Diaqua-bis-[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxyl-ato]magnesium(II) hexa-hydrate.

In the title compound, [Mg(C(16)H(17)FN(3)O(3))(2)(H(2)O)(2)]·6H(2)O, the Mg(2+) ion (site symmetry ) exhibits a distorted MgO(6) octa-hedral geometry defined by two O,O-bidentate 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazin-yl)-3-quinoline-carb-oxyl-ate (norf) anions and two water mol-ecules. 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 = 805.09

Triclinic,

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[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.249

S = 1.00

3203 reflections

278 parameters

14 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.41 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039437/hb5638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039437/hb5638Isup2.hkl

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

[Mg(C16H17FN3O3)2(H2O)2]·6H2O	Z = 1
Mr = 805.09	F(000) = 426
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.130P)2 + 1.1685P] where P = (Fo2 + 2Fc2)/3
3203 reflections	(Δ/σ)max < 0.001
278 parameters	Δρmax = 0.38 e Å−3
14 restraints	Δρmin = −0.41 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O3iv	0.82 (5)	1.98 (5)	2.749 (6)	156 (4)
O2W—H4W···N1v	0.82 (2)	2.36 (4)	3.121 (7)	154 (5)
O3W—H5W···O3iv	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···O3Wvi	0.82 (4)	2.31 (4)	2.888 (8)	128 (4)

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⋯N1iv	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⋯O3Wv	0.82 (4)	2.31 (4)	2.888 (8)	128 (4)

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