Tetra-aqua-(2,2'-bipyridine-κN,N')magnesium(II) bis-(4-fluoro-benzoate).

The title compound, [Mg(C(10)H(8)N(2))(H(2)O)(4)](C(7)H(4)FO(2))(2), consists of a bivalent [Mg(C(10)H(8)N(2))(H(2)O)(4)](2+) cation and two 4-fluorbenzoate anions. In the complex cation, the Mg(II) atom is coordinated by two N atoms from a 2,2'-bipyridine ligand and four water O atoms in a distorted MgN(2)O(4) octa-hedral geometry. The Mg(II) atom is located on a twofold rotation axis and thus a cation exhibits C(2) mol-ecular symmetry. The 2,2'-bipyridine ligands exhibit nearly perfect planarity (r.m.s. deviations = 0.0061 Å). In the crystal, O-H⋯O and C-H⋯O hydrogen bonds link the cations and anions into a three-dimensional supra-molecular network.

Related literature

For related magnesium(II) complexes with 1,10-phenanthroline and pyridine ligands, see: Halut-Desportes (1981 ▶); Hao et al. (2008 ▶); Zhang (2004 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

[Mg(C10H8N2)(H2O)4](C7H4FO2)2

M = 530.76

Orthorhombic,

a = 27.911 (6) Å

b = 12.423 (3) Å

c = 7.5895 (15) Å

V = 2631.6 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 290 K

0.18 × 0.13 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995) ▶ T min = 0.979, T max = 0.987

2316 measured reflections

2310 independent reflections

1741 reflections with I > 2σ(I)

R int = 0.096

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.207

S = 1.14

2310 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.32 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998) ▶; cell refinement: RAPID-AUTO ▶; data reduction: CrystalStructure (Rigaku/MSC, 2002) ▶; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047690/kp2287sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047690/kp2287Isup2.hkl

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

[Mg(C10H8N2)(H2O)4](C7H4FO2)2	F(000) = 1104
Mr = 530.76	Dx = 1.340 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2n 2ab	Cell parameters from 665 reflections
a = 27.911 (6) Å	θ = 3.2–25.0°
b = 12.423 (3) Å	µ = 0.13 mm−1
c = 7.5895 (15) Å	T = 290 K
V = 2631.6 (10) Å3	Block, colourless
Z = 4	0.18 × 0.13 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	2310 independent reflections
Radiation source: fine-focus sealed tube	1741 reflections with I > 2σ(I)
graphite	Rint = 0.096
ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −33→33
Tmin = 0.979, Tmax = 0.987	k = −14→14
2316 measured reflections	l = −8→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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.207	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0879P)2 + 2.3043P] where P = (Fo2 + 2Fc2)/3
2310 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.32 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
Mg1	0.0000	0.29487 (11)	0.2500	0.0347 (4)
O1	0.05496 (9)	0.4005 (2)	0.2115 (3)	0.0536 (7)
H1A	0.0576	0.4581	0.2632	0.080*
H1B	0.0657	0.4124	0.1128	0.080*
O2	−0.01046 (8)	0.2966 (2)	−0.0187 (3)	0.0509 (7)
H2A	−0.0378	0.2905	−0.0568	0.076*
H2B	0.0122	0.3254	−0.0688	0.076*
O3	0.40257 (9)	0.2093 (2)	0.1617 (4)	0.0680 (9)
O4	0.42874 (8)	0.0949 (2)	0.3633 (3)	0.0482 (7)
N1	0.04711 (9)	0.1555 (2)	0.2250 (4)	0.0418 (7)
F1	0.20665 (10)	0.0891 (3)	0.5077 (5)	0.1243 (14)
C1	0.09402 (13)	0.1603 (3)	0.1902 (5)	0.0544 (10)
H1	0.1090	0.2271	0.1896	0.065*
C2	0.12112 (15)	0.0689 (4)	0.1551 (6)	0.0682 (12)
H2	0.1537	0.0746	0.1312	0.082*
C3	0.09930 (15)	−0.0285 (4)	0.1561 (6)	0.0689 (12)
H3	0.1167	−0.0906	0.1313	0.083*
C4	0.05129 (15)	−0.0346 (3)	0.1944 (6)	0.0586 (10)
H4	0.0360	−0.1011	0.1969	0.070*
C5	0.02579 (12)	0.0585 (3)	0.2293 (4)	0.0415 (8)
C6	0.39599 (12)	0.1476 (3)	0.2874 (5)	0.0426 (8)
C7	0.34578 (6)	0.1330 (2)	0.3515 (3)	0.0454 (8)
C8	0.31097 (9)	0.20812 (19)	0.3063 (4)	0.0666 (12)
H8	0.3192	0.2683	0.2400	0.080*
C9	0.26384 (8)	0.1933 (2)	0.3604 (5)	0.0860 (16)
H9	0.2405	0.2436	0.3302	0.103*
C10	0.25153 (7)	0.1034 (3)	0.4595 (4)	0.0789 (14)
C11	0.28634 (10)	0.0283 (2)	0.5047 (4)	0.0844 (17)
H11	0.2781	−0.0319	0.5710	0.101*
C12	0.33346 (9)	0.0431 (2)	0.4506 (4)	0.0663 (12)
H12	0.3568	−0.0072	0.4808	0.080*

	U11	U22	U33	U12	U13	U23
Mg1	0.0374 (8)	0.0321 (8)	0.0346 (8)	0.000	−0.0008 (6)	0.000
O1	0.0681 (16)	0.0475 (14)	0.0450 (13)	−0.0212 (12)	0.0090 (12)	−0.0062 (12)
O2	0.0452 (14)	0.0697 (17)	0.0379 (13)	−0.0083 (12)	−0.0036 (10)	0.0040 (12)
O3	0.0505 (16)	0.076 (2)	0.0771 (19)	0.0115 (13)	0.0175 (14)	0.0332 (16)
O4	0.0473 (14)	0.0502 (15)	0.0472 (13)	0.0034 (11)	−0.0090 (11)	−0.0031 (11)
N1	0.0400 (16)	0.0406 (16)	0.0448 (15)	0.0030 (12)	−0.0008 (12)	−0.0011 (13)
F1	0.0611 (18)	0.169 (4)	0.143 (3)	−0.0280 (19)	0.0441 (18)	−0.016 (3)
C1	0.043 (2)	0.049 (2)	0.071 (3)	0.0030 (16)	0.0017 (18)	−0.0011 (19)
C2	0.047 (2)	0.072 (3)	0.085 (3)	0.015 (2)	0.010 (2)	−0.003 (2)
C3	0.066 (3)	0.052 (3)	0.089 (3)	0.024 (2)	0.006 (2)	−0.008 (2)
C4	0.070 (3)	0.036 (2)	0.070 (2)	0.0086 (18)	0.001 (2)	−0.0039 (18)
C5	0.0502 (19)	0.0371 (18)	0.0372 (17)	0.0012 (15)	−0.0021 (15)	−0.0001 (14)
C6	0.0430 (19)	0.0397 (19)	0.0451 (19)	0.0027 (15)	0.0018 (15)	−0.0051 (16)
C7	0.0430 (19)	0.050 (2)	0.0434 (18)	−0.0033 (16)	0.0019 (15)	−0.0017 (16)
C8	0.051 (2)	0.057 (2)	0.092 (3)	0.0051 (19)	0.013 (2)	0.007 (2)
C9	0.050 (3)	0.086 (4)	0.122 (4)	0.011 (2)	0.016 (3)	−0.004 (3)
C10	0.054 (3)	0.104 (4)	0.079 (3)	−0.017 (3)	0.023 (2)	−0.010 (3)
C11	0.073 (3)	0.112 (5)	0.068 (3)	−0.035 (3)	0.005 (2)	0.027 (3)
C12	0.059 (2)	0.081 (3)	0.059 (2)	−0.013 (2)	−0.0045 (19)	0.020 (2)

Mg1—O1i	2.040 (2)	C2—H2	0.9300
Mg1—O1	2.040 (2)	C3—C4	1.373 (6)
Mg1—O2	2.061 (2)	C3—H3	0.9300
Mg1—O2i	2.061 (2)	C4—C5	1.384 (5)
Mg1—N1i	2.183 (3)	C4—H4	0.9300
Mg1—N1	2.183 (3)	C5—C5i	1.473 (7)
O1—H1A	0.8200	C6—C7	1.494 (4)
O1—H1B	0.8200	C7—C8	1.3900
O2—H2A	0.8201	C7—C12	1.3900
O2—H2B	0.8198	C8—C9	1.3900
O3—C6	1.238 (4)	C8—H8	0.9300
O4—C6	1.263 (4)	C9—C10	1.3900
N1—C1	1.337 (4)	C9—H9	0.9300
N1—C5	1.344 (4)	C10—C11	1.3900
F1—C10	1.317 (3)	C11—C12	1.3900
C1—C2	1.390 (6)	C11—H11	0.9300
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.355 (6)
O1i—Mg1—O1	99.93 (16)	C2—C3—C4	119.3 (4)
O1i—Mg1—O2	91.62 (10)	C2—C3—H3	120.4
O1—Mg1—O2	87.60 (10)	C4—C3—H3	120.4
O1i—Mg1—O2i	87.60 (10)	C3—C4—C5	119.8 (4)
O1—Mg1—O2i	91.62 (10)	C3—C4—H4	120.1
O2—Mg1—O2i	178.78 (17)	C5—C4—H4	120.1
O1i—Mg1—N1i	92.57 (11)	N1—C5—C4	121.1 (3)
O1—Mg1—N1i	167.41 (12)	N1—C5—C5i	115.97 (18)
O2—Mg1—N1i	90.53 (10)	C4—C5—C5i	122.9 (2)
O2i—Mg1—N1i	90.44 (11)	O3—C6—O4	124.4 (3)
O1i—Mg1—N1	167.41 (12)	O3—C6—C7	117.7 (3)
O1—Mg1—N1	92.57 (11)	O4—C6—C7	117.9 (3)
O2—Mg1—N1	90.44 (11)	C8—C7—C12	120.0
O2i—Mg1—N1	90.53 (10)	C8—C7—C6	119.6 (2)
N1i—Mg1—N1	74.99 (15)	C12—C7—C6	120.4 (2)
Mg1—O1—H1A	124.2	C7—C8—C9	120.0
Mg1—O1—H1B	121.4	C7—C8—H8	120.0
H1A—O1—H1B	104.3	C9—C8—H8	120.0
Mg1—O2—H2A	118.7	C8—C9—C10	120.0
Mg1—O2—H2B	110.7	C8—C9—H9	120.0
H2A—O2—H2B	126.6	C10—C9—H9	120.0
C1—N1—C5	118.6 (3)	F1—C10—C11	120.4 (3)
C1—N1—Mg1	124.9 (2)	F1—C10—C9	119.6 (3)
C5—N1—Mg1	116.2 (2)	C11—C10—C9	120.0
N1—C1—C2	122.3 (4)	C10—C11—C12	120.0
N1—C1—H1	118.8	C10—C11—H11	120.0
C2—C1—H1	118.8	C12—C11—H11	120.0
C3—C2—C1	118.9 (4)	C11—C12—C7	120.0
C3—C2—H2	120.5	C11—C12—H12	120.0
C1—C2—H2	120.5	C7—C12—H12	120.0

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4ii	0.82	1.90	2.715 (4)	172
O1—H1B···O4iii	0.82	1.90	2.682 (4)	159
O2—H2A···O3iv	0.82	1.84	2.661 (3)	173
O2—H2B···O4iii	0.82	1.99	2.796 (5)	167
C3—H3···O3v	0.93	2.55	3.257 (6)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4i	0.82	1.90	2.715 (4)	172
O1—H1B⋯O4ii	0.82	1.90	2.682 (4)	159
O2—H2A⋯O3iii	0.82	1.84	2.661 (3)	173
O2—H2B⋯O4ii	0.82	1.99	2.796 (5)	167
C3—H3⋯O3iv	0.93	2.55	3.257 (6)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .