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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 7| July 2011| Pages m1003-m1004
doi:10.1107/S1600536811021921

Poly[[di­aqua­manganese(II)]-bis­­(μ-4-fluoro­benzoato-κ2O:O′)]

Hacali Necefoğlu,a Füreya Elif Özbek,a Vijdan Öztürk,a Barış Tercanb and Tuncer Hökelekc*

aKafkas University, Department of Chemistry, 36100 Kars, Turkey, bKarabük University, Department of Physics, 78050, Karabük, Turkey, and cHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 6 June 2011; accepted 7 June 2011; online 30 June 2011)

In the crystal structure of the title complex, [Mn(C7H4FO2)2(H2O)2]n, the MnII atom is located on an inversion centre. It is coordinated by two water mol­ecules in the apical directions and four 4-fluoro­benzoate (PFB) anions, bridging the symmetry related Mn atoms in the basal plane to form an infinite two-dimensional polymeric structure parallel to (100). The four O atoms of the PFB anions around the MnII atom form a slightly distorted square-planar arrangement, while the slightly distorted octa­hedral coordination is completed by the two O atoms of the water mol­ecules. The dihedral angle between the carboxyl­ate group and the adjacent benzene ring is 27.29 (16)°. The O—H⋯O hydrogen bonds further connect the manganese-carboxyl­ate units. π–π contacts between the benzene rings [centroid-centroid distance = 3.6894 (15) Å] further stabilize the crystal structure.

Related literature

For literature on niacin, see: Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For infomation on the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972[Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.]). For related structures, see: Hökelek et al. (2008[Hökelek, T., Çaylak, N. & Necefoğlu, H. (2008). Acta Cryst. E64, m505-m506.], 2009[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009). Acta Cryst. E65, m747-m748.]); Hökelek & Necefoğlu (2007[Hökelek, T. & Necefoğlu, H. (2007). Acta Cryst. E63, m821-m823.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc., Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • [Mn(C7H4FO2)2(H2O)2]

  • Mr = 369.18

  • Monoclinic, P 21 /c

  • a = 14.5065 (6) Å

  • b = 6.6107 (3) Å

  • c = 7.3708 (3) Å

  • β = 98.179 (2)°

  • V = 699.66 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.00 mm−1

  • T = 100 K

  • 0.34 × 0.27 × 0.24 mm
Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.728, Tmax = 0.786

  • 11656 measured reflections

  • 1758 independent reflections

  • 1720 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.111

  • S = 1.28

  • 1758 reflections

  • 114 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.24 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H32⋯O2i 0.79 (4) 2.51 (4) 3.039 (3) 125 (4)
O3—H32⋯O1i 0.79 (4) 2.18 (4) 2.935 (3) 158 (4)
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021921/su2282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021921/su2282Isup2.hkl

checkCIF report


Comment top

As a part of our ongoing investigations of transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

In the title two-dimensional polymeric structure the MnII atom is located on a centre of invesion, and surrounded by four 4-fluorobenzoate (PFB) anions and two water molecules (Fig. 1). The PFB anions bridge the symmetry related Mn atoms. The four O atoms [O1, O2, O1'' and O2'', symmetry code: ('') -x, -y, -z] in the equatorial plane around the Mn atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the symmetry related O atoms of the coordinated water molecules (O3 and O3'') in the axial positions (Fig. 1).

The near equalities of the C1—O1 [1.257 (3) Å] and C1—O2 [1.268 (3) Å] bonds in the carboxylate group indicate a delocalized bonding arrangement, rather than localized single and double bonds, and may be compared with the corresponding distances: 1.263 (2), 1.279 (2), 1.263 (2) and 1.278 (2) Å in {[Mn(C11H14NO2)2(H2O)3].2(H2O)}n, (II) (Hökelek et al., 2009), 1.256 (6) and 1.245 (6) Å in [Mn(DENA)2(C7H4ClO2)2(H2O)2], (III) (Hökelek et al., 2008) and 1.265 (6) and 1.275 (6) Å in [Mn(C9H10NO2)2(H2O)4].2(H2O), (IV) (Hökelek & Necefoğlu, 2007).

The Mn—O bond lengths are in the range of 2.1489 (17) - 2.1988 (19) Å, and are close to standard values (Allen et al., 1987) with an average Mn-O bond length of 2.1735 (18) Å. The Mn atom is displaced out of the least-square plane of the carboxylate group (O1/C1/O2) by -1.5976 (1) Å. The dihedral angle between the planar carboxylate group and the adjacent benzene ring A (C2—C7) is 27.29 (16)°.

In the crystal structure, (Fig. 2), intermolecular O—H···O hydrogen bonds (Table 1) link the manganese-carboxylate units, and may be effective in the stabilization of the structure. The π···π contacts between the benzene rings, Cg1—Cg1i [symmetry code: (i) x, 1/2 - y, z - 1/2, where Cg1 is the centroid of the ring A (C2—C7)] may further stabilize the structure, with a centroid-centroid distance of 3.6894 (15) Å.

Related literature top

For literature on niacin, see: Krishnamachari (1974). For infomation on the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek et al. (2008, 2009); Hökelek & Necefoğlu (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of MnSO4.H2O (0.85 g, 5 mmol) in H2O (100 ml) and isonicotinamide (1.22 g, 10 mmol) in H2O (50 ml) with sodium 4-fluorobenzoate (1.62 g, 10 mmol) in H2O (50 ml) at room temperature. The mixture was filtered and set aside to crystallize at ambient temperature for two weeks, giving blue single crystals.

Refinement top

Atoms H31 and H32 (for H2O) were located in a difference Fourier map and were freely refined. The C-bound H-atoms were positioned geometrically with C—H = 0.95 Å for aromatic H-atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry codes: (') -x, y + 1/2, 1/2 - z, ('') -x, -y, -z, (''') x, 1/2 - y, 1/2 + z]. Hydrogen atoms, except those of the water molecules, have been omitted for clarity.
[Figure 2] Fig. 2. A view along the a-axis of the crystal packing of the title compound [c-axis horizontal; b-axis vertical]. Hydrogen atoms, except those of the water molecules (violet balls), have been omitted for clarity.
Poly[[diaquamanganese(II)]-bis(µ-4-fluorobenzoato-κ2O:O')] top
Crystal data top
[Mn(C7H4FO2)2(H2O)2]F(000) = 374
Mr = 369.18Dx = 1.752 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9752 reflections
a = 14.5065 (6) Åθ = 2.8–28.5°
b = 6.6107 (3) ŵ = 1.00 mm−1
c = 7.3708 (3) ÅT = 100 K
β = 98.179 (2)°Block, blue
V = 699.66 (5) Å30.34 × 0.27 × 0.24 mm
Z = 2
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		1758 independent reflections
Radiation source: fine-focus sealed tube1720 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 28.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −19→19
Tmin = 0.728, Tmax = 0.786k = −8→7
11656 measured reflectionsl = −9→9
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.28 w = 1/[σ2(Fo2) + (0.031P)2 + 1.8232P]
where P = (Fo2 + 2Fc2)/3
1758 reflections(Δ/σ)max < 0.001
114 parametersΔρmax = 1.24 e Å−3
0 restraintsΔρmin = −0.45 e Å−3
Crystal data top
[Mn(C7H4FO2)2(H2O)2]V = 699.66 (5) Å3
Mr = 369.18Z = 2
Monoclinic, P21/cMo Kα radiation
a = 14.5065 (6) ŵ = 1.00 mm−1
b = 6.6107 (3) ÅT = 100 K
c = 7.3708 (3) Å0.34 × 0.27 × 0.24 mm
β = 98.179 (2)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		1758 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1720 reflections with I > 2σ(I)
Tmin = 0.728, Tmax = 0.786Rint = 0.029
11656 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.28Δρmax = 1.24 e Å−3
1758 reflectionsΔρmin = −0.45 e Å−3
114 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
xyzUiso*/Ueq
Mn10.50001.00000.50000.00934 (15)
O10.39762 (12)1.0833 (3)0.2723 (2)0.0133 (4)
O20.58287 (12)0.9092 (3)0.2904 (2)0.0133 (4)
O30.57162 (13)1.2939 (3)0.5150 (3)0.0146 (4)
H310.575 (3)1.370 (6)0.604 (6)0.027 (10)*
H320.566 (3)1.361 (6)0.425 (6)0.031 (10)*
F10.99509 (11)0.7768 (3)0.6699 (2)0.0279 (4)
C10.63126 (16)0.7488 (4)0.2983 (3)0.0099 (4)
C20.72835 (17)0.7562 (4)0.3993 (3)0.0123 (5)
C30.76860 (18)0.9415 (4)0.4534 (4)0.0169 (5)
H30.73401.06290.42850.020*
C40.85953 (19)0.9492 (4)0.5439 (4)0.0207 (5)
H40.88851.07480.57920.025*
C50.90623 (17)0.7696 (5)0.5807 (4)0.0184 (5)
C60.86858 (19)0.5840 (4)0.5321 (4)0.0200 (5)
H60.90300.46330.56140.024*
C70.77816 (18)0.5780 (4)0.4383 (4)0.0168 (5)
H70.75050.45170.40080.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0082 (2)0.0104 (3)0.0089 (2)0.00104 (17)−0.00066 (17)−0.00106 (17)
O10.0120 (8)0.0117 (8)0.0150 (8)0.0013 (6)−0.0025 (6)0.0011 (6)
O20.0145 (8)0.0125 (8)0.0131 (8)0.0030 (7)0.0025 (6)0.0003 (6)
O30.0200 (9)0.0128 (8)0.0106 (8)−0.0009 (7)0.0010 (7)0.0003 (7)
F10.0112 (7)0.0423 (11)0.0272 (9)−0.0031 (7)−0.0071 (6)−0.0018 (8)
C10.0092 (10)0.0115 (10)0.0091 (10)−0.0004 (8)0.0024 (8)0.0008 (8)
C20.0117 (10)0.0154 (11)0.0097 (10)−0.0011 (8)0.0010 (8)−0.0007 (8)
C30.0163 (12)0.0152 (12)0.0185 (12)−0.0015 (9)−0.0002 (9)−0.0012 (9)
C40.0176 (12)0.0210 (13)0.0226 (13)−0.0073 (10)−0.0003 (10)−0.0053 (10)
C50.0083 (10)0.0314 (15)0.0147 (11)−0.0023 (10)−0.0014 (9)−0.0008 (10)
C60.0153 (12)0.0219 (13)0.0216 (13)0.0046 (10)−0.0016 (10)0.0013 (10)
C70.0154 (11)0.0153 (12)0.0184 (12)0.0002 (9)−0.0016 (9)−0.0010 (9)
Geometric parameters (Å, º) top
Mn1—O12.1489 (17)C1—C21.498 (3)
Mn1—O1i2.1489 (17)C2—C31.391 (3)
Mn1—O22.1728 (17)C2—C71.390 (3)
Mn1—O2i2.1728 (17)C3—H30.9500
Mn1—O32.1988 (19)C4—C31.392 (4)
Mn1—O3i2.1988 (19)C4—H40.9500
O1—C1ii1.257 (3)C5—C41.375 (4)
O2—C11.268 (3)C6—C51.370 (4)
O3—H310.82 (4)C6—H60.9500
O3—H320.79 (4)C7—C61.394 (4)
F1—C51.362 (3)C7—H70.9500
C1—O1iii1.257 (3)
O1—Mn1—O1i180.0O1iii—C1—C2117.9 (2)
O1—Mn1—O284.62 (7)O2—C1—C2118.1 (2)
O1i—Mn1—O295.38 (7)C3—C2—C1119.9 (2)
O1—Mn1—O2i95.38 (7)C7—C2—C1120.0 (2)
O1i—Mn1—O2i84.62 (7)C7—C2—C3120.2 (2)
O1—Mn1—O394.69 (7)C2—C3—C4120.0 (2)
O1i—Mn1—O385.31 (7)C2—C3—H3120.0
O1—Mn1—O3i85.31 (7)C4—C3—H3120.0
O1i—Mn1—O3i94.69 (7)C3—C4—H4121.0
O2—Mn1—O2i180.0C5—C4—C3118.0 (2)
O2—Mn1—O388.55 (7)C5—C4—H4121.0
O2i—Mn1—O391.45 (7)F1—C5—C4118.1 (2)
O2—Mn1—O3i91.45 (7)F1—C5—C6118.2 (2)
O2i—Mn1—O3i88.55 (7)C6—C5—C4123.7 (2)
O3—Mn1—O3i180.00 (10)C5—C6—C7117.9 (2)
C1ii—O1—Mn1134.33 (16)C5—C6—H6121.1
C1—O2—Mn1123.85 (15)C7—C6—H6121.1
Mn1—O3—H31124 (3)C2—C7—C6120.2 (2)
Mn1—O3—H32118 (3)C2—C7—H7119.9
H31—O3—H32108 (4)C6—C7—H7119.9
O1iii—C1—O2124.0 (2)
O2—Mn1—O1—C1ii−106.1 (2)O2—C1—C2—C7169.1 (2)
O2i—Mn1—O1—C1ii73.9 (2)C1—C2—C3—C4−178.6 (2)
O3—Mn1—O1—C1ii−18.0 (2)C7—C2—C3—C41.1 (4)
O3i—Mn1—O1—C1ii162.0 (2)C1—C2—C7—C6179.9 (2)
O1i—Mn1—O2—C141.54 (19)C3—C2—C7—C60.2 (4)
O3—Mn1—O2—C1126.69 (19)C5—C4—C3—C2−1.4 (4)
O3i—Mn1—O2—C1−53.31 (19)F1—C5—C4—C3−179.8 (2)
Mn1—O2—C1—O1iii93.1 (3)C6—C5—C4—C30.5 (4)
Mn1—O2—C1—C2−86.2 (2)C7—C6—C5—F1−179.0 (2)
O1iii—C1—C2—C3169.5 (2)C7—C6—C5—C40.7 (4)
O1iii—C1—C2—C7−10.3 (3)C2—C7—C6—C5−1.1 (4)
O2—C1—C2—C3−11.2 (3)
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H32···O2ii0.79 (4)2.51 (4)3.039 (3)125 (4)
O3—H32···O1ii0.79 (4)2.18 (4)2.935 (3)158 (4)
Symmetry code: (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula[Mn(C7H4FO2)2(H2O)2]
Mr369.18
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)14.5065 (6), 6.6107 (3), 7.3708 (3)
β (°) 98.179 (2)
V (Å3)699.66 (5)
Z2
Radiation typeMo Kα
µ (mm−1)1.00
Crystal size (mm)0.34 × 0.27 × 0.24
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.728, 0.786
No. of measured, independent and
observed [I > 2σ(I)] reflections		11656, 1758, 1720
Rint0.029
(sin θ/λ)max (Å−1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.111, 1.28
No. of reflections1758
No. of parameters114
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)1.24, −0.45

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H32···O2i0.79 (4)2.51 (4)3.039 (3)125 (4)
O3—H32···O1i0.79 (4)2.18 (4)2.935 (3)158 (4)
Symmetry code: (i) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer. This work was supported financially by the Scientific and Technological Research Council of Turkey (grant No. 108 T657).

References

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 7| July 2011| Pages m1003-m1004
doi:10.1107/S1600536811021921
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