Bis(ethano­lato-κO)(5,10,15,20-tetra­phenyl­calix[4]pyrrole)manganese(III) hexa­fluoro­phosphate

Wang, S.; Li, Z.; Wang, X.; Yu, X.

doi:10.1107/S1600536808021879

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1232

doi:10.1107/S1600536808021879

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Bis(ethanolato-κO)(5,10,15,20-tetraphenylcalix[4]pyrrole)manganese(III) hexafluorophosphate

Suwen Wang,^a Zhongfang Li,^a ^* Xutao Wang ^a and Xianjin Yu ^a

^aCollege of Chemical Engineering, Shandong University of Technology, Zibo 255049, People's Republic of China
^*Correspondence e-mail: zhfli_sdut@yahoo.com.cn

(Received 22 June 2008; accepted 14 July 2008; online 6 September 2008)

The title compound, [Mn(C₂H₅O)₂(C₄₄H₂₈N₄)]PF₆, was synthesized from manganese(III) 2,4-pentanedionate and 5,10,15,20-tetraphenylcalix[4]pyrrole by a hydrothermal reaction. The Mn^III atom is located on an inversion centre and the asymmetric unit comprises one half-formula unit. The Mn^III ion is hexacoordinated by four N atoms from one 5,10,15,20-tetraphenylcalix[4]pyrrole ligand and two O atoms from two deprotonated ethanol molecules. The equatorially located atoms (the Mn and four N atoms) are planar. The dihedral angles between the planes of the phenyl rings and the equatorial plane are 53.3 (2) and 81.8 (2)°. One hexafluorophosphate anion balances the charge.

Related literature

For related literature, see: Church & Halvorson (1959 ); Chung et al. (1971 ); Okabe & Oya (2000 ); Serre et al. (2005 ); Pocker & Fong (1980 ); Scapin et al. (1997 ).

Experimental

Crystal data

[Mn(C₂H₅O)₂(C₄₄H₂₈N₄)]PF₆
M_r = 902.73
Monoclinic, P 2₁ /n
a = 10.7487 (8) Å
b = 16.8682 (14) Å
c = 11.9913 (19) Å
β = 109.412 (9)°
V = 2050.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 293 (2) K
0.43 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.835, T_max = 0.910
4407 measured reflections
3535 independent reflections
2142 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.214
S = 1.00
3535 reflections
284 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—N1	2.004 (3)
Mn1—N2	2.018 (3)
Mn1—O1	2.260 (3)

N1—Mn1—N2	90.13 (13)
N1—Mn1—O1ⁱ	90.70 (13)
N2—Mn1—O1ⁱ	90.25 (13)
N2—Mn1—O1	89.75 (13)
Symmetry code: (i) -x+2, -y, -z+2.

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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021879/kp2179sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021879/kp2179Isup2.hkl

checkCIF report

Comment top

In recent years, nitrogen-containing organics have been widely used as polydentate ligands, which can coordinate to transition or rare earth ions yielding complexes with interesting properties that are useful in materials science (Church & Halvorson, 1959; Chung et al., 1971) and in biological systems (Okabe & Oya, 2000; Serre et al., 2005; Pocker & Fong, 1980; Scapin et al., 1997). Herein, we report the synthesis and X-ray crystal structure analysis of the title compound, {[5,10,15,20-tetraphenyl-calix[4]pyrrole]manganese(III) bis-ethanol} hexafluorophosphate.

The Mn^III ion is hexa-coordinated with four N atoms from one 5,10,15,20-tetraphenyl-calix[4]pyrrole ligand and two O atoms from two ethanol molecules (Fig. 1). One hexafluorophosphate anion acts as charge balance. Mn^III is located at the inversion centre and the asymmetric unit comprises one-half molecule. The Mn^III ion is hexa-coordinated with four N atoms from one 5,10,15,20-tetraphenyl-calix[4]pyrrole ligand and two O atoms from two ethanol molecules. The equatorially located atoms Mn(1), N(1), N(2), N(1 A), and N(2 A) are planar. The dihedral angles between the planes of Ph rings [C(11), C(12), C(13), C(14), C(15), C(16)] and [C(17), C(18), C(19), C(20), C(21), C(22)] and quatorial plane are 53.3 (2) and 81.8 (2) Å, respectively. The Mn—N and Mn—O bond lengths are in the range of 2.004 (3)–2.018 (3) and 2.260 (3) Å, respectively (Table 1).

Related literature top

For related literature, see: Church & Halvorson (1959); Chung et al. (1971); Okabe & Oya (2000); Serre et al. (2005); Pocker & Fong (1980); Scapin et al. (1997).

Experimental top

A mixture of manganese(III) 2,4-pentanedionate (0.5 mmol), 5,10,15,20-tetraphenyl-calix[4]pyrrole (0.5 mmol), H₂O (8 ml) and ethanol (8 mL) in a 25 mL Teflon-lined stainless steel autoclave was kept at 433 K for three days. Red crystals were obtained after cooling to room temperature with a yield of 18%. Anal. Calc. for C₄₈H₃₈MnN₄O₂F₆P: C 66.61, H 3.82, N 6.48%; Found: C 66.65, H 3.78, N 6.52%.

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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) drawn with the 30% probability displacement ellipsoids for the non-hydrogen atoms. Symmetry codes used: - x + 2,-y,-z + 2; - x +1,-y,-z).

Bis(ethanolato-κO)(5,10,15,20-tetraphenylcalix[4]pyrrole)manganese(III) hexafluorophosphate top

Crystal data top

[Mn(C₂H₅O)₂(C₄₄H₂₈N₄)]PF₆	F(000) = 928
M_r = 902.73	D_x = 1.462 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3535 reflections
a = 10.7487 (8) Å	θ = 2.2–25.0°
b = 16.8682 (14) Å	µ = 0.44 mm⁻¹
c = 11.9913 (19) Å	T = 293 K
β = 109.412 (9)°	Block, yellow
V = 2050.6 (4) Å³	0.43 × 0.28 × 0.22 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	3535 independent reflections
Radiation source: fine-focus sealed tube	2142 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −1→12
T_min = 0.835, T_max = 0.910	k = −1→20
4407 measured reflections	l = −14→13

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.214	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.135P)²] where P = (F_o² + 2F_c²)/3
3535 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Mn(C₂H₅O)₂(C₄₄H₂₈N₄)]PF₆	V = 2050.6 (4) Å³
M_r = 902.73	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7487 (8) Å	µ = 0.44 mm⁻¹
b = 16.8682 (14) Å	T = 293 K
c = 11.9913 (19) Å	0.43 × 0.28 × 0.22 mm
β = 109.412 (9)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3535 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2142 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.910	R_int = 0.040
4407 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.214	H-atom parameters constrained
S = 1.00	Δρ_max = 0.33 e Å⁻³
3535 reflections	Δρ_min = −0.42 e Å⁻³
284 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	1.0000	0.0000	1.0000	0.0507 (3)
C1	0.8291 (4)	0.0451 (2)	0.7085 (3)	0.0579 (10)
C2	0.8243 (4)	0.0985 (2)	0.7966 (4)	0.0572 (10)
C3	0.7590 (4)	0.1738 (3)	0.7732 (4)	0.0670 (12)
H3A	0.7183	0.1961	0.6991	0.080*
C4	0.7671 (5)	0.2059 (3)	0.8768 (4)	0.0680 (12)
H4A	0.7311	0.2541	0.8881	0.082*
C5	0.8417 (4)	0.1524 (2)	0.9685 (4)	0.0572 (10)
C6	0.8735 (4)	0.1665 (2)	1.0892 (4)	0.0570 (10)
C7	0.9596 (4)	0.1198 (2)	1.1763 (4)	0.0551 (9)
C8	1.0066 (4)	0.1385 (3)	1.2992 (4)	0.0617 (10)
H8A	0.9820	0.1821	1.3345	0.074*
C9	1.0931 (4)	0.0817 (3)	1.3555 (4)	0.0598 (10)
H9A	1.1410	0.0798	1.4358	0.072*
C10	1.0973 (4)	0.0248 (2)	1.2677 (3)	0.0542 (9)
C11	0.7496 (4)	0.0648 (2)	0.5827 (4)	0.0594 (10)
C12	0.8044 (5)	0.0722 (3)	0.4937 (4)	0.0697 (12)
H12A	0.8948	0.0654	0.5115	0.084*
C13	0.7273 (6)	0.0893 (3)	0.3793 (5)	0.0814 (14)
H13A	0.7655	0.0920	0.3202	0.098*
C14	0.5958 (6)	0.1024 (3)	0.3521 (5)	0.0864 (16)
H14A	0.5448	0.1156	0.2752	0.104*
C15	0.5383 (5)	0.0959 (3)	0.4383 (5)	0.0862 (15)
H15A	0.4481	0.1041	0.4193	0.103*
C16	0.6152 (5)	0.0771 (3)	0.5547 (4)	0.0701 (12)
H16A	0.5761	0.0728	0.6129	0.084*
C17	0.8100 (4)	0.2373 (2)	1.1233 (4)	0.0560 (10)
C18	0.6787 (5)	0.2366 (3)	1.1115 (4)	0.0735 (12)
H18A	0.6285	0.1915	1.0830	0.088*
C19	0.6202 (5)	0.3030 (3)	1.1418 (5)	0.0822 (14)
H19A	0.5314	0.3019	1.1346	0.099*
C20	0.6936 (6)	0.3702 (3)	1.1824 (4)	0.0824 (15)
H20A	0.6543	0.4145	1.2027	0.099*
C21	0.8222 (6)	0.3720 (3)	1.1929 (5)	0.0829 (14)
H21A	0.8712	0.4178	1.2197	0.099*
C22	0.8817 (5)	0.3065 (3)	1.1642 (5)	0.0742 (13)
H22A	0.9707	0.3084	1.1723	0.089*
C23	1.2032 (10)	0.1503 (5)	1.0298 (13)	0.204 (6)
H23A	1.1197	0.1743	1.0256	0.245*
H23B	1.2537	0.1461	1.1133	0.245*
C24	1.2665 (15)	0.2060 (6)	0.9868 (11)	0.227 (6)
H24A	1.2841	0.2517	1.0374	0.341*
H24B	1.2119	0.2210	0.9086	0.341*
H24C	1.3481	0.1846	0.9839	0.341*
P1	0.5000	0.0000	0.0000	0.1018 (9)
N1	0.8781 (3)	0.0872 (2)	0.9162 (3)	0.0541 (8)
N2	1.0169 (3)	0.05011 (19)	1.1572 (3)	0.0552 (8)
F1	0.6259 (11)	0.0076 (5)	0.0792 (8)	0.217 (3)
F2	0.4786 (14)	0.0803 (9)	−0.0209 (16)	0.350 (8)
F3	0.460 (2)	0.0081 (15)	0.0848 (14)	0.387 (10)
O1	1.1729 (3)	0.07288 (19)	0.9912 (3)	0.0787 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0513 (5)	0.0471 (5)	0.0521 (5)	0.0032 (3)	0.0152 (4)	−0.0035 (3)
C1	0.062 (2)	0.057 (2)	0.052 (2)	0.0003 (19)	0.0165 (19)	−0.0015 (18)
C2	0.056 (2)	0.058 (2)	0.055 (2)	0.0046 (19)	0.0136 (18)	0.0003 (18)
C3	0.077 (3)	0.055 (2)	0.059 (2)	0.014 (2)	0.010 (2)	0.0028 (19)
C4	0.076 (3)	0.056 (2)	0.069 (3)	0.017 (2)	0.021 (2)	0.000 (2)
C5	0.057 (2)	0.054 (2)	0.060 (2)	0.0050 (18)	0.0173 (19)	−0.0075 (18)
C6	0.058 (2)	0.049 (2)	0.064 (2)	−0.0013 (18)	0.0195 (19)	−0.0075 (18)
C7	0.057 (2)	0.052 (2)	0.059 (2)	0.0011 (18)	0.0225 (19)	−0.0026 (18)
C8	0.073 (3)	0.054 (2)	0.060 (2)	0.003 (2)	0.024 (2)	−0.0111 (19)
C9	0.066 (3)	0.057 (2)	0.053 (2)	0.004 (2)	0.0163 (19)	−0.0026 (19)
C10	0.058 (2)	0.051 (2)	0.053 (2)	−0.0007 (19)	0.0185 (19)	−0.0005 (17)
C11	0.068 (3)	0.050 (2)	0.057 (2)	−0.0011 (19)	0.016 (2)	−0.0018 (18)
C12	0.071 (3)	0.071 (3)	0.065 (3)	−0.001 (2)	0.019 (2)	0.005 (2)
C13	0.098 (4)	0.078 (3)	0.066 (3)	0.001 (3)	0.026 (3)	0.010 (2)
C14	0.095 (4)	0.089 (4)	0.060 (3)	−0.005 (3)	0.005 (3)	0.008 (3)
C15	0.071 (3)	0.086 (4)	0.083 (3)	0.008 (3)	0.002 (3)	0.004 (3)
C16	0.062 (3)	0.078 (3)	0.065 (3)	0.003 (2)	0.014 (2)	0.002 (2)
C17	0.056 (2)	0.054 (2)	0.057 (2)	0.0087 (19)	0.0183 (18)	−0.0007 (18)
C18	0.067 (3)	0.061 (3)	0.092 (3)	0.004 (2)	0.026 (2)	−0.009 (2)
C19	0.073 (3)	0.083 (3)	0.098 (4)	0.019 (3)	0.038 (3)	0.000 (3)
C20	0.115 (5)	0.065 (3)	0.070 (3)	0.031 (3)	0.035 (3)	−0.004 (2)
C21	0.095 (4)	0.062 (3)	0.093 (4)	0.006 (3)	0.031 (3)	−0.015 (3)
C22	0.074 (3)	0.057 (3)	0.093 (3)	−0.004 (2)	0.030 (3)	−0.015 (2)
C23	0.187 (9)	0.105 (6)	0.404 (18)	−0.072 (6)	0.210 (11)	−0.095 (9)
C24	0.39 (2)	0.111 (7)	0.234 (13)	−0.052 (10)	0.170 (13)	−0.041 (7)
P1	0.0807 (16)	0.1047 (19)	0.1054 (19)	0.0316 (13)	0.0113 (14)	−0.0304 (15)
N1	0.0532 (18)	0.0542 (18)	0.0538 (18)	0.0027 (15)	0.0164 (15)	−0.0062 (14)
N2	0.0538 (19)	0.0549 (19)	0.0559 (18)	0.0009 (15)	0.0171 (15)	−0.0046 (15)
F1	0.216 (9)	0.238 (8)	0.206 (8)	−0.015 (6)	0.080 (7)	−0.014 (5)
F2	0.338 (16)	0.247 (13)	0.40 (2)	0.005 (12)	0.030 (15)	−0.013 (13)
F3	0.346 (19)	0.47 (2)	0.288 (18)	0.205 (16)	0.030 (14)	0.022 (15)
O1	0.0648 (19)	0.0609 (19)	0.116 (3)	−0.0143 (15)	0.0377 (19)	−0.0146 (18)

Geometric parameters (Å, º) top

Mn1—N1	2.004 (3)	C13—C14	1.358 (8)
Mn1—N1ⁱ	2.004 (3)	C13—H13A	0.9300
Mn1—N2	2.018 (3)	C14—C15	1.373 (8)
Mn1—N2ⁱ	2.018 (3)	C14—H14A	0.9300
Mn1—O1ⁱ	2.260 (3)	C15—C16	1.402 (7)
Mn1—O1	2.260 (3)	C15—H15A	0.9300
C1—C10ⁱ	1.395 (6)	C16—H16A	0.9300
C1—C2	1.403 (6)	C17—C18	1.371 (6)
C1—C11	1.504 (6)	C17—C22	1.394 (6)
C2—N1	1.369 (5)	C18—C19	1.390 (7)
C2—C3	1.432 (6)	C18—H18A	0.9300
C3—C4	1.331 (6)	C19—C20	1.375 (8)
C3—H3A	0.9300	C19—H19A	0.9300
C4—C5	1.442 (6)	C20—C21	1.346 (8)
C4—H4A	0.9300	C20—H20A	0.9300
C5—N1	1.386 (5)	C21—C22	1.377 (7)
C5—C6	1.393 (6)	C21—H21A	0.9300
C6—C7	1.388 (6)	C22—H22A	0.9300
C6—C17	1.497 (5)	C23—C24	1.358 (11)
C7—N2	1.381 (5)	C23—O1	1.388 (8)
C7—C8	1.425 (6)	C23—H23A	0.9700
C8—C9	1.348 (6)	C23—H23B	0.9700
C8—H8A	0.9300	C24—H24A	0.9600
C9—C10	1.436 (6)	C24—H24B	0.9600
C9—H9A	0.9300	C24—H24C	0.9600
C10—N2	1.387 (5)	P1—F3	1.23 (2)
C10—C1ⁱ	1.395 (6)	P1—F3ⁱⁱ	1.23 (2)
C11—C12	1.385 (6)	P1—F1ⁱⁱ	1.376 (11)
C11—C16	1.385 (6)	P1—F1	1.376 (11)
C12—C13	1.378 (7)	P1—F2	1.382 (15)
C12—H12A	0.9300	P1—F2ⁱⁱ	1.382 (15)

N1—Mn1—N1ⁱ	180.000 (1)	C14—C15—H15A	119.9
N1—Mn1—N2	90.13 (13)	C16—C15—H15A	119.9
N1ⁱ—Mn1—N2	89.87 (13)	C11—C16—C15	119.8 (5)
N1—Mn1—N2ⁱ	89.87 (13)	C11—C16—H16A	120.1
N1ⁱ—Mn1—N2ⁱ	90.13 (13)	C15—C16—H16A	120.1
N2—Mn1—N2ⁱ	180.000 (1)	C18—C17—C22	118.2 (4)
N1—Mn1—O1ⁱ	90.70 (13)	C18—C17—C6	120.8 (4)
N1ⁱ—Mn1—O1ⁱ	89.30 (13)	C22—C17—C6	121.0 (4)
N2—Mn1—O1ⁱ	90.25 (13)	C17—C18—C19	120.4 (5)
N2ⁱ—Mn1—O1ⁱ	89.75 (13)	C17—C18—H18A	119.8
N1—Mn1—O1	89.30 (13)	C19—C18—H18A	119.8
N1ⁱ—Mn1—O1	90.70 (13)	C20—C19—C18	120.0 (5)
N2—Mn1—O1	89.75 (13)	C20—C19—H19A	120.0
N2ⁱ—Mn1—O1	90.25 (13)	C18—C19—H19A	120.0
O1ⁱ—Mn1—O1	180.0	C21—C20—C19	120.2 (5)
C10ⁱ—C1—C2	123.3 (4)	C21—C20—H20A	119.9
C10ⁱ—C1—C11	119.2 (4)	C19—C20—H20A	119.9
C2—C1—C11	117.5 (4)	C20—C21—C22	120.4 (5)
N1—C2—C1	126.2 (4)	C20—C21—H21A	119.8
N1—C2—C3	109.7 (4)	C22—C21—H21A	119.8
C1—C2—C3	124.1 (4)	C21—C22—C17	120.8 (5)
C4—C3—C2	107.6 (4)	C21—C22—H22A	119.6
C4—C3—H3A	126.2	C17—C22—H22A	119.6
C2—C3—H3A	126.2	C24—C23—O1	128.0 (9)
C3—C4—C5	107.7 (4)	C24—C23—H23A	105.3
C3—C4—H4A	126.1	O1—C23—H23A	105.3
C5—C4—H4A	126.1	C24—C23—H23B	105.3
N1—C5—C6	126.7 (4)	O1—C23—H23B	105.3
N1—C5—C4	108.7 (3)	H23A—C23—H23B	106.0
C6—C5—C4	124.6 (4)	C23—C24—H24A	109.5
C7—C6—C5	123.8 (4)	C23—C24—H24B	109.5
C7—C6—C17	119.9 (4)	H24A—C24—H24B	109.5
C5—C6—C17	116.3 (4)	C23—C24—H24C	109.5
N2—C7—C6	125.6 (4)	H24A—C24—H24C	109.5
N2—C7—C8	109.6 (3)	H24B—C24—H24C	109.5
C6—C7—C8	124.8 (4)	F3—P1—F3ⁱⁱ	180 (2)
C9—C8—C7	108.0 (4)	F3—P1—F1ⁱⁱ	92.8 (9)
C9—C8—H8A	126.0	F3ⁱⁱ—P1—F1ⁱⁱ	87.2 (9)
C7—C8—H8A	126.0	F3—P1—F1	87.2 (9)
C8—C9—C10	107.0 (4)	F3ⁱⁱ—P1—F1	92.8 (9)
C8—C9—H9A	126.5	F1ⁱⁱ—P1—F1	180.0 (13)
C10—C9—H9A	126.5	F3—P1—F2	87.6 (9)
N2—C10—C1ⁱ	125.9 (4)	F3ⁱⁱ—P1—F2	92.4 (9)
N2—C10—C9	109.4 (4)	F1ⁱⁱ—P1—F2	84.2 (6)
C1ⁱ—C10—C9	124.7 (4)	F1—P1—F2	95.8 (6)
C12—C11—C16	118.4 (4)	F3—P1—F2ⁱⁱ	92.4 (9)
C12—C11—C1	123.1 (4)	F3ⁱⁱ—P1—F2ⁱⁱ	87.6 (9)
C16—C11—C1	118.4 (4)	F1ⁱⁱ—P1—F2ⁱⁱ	95.8 (6)
C13—C12—C11	121.1 (5)	F1—P1—F2ⁱⁱ	84.2 (6)
C13—C12—H12A	119.4	F2—P1—F2ⁱⁱ	180.0 (3)
C11—C12—H12A	119.4	C2—N1—C5	106.2 (3)
C14—C13—C12	120.4 (5)	C2—N1—Mn1	127.3 (3)
C14—C13—H13A	119.8	C5—N1—Mn1	126.3 (3)
C12—C13—H13A	119.8	C7—N2—C10	105.9 (3)
C13—C14—C15	120.0 (5)	C7—N2—Mn1	127.2 (3)
C13—C14—H14A	120.0	C10—N2—Mn1	126.7 (3)
C15—C14—H14A	120.0	C23—O1—Mn1	127.0 (4)
C14—C15—C16	120.2 (5)

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

Experimental details

Crystal data
Chemical formula	[Mn(C₂H₅O)₂(C₄₄H₂₈N₄)]PF₆
M_r	902.73
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.7487 (8), 16.8682 (14), 11.9913 (19)
β (°)	109.412 (9)
V (Å³)	2050.6 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.43 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.835, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	4407, 3535, 2142
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.214, 1.00
No. of reflections	3535
No. of parameters	284
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.42

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

Selected geometric parameters (Å, º) top

Mn1—N1	2.004 (3)	Mn1—O1	2.260 (3)
Mn1—N2	2.018 (3)

N1—Mn1—N2	90.13 (13)	N2—Mn1—O1ⁱ	90.25 (13)
N1—Mn1—O1ⁱ	90.70 (13)	N2—Mn1—O1	89.75 (13)

Symmetry code: (i) −x+2, −y, −z+2.

Acknowledgements

The authors thank the NSFC (grant No. 20776081).

References

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