	1.5559	0.2449	0.3158	0.039*
H22B	1.4464	0.3547	0.2590	0.039*
C23	1.6420 (4)	0.2913 (4)	0.1774 (3)	0.0344 (9)
H23	1.7047	0.2070	0.1790	0.041*
C24	1.7540 (5)	0.3865 (4)	0.1871 (3)	0.0371 (10)
C25	1.5739 (5)	0.3280 (4)	0.0842 (3)	0.0389 (10)
H25A	1.5112	0.4115	0.0797	0.047*
H25B	1.6598	0.3359	0.0340	0.047*
C26	1.4706 (5)	0.2260 (5)	0.0744 (3)	0.0416 (10)
H26A	1.5359	0.1447	0.0726	0.050*
H26B	1.4248	0.2535	0.0161	0.050*
C27	0.9657 (5)	0.7352 (4)	0.0992 (3)	0.0360 (9)
C28	0.9835 (5)	0.8607 (4)	0.0286 (3)	0.0426 (10)
H28	1.0018	0.8391	−0.0332	0.051*
C29	1.1322 (5)	0.9177 (4)	0.0430 (3)	0.0400 (10)
H29A	1.1198	0.9368	0.1047	0.048*
H29B	1.2236	0.8544	0.0383	0.048*
C30	0.8404 (5)	0.9579 (4)	0.0298 (3)	0.0423 (10)
H30A	0.8166	0.9787	0.0910	0.051*
H30B	0.7501	0.9206	0.0172	0.051*
N1	1.1746 (4)	0.6163 (3)	0.2743 (2)	0.0364 (8)
N2	0.8915 (4)	0.5678 (3)	0.3718 (2)	0.0340 (8)
N3	1.2766 (4)	0.8696 (4)	0.4881 (3)	0.0407 (9)
N4	0.9733 (4)	0.8249 (3)	0.5858 (2)	0.0380 (8)
O1	1.1606 (4)	0.3541 (3)	0.0659 (2)	0.0532 (9)
O2	1.1563 (3)	0.3674 (3)	0.2134 (2)	0.0397 (7)
O3	1.8227 (4)	0.4527 (4)	0.1177 (3)	0.0595 (10)
O4	1.7807 (4)	0.3935 (3)	0.2666 (2)	0.0532 (9)
O5	0.8733 (4)	0.7288 (3)	0.1720 (2)	0.0461 (8)
O6	1.0573 (3)	0.6357 (3)	0.0822 (2)	0.0365 (7)
Mn1	0.97563 (7)	0.51832 (6)	0.22819 (4)	0.02964 (19)
Mn2	1.0000	0.5000	0.0000	0.0292 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.043 (2)	0.049 (3)	0.057 (3)	−0.008 (2)	0.005 (2)	−0.025 (2)
C2	0.038 (2)	0.069 (3)	0.063 (3)	−0.019 (2)	0.008 (2)	−0.031 (3)
C3	0.039 (2)	0.059 (3)	0.066 (3)	−0.016 (2)	0.001 (2)	−0.031 (3)
C4	0.036 (2)	0.034 (2)	0.040 (2)	−0.0096 (17)	0.0023 (18)	−0.0130 (19)
C5	0.033 (2)	0.031 (2)	0.036 (2)	−0.0062 (16)	−0.0048 (17)	−0.0108 (18)
C6	0.038 (2)	0.0253 (19)	0.033 (2)	−0.0071 (16)	−0.0100 (17)	−0.0067 (17)
C7	0.042 (2)	0.041 (2)	0.050 (3)	−0.0163 (19)	−0.006 (2)	−0.013 (2)
C8	0.035 (2)	0.057 (3)	0.047 (3)	−0.017 (2)	0.007 (2)	−0.020 (2)
C9	0.042 (2)	0.044 (3)	0.039 (2)	−0.0143 (19)	0.0044 (19)	−0.015 (2)
C10	0.036 (2)	0.029 (2)	0.038 (2)	−0.0105 (16)	−0.0045 (18)	−0.0087 (18)
C11	0.038 (2)	0.029 (2)	0.033 (2)	−0.0069 (16)	−0.0070 (17)	−0.0105 (17)
C12	0.036 (2)	0.035 (2)	0.042 (2)	−0.0061 (17)	−0.0077 (18)	−0.015 (2)
C13	0.038 (2)	0.032 (2)	0.044 (3)	−0.0054 (17)	−0.0104 (19)	−0.0127 (19)
C14	0.037 (2)	0.054 (3)	0.058 (3)	−0.010 (2)	−0.005 (2)	−0.028 (2)
C15	0.047 (3)	0.042 (3)	0.057 (3)	−0.008 (2)	−0.013 (2)	−0.023 (2)
C16	0.057 (3)	0.043 (3)	0.042 (3)	−0.007 (2)	−0.007 (2)	−0.020 (2)
C17	0.052 (3)	0.051 (3)	0.040 (3)	−0.019 (2)	0.004 (2)	−0.020 (2)
C18	0.041 (2)	0.034 (2)	0.040 (2)	−0.0120 (18)	−0.0062 (19)	−0.0084 (19)
C19	0.033 (2)	0.0235 (19)	0.044 (2)	−0.0064 (16)	−0.0099 (18)	−0.0058 (18)
C20	0.031 (2)	0.0238 (19)	0.047 (2)	−0.0073 (15)	−0.0061 (18)	−0.0107 (18)
C21	0.036 (2)	0.030 (2)	0.044 (3)	−0.0092 (17)	−0.0082 (18)	0.0013 (19)
C22	0.0299 (19)	0.037 (2)	0.034 (2)	−0.0113 (16)	−0.0075 (16)	−0.0051 (18)
C23	0.0288 (19)	0.030 (2)	0.047 (3)	−0.0068 (16)	−0.0013 (18)	−0.0136 (19)
C24	0.031 (2)	0.037 (2)	0.047 (3)	−0.0098 (17)	0.0017 (19)	−0.017 (2)
C25	0.038 (2)	0.044 (2)	0.037 (2)	−0.0093 (18)	−0.0001 (18)	−0.013 (2)
C26	0.035 (2)	0.052 (3)	0.044 (3)	−0.0067 (19)	−0.0022 (19)	−0.022 (2)
C27	0.047 (2)	0.028 (2)	0.037 (2)	−0.0106 (18)	−0.009 (2)	−0.0073 (18)
C28	0.053 (3)	0.026 (2)	0.048 (3)	−0.0078 (18)	−0.001 (2)	−0.0045 (19)
C29	0.039 (2)	0.031 (2)	0.047 (3)	−0.0050 (18)	−0.003 (2)	−0.003 (2)
C30	0.045 (2)	0.032 (2)	0.050 (3)	−0.0124 (18)	−0.005 (2)	−0.004 (2)
N1	0.0386 (18)	0.0342 (19)	0.039 (2)	−0.0080 (15)	−0.0005 (15)	−0.0128 (16)
N2	0.0337 (17)	0.0320 (18)	0.040 (2)	−0.0101 (14)	−0.0060 (15)	−0.0099 (16)
N3	0.0353 (18)	0.045 (2)	0.049 (2)	−0.0119 (15)	−0.0009 (16)	−0.0233 (19)
N4	0.0442 (19)	0.041 (2)	0.0338 (19)	−0.0150 (16)	−0.0048 (16)	−0.0112 (16)
O1	0.069 (2)	0.0470 (19)	0.048 (2)	0.0177 (16)	−0.0304 (17)	−0.0172 (16)
O2	0.0408 (16)	0.0360 (16)	0.0435 (18)	0.0027 (12)	−0.0073 (14)	−0.0129 (14)
O3	0.055 (2)	0.063 (2)	0.063 (2)	−0.0343 (18)	0.0056 (17)	−0.0086 (19)
O4	0.0518 (19)	0.061 (2)	0.059 (2)	−0.0265 (16)	−0.0042 (16)	−0.0263 (18)
O5	0.0587 (19)	0.0331 (16)	0.0444 (19)	−0.0054 (14)	0.0034 (16)	−0.0088 (14)
O6	0.0482 (16)	0.0239 (14)	0.0425 (17)	−0.0089 (12)	−0.0098 (13)	−0.0115 (13)
Mn1	0.0326 (3)	0.0273 (3)	0.0316 (4)	−0.0081 (2)	−0.0036 (3)	−0.0088 (3)
Mn2	0.0341 (4)	0.0253 (4)	0.0306 (5)	−0.0070 (3)	−0.0073 (4)	−0.0067 (4)

Geometric parameters (Å, º) top

C1—N1	1.329 (5)	C21—H21A	0.9700
C1—C2	1.383 (6)	C21—H21B	0.9700
C1—H1	0.9300	C22—C23	1.523 (6)
C2—C3	1.379 (6)	C22—H22A	0.9700
C2—H2	0.9300	C22—H22B	0.9700
C3—C4	1.403 (6)	C23—C24	1.520 (5)
C3—H3	0.9300	C23—C25	1.529 (6)
C4—C5	1.396 (5)	C23—H23	0.9800
C4—C12	1.472 (5)	C24—O3	1.234 (5)
C5—N1	1.351 (5)	C24—O4	1.253 (5)
C5—C6	1.464 (5)	C25—C26	1.526 (6)
C6—N2	1.351 (5)	C25—H25A	0.9700
C6—C10	1.397 (5)	C25—H25B	0.9700
C7—N2	1.337 (5)	C26—H26A	0.9700
C7—C8	1.389 (6)	C26—H26B	0.9700
C7—H7	0.9300	C27—O5	1.243 (5)
C8—C9	1.368 (6)	C27—O6	1.283 (5)
C8—H8	0.9300	C27—C28	1.514 (6)
C9—C10	1.391 (6)	C28—C30	1.500 (6)
C9—H9	0.9300	C28—C29	1.539 (6)
C10—C11	1.461 (5)	C28—H28	0.9800
C11—N4	1.325 (5)	C29—C30ⁱ	1.533 (6)
C11—C12	1.428 (6)	C29—H29A	0.9700
C12—N3	1.322 (5)	C29—H29B	0.9700
C13—N3	1.365 (5)	C30—C29ⁱ	1.533 (6)
C13—C18	1.411 (6)	C30—H30A	0.9700
C13—C14	1.414 (6)	C30—H30B	0.9700
C14—C15	1.360 (6)	N1—Mn1	2.356 (3)
C14—H14	0.9300	N2—Mn1	2.303 (3)
C15—C16	1.395 (7)	O1—Mn2	2.102 (3)
C15—H15	0.9300	O2—Mn1	2.107 (3)
C16—C17	1.356 (6)	O3—Mn2ⁱⁱ	2.165 (3)
C16—H16	0.9300	O3—Mn1ⁱⁱ	2.495 (4)
C17—C18	1.408 (6)	O4—Mn1ⁱⁱ	2.200 (3)
C17—H17	0.9300	O5—Mn1	2.312 (3)
C18—N4	1.364 (5)	O6—Mn2	2.218 (3)
C19—O1	1.251 (5)	O6—Mn1	2.314 (3)
C19—O2	1.253 (5)	Mn1—O4ⁱⁱⁱ	2.200 (3)
C19—C20	1.531 (5)	Mn1—O3ⁱⁱⁱ	2.495 (4)
C20—C26	1.531 (6)	Mn2—O1^iv	2.102 (3)
C20—C21	1.536 (6)	Mn2—O3^v	2.165 (3)
C20—H20	0.9800	Mn2—O3ⁱⁱⁱ	2.165 (3)
C21—C22	1.521 (5)	Mn2—O6^iv	2.218 (3)

N1—C1—C2	123.2 (4)	C23—C25—H25A	109.5
N1—C1—H1	118.4	C26—C25—H25B	109.5
C2—C1—H1	118.4	C23—C25—H25B	109.5
C3—C2—C1	119.0 (4)	H25A—C25—H25B	108.0
C3—C2—H2	120.5	C25—C26—C20	111.9 (3)
C1—C2—H2	120.5	C25—C26—H26A	109.2
C2—C3—C4	119.0 (4)	C20—C26—H26A	109.2
C2—C3—H3	120.5	C25—C26—H26B	109.2
C4—C3—H3	120.5	C20—C26—H26B	109.2
C5—C4—C3	118.0 (4)	H26A—C26—H26B	107.9
C5—C4—C12	120.2 (3)	O5—C27—O6	121.1 (4)
C3—C4—C12	121.8 (4)	O5—C27—C28	122.5 (4)
N1—C5—C4	122.5 (4)	O6—C27—C28	116.3 (4)
N1—C5—C6	116.7 (3)	C30—C28—C27	114.1 (4)
C4—C5—C6	120.8 (3)	C30—C28—C29	111.5 (3)
N2—C6—C10	122.6 (4)	C27—C28—C29	108.7 (4)
N2—C6—C5	117.5 (3)	C30—C28—H28	107.4
C10—C6—C5	119.9 (3)	C27—C28—H28	107.4
N2—C7—C8	122.9 (4)	C29—C28—H28	107.4
N2—C7—H7	118.5	C30ⁱ—C29—C28	110.7 (4)
C8—C7—H7	118.5	C30ⁱ—C29—H29A	109.5
C9—C8—C7	119.5 (4)	C28—C29—H29A	109.5
C9—C8—H8	120.3	C30ⁱ—C29—H29B	109.5
C7—C8—H8	120.3	C28—C29—H29B	109.5
C8—C9—C10	118.8 (4)	H29A—C29—H29B	108.1
C8—C9—H9	120.6	C28—C30—C29ⁱ	111.0 (4)
C10—C9—H9	120.6	C28—C30—H30A	109.4
C9—C10—C6	118.5 (4)	C29ⁱ—C30—H30A	109.4
C9—C10—C11	121.6 (4)	C28—C30—H30B	109.4
C6—C10—C11	119.9 (3)	C29ⁱ—C30—H30B	109.4
N4—C11—C12	121.9 (4)	H30A—C30—H30B	108.0
N4—C11—C10	117.4 (4)	C1—N1—C5	118.2 (4)
C12—C11—C10	120.6 (3)	C1—N1—Mn1	125.1 (3)
N3—C12—C11	122.4 (3)	C5—N1—Mn1	116.4 (2)
N3—C12—C4	119.1 (4)	C7—N2—C6	117.6 (3)
C11—C12—C4	118.5 (3)	C7—N2—Mn1	124.1 (3)
N3—C13—C18	121.2 (4)	C6—N2—Mn1	117.8 (3)
N3—C13—C14	120.0 (4)	C12—N3—C13	116.4 (3)
C18—C13—C14	118.8 (4)	C11—N4—C18	116.3 (3)
C15—C14—C13	119.8 (4)	C19—O1—Mn2	137.6 (3)
C15—C14—H14	120.1	C19—O2—Mn1	130.2 (3)
C13—C14—H14	120.1	C24—O3—Mn2ⁱⁱ	158.1 (3)
C14—C15—C16	121.5 (4)	C24—O3—Mn1ⁱⁱ	86.0 (3)
C14—C15—H15	119.3	Mn2ⁱⁱ—O3—Mn1ⁱⁱ	93.87 (12)
C16—C15—H15	119.3	C24—O4—Mn1ⁱⁱ	99.5 (3)
C17—C16—C15	120.0 (4)	C27—O5—Mn1	91.5 (2)
C17—C16—H16	120.0	C27—O6—Mn2	124.5 (3)
C15—C16—H16	120.0	C27—O6—Mn1	90.3 (2)
C16—C17—C18	120.5 (4)	Mn2—O6—Mn1	97.62 (11)
C16—C17—H17	119.8	O2—Mn1—O4ⁱⁱⁱ	95.86 (12)
C18—C17—H17	119.8	O2—Mn1—N2	120.52 (12)
N4—C18—C17	118.7 (4)	O4ⁱⁱⁱ—Mn1—N2	82.87 (12)
N4—C18—C13	121.8 (4)	O2—Mn1—O5	147.38 (12)
C17—C18—C13	119.5 (4)	O4ⁱⁱⁱ—Mn1—O5	108.96 (13)
O1—C19—O2	124.9 (4)	N2—Mn1—O5	84.24 (12)
O1—C19—C20	116.1 (3)	O2—Mn1—O6	91.43 (11)
O2—C19—C20	118.9 (4)	O4ⁱⁱⁱ—Mn1—O6	127.44 (12)
C19—C20—C26	110.3 (4)	N2—Mn1—O6	135.18 (11)
C19—C20—C21	114.4 (3)	O5—Mn1—O6	56.78 (10)
C26—C20—C21	110.8 (3)	O2—Mn1—N1	84.36 (11)
C19—C20—H20	107.0	O4ⁱⁱⁱ—Mn1—N1	148.93 (13)
C26—C20—H20	107.0	N2—Mn1—N1	70.66 (12)
C21—C20—H20	107.0	O5—Mn1—N1	84.83 (12)
C22—C21—C20	112.2 (3)	O6—Mn1—N1	83.54 (12)
C22—C21—H21A	109.2	O2—Mn1—O3ⁱⁱⁱ	91.42 (12)
C20—C21—H21A	109.2	O4ⁱⁱⁱ—Mn1—O3ⁱⁱⁱ	54.17 (12)
C22—C21—H21B	109.2	N2—Mn1—O3ⁱⁱⁱ	129.79 (12)
C20—C21—H21B	109.2	O5—Mn1—O3ⁱⁱⁱ	86.59 (12)
H21A—C21—H21B	107.9	O6—Mn1—O3ⁱⁱⁱ	73.72 (11)
C21—C22—C23	111.7 (3)	N1—Mn1—O3ⁱⁱⁱ	156.77 (12)
C21—C22—H22A	109.3	O1^iv—Mn2—O1	180.00 (17)
C23—C22—H22A	109.3	O1^iv—Mn2—O3^v	89.57 (15)
C21—C22—H22B	109.3	O1—Mn2—O3^v	90.43 (15)
C23—C22—H22B	109.3	O1^iv—Mn2—O3ⁱⁱⁱ	90.43 (15)
H22A—C22—H22B	107.9	O1—Mn2—O3ⁱⁱⁱ	89.57 (15)
C24—C23—C22	112.7 (3)	O3^v—Mn2—O3ⁱⁱⁱ	180.0 (2)
C24—C23—C25	112.4 (4)	O1^iv—Mn2—O6	89.89 (11)
C22—C23—C25	110.7 (3)	O1—Mn2—O6	90.11 (11)
C24—C23—H23	106.9	O3^v—Mn2—O6	97.56 (12)
C22—C23—H23	106.9	O3ⁱⁱⁱ—Mn2—O6	82.44 (12)
C25—C23—H23	106.9	O1^iv—Mn2—O6^iv	90.11 (11)
O3—C24—O4	120.0 (4)	O1—Mn2—O6^iv	89.89 (11)
O3—C24—C23	120.7 (4)	O3^v—Mn2—O6^iv	82.44 (12)
O4—C24—C23	119.2 (4)	O3ⁱⁱⁱ—Mn2—O6^iv	97.56 (12)
C26—C25—C23	110.9 (4)	O6—Mn2—O6^iv	180.00 (11)
C26—C25—H25A	109.5

Symmetry codes: (i) −x+2, −y+2, −z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+2, −y+1, −z; (v) −x+3, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Mn₃(C₈H₁₀O₄)₃(C₁₈H₁₀N₄)₂]
M_r	1239.90
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5730 (17), 10.614 (2), 14.846 (3)
α, β, γ (°)	77.34 (3), 81.99 (3), 82.67 (3)
V (Å³)	1298.6 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.33 × 0.22 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.762, 0.863
No. of measured, independent and observed [I > 2σ(I)] reflections	12776, 5830, 3707
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.176, 1.05
No. of reflections	5830
No. of parameters	376
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.74

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Acknowledgements

The work was supported by the Program for Young Academic Backbone in Heilongjiang Provincial University (No. 1152 G053).

References

De, G. (2007). Acta Cryst. E63, m1748–m1749. Web of Science CSD CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Li, Y.-J. (2007). Acta Cryst. E63, m1654–m1655. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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