Poly[[diaqua-manganese(II)]-bis-(μ-4-fluoro-benzoato-κO:O')].

In the crystal structure of the title complex, [Mn(C(7)H(4)FO(2))(2)(H(2)O)(2)](n), the Mn(II) atom is located on an inversion centre. It is coordinated by two water mol-ecules in the apical directions and four 4-fluoro-benzoate (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 Mn(II) atom form a slightly distorted square-planar arrangement, while the slightly distorted octa-hedral coordination is completed by the two O atoms of the water mol-ecules. The dihedral angle between the carboxyl-ate group and the adjacent benzene ring is 27.29 (16)°. The O-H⋯O hydrogen bonds further connect the manganese-carboxyl-ate 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 ▶). 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

Crystal data

[Mn(C7H4FO2)2(H2O)2]

M = 369.18

Monoclinic,

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 ▶) T min = 0.728, T max = 0.786

11656 measured reflections

1758 independent reflections

1720 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021921/su2282sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C7H4FO2)2(H2O)2]	F(000) = 374
Mr = 369.18	Dx = 1.752 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9752 reflections
a = 14.5065 (6) Å	θ = 2.8–28.5°
b = 6.6107 (3) Å	µ = 1.00 mm−1
c = 7.3708 (3) Å	T = 100 K
β = 98.179 (2)°	Block, blue
V = 699.66 (5) Å3	0.34 × 0.27 × 0.24 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	1758 independent reflections
Radiation source: fine-focus sealed tube	1720 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 28.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→19
Tmin = 0.728, Tmax = 0.786	k = −8→7
11656 measured reflections	l = −9→9

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H 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 parameters	Δρmax = 1.24 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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.

	x	y	z	Uiso*/Ueq
Mn1	0.5000	1.0000	0.5000	0.00934 (15)
O1	0.39762 (12)	1.0833 (3)	0.2723 (2)	0.0133 (4)
O2	0.58287 (12)	0.9092 (3)	0.2904 (2)	0.0133 (4)
O3	0.57162 (13)	1.2939 (3)	0.5150 (3)	0.0146 (4)
H31	0.575 (3)	1.370 (6)	0.604 (6)	0.027 (10)*
H32	0.566 (3)	1.361 (6)	0.425 (6)	0.031 (10)*
F1	0.99509 (11)	0.7768 (3)	0.6699 (2)	0.0279 (4)
C1	0.63126 (16)	0.7488 (4)	0.2983 (3)	0.0099 (4)
C2	0.72835 (17)	0.7562 (4)	0.3993 (3)	0.0123 (5)
C3	0.76860 (18)	0.9415 (4)	0.4534 (4)	0.0169 (5)
H3	0.7340	1.0629	0.4285	0.020*
C4	0.85953 (19)	0.9492 (4)	0.5439 (4)	0.0207 (5)
H4	0.8885	1.0748	0.5792	0.025*
C5	0.90623 (17)	0.7696 (5)	0.5807 (4)	0.0184 (5)
C6	0.86858 (19)	0.5840 (4)	0.5321 (4)	0.0200 (5)
H6	0.9030	0.4633	0.5614	0.024*
C7	0.77816 (18)	0.5780 (4)	0.4383 (4)	0.0168 (5)
H7	0.7505	0.4517	0.4008	0.020*

	U11	U22	U33	U12	U13	U23
Mn1	0.0082 (2)	0.0104 (3)	0.0089 (2)	0.00104 (17)	−0.00066 (17)	−0.00106 (17)
O1	0.0120 (8)	0.0117 (8)	0.0150 (8)	0.0013 (6)	−0.0025 (6)	0.0011 (6)
O2	0.0145 (8)	0.0125 (8)	0.0131 (8)	0.0030 (7)	0.0025 (6)	0.0003 (6)
O3	0.0200 (9)	0.0128 (8)	0.0106 (8)	−0.0009 (7)	0.0010 (7)	0.0003 (7)
F1	0.0112 (7)	0.0423 (11)	0.0272 (9)	−0.0031 (7)	−0.0071 (6)	−0.0018 (8)
C1	0.0092 (10)	0.0115 (10)	0.0091 (10)	−0.0004 (8)	0.0024 (8)	0.0008 (8)
C2	0.0117 (10)	0.0154 (11)	0.0097 (10)	−0.0011 (8)	0.0010 (8)	−0.0007 (8)
C3	0.0163 (12)	0.0152 (12)	0.0185 (12)	−0.0015 (9)	−0.0002 (9)	−0.0012 (9)
C4	0.0176 (12)	0.0210 (13)	0.0226 (13)	−0.0073 (10)	−0.0003 (10)	−0.0053 (10)
C5	0.0083 (10)	0.0314 (15)	0.0147 (11)	−0.0023 (10)	−0.0014 (9)	−0.0008 (10)
C6	0.0153 (12)	0.0219 (13)	0.0216 (13)	0.0046 (10)	−0.0016 (10)	0.0013 (10)
C7	0.0154 (11)	0.0153 (12)	0.0184 (12)	0.0002 (9)	−0.0016 (9)	−0.0010 (9)

Mn1—O1	2.1489 (17)	C1—C2	1.498 (3)
Mn1—O1i	2.1489 (17)	C2—C3	1.391 (3)
Mn1—O2	2.1728 (17)	C2—C7	1.390 (3)
Mn1—O2i	2.1728 (17)	C3—H3	0.9500
Mn1—O3	2.1988 (19)	C4—C3	1.392 (4)
Mn1—O3i	2.1988 (19)	C4—H4	0.9500
O1—C1ii	1.257 (3)	C5—C4	1.375 (4)
O2—C1	1.268 (3)	C6—C5	1.370 (4)
O3—H31	0.82 (4)	C6—H6	0.9500
O3—H32	0.79 (4)	C7—C6	1.394 (4)
F1—C5	1.362 (3)	C7—H7	0.9500
C1—O1iii	1.257 (3)
O1—Mn1—O1i	180.0	O1iii—C1—C2	117.9 (2)
O1—Mn1—O2	84.62 (7)	O2—C1—C2	118.1 (2)
O1i—Mn1—O2	95.38 (7)	C3—C2—C1	119.9 (2)
O1—Mn1—O2i	95.38 (7)	C7—C2—C1	120.0 (2)
O1i—Mn1—O2i	84.62 (7)	C7—C2—C3	120.2 (2)
O1—Mn1—O3	94.69 (7)	C2—C3—C4	120.0 (2)
O1i—Mn1—O3	85.31 (7)	C2—C3—H3	120.0
O1—Mn1—O3i	85.31 (7)	C4—C3—H3	120.0
O1i—Mn1—O3i	94.69 (7)	C3—C4—H4	121.0
O2—Mn1—O2i	180.0	C5—C4—C3	118.0 (2)
O2—Mn1—O3	88.55 (7)	C5—C4—H4	121.0
O2i—Mn1—O3	91.45 (7)	F1—C5—C4	118.1 (2)
O2—Mn1—O3i	91.45 (7)	F1—C5—C6	118.2 (2)
O2i—Mn1—O3i	88.55 (7)	C6—C5—C4	123.7 (2)
O3—Mn1—O3i	180.00 (10)	C5—C6—C7	117.9 (2)
C1ii—O1—Mn1	134.33 (16)	C5—C6—H6	121.1
C1—O2—Mn1	123.85 (15)	C7—C6—H6	121.1
Mn1—O3—H31	124 (3)	C2—C7—C6	120.2 (2)
Mn1—O3—H32	118 (3)	C2—C7—H7	119.9
H31—O3—H32	108 (4)	C6—C7—H7	119.9
O1iii—C1—O2	124.0 (2)
O2—Mn1—O1—C1ii	−106.1 (2)	O2—C1—C2—C7	169.1 (2)
O2i—Mn1—O1—C1ii	73.9 (2)	C1—C2—C3—C4	−178.6 (2)
O3—Mn1—O1—C1ii	−18.0 (2)	C7—C2—C3—C4	1.1 (4)
O3i—Mn1—O1—C1ii	162.0 (2)	C1—C2—C7—C6	179.9 (2)
O1i—Mn1—O2—C1	41.54 (19)	C3—C2—C7—C6	0.2 (4)
O3—Mn1—O2—C1	126.69 (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—O1iii	93.1 (3)	C6—C5—C4—C3	0.5 (4)
Mn1—O2—C1—C2	−86.2 (2)	C7—C6—C5—F1	−179.0 (2)
O1iii—C1—C2—C3	169.5 (2)	C7—C6—C5—C4	0.7 (4)
O1iii—C1—C2—C7	−10.3 (3)	C2—C7—C6—C5	−1.1 (4)
O2—C1—C2—C3	−11.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H32···O2ii	0.79 (4)	2.51 (4)	3.039 (3)	125 (4)
O3—H32···O1ii	0.79 (4)	2.18 (4)	2.935 (3)	158 (4)

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) .