Diaqua­bis­[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxyl­ato]magnesium(II) hexa­hydrate

Wen, J.-F.; Yin, W.-Z.; Qiao, Y.-X.

doi:10.1107/S1600536810039437

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1388

https://doi.org/10.1107/S1600536810039437

Open

access

Diaquabis[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylato]magnesium(II) hexahydrate

Ji-Feng Wen,^a Wen-Zhe Yin ^a ^* and Ya-Xian Qiao ^b

^aThe Second Affiliated Hospital, Harbin Medical University, Harbin, 150086, People's Republic of China, and ^bScientific and Technical Department, Harbin Medical University, Harbin, 150086, People's Republic of China
^*Correspondence e-mail: yinwenzhe@126.com

(Received 11 September 2010; accepted 1 October 2010; online 13 October 2010)

In the title compound, [Mg(C₁₆H₁₇FN₃O₃)₂(H₂O)₂]·6H₂O, the Mg²⁺ ion (site symmetry $[\overline{1}]$ ) exhibits a distorted MgO₆ octahedral geometry defined by two O,O-bidentate 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline-carboxylate (norf) anions and two water molecules. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds help to establish the packing.

Related literature

For the cadmium, zinc and cobalt(II) complexes of the norf anion, see: Chen et al. (2001 ), Wang et al. (2004 ) and An et al. (2007 ), respectively. For background to the medicinal uses of Norfloxacin [H-norf or 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid], which is used to treat infections, see: Mizuki et al. (1996 ).

Experimental

Crystal data

[Mg(C₁₆H₁₇FN₃O₃)₂(H₂O)₂]·6H₂O
M_r = 805.09
Triclinic, $[P \overline 1]$
a = 5.0944 (10) Å
b = 13.785 (3) Å
c = 14.351 (3) Å
α = 112.06 (3)°
β = 97.59 (3)°
γ = 93.74 (3)°
V = 918.6 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 295 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.984, T_max = 0.989
7196 measured reflections
3203 independent reflections
1774 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.249
S = 1.00
3203 reflections
278 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Selected bond lengths (Å)

Mg1—O2	2.001 (3)
Mg1—O1	2.085 (3)
Mg1—O1W	2.094 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2Wⁱ	0.86	2.20	2.787 (7)	126
O1W—H1W⋯O2W	0.82 (1)	1.97 (1)	2.786 (6)	175 (3)
O1W—H2W⋯O1ⁱⁱ	0.82 (2)	2.09 (2)	2.901 (5)	175 (2)
O2W—H3W⋯O3ⁱⁱⁱ	0.82 (5)	1.98 (5)	2.749 (6)	156 (4)
O2W—H4W⋯N1^iv	0.82 (2)	2.36 (4)	3.121 (7)	154 (5)
O3W—H5W⋯O3ⁱⁱⁱ	0.82 (4)	2.18 (4)	2.835 (6)	137 (5)
O3W—H6W⋯O4W	0.81 (15)	2.3 (2)	2.890 (8)	131 (19)
O4W—H8W⋯O3W^v	0.82 (4)	2.31 (4)	2.888 (8)	128 (4)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z; (iv) x-1, y-1, z; (v) x-1, y, z.

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 I, global. DOI: https://doi.org/10.1107/S1600536810039437/hb5638sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039437/hb5638Isup2.hkl

checkCIF report

Comment top

Norfloxacin (H-norf, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl) -3-quinoline carboxylic acid) is member of the class of quinolones that is used to treat infections (Mizuki et al., 1996). Cadmium(II), zinc(II) and cobalt(II) derivatives of norf have been reported (Chen et al., 2001; Wang et al., 2004; An et al.,2007).

The title magnesium(II)-containing complex of norf, (I), is reported here.(Fig. 1).

The structure of (I) is built up from Mg²⁺ cations, norf ligands, coordinated water molecules, uncoordinated water molecules (Fig. 1). The manganese geometry is a slightly distorted octahedron.

The components of (I) are linked by O—H···O and O—H···N hydrogen bonds involving all the potential donors, generating a three-dimensional supramolecular network.

Related literature top

For the cadmium, zinc and cobalt(II) complexes of the norf anion, see: Chen et al. (2001), Wang et al. (2004) and An et al. (2007), respectively. For background to the medicinal uses of Norfloxacin [H-norf or 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid], which is used to treat infections, see: Mizuki et al. (1996).

Experimental top

A mixture of Mg(NO₃)₂.2H₂O (0.5 mmol), H-norf(0.6 mmol), and water (12 ml) was stirred for 30 min in air. The mixture was then transferred to a 25 ml Teflon reactor and kept at 433 K for 72 h under autogenous pressure. Upon cooling, colorless blocks of (I) were obtained from the reaction mixture.

Structure description top

The title magnesium(II)-containing complex of norf, (I), is reported here.(Fig. 1).

The structure of (I) is built up from Mg²⁺ cations, norf ligands, coordinated water molecules, uncoordinated water molecules (Fig. 1). The manganese geometry is a slightly distorted octahedron.

The components of (I) are linked by O—H···O and O—H···N hydrogen bonds involving all the potential donors, generating a three-dimensional supramolecular network.

For the cadmium, zinc and cobalt(II) complexes of the norf anion, see: Chen et al. (2001), Wang et al. (2004) and An et al. (2007), respectively. For background to the medicinal uses of Norfloxacin [H-norf or 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid], which is used to treat infections, see: Mizuki et al. (1996).

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), showing the Mg coordination with 50% displacement ellipsoids. Symmetry code: (i) -x, -y, 1 - z.

Diaquabis[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylato]magnesium(II) hexahydrate top

Crystal data top

[Mg(C₁₆H₁₇FN₃O₃)₂(H₂O)₂]·6H₂O	Z = 1
M_r = 805.09	F(000) = 426
Triclinic, P1	D_x = 1.455 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0944 (10) Å	Cell parameters from 3203 reflections
b = 13.785 (3) Å	θ = 3.1–25.0°
c = 14.351 (3) Å	µ = 0.14 mm⁻¹
α = 112.06 (3)°	T = 295 K
β = 97.59 (3)°	Block, colorless
γ = 93.74 (3)°	0.12 × 0.10 × 0.08 mm
V = 918.6 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	3203 independent reflections
Radiation source: fine-focus sealed tube	1774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
phi and ω scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −5→6
T_min = 0.984, T_max = 0.989	k = −16→15
7196 measured reflections	l = −17→17

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.249	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.130P)² + 1.1685P] where P = (F_o² + 2F_c²)/3
3203 reflections	(Δ/σ)_max < 0.001
278 parameters	Δρ_max = 0.38 e Å⁻³
14 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Mg(C₁₆H₁₇FN₃O₃)₂(H₂O)₂]·6H₂O	γ = 93.74 (3)°
M_r = 805.09	V = 918.6 (3) Å³
Triclinic, P1	Z = 1
a = 5.0944 (10) Å	Mo Kα radiation
b = 13.785 (3) Å	µ = 0.14 mm⁻¹
c = 14.351 (3) Å	T = 295 K
α = 112.06 (3)°	0.12 × 0.10 × 0.08 mm
β = 97.59 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3203 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1774 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.989	R_int = 0.053
7196 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	14 restraints
wR(F²) = 0.249	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.38 e Å⁻³
3203 reflections	Δρ_min = −0.41 e Å⁻³
278 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
C1	0.6643 (11)	1.0494 (5)	0.1860 (4)	0.0542 (15)
H1A	0.8374	1.0250	0.1780	0.065*
H1B	0.5932	1.0600	0.1249	0.065*
C2	0.4804 (10)	0.9679 (4)	0.1990 (4)	0.0434 (12)
H2A	0.3051	0.9910	0.2043	0.052*
H2B	0.4622	0.9021	0.1399	0.052*
C3	0.6286 (11)	1.0513 (4)	0.3807 (4)	0.0485 (13)
H3A	0.7095	1.0396	0.4401	0.058*
H3B	0.4582	1.0765	0.3932	0.058*
C4	0.8076 (12)	1.1339 (4)	0.3651 (5)	0.0563 (15)
H4A	0.8267	1.2000	0.4239	0.068*
H4B	0.9833	1.1117	0.3584	0.068*
C5	0.4638 (9)	0.8637 (3)	0.3026 (3)	0.0347 (11)
C6	0.2314 (9)	0.8028 (4)	0.2407 (4)	0.0379 (11)
H6	0.1484	0.8213	0.1891	0.046*
C7	0.1195 (9)	0.7150 (3)	0.2534 (3)	0.0336 (11)
C8	0.2283 (9)	0.6871 (3)	0.3335 (3)	0.0333 (11)
C9	0.4682 (9)	0.7473 (4)	0.3948 (3)	0.0360 (11)
H9	0.5519	0.7296	0.4469	0.043*
C10	0.5770 (9)	0.8300 (4)	0.3787 (4)	0.0385 (11)
C11	0.1060 (8)	0.6013 (3)	0.3537 (3)	0.0324 (10)
C12	−0.1318 (9)	0.5427 (4)	0.2836 (3)	0.0370 (11)
C13	−0.2237 (10)	0.5729 (4)	0.2062 (4)	0.0390 (12)
H13	−0.3732	0.5321	0.1601	0.047*
C14	−0.2863 (10)	0.4475 (4)	0.2873 (4)	0.0413 (12)
C15	−0.2428 (10)	0.6777 (4)	0.1028 (4)	0.0435 (12)
H15A	−0.2341	0.7535	0.1229	0.052*
H15B	−0.4297	0.6488	0.0853	0.052*
C16	−0.1147 (13)	0.6332 (5)	0.0103 (4)	0.0629 (16)
H16A	0.0675	0.6649	0.0255	0.094*
H16B	−0.2094	0.6480	−0.0444	0.094*
H16C	−0.1201	0.5583	−0.0097	0.094*
F1	0.8150 (5)	0.8827 (2)	0.4368 (2)	0.0517 (8)
Mg1	0.0000	0.5000	0.5000	0.0334 (6)
N1	0.6945 (10)	1.1490 (3)	0.2742 (4)	0.0570 (13)
H1	0.6518	1.2077	0.2725	0.068*
N2	0.5853 (8)	0.9511 (3)	0.2908 (3)	0.0410 (10)
N3	−0.1186 (8)	0.6557 (3)	0.1905 (3)	0.0392 (10)
O1	0.2033 (6)	0.5828 (3)	0.4305 (2)	0.0373 (8)
O2	−0.2364 (6)	0.4254 (3)	0.3645 (2)	0.0440 (9)
O3	−0.4641 (8)	0.3955 (3)	0.2116 (3)	0.0572 (11)
O1W	0.2550 (7)	0.3831 (3)	0.4608 (3)	0.0438 (9)
O2W	0.2443 (8)	0.2500 (3)	0.2582 (3)	0.0632 (12)
O3W	0.5868 (10)	0.2135 (4)	0.0401 (3)	0.0759 (13)
O4W	0.0637 (12)	0.1102 (5)	0.0279 (6)	0.1083 (19)
H3W	0.292 (7)	0.302 (3)	0.247 (5)	0.080*
H7W	0.027 (14)	0.105 (5)	−0.0312 (14)	0.080*
H1W	0.241 (5)	0.3441 (18)	0.4005 (5)	0.080*
H5W	0.660 (10)	0.263 (3)	0.092 (3)	0.080*
H4W	0.0823 (16)	0.237 (4)	0.253 (5)	0.080*
H6W	0.51 (5)	0.166 (11)	0.050 (5)	0.080*
H2W	0.407 (2)	0.3970 (11)	0.4929 (19)	0.08 (2)*
H8W	−0.008 (8)	0.155 (3)	0.069 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.052 (3)	0.070 (4)	0.059 (4)	0.008 (3)	0.013 (3)	0.045 (3)
C2	0.049 (3)	0.044 (3)	0.041 (3)	0.000 (2)	0.006 (2)	0.022 (2)
C3	0.056 (3)	0.042 (3)	0.039 (3)	−0.008 (3)	0.000 (2)	0.011 (2)
C4	0.059 (3)	0.047 (3)	0.059 (4)	−0.009 (3)	−0.006 (3)	0.025 (3)
C5	0.040 (3)	0.034 (2)	0.030 (3)	−0.002 (2)	0.004 (2)	0.015 (2)
C6	0.047 (3)	0.036 (3)	0.034 (3)	0.000 (2)	0.004 (2)	0.018 (2)
C7	0.038 (3)	0.030 (2)	0.030 (3)	−0.002 (2)	0.000 (2)	0.011 (2)
C8	0.036 (2)	0.034 (2)	0.028 (2)	−0.003 (2)	0.0006 (19)	0.012 (2)
C9	0.035 (2)	0.042 (3)	0.032 (3)	−0.001 (2)	0.000 (2)	0.018 (2)
C10	0.041 (3)	0.040 (3)	0.033 (3)	0.000 (2)	0.001 (2)	0.014 (2)
C11	0.031 (2)	0.037 (2)	0.029 (2)	−0.002 (2)	0.0013 (19)	0.015 (2)
C12	0.040 (3)	0.037 (3)	0.033 (3)	−0.004 (2)	−0.001 (2)	0.016 (2)
C13	0.044 (3)	0.039 (3)	0.033 (3)	0.002 (2)	−0.004 (2)	0.017 (2)
C14	0.053 (3)	0.038 (3)	0.030 (3)	−0.006 (2)	−0.001 (2)	0.015 (2)
C15	0.049 (3)	0.048 (3)	0.037 (3)	0.004 (2)	−0.007 (2)	0.024 (2)
C16	0.076 (4)	0.073 (4)	0.045 (3)	0.023 (3)	0.001 (3)	0.030 (3)
F1	0.0444 (16)	0.0568 (18)	0.0516 (19)	−0.0141 (14)	−0.0135 (13)	0.0289 (15)
Mg1	0.0354 (12)	0.0384 (12)	0.0304 (12)	−0.0011 (10)	0.0002 (9)	0.0205 (10)
N1	0.068 (3)	0.041 (3)	0.068 (3)	0.006 (2)	0.007 (3)	0.030 (2)
N2	0.053 (3)	0.039 (2)	0.033 (2)	−0.0024 (19)	0.0064 (19)	0.0177 (19)
N3	0.045 (2)	0.039 (2)	0.035 (2)	−0.0019 (19)	−0.0020 (18)	0.0209 (19)
O1	0.0381 (17)	0.0481 (19)	0.0322 (18)	0.0006 (15)	0.0023 (14)	0.0247 (15)
O2	0.0458 (19)	0.049 (2)	0.038 (2)	−0.0101 (16)	−0.0070 (15)	0.0251 (16)
O3	0.072 (3)	0.051 (2)	0.042 (2)	−0.020 (2)	−0.0172 (19)	0.0236 (18)
O1W	0.042 (2)	0.048 (2)	0.044 (2)	0.0087 (17)	0.0063 (16)	0.0205 (17)
O2W	0.056 (2)	0.059 (3)	0.075 (3)	−0.011 (2)	0.010 (2)	0.030 (2)
O3W	0.089 (3)	0.071 (3)	0.057 (3)	0.015 (3)	0.009 (2)	0.013 (2)
O4W	0.093 (4)	0.090 (4)	0.151 (6)	0.023 (3)	0.041 (4)	0.049 (4)

Geometric parameters (Å, º) top

C1—N1	1.458 (8)	C12—C13	1.366 (6)
C1—C2	1.498 (6)	C12—C14	1.508 (6)
C1—H1A	0.9700	C13—N3	1.335 (6)
C1—H1B	0.9700	C13—H13	0.9300
C2—N2	1.461 (6)	C14—O2	1.254 (5)
C2—H2A	0.9700	C14—O3	1.259 (6)
C2—H2B	0.9700	C15—N3	1.476 (6)
C3—N2	1.472 (6)	C15—C16	1.495 (8)
C3—C4	1.512 (7)	C15—H15A	0.9700
C3—H3A	0.9700	C15—H15B	0.9700
C3—H3B	0.9700	C16—H16A	0.9600
C4—N1	1.449 (7)	C16—H16B	0.9600
C4—H4A	0.9700	C16—H16C	0.9600
C4—H4B	0.9700	Mg1—O2ⁱ	2.001 (3)
C5—C6	1.389 (6)	Mg1—O2	2.001 (3)
C5—N2	1.394 (5)	Mg1—O1ⁱ	2.085 (3)
C5—C10	1.412 (6)	Mg1—O1	2.085 (3)
C6—C7	1.388 (6)	Mg1—O1Wⁱ	2.094 (3)
C6—H6	0.9300	Mg1—O1W	2.094 (3)
C7—C8	1.403 (6)	N1—H1	0.8600
C7—N3	1.408 (6)	O1W—H1W	0.820 (10)
C8—C9	1.411 (6)	O1W—H2W	0.818 (17)
C8—C11	1.443 (6)	O2W—H3W	0.82 (5)
C9—C10	1.345 (6)	O2W—H4W	0.821 (16)
C9—H9	0.9300	O3W—H5W	0.82 (4)
C10—F1	1.362 (5)	O3W—H6W	0.81 (15)
C11—O1	1.268 (5)	O4W—H8W	0.82 (4)
C11—C12	1.439 (6)	O4W—H7W	0.82 (3)

N1—C1—C2	110.5 (4)	N3—C13—C12	126.0 (4)
N1—C1—H1A	109.5	N3—C13—H13	117.0
C2—C1—H1A	109.5	C12—C13—H13	117.0
N1—C1—H1B	109.5	O2—C14—O3	123.8 (4)
C2—C1—H1B	109.5	O2—C14—C12	119.4 (4)
H1A—C1—H1B	108.1	O3—C14—C12	116.7 (4)
N2—C2—C1	110.1 (4)	N3—C15—C16	113.9 (4)
N2—C2—H2A	109.6	N3—C15—H15A	108.8
C1—C2—H2A	109.6	C16—C15—H15A	108.8
N2—C2—H2B	109.6	N3—C15—H15B	108.8
C1—C2—H2B	109.6	C16—C15—H15B	108.8
H2A—C2—H2B	108.1	H15A—C15—H15B	107.7
N2—C3—C4	111.2 (4)	C15—C16—H16A	109.5
N2—C3—H3A	109.4	C15—C16—H16B	109.5
C4—C3—H3A	109.4	H16A—C16—H16B	109.5
N2—C3—H3B	109.4	C15—C16—H16C	109.5
C4—C3—H3B	109.4	H16A—C16—H16C	109.5
H3A—C3—H3B	108.0	H16B—C16—H16C	109.5
N1—C4—C3	110.0 (4)	O2ⁱ—Mg1—O2	180.0
N1—C4—H4A	109.7	O2ⁱ—Mg1—O1ⁱ	86.80 (12)
C3—C4—H4A	109.7	O2—Mg1—O1ⁱ	93.20 (13)
N1—C4—H4B	109.7	O2ⁱ—Mg1—O1	93.20 (13)
C3—C4—H4B	109.7	O2—Mg1—O1	86.80 (12)
H4A—C4—H4B	108.2	O1ⁱ—Mg1—O1	180.0
C6—C5—N2	123.6 (4)	O2ⁱ—Mg1—O1Wⁱ	90.04 (15)
C6—C5—C10	115.4 (4)	O2—Mg1—O1Wⁱ	89.96 (15)
N2—C5—C10	121.0 (4)	O1ⁱ—Mg1—O1Wⁱ	90.47 (13)
C5—C6—C7	122.0 (4)	O1—Mg1—O1Wⁱ	89.53 (13)
C5—C6—H6	119.0	O2ⁱ—Mg1—O1W	89.96 (15)
C7—C6—H6	119.0	O2—Mg1—O1W	90.04 (14)
C6—C7—C8	121.3 (4)	O1ⁱ—Mg1—O1W	89.53 (13)
C6—C7—N3	120.7 (4)	O1—Mg1—O1W	90.47 (13)
C8—C7—N3	117.9 (4)	O1Wⁱ—Mg1—O1W	180.0
C7—C8—C9	116.7 (4)	C4—N1—C1	109.6 (4)
C7—C8—C11	122.8 (4)	C4—N1—H1	125.2
C9—C8—C11	120.5 (4)	C1—N1—H1	125.2
C10—C9—C8	120.6 (4)	C5—N2—C2	116.5 (4)
C10—C9—H9	119.7	C5—N2—C3	116.4 (4)
C8—C9—H9	119.7	C2—N2—C3	110.4 (4)
C9—C10—F1	118.5 (4)	C13—N3—C7	119.1 (4)
C9—C10—C5	123.9 (4)	C13—N3—C15	119.2 (4)
F1—C10—C5	117.6 (4)	C7—N3—C15	121.4 (4)
O1—C11—C12	123.8 (4)	C11—O1—Mg1	125.9 (3)
O1—C11—C8	120.5 (4)	C14—O2—Mg1	132.8 (3)
C12—C11—C8	115.6 (4)	H1W—O1W—H2W	115 (2)
C13—C12—C11	118.4 (4)	H3W—O2W—H4W	115 (5)
C13—C12—C14	116.7 (4)	H5W—O3W—H6W	115 (7)
C11—C12—C14	124.9 (4)	H8W—O4W—H7W	115 (6)

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
N1—H1···O2Wⁱⁱ	0.86	2.20	2.787 (7)	126
O1W—H1W···O2W	0.82 (1)	1.97 (1)	2.786 (6)	175 (3)
O1W—H2W···O1ⁱⁱⁱ	0.82 (2)	2.09 (2)	2.901 (5)	175 (2)
O2W—H3W···O3^iv	0.82 (5)	1.98 (5)	2.749 (6)	156 (4)
O2W—H4W···N1^v	0.82 (2)	2.36 (4)	3.121 (7)	154 (5)
O3W—H5W···O3^iv	0.82 (4)	2.18 (4)	2.835 (6)	137 (5)
O3W—H6W···O4W	0.81 (15)	2.3 (2)	2.890 (8)	131 (19)
O4W—H8W···O3W^vi	0.82 (4)	2.31 (4)	2.888 (8)	128 (4)

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

Experimental details

Crystal data
Chemical formula	[Mg(C₁₆H₁₇FN₃O₃)₂(H₂O)₂]·6H₂O
M_r	805.09
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	5.0944 (10), 13.785 (3), 14.351 (3)
α, β, γ (°)	112.06 (3), 97.59 (3), 93.74 (3)
V (Å³)	918.6 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.984, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	7196, 3203, 1774
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.249, 1.00
No. of reflections	3203
No. of parameters	278
No. of restraints	14
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.41

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

Selected bond lengths (Å) top

Mg1—O2	2.001 (3)	Mg1—O1W	2.094 (3)
Mg1—O1	2.085 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2Wⁱ	0.86	2.20	2.787 (7)	126
O1W—H1W···O2W	0.820 (10)	1.969 (11)	2.786 (6)	175 (3)
O1W—H2W···O1ⁱⁱ	0.818 (17)	2.085 (16)	2.901 (5)	175 (2)
O2W—H3W···O3ⁱⁱⁱ	0.82 (5)	1.98 (5)	2.749 (6)	156 (4)
O2W—H4W···N1^iv	0.821 (16)	2.36 (4)	3.121 (7)	154 (5)
O3W—H5W···O3ⁱⁱⁱ	0.82 (4)	2.18 (4)	2.835 (6)	137 (5)
O3W—H6W···O4W	0.81 (15)	2.3 (2)	2.890 (8)	131 (19)
O4W—H8W···O3W^v	0.82 (4)	2.31 (4)	2.888 (8)	128 (4)

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

Acknowledgements

The authors acknowledge financial support by Harbin Medical University.

References

An, Z., Xu, W. & Wang, R.-S. (2007). Acta Cryst. E63, m507–m508. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-F., Xiong, R.-G., Zhang, J., Chen, X.-T., Xue, Z.-L. & You, X.-Z. (2001). Inorg. Chem. 40, 4075–4077. Web of Science CSD CrossRef PubMed CAS Google Scholar
Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 Suppl. A, 41–55. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y.-C., Zhao, H., Ye, Q., Chen, Z.-F., Xiong, R.-G. & Fun, H.-K. (2004). Inorg. Chim. Acta. 357, 4303–4308. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1388

https://doi.org/10.1107/S1600536810039437

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Di­aqua­bis­­[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-di­hydro­quinoline-3-carboxyl­ato]magnesium(II) hexa­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Diaquabis[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylato]magnesium(II) hexahydrate