Diaqua­bis­(4,4′-bipyridine-κN)bis­(2,4,5-trifluoro-3-hy­droxy­benzoato-κO1)manganese(II)

Min, C.-G.; Yang, X.-K.

doi:10.1107/S1600536811049610

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1826

https://doi.org/10.1107/S1600536811049610

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Diaquabis(4,4′-bipyridine-κN)bis(2,4,5-trifluoro-3-hydroxybenzoato-κO¹)manganese(II)

Chun-Gang Min ^a ^* and Xi-Kun Yang ^a

^aResearch Center for Analysis and Measurement, Kunming University of Science and Technology, 650093 Kunming, Yunnan, People's Republic of China
^*Correspondence e-mail: minchungang@163.com

(Received 1 September 2011; accepted 21 November 2011; online 25 November 2011)

In the title compound, [Mn(C₇H₂F₃O₃)₂(C₁₀H₈N₂)₂(H₂O)₂], the Mn^II ion, situated on a centre of inversion, has a distorted octahedral coordination geometry and is coordinated by two N atoms from two 4,4′-bipyridine ligands, two O atoms from two 2,4,5-trifluoro-3-hydroxybenzoate ligands and two water molecules. Intermolecular O—H⋯N hydrogen bonds link the molecules into a chain along the a axis. Interactions between neighboring chains occur through O—H⋯O hydrogen bonds, which link the chains into a two-dimensional supramolecular network parallel to the ac plane. In addition, O—H⋯O hydrogen bonds between the water molecules and carboxylate groups also exist in the the crystal structure.

Related literature

For general background to the design and synthesis of novel metal-organic coordination polymers based on fluorobenzoic acid, see: Gielen et al. (1992 ); Ma et al. (2006 ); Shi et al. (2011 ). For a related structure, see: Zhu (2009 ).

Experimental

Crystal data

[Mn(C₇H₂F₃O₃)₂(C₁₀H₈N₂)₂(H₂O)₂]
M_r = 785.51
Triclinic, $[P \overline 1]$
a = 7.0706 (6) Å
b = 8.2939 (7) Å
c = 13.9856 (12) Å
α = 79.200 (1)°
β = 88.338 (1)°
γ = 79.830 (2)°
V = 792.96 (12) Å³
Z = 1
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 298 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.861, T_max = 0.904
4185 measured reflections
2792 independent reflections
2101 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.084
S = 1.01
2792 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯O2	0.85	2.04	2.839 (2)	155
O1W—H1W⋯O2ⁱ	0.84	1.97	2.773 (2)	159
O3—H3⋯N2ⁱⁱ	0.82	1.89	2.641 (3)	152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+2, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811049610/rn2092sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049610/rn2092Isup2.hkl

checkCIF report

Comment top

In recent years, the design and synthesis of novel metal-organic coordination polymers based on fluorobenzoic acids have attracted much attention (Gielen et al., 1992; Ma et al., 2006; Zhu, 2009; Shi et al., 2011). We report herein the crystal structure (Fig. 1) of the title compound (I) based on 2,4,5-trifluoro-3-hydroxy-benzoic and 4,4'-bipyridine. In the crystal packing, the adjacent mononuclear units are linked into a linear chain along a axis via O—H···N hydrogen bonds (Fig. 2). Furthermore, additional interactions within neighboring chains occur through O—H···O hydrogen bonds, thus a two-dimensional supramolecular network parallel to ac plane is formed, as shown in Fig. 3. In addition, intramolecular O—H···O hydrogen bonds (O1W—H2W···O2) between the water molecules and carboxylate groups also exist in the the crystal structure.

Related literature top

For general background to the design and synthesis of novel metal-organic coordination polymers based on fluorobenzoic acid, see: Gielen et al. (1992); Ma et al. (2006); Shi et al. (2011). For a related structure, see: Zhu (2009).

Experimental top

A mixture of Mn(CH₃COO)₂^.4H₂O (0.1 mmol), 2,4,5-trifluoro-3-hydroxy-benzoic acid (0.2 mmol), Et₃N (0.1 ml), EtOH (3 ml) and H₂O (2 ml) was sealed in a 10 ml Teflon-lined stainless-steel reactor, heated to 393 K for 72 h, and then slowly cooled to room temperature. Light yellow block crystals suitable for X-ray diffraction analysis were collected by filtration.

Structure description top

For general background to the design and synthesis of novel metal-organic coordination polymers based on fluorobenzoic acid, see: Gielen et al. (1992); Ma et al. (2006); Shi et al. (2011). For a related structure, see: Zhu (2009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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), with displacement ellipsoids drawn at the 30% probability level [symmetry codes: (A) -x, 1 - y, 1 - z].
	Fig. 2. The linear chain of (I). All H atoms have been omitted for clarity
	Fig. 3. The two-dimensional of (I). All H atoms have been omitted for clarity

Diaquabis(4,4'-bipyridine-κN)bis(2,4,5-trifluoro-3- hydroxybenzoato-κO¹)manganese(II) top

Crystal data top

[Mn(C₇H₂F₃O₃)₂(C₁₀H₈N₂)₂(H₂O)₂]	Z = 1
M_r = 785.51	F(000) = 399
Triclinic, P1	D_x = 1.645 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0706 (6) Å	Cell parameters from 1483 reflections
b = 8.2939 (7) Å	θ = 2.9–26.6°
c = 13.9856 (12) Å	µ = 0.51 mm⁻¹
α = 79.200 (1)°	T = 298 K
β = 88.338 (1)°	Block, light yellow
γ = 79.830 (2)°	0.30 × 0.25 × 0.20 mm
V = 792.96 (12) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2792 independent reflections
Radiation source: fine-focus sealed tube	2101 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.861, T_max = 0.904	k = −8→9
4185 measured reflections	l = −15→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0281P)² + 0.0001P] where P = (F_o² + 2F_c²)/3
2792 reflections	(Δ/σ)_max < 0.001
241 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Mn(C₇H₂F₃O₃)₂(C₁₀H₈N₂)₂(H₂O)₂]	γ = 79.830 (2)°
M_r = 785.51	V = 792.96 (12) Å³
Triclinic, P1	Z = 1
a = 7.0706 (6) Å	Mo Kα radiation
b = 8.2939 (7) Å	µ = 0.51 mm⁻¹
c = 13.9856 (12) Å	T = 298 K
α = 79.200 (1)°	0.30 × 0.25 × 0.20 mm
β = 88.338 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2792 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2101 reflections with I > 2σ(I)
T_min = 0.861, T_max = 0.904	R_int = 0.041
4185 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
2792 reflections	Δρ_min = −0.28 e Å⁻³
241 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	0.0000	0.5000	0.5000	0.03192 (17)
F1	0.2679 (2)	0.40469 (16)	0.18986 (10)	0.0502 (4)
F2	0.4119 (2)	−0.13268 (18)	0.11722 (11)	0.0654 (5)
F3	0.4709 (2)	−0.26309 (17)	0.30543 (11)	0.0653 (5)
O1	0.1454 (2)	0.3687 (2)	0.39423 (11)	0.0390 (4)
O1W	0.2747 (2)	0.5272 (2)	0.55884 (12)	0.0481 (5)
H1W	0.3355	0.6075	0.5531	0.072*
H2W	0.3528	0.4491	0.5395	0.072*
O2	0.4427 (2)	0.2766 (2)	0.45383 (12)	0.0452 (5)
O3	0.3067 (3)	0.1957 (2)	0.05414 (12)	0.0541 (5)
H3	0.2740	0.2973	0.0440	0.081*
N1	−0.0323 (3)	0.7434 (2)	0.38644 (14)	0.0371 (5)
N2	−0.2524 (3)	1.4900 (3)	0.03585 (15)	0.0475 (6)
C9	−0.2397 (4)	1.3428 (3)	0.01136 (19)	0.0573 (8)
H9	−0.2601	1.3389	−0.0535	0.069*
C10	−0.1977 (4)	1.1936 (3)	0.07644 (19)	0.0513 (7)
H10	−0.1919	1.0933	0.0549	0.062*
C6	−0.1646 (3)	1.1932 (3)	0.17280 (17)	0.0340 (6)
C7	−0.1801 (4)	1.3478 (3)	0.19819 (19)	0.0562 (8)
H7	−0.1596	1.3557	0.2624	0.067*
C8	−0.2257 (5)	1.4904 (3)	0.1290 (2)	0.0617 (9)
H8	−0.2384	1.5927	0.1488	0.074*
C3	−0.1171 (3)	1.0381 (3)	0.24554 (17)	0.0327 (6)
C4	−0.0622 (4)	0.8826 (3)	0.22071 (18)	0.0458 (7)
H4	−0.0530	0.8736	0.1554	0.055*
C5	−0.0210 (4)	0.7414 (3)	0.29101 (18)	0.0465 (7)
H5	0.0164	0.6394	0.2713	0.056*
C1	−0.0822 (4)	0.8925 (3)	0.41036 (17)	0.0409 (6)
H1	−0.0885	0.8980	0.4762	0.049*
C2	−0.1251 (4)	1.0389 (3)	0.34485 (17)	0.0407 (6)
H2	−0.1597	1.1390	0.3669	0.049*
C11	0.3130 (4)	0.2840 (3)	0.39429 (16)	0.0322 (6)
C12	0.3486 (3)	0.1745 (3)	0.31840 (16)	0.0305 (5)
C13	0.3175 (3)	0.2371 (3)	0.22071 (17)	0.0331 (6)
C15	0.3911 (4)	−0.0307 (3)	0.18248 (18)	0.0396 (6)
C16	0.4213 (3)	−0.0955 (3)	0.27927 (18)	0.0395 (6)
C17	0.4035 (3)	0.0031 (3)	0.34792 (17)	0.0355 (6)
H17	0.4276	−0.0432	0.4132	0.043*
C14	0.3377 (3)	0.1397 (3)	0.14978 (17)	0.0350 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0402 (3)	0.0269 (3)	0.0264 (3)	−0.0019 (2)	−0.0003 (2)	−0.0029 (2)
F1	0.0817 (11)	0.0280 (8)	0.0353 (8)	−0.0021 (7)	0.0036 (8)	0.0012 (6)
F2	0.1059 (14)	0.0421 (10)	0.0487 (10)	0.0014 (9)	−0.0030 (9)	−0.0223 (8)
F3	0.0996 (13)	0.0275 (9)	0.0604 (11)	0.0124 (8)	−0.0129 (9)	−0.0065 (8)
O1	0.0435 (11)	0.0392 (10)	0.0310 (10)	0.0052 (8)	−0.0003 (8)	−0.0096 (8)
O1W	0.0412 (11)	0.0415 (11)	0.0618 (12)	−0.0062 (8)	−0.0004 (9)	−0.0109 (9)
O2	0.0460 (11)	0.0439 (11)	0.0478 (11)	−0.0067 (8)	−0.0111 (9)	−0.0128 (9)
O3	0.0902 (15)	0.0395 (11)	0.0288 (10)	−0.0025 (10)	−0.0028 (10)	−0.0042 (8)
N1	0.0477 (13)	0.0311 (12)	0.0310 (12)	−0.0070 (10)	0.0016 (10)	−0.0018 (9)
N2	0.0673 (16)	0.0354 (13)	0.0365 (13)	−0.0076 (11)	−0.0104 (11)	0.0021 (11)
C9	0.095 (2)	0.0457 (18)	0.0285 (15)	−0.0092 (16)	−0.0113 (15)	0.0005 (13)
C10	0.082 (2)	0.0330 (16)	0.0375 (16)	−0.0059 (14)	−0.0067 (14)	−0.0051 (13)
C6	0.0353 (14)	0.0322 (14)	0.0320 (14)	−0.0039 (11)	−0.0009 (11)	−0.0015 (11)
C7	0.095 (2)	0.0367 (17)	0.0334 (16)	−0.0049 (15)	−0.0119 (15)	−0.0031 (13)
C8	0.107 (3)	0.0311 (16)	0.0451 (18)	−0.0064 (16)	−0.0170 (17)	−0.0033 (14)
C3	0.0331 (14)	0.0309 (14)	0.0329 (14)	−0.0065 (11)	0.0002 (11)	−0.0024 (11)
C4	0.072 (2)	0.0352 (16)	0.0276 (14)	−0.0041 (13)	0.0043 (13)	−0.0038 (12)
C5	0.073 (2)	0.0285 (15)	0.0345 (16)	−0.0011 (13)	0.0019 (14)	−0.0046 (12)
C1	0.0605 (18)	0.0342 (15)	0.0283 (14)	−0.0101 (12)	0.0006 (12)	−0.0046 (12)
C2	0.0596 (17)	0.0270 (14)	0.0339 (15)	−0.0057 (12)	0.0003 (12)	−0.0038 (12)
C11	0.0408 (15)	0.0265 (13)	0.0274 (13)	−0.0059 (11)	0.0026 (12)	−0.0002 (10)
C12	0.0277 (13)	0.0318 (14)	0.0308 (13)	−0.0026 (10)	0.0028 (10)	−0.0061 (11)
C13	0.0363 (14)	0.0219 (13)	0.0371 (14)	−0.0003 (10)	0.0027 (11)	−0.0002 (11)
C15	0.0461 (16)	0.0366 (16)	0.0371 (15)	−0.0008 (12)	0.0003 (12)	−0.0153 (13)
C16	0.0455 (16)	0.0244 (14)	0.0444 (16)	0.0020 (11)	−0.0035 (12)	−0.0030 (12)
C17	0.0385 (14)	0.0330 (14)	0.0307 (14)	0.0009 (11)	−0.0038 (11)	−0.0015 (11)
C14	0.0423 (15)	0.0346 (15)	0.0274 (14)	−0.0040 (11)	0.0009 (11)	−0.0062 (11)

Geometric parameters (Å, º) top

Mn1—O1	2.1335 (15)	C10—H10	0.9300
Mn1—O1ⁱ	2.1335 (15)	C6—C7	1.378 (3)
Mn1—O1Wⁱ	2.1949 (16)	C6—C3	1.476 (3)
Mn1—O1W	2.1949 (16)	C7—C8	1.377 (4)
Mn1—N1	2.3038 (19)	C7—H7	0.9300
Mn1—N1ⁱ	2.3038 (19)	C8—H8	0.9300
F1—C13	1.361 (3)	C3—C4	1.385 (3)
F2—C15	1.345 (3)	C3—C2	1.389 (3)
F3—C16	1.354 (3)	C4—C5	1.374 (3)
O1—C11	1.266 (3)	C4—H4	0.9300
O1W—H1W	0.8445	C5—H5	0.9300
O1W—H2W	0.8541	C1—C2	1.369 (3)
O2—C11	1.242 (3)	C1—H1	0.9300
O3—C14	1.342 (3)	C2—H2	0.9300
O3—H3	0.8200	C11—C12	1.510 (3)
N1—C1	1.326 (3)	C12—C13	1.377 (3)
N1—C5	1.338 (3)	C12—C17	1.392 (3)
N2—C9	1.316 (3)	C13—C14	1.382 (3)
N2—C8	1.323 (3)	C15—C16	1.368 (3)
C9—C10	1.383 (4)	C15—C14	1.388 (3)
C9—H9	0.9300	C16—C17	1.363 (3)
C10—C6	1.374 (3)	C17—H17	0.9300

O1—Mn1—O1ⁱ	180.0	C7—C8—H8	118.2
O1—Mn1—O1Wⁱ	88.91 (6)	C4—C3—C2	115.2 (2)
O1ⁱ—Mn1—O1Wⁱ	91.09 (6)	C4—C3—C6	123.1 (2)
O1—Mn1—O1W	91.09 (6)	C2—C3—C6	121.7 (2)
O1ⁱ—Mn1—O1W	88.91 (6)	C5—C4—C3	121.1 (2)
O1Wⁱ—Mn1—O1W	180.00 (8)	C5—C4—H4	119.5
O1—Mn1—N1	89.39 (6)	C3—C4—H4	119.5
O1ⁱ—Mn1—N1	90.61 (6)	N1—C5—C4	123.2 (2)
O1Wⁱ—Mn1—N1	84.76 (7)	N1—C5—H5	118.4
O1W—Mn1—N1	95.24 (7)	C4—C5—H5	118.4
O1—Mn1—N1ⁱ	90.61 (6)	N1—C1—C2	124.6 (2)
O1ⁱ—Mn1—N1ⁱ	89.39 (6)	N1—C1—H1	117.7
O1Wⁱ—Mn1—N1ⁱ	95.24 (7)	C2—C1—H1	117.7
O1W—Mn1—N1ⁱ	84.76 (7)	C1—C2—C3	120.2 (2)
N1—Mn1—N1ⁱ	180.0	C1—C2—H2	119.9
C11—O1—Mn1	130.94 (15)	C3—C2—H2	119.9
Mn1—O1W—H1W	133.3	O2—C11—O1	125.9 (2)
Mn1—O1W—H2W	102.0	O2—C11—C12	118.6 (2)
H1W—O1W—H2W	104.9	O1—C11—C12	115.3 (2)
C14—O3—H3	109.5	C13—C12—C17	118.4 (2)
C1—N1—C5	115.8 (2)	C13—C12—C11	122.2 (2)
C1—N1—Mn1	122.51 (15)	C17—C12—C11	119.3 (2)
C5—N1—Mn1	121.30 (16)	F1—C13—C12	119.4 (2)
C9—N2—C8	116.3 (2)	F1—C13—C14	116.7 (2)
N2—C9—C10	123.8 (2)	C12—C13—C14	123.9 (2)
N2—C9—H9	118.1	F2—C15—C16	119.9 (2)
C10—C9—H9	118.1	F2—C15—C14	118.9 (2)
C6—C10—C9	120.1 (3)	C16—C15—C14	121.2 (2)
C6—C10—H10	119.9	F3—C16—C17	120.4 (2)
C9—C10—H10	119.9	F3—C16—C15	117.6 (2)
C10—C6—C7	115.8 (2)	C17—C16—C15	122.0 (2)
C10—C6—C3	122.7 (2)	C16—C17—C12	118.7 (2)
C7—C6—C3	121.5 (2)	C16—C17—H17	120.6
C8—C7—C6	120.4 (3)	C12—C17—H17	120.6
C8—C7—H7	119.8	O3—C14—C13	125.6 (2)
C6—C7—H7	119.8	O3—C14—C15	118.5 (2)
N2—C8—C7	123.6 (3)	C13—C14—C15	115.9 (2)
N2—C8—H8	118.2

O1Wⁱ—Mn1—O1—C11	−155.2 (2)	Mn1—N1—C1—C2	−171.9 (2)
O1W—Mn1—O1—C11	24.8 (2)	N1—C1—C2—C3	−0.3 (4)
N1—Mn1—O1—C11	120.1 (2)	C4—C3—C2—C1	−0.6 (4)
N1ⁱ—Mn1—O1—C11	−59.9 (2)	C6—C3—C2—C1	179.3 (2)
O1—Mn1—N1—C1	−165.93 (19)	Mn1—O1—C11—O2	−10.1 (4)
O1ⁱ—Mn1—N1—C1	14.07 (19)	Mn1—O1—C11—C12	165.38 (14)
O1Wⁱ—Mn1—N1—C1	105.11 (19)	O2—C11—C12—C13	−128.6 (2)
O1W—Mn1—N1—C1	−74.89 (19)	O1—C11—C12—C13	55.6 (3)
O1—Mn1—N1—C5	21.15 (19)	O2—C11—C12—C17	55.3 (3)
O1ⁱ—Mn1—N1—C5	−158.85 (19)	O1—C11—C12—C17	−120.5 (2)
O1Wⁱ—Mn1—N1—C5	−67.81 (19)	C17—C12—C13—F1	−178.5 (2)
O1W—Mn1—N1—C5	112.19 (19)	C11—C12—C13—F1	5.4 (3)
C8—N2—C9—C10	−1.1 (5)	C17—C12—C13—C14	0.0 (4)
N2—C9—C10—C6	−0.6 (5)	C11—C12—C13—C14	−176.1 (2)
C9—C10—C6—C7	1.2 (4)	F2—C15—C16—F3	−0.3 (4)
C9—C10—C6—C3	−179.3 (2)	C14—C15—C16—F3	179.2 (2)
C10—C6—C7—C8	−0.2 (4)	F2—C15—C16—C17	179.4 (2)
C3—C6—C7—C8	−179.6 (3)	C14—C15—C16—C17	−1.0 (4)
C9—N2—C8—C7	2.3 (5)	F3—C16—C17—C12	−178.7 (2)
C6—C7—C8—N2	−1.7 (5)	C15—C16—C17—C12	1.5 (4)
C10—C6—C3—C4	14.1 (4)	C13—C12—C17—C16	−1.0 (3)
C7—C6—C3—C4	−166.5 (3)	C11—C12—C17—C16	175.2 (2)
C10—C6—C3—C2	−165.7 (2)	F1—C13—C14—O3	−2.3 (4)
C7—C6—C3—C2	13.6 (4)	C12—C13—C14—O3	179.2 (2)
C2—C3—C4—C5	0.5 (4)	F1—C13—C14—C15	179.1 (2)
C6—C3—C4—C5	−179.4 (2)	C12—C13—C14—C15	0.5 (4)
C1—N1—C5—C4	−1.5 (4)	F2—C15—C14—O3	0.7 (4)
Mn1—N1—C5—C4	171.9 (2)	C16—C15—C14—O3	−178.8 (2)
C3—C4—C5—N1	0.6 (4)	F2—C15—C14—C13	179.5 (2)
C5—N1—C1—C2	1.3 (4)	C16—C15—C14—C13	0.0 (4)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O2	0.85	2.04	2.839 (2)	155
O1W—H1W···O2ⁱⁱ	0.84	1.97	2.773 (2)	159
O3—H3···N2ⁱⁱⁱ	0.82	1.89	2.641 (3)	152

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

Experimental details

Crystal data
Chemical formula	[Mn(C₇H₂F₃O₃)₂(C₁₀H₈N₂)₂(H₂O)₂]
M_r	785.51
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.0706 (6), 8.2939 (7), 13.9856 (12)
α, β, γ (°)	79.200 (1), 88.338 (1), 79.830 (2)
V (Å³)	792.96 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.861, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	4185, 2792, 2101
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.084, 1.01
No. of reflections	2792
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O2	0.85	2.04	2.839 (2)	155.4
O1W—H1W···O2ⁱ	0.84	1.97	2.773 (2)	158.5
O3—H3···N2ⁱⁱ	0.82	1.89	2.641 (3)	152.4

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20863003).

References

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Ma, C. L., Sun, J. S. & Zhang, R. F. (2006). J. Organomet. Chem. 691, 5885–5898. Google Scholar
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