Poly[(μ3-biphenyl-3,4′-dicarboxyl­ato-κ4O3:O3′:O4′,O4′′)(1H-imidazo[4,5-f][1,10]phenanthroline-κ2N7,N8)manganese(II)]

Wang, F.-M.

doi:10.1107/S1600536810045587

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1677

https://doi.org/10.1107/S1600536810045587

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Poly[(μ₃-biphenyl-3,4′-dicarboxylato-κ⁴O³:O^3′:O^4′,O^4′′)(1H-imidazo[4,5-f][1,10]phenanthroline-κ²N⁷,N⁸)manganese(II)]

Fu-Ming Wang ^a ^*

^aDepartment of Chemistry, Dezhou University, Shandong 253023, People's Republic of China
^*Correspondence e-mail: dzwangfm@163.com

(Received 20 October 2010; accepted 6 November 2010; online 27 November 2010)

In the title compound, [Mn(C₁₄H₈O₄)(C₁₃H₈N₄)]_n, the Mn^II atom is six-coordinated in a distorted octahedral geometry by four O atoms from three different carboxylate groups and two N atoms from one imidazo[4,5-f][1,10]phenanthroline molecule. The organic ligands link inorganic Mn^II nodes, forming a zigzag chain along the c axis.

Related literature

For the use of diphenic acid as an O-donor ligand in the design and synthesis of coordination polymers, see: Wang et al. (2006 ); Yin et al. (2005 ). The distortion of the diphenyl spacer about the central bond allows the carboxylate ligand to link metal ions into helical chains or one dimensional chains, see: Guo et al. (2010 ).

Experimental

Crystal data

[Mn(C₁₄H₈O₄)(C₁₃H₈N₄)]
M_r = 515.38
Monoclinic, P 2/c
a = 8.0634 (13) Å
b = 11.705 (2) Å
c = 22.807 (4) Å
β = 94.307 (2)°
V = 2146.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.915, T_max = 0.949
12211 measured reflections
3997 independent reflections
2211 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.107
S = 1.00
3997 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—O4	2.106 (3)
Mn1—O3	2.124 (3)
Mn1—O2ⁱ	2.208 (3)
Mn1—N4	2.273 (3)
Mn1—N3	2.281 (3)
Mn1—O1ⁱ	2.313 (3)

O4—Mn1—O3	97.67 (11)
O4—Mn1—O2ⁱ	89.59 (11)
O3—Mn1—O2ⁱ	98.36 (11)
O4—Mn1—N4	120.65 (11)
O3—Mn1—N4	94.32 (11)
O2ⁱ—Mn1—N4	145.23 (11)
O4—Mn1—N3	84.57 (11)
O3—Mn1—N3	165.21 (11)
O2ⁱ—Mn1—N3	96.26 (11)
N4—Mn1—N3	72.22 (11)
O4—Mn1—O1ⁱ	144.17 (10)
O3—Mn1—O1ⁱ	100.92 (10)
O2ⁱ—Mn1—O1ⁱ	57.65 (10)
N4—Mn1—O1ⁱ	88.24 (10)
N3—Mn1—O1ⁱ	85.10 (11)
Symmetry codes: (i) $[x, -y, z-{\script{1\over 2}}]$ ; (ii) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045587/jh2224sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045587/jh2224Isup2.hkl

checkCIF report

Comment top

Diphenic acid as O-donor ligand has received much more attention in the designed synthesis of coordination polymers (Wang, et al., 2006; Yin, et al., 2005). I select 3,4'-biphenyldicarboxylicacid as the ligand based on the following consideratons. First, the two functional carboxylate groups can adopt different coordination modes. Second, two phenyl rings are not coplanar with each other owing to the steric hindrance of carboxylate groups in coordinaton process. The distortion of diphenyl spacer about the central bond allows the carboxylate ligand to link metal ions into helical chains or one dimensional chains (Guo, et al., 2010).

The title compound,(I), was synthesized by the hydrothermal reaction of 3,4'-biphenyldicarboxylic acid with imidazo[4,5-f][1,10]phenanthroline and manganese chloride terahydrate. The central Mn^II exhibits an octahedral geometry with N2O4 coordination sphere from three carboxylate ligands and one imidazo[4,5-f][1,10]phenanthroline ligand. The carboxylate groups act as m₃-ligand with one carboxylate group bridging two Mn^II ions in a bis-monodetate fashion, and the other carboxylate group bridging Mn^II in a bidentate chelating mode. The dihedral angle two phenyl rings in carboxylate ligand is 9.33°. The carboxylate ligands link Mn^II nodes to form one-dimensional zigzag chain along c axis.

Related literature top

For the use of diphenic acid as an O-donor ligand in the design and synthesis of coordination polymers, see: Wang et al. (2006); Yin et al. (2005). The distortion of the diphenyl spacer about the central bond allows the carboxylate ligand to link metal ions into helical chains or one dimensional chains, see: Guo et al. (2010).

Experimental top

A mixture of MnCl₂.4H₂O (0.099 g, 0.5 mmol), 3,4'-biphenyldicarboxylic acid (0.121 g,0.5 mmol), NaOH (0.04 g, 1 mmol), imidazo[4,5-f][1,10]phenanthroline (0.110 g,0.5 mmol)and distillated water (15 ml) was heated to 433 K for 96 h in a 25 ml stainless steel reactor with a Teflon liner. Yellow block crystals were obtained with 52% yield on Mn basis.

Structure description top

For the use of diphenic acid as an O-donor ligand in the design and synthesis of coordination polymers, see: Wang et al. (2006); Yin et al. (2005). The distortion of the diphenyl spacer about the central bond allows the carboxylate ligand to link metal ions into helical chains or one dimensional chains, see: Guo et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The coordination environments of manganese(II) atom. All hydrogen atoms are omitted for clarity.
	Fig. 2. View of the one-dimensional zigzag chain running along c axis in compound

Poly[(µ₃-biphenyl-3,4'-dicarboxylato- κ⁴O³:O^3':O^4',O^4'')(1H- imidazo[4,5-f][1,10]phenanthroline- κ²N⁷,N⁸)manganese(II)] top

Crystal data top

[Mn(C₁₄H₈O₄)(C₁₃H₈N₄)]	F(000) = 1052
M_r = 515.38	D_x = 1.595 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0634 (13) Å	Cell parameters from 1052 reflections
b = 11.705 (2) Å	θ = 2.5–19.6°
c = 22.807 (4) Å	µ = 0.66 mm⁻¹
β = 94.307 (2)°	T = 296 K
V = 2146.5 (6) Å³	Block, yellow
Z = 4	0.30 × 0.25 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3997 independent reflections
Radiation source: fine-focus sealed tube	2211 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
φ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.915, T_max = 0.949	k = −14→13
12211 measured reflections	l = −27→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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.026P)² + 0.6105P] where P = (F_o² + 2F_c²)/3
3997 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Mn(C₁₄H₈O₄)(C₁₃H₈N₄)]	V = 2146.5 (6) Å³
M_r = 515.38	Z = 4
Monoclinic, P2/c	Mo Kα radiation
a = 8.0634 (13) Å	µ = 0.66 mm⁻¹
b = 11.705 (2) Å	T = 296 K
c = 22.807 (4) Å	0.30 × 0.25 × 0.15 mm
β = 94.307 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3997 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2211 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.949	R_int = 0.079
12211 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.00	Δρ_max = 0.27 e Å⁻³
3997 reflections	Δρ_min = −0.26 e Å⁻³
325 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
C1	0.3326 (5)	−0.2910 (3)	0.59868 (17)	0.0397 (10)
C2	0.4198 (5)	−0.2655 (3)	0.54479 (16)	0.0366 (10)
C3	0.5437 (5)	−0.3374 (4)	0.52782 (18)	0.0544 (12)
H3	0.5755	−0.4007	0.5507	0.065*
C4	0.6200 (6)	−0.3150 (4)	0.4769 (2)	0.0653 (14)
H4	0.7027	−0.3635	0.4653	0.078*
C5	0.5739 (5)	−0.2205 (4)	0.44316 (19)	0.0583 (13)
H5	0.6266	−0.2068	0.4089	0.070*
C6	0.4504 (5)	−0.1452 (3)	0.45896 (16)	0.0384 (10)
C7	0.3743 (5)	−0.1712 (3)	0.51070 (15)	0.0360 (9)
H7	0.2906	−0.1235	0.5224	0.043*
C8	0.3964 (5)	−0.0463 (3)	0.42123 (16)	0.0359 (10)
C9	0.4790 (5)	−0.0157 (3)	0.37261 (17)	0.0454 (11)
H9	0.5760	−0.0543	0.3651	0.054*
C10	0.4217 (5)	0.0706 (3)	0.33468 (17)	0.0445 (11)
H10	0.4795	0.0887	0.3021	0.053*
C11	0.2787 (5)	0.1298 (3)	0.34526 (16)	0.0348 (10)
C12	0.2034 (5)	0.2153 (3)	0.30153 (18)	0.0395 (10)
C13	0.2002 (5)	0.1057 (3)	0.39553 (17)	0.0455 (11)
H13	0.1078	0.1481	0.4044	0.055*
C14	0.2582 (5)	0.0185 (3)	0.43296 (17)	0.0479 (12)
H14	0.2035	0.0032	0.4666	0.058*
C15	0.3314 (5)	0.4924 (4)	0.29153 (17)	0.0449 (11)
H15	0.3656	0.4221	0.3072	0.054*
C16	0.3820 (5)	0.5911 (4)	0.32141 (17)	0.0499 (12)
H16	0.4483	0.5865	0.3565	0.060*
C17	0.3340 (5)	0.6951 (4)	0.29906 (17)	0.0478 (12)
H17	0.3654	0.7617	0.3191	0.057*
C18	0.2367 (5)	0.7004 (3)	0.24547 (16)	0.0335 (9)
C19	0.1832 (5)	0.8018 (3)	0.21576 (19)	0.0428 (11)
C20	0.1350 (6)	0.9765 (4)	0.1863 (3)	0.0705 (15)
H20	0.1350	1.0560	0.1855	0.085*
C21	0.0931 (5)	0.8014 (4)	0.16250 (19)	0.0437 (11)
C22	0.0414 (5)	0.6983 (3)	0.13349 (17)	0.0388 (10)
C23	−0.0542 (5)	0.6908 (4)	0.08015 (18)	0.0535 (12)
H23	−0.0876	0.7567	0.0598	0.064*
C24	−0.0983 (5)	0.5857 (4)	0.05792 (18)	0.0519 (12)
H24	−0.1626	0.5793	0.0225	0.062*
C25	−0.0458 (5)	0.4885 (4)	0.08908 (17)	0.0464 (11)
H25	−0.0780	0.4174	0.0739	0.056*
C26	0.0901 (5)	0.5956 (3)	0.16214 (16)	0.0336 (10)
C27	0.1912 (4)	0.5964 (3)	0.21789 (16)	0.0315 (9)
Mn1	0.15985 (8)	0.33674 (5)	0.18767 (2)	0.03702 (19)
N1	0.2089 (4)	0.9153 (3)	0.23044 (17)	0.0551 (10)
H1	0.2618	0.9414	0.2617	0.066*
N2	0.0616 (5)	0.9125 (3)	0.14389 (18)	0.0655 (12)
N3	0.0475 (4)	0.4922 (3)	0.13919 (13)	0.0372 (8)
N4	0.2358 (4)	0.4944 (3)	0.24136 (13)	0.0358 (8)
O1	0.3863 (3)	−0.3680 (2)	0.63325 (12)	0.0545 (8)
O2	0.2030 (4)	−0.2362 (2)	0.60829 (12)	0.0541 (8)
O3	0.2624 (3)	0.2201 (2)	0.25189 (11)	0.0486 (8)
O4	−0.0869 (4)	0.2767 (2)	0.18362 (12)	0.0510 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.045 (3)	0.038 (3)	0.036 (2)	−0.001 (2)	−0.004 (2)	0.005 (2)
C2	0.040 (3)	0.036 (2)	0.033 (2)	−0.002 (2)	−0.003 (2)	0.0031 (19)
C3	0.054 (3)	0.058 (3)	0.052 (3)	0.006 (3)	0.009 (2)	0.017 (2)
C4	0.062 (3)	0.070 (4)	0.067 (3)	0.030 (3)	0.023 (3)	0.020 (3)
C5	0.061 (3)	0.069 (3)	0.046 (3)	0.014 (3)	0.015 (2)	0.022 (3)
C6	0.034 (2)	0.042 (3)	0.039 (2)	−0.002 (2)	−0.0045 (19)	0.000 (2)
C7	0.036 (2)	0.037 (2)	0.034 (2)	0.003 (2)	−0.0036 (18)	0.000 (2)
C8	0.038 (3)	0.037 (2)	0.032 (2)	−0.001 (2)	−0.006 (2)	−0.0001 (18)
C9	0.054 (3)	0.045 (3)	0.039 (2)	0.008 (2)	0.009 (2)	0.007 (2)
C10	0.054 (3)	0.045 (3)	0.036 (2)	0.003 (2)	0.009 (2)	0.003 (2)
C11	0.040 (3)	0.032 (2)	0.031 (2)	0.001 (2)	−0.0053 (19)	0.0021 (17)
C12	0.048 (3)	0.030 (2)	0.040 (3)	−0.006 (2)	0.003 (2)	−0.002 (2)
C13	0.044 (3)	0.042 (3)	0.050 (3)	0.009 (2)	0.007 (2)	0.006 (2)
C14	0.047 (3)	0.054 (3)	0.044 (3)	0.007 (2)	0.011 (2)	0.018 (2)
C15	0.048 (3)	0.047 (3)	0.040 (3)	0.001 (2)	−0.004 (2)	−0.001 (2)
C16	0.054 (3)	0.058 (3)	0.036 (3)	−0.001 (3)	−0.009 (2)	0.000 (2)
C17	0.048 (3)	0.046 (3)	0.048 (3)	−0.009 (2)	0.000 (2)	−0.013 (2)
C18	0.032 (2)	0.029 (2)	0.039 (2)	−0.0037 (19)	0.0022 (19)	−0.0025 (19)
C19	0.044 (3)	0.031 (3)	0.054 (3)	0.002 (2)	0.009 (2)	−0.005 (2)
C20	0.076 (4)	0.032 (3)	0.103 (4)	0.004 (3)	0.005 (3)	0.000 (3)
C21	0.048 (3)	0.033 (3)	0.050 (3)	0.003 (2)	0.006 (2)	0.006 (2)
C22	0.038 (3)	0.038 (3)	0.040 (2)	0.006 (2)	0.005 (2)	0.006 (2)
C23	0.057 (3)	0.052 (3)	0.050 (3)	0.007 (2)	−0.007 (2)	0.012 (2)
C24	0.055 (3)	0.059 (3)	0.039 (3)	0.001 (3)	−0.017 (2)	0.005 (2)
C25	0.057 (3)	0.042 (3)	0.038 (3)	−0.005 (2)	−0.012 (2)	−0.004 (2)
C26	0.032 (2)	0.029 (2)	0.039 (2)	−0.002 (2)	0.0015 (19)	−0.0043 (19)
C27	0.032 (2)	0.030 (2)	0.033 (2)	0.000 (2)	0.0014 (18)	0.0004 (19)
Mn1	0.0488 (4)	0.0288 (3)	0.0331 (3)	−0.0021 (3)	0.0009 (3)	0.0000 (3)
N1	0.063 (3)	0.033 (2)	0.068 (3)	−0.005 (2)	0.002 (2)	−0.011 (2)
N2	0.077 (3)	0.033 (2)	0.084 (3)	0.004 (2)	−0.008 (2)	0.006 (2)
N3	0.041 (2)	0.035 (2)	0.035 (2)	−0.0062 (17)	−0.0028 (16)	0.0010 (16)
N4	0.039 (2)	0.035 (2)	0.0322 (19)	0.0018 (17)	−0.0042 (16)	0.0014 (16)
O1	0.055 (2)	0.061 (2)	0.0474 (18)	0.0062 (16)	0.0023 (15)	0.0234 (16)
O2	0.057 (2)	0.053 (2)	0.0532 (19)	0.0139 (17)	0.0165 (16)	0.0146 (15)
O3	0.064 (2)	0.0449 (18)	0.0371 (16)	0.0085 (15)	0.0060 (15)	0.0079 (14)
O4	0.051 (2)	0.0479 (19)	0.0544 (19)	−0.0143 (16)	0.0055 (15)	−0.0037 (15)

Geometric parameters (Å, º) top

C1—O1	1.253 (4)	C17—H17	0.9300
C1—O2	1.259 (4)	C18—C27	1.406 (5)
C1—C2	1.491 (5)	C18—C19	1.417 (5)
C2—C3	1.384 (5)	C19—C21	1.368 (5)
C2—C7	1.385 (5)	C19—N1	1.382 (5)
C3—C4	1.379 (5)	C20—N2	1.328 (5)
C3—H3	0.9300	C20—N1	1.338 (5)
C4—C5	1.382 (5)	C20—H20	0.9300
C4—H4	0.9300	C21—N2	1.386 (5)
C5—C6	1.398 (5)	C21—C22	1.424 (5)
C5—H5	0.9300	C22—C23	1.393 (5)
C6—C7	1.404 (5)	C22—C26	1.410 (5)
C6—C8	1.487 (5)	C23—C24	1.367 (5)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.383 (5)	C24—C25	1.391 (5)
C8—C14	1.391 (5)	C24—H24	0.9300
C9—C10	1.387 (5)	C25—N3	1.321 (4)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.382 (5)	C26—N3	1.352 (4)
C10—H10	0.9300	C26—C27	1.458 (5)
C11—C13	1.380 (5)	C27—N4	1.347 (4)
C11—C12	1.508 (5)	Mn1—O4	2.106 (3)
C12—O4ⁱ	1.250 (4)	Mn1—O3	2.124 (3)
C12—O3	1.262 (4)	Mn1—O2ⁱⁱ	2.208 (3)
C13—C14	1.388 (5)	Mn1—N4	2.273 (3)
C13—H13	0.9300	Mn1—N3	2.281 (3)
C14—H14	0.9300	Mn1—O1ⁱⁱ	2.313 (3)
C15—N4	1.331 (4)	Mn1—C1ⁱⁱ	2.602 (4)
C15—C16	1.387 (5)	N1—H1	0.8600
C15—H15	0.9300	O1—Mn1ⁱⁱⁱ	2.313 (3)
C16—C17	1.364 (5)	O2—Mn1ⁱⁱⁱ	2.208 (3)
C16—H16	0.9300	O4—C12ⁱ	1.250 (4)
C17—C18	1.403 (5)

O1—C1—O2	120.6 (4)	N2—C20—N1	113.2 (4)
O1—C1—C2	120.0 (4)	N2—C20—H20	123.4
O2—C1—C2	119.4 (4)	N1—C20—H20	123.4
O1—C1—Mn1ⁱⁱⁱ	62.7 (2)	C19—C21—N2	110.0 (4)
O2—C1—Mn1ⁱⁱⁱ	57.9 (2)	C19—C21—C22	122.2 (4)
C2—C1—Mn1ⁱⁱⁱ	175.7 (3)	N2—C21—C22	127.8 (4)
C3—C2—C7	119.6 (4)	C23—C22—C26	117.9 (4)
C3—C2—C1	120.3 (4)	C23—C22—C21	125.6 (4)
C7—C2—C1	120.1 (4)	C26—C22—C21	116.5 (4)
C4—C3—C2	119.8 (4)	C24—C23—C22	119.5 (4)
C4—C3—H3	120.1	C24—C23—H23	120.3
C2—C3—H3	120.1	C22—C23—H23	120.3
C3—C4—C5	120.2 (4)	C23—C24—C25	119.1 (4)
C3—C4—H4	119.9	C23—C24—H24	120.5
C5—C4—H4	119.9	C25—C24—H24	120.5
C4—C5—C6	121.9 (4)	N3—C25—C24	123.2 (4)
C4—C5—H5	119.1	N3—C25—H25	118.4
C6—C5—H5	119.1	C24—C25—H25	118.4
C5—C6—C7	116.4 (4)	N3—C26—C22	122.0 (3)
C5—C6—C8	121.7 (4)	N3—C26—C27	116.9 (4)
C7—C6—C8	121.8 (4)	C22—C26—C27	121.1 (4)
C2—C7—C6	122.1 (4)	N4—C27—C18	122.5 (3)
C2—C7—H7	119.0	N4—C27—C26	117.1 (3)
C6—C7—H7	119.0	C18—C27—C26	120.4 (4)
C9—C8—C14	117.0 (4)	O4—Mn1—O3	97.67 (11)
C9—C8—C6	121.8 (4)	O4—Mn1—O2ⁱⁱ	89.59 (11)
C14—C8—C6	121.2 (4)	O3—Mn1—O2ⁱⁱ	98.36 (11)
C8—C9—C10	122.1 (4)	O4—Mn1—N4	120.65 (11)
C8—C9—H9	119.0	O3—Mn1—N4	94.32 (11)
C10—C9—H9	119.0	O2ⁱⁱ—Mn1—N4	145.23 (11)
C11—C10—C9	120.0 (4)	O4—Mn1—N3	84.57 (11)
C11—C10—H10	120.0	O3—Mn1—N3	165.21 (11)
C9—C10—H10	120.0	O2ⁱⁱ—Mn1—N3	96.26 (11)
C13—C11—C10	118.9 (4)	N4—Mn1—N3	72.22 (11)
C13—C11—C12	119.9 (4)	O4—Mn1—O1ⁱⁱ	144.17 (10)
C10—C11—C12	121.1 (4)	O3—Mn1—O1ⁱⁱ	100.92 (10)
O4ⁱ—C12—O3	124.0 (4)	O2ⁱⁱ—Mn1—O1ⁱⁱ	57.65 (10)
O4ⁱ—C12—C11	118.4 (4)	N4—Mn1—O1ⁱⁱ	88.24 (10)
O3—C12—C11	117.6 (4)	N3—Mn1—O1ⁱⁱ	85.10 (11)
C11—C13—C14	120.5 (4)	O4—Mn1—C1ⁱⁱ	117.17 (12)
C11—C13—H13	119.8	O3—Mn1—C1ⁱⁱ	101.66 (11)
C14—C13—H13	119.8	O2ⁱⁱ—Mn1—C1ⁱⁱ	28.90 (10)
C13—C14—C8	121.4 (4)	N4—Mn1—C1ⁱⁱ	116.67 (12)
C13—C14—H14	119.3	N3—Mn1—C1ⁱⁱ	90.13 (11)
C8—C14—H14	119.3	O1ⁱⁱ—Mn1—C1ⁱⁱ	28.77 (10)
N4—C15—C16	122.5 (4)	C20—N1—C19	106.4 (4)
N4—C15—H15	118.7	C20—N1—H1	126.8
C16—C15—H15	118.7	C19—N1—H1	126.8
C17—C16—C15	119.7 (4)	C20—N2—C21	104.2 (4)
C17—C16—H16	120.2	C25—N3—C26	118.4 (3)
C15—C16—H16	120.2	C25—N3—Mn1	124.9 (3)
C16—C17—C18	119.3 (4)	C26—N3—Mn1	116.5 (2)
C16—C17—H17	120.3	C15—N4—C27	118.5 (3)
C18—C17—H17	120.3	C15—N4—Mn1	124.3 (3)
C17—C18—C27	117.5 (4)	C27—N4—Mn1	116.9 (2)
C17—C18—C19	125.7 (4)	C1—O1—Mn1ⁱⁱⁱ	88.5 (3)
C27—C18—C19	116.8 (4)	C1—O2—Mn1ⁱⁱⁱ	93.2 (2)
C21—C19—N1	106.2 (4)	C12—O3—Mn1	119.6 (3)
C21—C19—C18	123.0 (4)	C12ⁱ—O4—Mn1	155.1 (3)
N1—C19—C18	130.9 (4)

O1—C1—C2—C3	10.1 (6)	C22—C26—C27—N4	−178.2 (3)
O2—C1—C2—C3	−168.5 (4)	N3—C26—C27—C18	−178.2 (3)
Mn1ⁱⁱⁱ—C1—C2—C3	−118 (4)	C22—C26—C27—C18	2.6 (6)
O1—C1—C2—C7	−171.5 (4)	N2—C20—N1—C19	0.5 (6)
O2—C1—C2—C7	10.0 (6)	C21—C19—N1—C20	−0.1 (5)
Mn1ⁱⁱⁱ—C1—C2—C7	60 (4)	C18—C19—N1—C20	178.4 (4)
C7—C2—C3—C4	−0.5 (6)	N1—C20—N2—C21	−0.6 (6)
C1—C2—C3—C4	178.0 (4)	C19—C21—N2—C20	0.5 (5)
C2—C3—C4—C5	0.5 (7)	C22—C21—N2—C20	179.6 (4)
C3—C4—C5—C6	0.1 (7)	C24—C25—N3—C26	1.9 (6)
C4—C5—C6—C7	−0.7 (6)	C24—C25—N3—Mn1	−173.4 (3)
C4—C5—C6—C8	−177.5 (4)	C22—C26—N3—C25	−1.6 (6)
C3—C2—C7—C6	−0.2 (6)	C27—C26—N3—C25	179.2 (3)
C1—C2—C7—C6	−178.6 (3)	C22—C26—N3—Mn1	174.1 (3)
C5—C6—C7—C2	0.7 (5)	C27—C26—N3—Mn1	−5.1 (4)
C8—C6—C7—C2	177.5 (3)	O4—Mn1—N3—C25	−54.9 (3)
C5—C6—C8—C9	−8.1 (6)	O3—Mn1—N3—C25	−154.4 (4)
C7—C6—C8—C9	175.2 (4)	O2ⁱⁱ—Mn1—N3—C25	34.1 (3)
C5—C6—C8—C14	170.9 (4)	N4—Mn1—N3—C25	−179.5 (3)
C7—C6—C8—C14	−5.8 (6)	O1ⁱⁱ—Mn1—N3—C25	90.8 (3)
C14—C8—C9—C10	−4.2 (6)	C1ⁱⁱ—Mn1—N3—C25	62.4 (3)
C6—C8—C9—C10	174.9 (4)	O4—Mn1—N3—C26	129.7 (3)
C8—C9—C10—C11	0.6 (6)	O3—Mn1—N3—C26	30.2 (6)
C9—C10—C11—C13	3.5 (6)	O2ⁱⁱ—Mn1—N3—C26	−141.3 (3)
C9—C10—C11—C12	−173.4 (3)	N4—Mn1—N3—C26	5.1 (3)
C13—C11—C12—O4ⁱ	12.0 (5)	O1ⁱⁱ—Mn1—N3—C26	−84.6 (3)
C10—C11—C12—O4ⁱ	−171.1 (4)	C1ⁱⁱ—Mn1—N3—C26	−113.0 (3)
C13—C11—C12—O3	−167.9 (4)	C16—C15—N4—C27	2.2 (6)
C10—C11—C12—O3	9.0 (5)	C16—C15—N4—Mn1	176.6 (3)
C10—C11—C13—C14	−3.9 (6)	C18—C27—N4—C15	−2.4 (6)
C12—C11—C13—C14	173.0 (4)	C26—C27—N4—C15	178.4 (3)
C11—C13—C14—C8	0.3 (6)	C18—C27—N4—Mn1	−177.2 (3)
C9—C8—C14—C13	3.7 (6)	C26—C27—N4—Mn1	3.6 (4)
C6—C8—C14—C13	−175.3 (4)	O4—Mn1—N4—C15	108.8 (3)
N4—C15—C16—C17	−0.4 (7)	O3—Mn1—N4—C15	7.2 (3)
C15—C16—C17—C18	−1.3 (6)	O2ⁱⁱ—Mn1—N4—C15	−104.2 (3)
C16—C17—C18—C27	1.1 (6)	N3—Mn1—N4—C15	−179.0 (3)
C16—C17—C18—C19	−177.3 (4)	O1ⁱⁱ—Mn1—N4—C15	−93.6 (3)
C17—C18—C19—C21	177.7 (4)	C1ⁱⁱ—Mn1—N4—C15	−98.1 (3)
C27—C18—C19—C21	−0.7 (6)	O4—Mn1—N4—C27	−76.8 (3)
C17—C18—C19—N1	−0.6 (7)	O3—Mn1—N4—C27	−178.3 (3)
C27—C18—C19—N1	−179.0 (4)	O2ⁱⁱ—Mn1—N4—C27	70.3 (3)
N1—C19—C21—N2	−0.2 (5)	N3—Mn1—N4—C27	−4.6 (3)
C18—C19—C21—N2	−178.9 (4)	O1ⁱⁱ—Mn1—N4—C27	80.9 (3)
N1—C19—C21—C22	−179.4 (4)	C1ⁱⁱ—Mn1—N4—C27	76.3 (3)
C18—C19—C21—C22	2.0 (7)	O2—C1—O1—Mn1ⁱⁱⁱ	2.3 (4)
C19—C21—C22—C23	178.2 (4)	C2—C1—O1—Mn1ⁱⁱⁱ	−176.2 (3)
N2—C21—C22—C23	−0.8 (7)	O1—C1—O2—Mn1ⁱⁱⁱ	−2.4 (4)
C19—C21—C22—C26	−0.9 (6)	C2—C1—O2—Mn1ⁱⁱⁱ	176.1 (3)
N2—C21—C22—C26	−179.9 (4)	O4ⁱ—C12—O3—Mn1	−0.8 (5)
C26—C22—C23—C24	0.6 (6)	C11—C12—O3—Mn1	179.1 (2)
C21—C22—C23—C24	−178.4 (4)	O4—Mn1—O3—C12	−57.7 (3)
C22—C23—C24—C25	−0.3 (7)	O2ⁱⁱ—Mn1—O3—C12	−148.5 (3)
C23—C24—C25—N3	−1.0 (7)	N4—Mn1—O3—C12	64.0 (3)
C23—C22—C26—N3	0.4 (6)	N3—Mn1—O3—C12	40.1 (6)
C21—C22—C26—N3	179.5 (3)	O1ⁱⁱ—Mn1—O3—C12	153.0 (3)
C23—C22—C26—C27	179.6 (4)	C1ⁱⁱ—Mn1—O3—C12	−177.6 (3)
C21—C22—C26—C27	−1.3 (6)	O3—Mn1—O4—C12ⁱ	4.0 (7)
C17—C18—C27—N4	0.8 (6)	O2ⁱⁱ—Mn1—O4—C12ⁱ	102.4 (6)
C19—C18—C27—N4	179.3 (3)	N4—Mn1—O4—C12ⁱ	−95.7 (7)
C17—C18—C27—C26	179.9 (3)	N3—Mn1—O4—C12ⁱ	−161.3 (7)
C19—C18—C27—C26	−1.5 (5)	O1ⁱⁱ—Mn1—O4—C12ⁱ	124.8 (6)
N3—C26—C27—N4	1.0 (5)	C1ⁱⁱ—Mn1—O4—C12ⁱ	111.3 (6)

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

Experimental details

Crystal data
Chemical formula	[Mn(C₁₄H₈O₄)(C₁₃H₈N₄)]
M_r	515.38
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	296
a, b, c (Å)	8.0634 (13), 11.705 (2), 22.807 (4)
β (°)	94.307 (2)
V (Å³)	2146.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.30 × 0.25 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.915, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	12211, 3997, 2211
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.107, 1.00
No. of reflections	3997
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Mn1—O4	2.106 (3)	Mn1—O1ⁱ	2.313 (3)
Mn1—O3	2.124 (3)	Mn1—C1ⁱ	2.602 (4)
Mn1—O2ⁱ	2.208 (3)	O1—Mn1ⁱⁱ	2.313 (3)
Mn1—N4	2.273 (3)	O2—Mn1ⁱⁱ	2.208 (3)
Mn1—N3	2.281 (3)

O4—Mn1—O3	97.67 (11)	O2ⁱ—Mn1—N3	96.26 (11)
O4—Mn1—O2ⁱ	89.59 (11)	N4—Mn1—N3	72.22 (11)
O3—Mn1—O2ⁱ	98.36 (11)	O4—Mn1—O1ⁱ	144.17 (10)
O4—Mn1—N4	120.65 (11)	O3—Mn1—O1ⁱ	100.92 (10)
O3—Mn1—N4	94.32 (11)	O2ⁱ—Mn1—O1ⁱ	57.65 (10)
O2ⁱ—Mn1—N4	145.23 (11)	N4—Mn1—O1ⁱ	88.24 (10)
O4—Mn1—N3	84.57 (11)	N3—Mn1—O1ⁱ	85.10 (11)
O3—Mn1—N3	165.21 (11)

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

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Guo, F., Zhu, B. Y. & Zhang, X. L. (2010). J. Inorg. Organomet. Polym. 20, 118–123. Web of Science CSD CrossRef CAS Google Scholar
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