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Acta Cryst. (2007). E63, m2084-m2085    [ doi:10.1107/S1600536807032072 ]

Diaquabis[1-ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato-[kappa]2O3,O4]manganese(II) benzene-1,4-dicarboxylate tetradecahydrate

Z. An, W. Qi and J. Huang

Abstract top

In the title compound, [Mn(C17H20FN3O3)2(H2O)2](C8H4O4).14H2O, the MnII atom (site symmetry \overline{1}) exhibits a distorted MnO6 octahedral geometry defined by two neutral bidentate O,O-bonded 1-ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (Hpef) zwitterions and two water molecules. The charge-balancing benzene-1,4-dicarboxylate (1,4-bdc) anion is also centrosymmetric. An extensive network of O-H...O and O-H...N hydrogen bonds helps to establish the crystal packing.

Comment top

Pefloxacin (Hpef, C17H20FN3O3, 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The silver(I) derivative of the pefloxacin (pef) anion has been reported (Baenziger et al., 1986). The title manganese(II)-containing complex of Hper, (I), is reported here.

The structure of (I) is built up from Mn2+ cations (site symmetry 1) neutral Hpef ligands in their zwittrionic form (i.e. nominal proton transfer from the carboxylic acid group to a piperizine H atom), coordinated water molecules, a centrosymmetric 1,4-bdc anion and uncoordinated water molecules (Fig. 1). The manganese geometry is a slightly distorted octahedron (Table 1).

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 (Table 2).

Related literature top

For the silver and cobalt complexes of the pef anion, see: Baenziger et al. (1986); An et al. (2007). For background literature on the medicinal uses of Hpef, see: Mizuki et al. (1996).

Experimental top

A mixture of Mn(CH3COO)2.4H2O (0.061 g, 0.25 mmol), Hpef (0.17 g, 0.5 mmol), 1,4-benzenedicarboxylic acid (1,4-bdc, 0.04 g, 0.25 mmol) and water (12 ml) was stirred for 30 min in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 433 K for 72 h under autogenous pressure. Upon cooling, colorless prisms of (I) were obtained from the reaction mixture.

Refinement top

The carbon-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The H atoms on the N and water molecules were located in a difference map and refined with a distance restraint of N—H = 0.90 (1) Å, O—H = 0.85 (1) Å,and the constraint Uiso(H) = 1.5Ueq(N,O).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), show the Mn coordination, showing 50% displacement ellipsoids.(The uncoordinated water molecules are omitted for clarity). Symmetry code: (i) -x, -y, 1 - z. Yhe unlabelled atoms of the 1,4-bdc dianion are generated by the symmetry operation (1 - x, 1 - y, 2 - z).
Diaquabis[1-ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl)-4-oxo-1,4- dihydroquinoline-3-carboxylato-κ2O3,O4]manganese(II) benzene-1,4-dicarboxylate tetradecahydrate top
Crystal data top
[Mn(C17H20FN3O3)2(H2O)2](C8H4O4)·14H2OZ = 1
Mr = 1174.03F(000) = 621
Triclinic, P1Dx = 1.426 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.147 (3) ÅCell parameters from 10985 reflections
b = 11.500 (3) Åθ = 2.5–26.0°
c = 11.832 (3) ŵ = 0.34 mm−1
α = 111.722 (4)°T = 295 K
β = 92.011 (4)°Prism, colorless
γ = 102.066 (4)°0.34 × 0.26 × 0.18 mm
V = 1367.3 (6) Å3
Data collection top
Bruker SMART CCD
diffractometer		5353 independent reflections
Radiation source: fine-focus sealed tube4645 reflections with I > 2σ(I)
graphiteRint = 0.013
ω scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.894, Tmax = 0.942k = −13→14
11720 measured reflectionsl = −14→14
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)] = 0.036Hydrogen site location: difmap and geom
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.048P)2 + 0.5532P]
where P = (Fo2 + 2Fc2)/3
5353 reflections(Δ/σ)max < 0.001
402 parametersΔρmax = 0.38 e Å−3
25 restraintsΔρmin = −0.35 e Å−3
Crystal data top
[Mn(C17H20FN3O3)2(H2O)2](C8H4O4)·14H2Oγ = 102.066 (4)°
Mr = 1174.03V = 1367.3 (6) Å3
Triclinic, P1Z = 1
a = 11.147 (3) ÅMo Kα radiation
b = 11.500 (3) ŵ = 0.34 mm−1
c = 11.832 (3) ÅT = 295 K
α = 111.722 (4)°0.34 × 0.26 × 0.18 mm
β = 92.011 (4)°
Data collection top
Bruker SMART CCD
diffractometer		5353 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4645 reflections with I > 2σ(I)
Tmin = 0.894, Tmax = 0.942Rint = 0.013
11720 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098Δρmax = 0.38 e Å−3
S = 1.03Δρmin = −0.35 e Å−3
5353 reflectionsAbsolute structure: ?
402 parametersFlack parameter: ?
25 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.00000.00000.50000.03248 (11)
F10.46666 (10)0.53125 (9)0.63639 (11)0.0466 (3)
O10.08828 (11)−0.14497 (11)0.51391 (13)0.0442 (3)
O1W0.0623 (2)0.60894 (17)0.6358 (2)0.0861 (7)
O20.22468 (12)−0.23558 (13)0.56627 (17)0.0632 (5)
O2W0.14371 (15)0.64240 (17)0.92704 (17)0.0661 (4)
O30.18601 (10)0.10280 (11)0.51526 (11)0.0370 (3)
O3W0.28264 (18)0.06305 (16)0.96455 (16)0.0685 (5)
O40.01341 (12)0.08480 (13)0.70334 (12)0.0460 (3)
O4W0.54654 (17)0.79875 (16)0.82458 (17)0.0690 (5)
O50.23622 (11)0.22196 (11)0.84581 (12)0.0427 (3)
O5W0.30062 (16)0.81047 (17)0.83005 (15)0.0673 (4)
O60.18210 (11)0.39621 (12)0.84330 (13)0.0475 (3)
O6W0.91289 (15)0.29089 (17)0.83310 (16)0.0660 (4)
O7W0.91049 (14)0.62388 (13)0.39048 (14)0.0551 (4)
N10.51219 (12)0.07432 (13)0.66259 (13)0.0324 (3)
N20.69176 (12)0.52516 (14)0.72389 (13)0.0353 (3)
N30.91188 (13)0.72584 (14)0.77586 (14)0.0364 (3)
C10.19619 (15)−0.14347 (15)0.55046 (16)0.0339 (4)
C20.29724 (14)−0.02282 (15)0.58101 (15)0.0300 (3)
C30.28289 (14)0.09020 (15)0.56370 (14)0.0283 (3)
C40.39132 (14)0.19783 (15)0.60438 (14)0.0278 (3)
C50.38087 (14)0.31463 (15)0.59749 (15)0.0314 (3)
H5A0.30630.32210.56640.038*
C60.48032 (15)0.41633 (15)0.63654 (15)0.0332 (4)
C70.59673 (14)0.41172 (16)0.68282 (14)0.0315 (3)
C80.60684 (14)0.29760 (16)0.69184 (15)0.0321 (3)
H8A0.68190.29140.72320.039*
C90.50454 (14)0.19059 (15)0.65399 (14)0.0288 (3)
C100.41142 (15)−0.02378 (16)0.62819 (15)0.0329 (4)
H10A0.4194−0.09900.63700.039*
C110.62620 (16)0.05826 (17)0.71744 (17)0.0382 (4)
H11A0.69770.10310.69290.046*
H11B0.6262−0.03250.68640.046*
C120.6364 (2)0.1097 (2)0.85510 (18)0.0512 (5)
H12A0.64130.20060.88650.077*
H12B0.70950.09450.88690.077*
H12C0.56500.06680.87980.077*
C130.79810 (16)0.53132 (17)0.80351 (17)0.0380 (4)
H13A0.85150.48070.75530.046*
H13B0.77050.49640.86380.046*
C140.86825 (16)0.67091 (17)0.86713 (16)0.0391 (4)
H14A0.81490.72050.91660.047*
H14B0.93860.67670.92120.047*
C150.80610 (17)0.71083 (18)0.68622 (18)0.0432 (4)
H15A0.83710.73960.62310.052*
H15B0.75150.76390.72790.052*
C160.73510 (17)0.57148 (18)0.62816 (17)0.0434 (4)
H16A0.66480.56330.57270.052*
H16B0.78790.51920.58110.052*
C170.9810 (2)0.86274 (19)0.8371 (2)0.0587 (6)
H17A0.92720.91310.88260.088*
H17B1.01050.89470.77630.088*
H17C1.04980.86900.89180.088*
C180.25857 (15)0.34060 (16)0.86950 (s15)0.0335 (4)
C190.38438 (14)0.42305 (15)0.93586 (14)0.0311 (3)
C200.46415 (16)0.37370 (17)0.98691 (18)0.0426 (4)
H20A0.44120.28800.97830.051*
C210.57784 (16)0.44940 (17)1.05081 (19)0.0434 (4)
H21A0.62950.41411.08520.052*
H1W10.1161 (17)0.6498 (18)0.607 (2)0.065*
H1W20.076 (2)0.5375 (13)0.629 (2)0.065*
H2W10.161 (2)0.5696 (12)0.907 (2)0.065*
H3W10.271 (2)0.1053 (18)0.9211 (17)0.065*
H4W10.550 (2)0.7200 (10)0.7995 (19)0.065*
H5W10.2664 (17)0.787 (2)0.7574 (12)0.065*
H2W20.1932 (19)0.6898 (17)0.900 (2)0.065*
H5W20.3756 (10)0.805 (2)0.8276 (19)0.065*
H4W20.591 (2)0.8406 (17)0.8935 (13)0.065*
H3W20.303 (2)−0.0048 (15)0.9206 (18)0.065*
H1O0.0850 (10)0.1230 (19)0.7420 (19)0.065*
H3N0.9643 (18)0.682 (2)0.7304 (19)0.065*
H2O−0.0366 (15)0.1318 (19)0.734 (2)0.065*
H7W10.887 (2)0.624 (2)0.3214 (12)0.065*
H7W20.9690 (16)0.6912 (16)0.4274 (17)0.065*
H6W10.8902 (18)0.311 (2)0.9050 (12)0.065*
H6W20.9887 (11)0.330 (2)0.8411 (19)0.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.02475 (18)0.02569 (18)0.0422 (2)−0.00318 (13)−0.00723 (14)0.01368 (15)
F10.0427 (6)0.0294 (5)0.0652 (7)−0.0028 (4)−0.0135 (5)0.0234 (5)
O10.0340 (6)0.0271 (6)0.0653 (9)−0.0040 (5)−0.0115 (6)0.0185 (6)
O1W0.1294 (17)0.0606 (11)0.1088 (15)0.0548 (11)0.0819 (13)0.0552 (11)
O20.0359 (7)0.0407 (8)0.1243 (14)0.0035 (6)0.0029 (8)0.0481 (9)
O2W0.0527 (9)0.0580 (10)0.0800 (12)0.0161 (8)0.0081 (8)0.0166 (9)
O30.0257 (6)0.0328 (6)0.0523 (7)−0.0024 (5)−0.0070 (5)0.0225 (6)
O3W0.0795 (11)0.0500 (9)0.0772 (12)0.0130 (8)−0.0082 (9)0.0290 (8)
O40.0378 (7)0.0445 (7)0.0446 (8)0.0001 (6)−0.0074 (6)0.0110 (6)
O4W0.0744 (11)0.0449 (9)0.0718 (11)0.0043 (8)−0.0024 (9)0.0109 (8)
O50.0393 (7)0.0338 (6)0.0463 (7)−0.0006 (5)−0.0086 (5)0.0122 (6)
O5W0.0653 (10)0.0660 (10)0.0599 (10)0.0114 (9)−0.0115 (8)0.0163 (8)
O60.0359 (7)0.0423 (7)0.0594 (8)0.0026 (5)−0.0121 (6)0.0195 (6)
O6W0.0509 (9)0.0728 (11)0.0716 (11)0.0146 (8)0.0112 (8)0.0246 (9)
O7W0.0614 (9)0.0354 (7)0.0620 (9)−0.0024 (6)−0.0176 (7)0.0213 (7)
N10.0278 (7)0.0320 (7)0.0379 (8)0.0044 (5)0.0000 (5)0.0158 (6)
N20.0293 (7)0.0371 (8)0.0362 (8)−0.0074 (6)−0.0069 (6)0.0198 (6)
N30.0276 (7)0.0309 (7)0.0444 (8)−0.0012 (6)0.0038 (6)0.0120 (6)
C10.0309 (8)0.0268 (8)0.0438 (10)0.0025 (6)0.0042 (7)0.0157 (7)
C20.0276 (8)0.0276 (8)0.0328 (8)0.0016 (6)0.0027 (6)0.0121 (7)
C30.0261 (7)0.0276 (8)0.0293 (8)0.0006 (6)0.0021 (6)0.0120 (6)
C40.0251 (7)0.0277 (8)0.0288 (8)0.0010 (6)0.0006 (6)0.0120 (6)
C50.0265 (8)0.0323 (8)0.0342 (8)0.0008 (6)−0.0040 (6)0.0157 (7)
C60.0357 (9)0.0270 (8)0.0363 (9)0.0003 (7)−0.0027 (7)0.0160 (7)
C70.0282 (8)0.0325 (8)0.0300 (8)−0.0033 (6)−0.0011 (6)0.0138 (7)
C80.0240 (7)0.0366 (9)0.0342 (8)0.0009 (6)−0.0008 (6)0.0158 (7)
C90.0273 (8)0.0296 (8)0.0292 (8)0.0021 (6)0.0019 (6)0.0137 (6)
C100.0322 (8)0.0297 (8)0.0388 (9)0.0051 (7)0.0038 (7)0.0168 (7)
C110.0314 (8)0.0373 (9)0.0473 (10)0.0084 (7)−0.0021 (7)0.0187 (8)
C120.0513 (11)0.0531 (12)0.0483 (11)0.0085 (9)−0.0065 (9)0.0220 (10)
C130.0311 (8)0.0408 (9)0.0410 (10)−0.0034 (7)−0.0049 (7)0.0218 (8)
C140.0310 (8)0.0426 (10)0.0376 (9)−0.0021 (7)−0.0031 (7)0.0153 (8)
C150.0372 (9)0.0433 (10)0.0513 (11)−0.0016 (8)−0.0008 (8)0.0272 (9)
C160.0411 (10)0.0461 (10)0.0386 (10)−0.0087 (8)−0.0050 (8)0.0227 (8)
C170.0507 (12)0.0362 (10)0.0724 (15)−0.0085 (9)−0.0010 (10)0.0129 (10)
C180.0311 (8)0.0363 (9)0.0295 (8)0.0024 (7)0.0008 (6)0.0118 (7)
C190.0279 (8)0.0331 (8)0.0289 (8)0.0036 (6)0.0020 (6)0.0103 (7)
C200.0350 (9)0.0318 (9)0.0586 (12)0.0017 (7)−0.0048 (8)0.0193 (8)
C210.0328 (9)0.0392 (10)0.0603 (12)0.0035 (7)−0.0081 (8)0.0253 (9)
Geometric parameters (Å, °) top
Mn1—O32.1261 (12)C2—C101.376 (2)
Mn1—O3i2.1261 (12)C2—C31.428 (2)
Mn1—O12.1569 (13)C3—C41.455 (2)
Mn1—O1i2.1569 (13)C4—C51.404 (2)
Mn1—O4i2.2223 (15)C4—C91.404 (2)
Mn1—O42.2223 (15)C5—C61.354 (2)
F1—C61.3621 (19)C5—H5A0.9300
O1—C11.258 (2)C6—C71.410 (2)
O1W—H1W10.841 (9)C7—C81.382 (2)
O1W—H1W20.840 (9)C8—C91.409 (2)
O2—C11.241 (2)C8—H8A0.9300
O2W—H2W10.846 (9)C10—H10A0.9300
O2W—H2W20.849 (9)C11—C121.504 (3)
O3—C31.2646 (19)C11—H11A0.9700
O3W—H3W10.851 (9)C11—H11B0.9700
O3W—H3W20.843 (9)C12—H12A0.9600
O4—H1O0.848 (9)C12—H12B0.9600
O4—H2O0.853 (9)C12—H12C0.9600
O4W—H4W10.853 (9)C13—C141.515 (2)
O4W—H4W20.849 (9)C13—H13A0.9700
O5—C181.254 (2)C13—H13B0.9700
O5W—H5W10.848 (9)C14—H14A0.9700
O5W—H5W20.852 (9)C14—H14B0.9700
O6—C181.260 (2)C15—C161.511 (2)
O6W—H6W10.857 (9)C15—H15A0.9700
O6W—H6W20.855 (9)C15—H15B0.9700
O7W—H7W10.849 (9)C16—H16A0.9700
O7W—H7W20.857 (9)C16—H16B0.9700
N1—C101.341 (2)C17—H17A0.9600
N1—C91.398 (2)C17—H17B0.9600
N1—C111.483 (2)C17—H17C0.9600
N2—C71.406 (2)C18—C191.516 (2)
N2—C131.461 (2)C19—C201.380 (2)
N2—C161.476 (2)C19—C21ii1.385 (2)
N3—C171.485 (2)C20—C211.386 (2)
N3—C141.488 (2)C20—H20A0.9300
N3—C151.496 (2)C21—C19ii1.385 (2)
N3—H3N0.911 (10)C21—H21A0.9300
C1—C21.507 (2)
O3—Mn1—O3i180.0C9—C8—H8A119.7
O3—Mn1—O182.48 (5)N1—C9—C4117.96 (13)
O3i—Mn1—O197.52 (5)N1—C9—C8121.74 (14)
O3—Mn1—O1i97.52 (5)C4—C9—C8120.29 (14)
O3i—Mn1—O1i82.48 (5)N1—C10—C2125.66 (15)
O1—Mn1—O1i180.0N1—C10—H10A117.2
O3—Mn1—O4i91.74 (5)C2—C10—H10A117.2
O3i—Mn1—O4i88.26 (5)N1—C11—C12111.96 (15)
O1—Mn1—O4i91.32 (5)N1—C11—H11A109.2
O1i—Mn1—O4i88.68 (5)C12—C11—H11A109.2
O3—Mn1—O488.26 (5)N1—C11—H11B109.2
O3i—Mn1—O491.74 (5)C12—C11—H11B109.2
O1—Mn1—O488.68 (5)H11A—C11—H11B107.9
O1i—Mn1—O491.32 (5)C11—C12—H12A109.5
O4i—Mn1—O4180.0C11—C12—H12B109.5
C1—O1—Mn1134.01 (10)H12A—C12—H12B109.5
H1W1—O1W—H1W2112.1 (15)C11—C12—H12C109.5
H2W1—O2W—H2W2109.9 (15)H12A—C12—H12C109.5
C3—O3—Mn1128.61 (10)H12B—C12—H12C109.5
H3W1—O3W—H3W2109.5 (15)N2—C13—C14108.54 (14)
Mn1—O4—H1O116.7 (15)N2—C13—H13A110.0
Mn1—O4—H2O116.2 (16)C14—C13—H13A110.0
H1O—O4—H2O108.8 (14)N2—C13—H13B110.0
H4W1—O4W—H4W2109.3 (14)C14—C13—H13B110.0
H5W1—O5W—H5W2108.8 (14)H13A—C13—H13B108.4
H6W1—O6W—H6W2107.5 (14)N3—C14—C13110.71 (14)
H7W1—O7W—H7W2108.5 (14)N3—C14—H14A109.5
C10—N1—C9119.52 (14)C13—C14—H14A109.5
C10—N1—C11118.21 (14)N3—C14—H14B109.5
C9—N1—C11122.10 (13)C13—C14—H14B109.5
C7—N2—C13117.36 (13)H14A—C14—H14B108.1
C7—N2—C16115.44 (13)N3—C15—C16110.30 (15)
C13—N2—C16109.53 (13)N3—C15—H15A109.6
C17—N3—C14111.28 (15)C16—C15—H15A109.6
C17—N3—C15111.36 (15)N3—C15—H15B109.6
C14—N3—C15110.75 (13)C16—C15—H15B109.6
C17—N3—H3N107.0 (15)H15A—C15—H15B108.1
C14—N3—H3N110.6 (15)N2—C16—C15110.04 (15)
C15—N3—H3N105.7 (15)N2—C16—H16A109.7
O2—C1—O1123.65 (15)C15—C16—H16A109.7
O2—C1—C2117.11 (15)N2—C16—H16B109.7
O1—C1—C2119.21 (14)C15—C16—H16B109.7
C10—C2—C3118.45 (14)H16A—C16—H16B108.2
C10—C2—C1116.66 (14)N3—C17—H17A109.5
C3—C2—C1124.89 (14)N3—C17—H17B109.5
O3—C3—C2125.65 (14)H17A—C17—H17B109.5
O3—C3—C4118.56 (14)N3—C17—H17C109.5
C2—C3—C4115.78 (14)H17A—C17—H17C109.5
C5—C4—C9118.85 (14)H17B—C17—H17C109.5
C5—C4—C3118.57 (14)O5—C18—O6124.04 (15)
C9—C4—C3122.54 (14)O5—C18—C19118.20 (15)
C6—C5—C4119.38 (15)O6—C18—C19117.75 (15)
C6—C5—H5A120.3C20—C19—C21ii117.87 (15)
C4—C5—H5A120.3C20—C19—C18120.83 (15)
C5—C6—F1118.66 (15)C21ii—C19—C18121.29 (15)
C5—C6—C7123.54 (15)C19—C20—C21121.25 (16)
F1—C6—C7117.73 (14)C19—C20—H20A119.4
C8—C7—N2124.55 (15)C21—C20—H20A119.4
C8—C7—C6117.26 (14)C19ii—C21—C20120.88 (17)
N2—C7—C6118.06 (15)C19ii—C21—H21A119.6
C7—C8—C9120.62 (15)C20—C21—H21A119.6
C7—C8—H8A119.7
O3—Mn1—O1—C117.92 (17)F1—C6—C7—N2−1.0 (2)
O3i—Mn1—O1—C1−162.08 (17)N2—C7—C8—C9176.65 (15)
O1i—Mn1—O1—C122 (19)C6—C7—C8—C91.0 (2)
O4i—Mn1—O1—C1109.51 (17)C10—N1—C9—C4−2.6 (2)
O4—Mn1—O1—C1−70.49 (17)C11—N1—C9—C4−177.88 (14)
O3i—Mn1—O3—C3149 (31)C10—N1—C9—C8178.36 (15)
O1—Mn1—O3—C3−24.78 (14)C11—N1—C9—C83.0 (2)
O1i—Mn1—O3—C3155.22 (14)C5—C4—C9—N1178.58 (14)
O4i—Mn1—O3—C3−115.88 (14)C3—C4—C9—N10.8 (2)
O4—Mn1—O3—C364.12 (14)C5—C4—C9—C8−2.3 (2)
Mn1—O1—C1—O2169.97 (15)C3—C4—C9—C8179.90 (15)
Mn1—O1—C1—C2−8.1 (3)C7—C8—C9—N1−179.75 (15)
O2—C1—C2—C10−2.4 (2)C7—C8—C9—C41.2 (2)
O1—C1—C2—C10175.82 (16)C9—N1—C10—C21.5 (3)
O2—C1—C2—C3177.16 (17)C11—N1—C10—C2177.01 (16)
O1—C1—C2—C3−4.7 (3)C3—C2—C10—N11.5 (3)
Mn1—O3—C3—C223.6 (2)C1—C2—C10—N1−178.98 (16)
Mn1—O3—C3—C4−157.54 (11)C10—N1—C11—C12−93.51 (19)
C10—C2—C3—O3175.89 (16)C9—N1—C11—C1281.9 (2)
C1—C2—C3—O3−3.6 (3)C7—N2—C13—C14−162.98 (15)
C10—C2—C3—C4−3.0 (2)C16—N2—C13—C1462.85 (19)
C1—C2—C3—C4177.45 (15)C17—N3—C14—C13−179.95 (16)
O3—C3—C4—C55.2 (2)C15—N3—C14—C1355.6 (2)
C2—C3—C4—C5−175.80 (14)N2—C13—C14—N3−59.88 (19)
O3—C3—C4—C9−177.03 (15)C17—N3—C15—C16−178.28 (16)
C2—C3—C4—C92.0 (2)C14—N3—C15—C16−53.9 (2)
C9—C4—C5—C61.2 (2)C7—N2—C16—C15162.65 (15)
C3—C4—C5—C6179.08 (15)C13—N2—C16—C15−62.2 (2)
C4—C5—C6—F1−175.97 (14)N3—C15—C16—N257.0 (2)
C4—C5—C6—C71.1 (3)O5—C18—C19—C20−10.7 (2)
C13—N2—C7—C8−13.3 (2)O6—C18—C19—C20168.18 (17)
C16—N2—C7—C8118.21 (19)O5—C18—C19—C21ii170.47 (17)
C13—N2—C7—C6162.27 (16)O6—C18—C19—C21ii−10.7 (2)
C16—N2—C7—C6−66.2 (2)C21ii—C19—C20—C210.8 (3)
C5—C6—C7—C8−2.2 (3)C18—C19—C20—C21−178.11 (17)
F1—C6—C7—C8174.87 (15)C19—C20—C21—C19ii−0.8 (3)
C5—C6—C7—N2−178.13 (16)
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y+1, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H1O···O50.85 (1)1.91 (1)2.7565 (18)173 (2)
N3—H3N···O1Wiii0.91 (1)1.71 (1)2.618 (2)174 (2)
O1W—H1W1···O2iv0.84 (1)1.81 (1)2.644 (2)169 (2)
O4—H2O···O6Wv0.85 (1)1.98 (1)2.787 (2)157 (2)
O7W—H7W1···O6vi0.85 (1)1.98 (1)2.828 (2)173 (2)
O7W—H7W2···O1vii0.86 (1)1.95 (1)2.8013 (18)174 (2)
O1W—H1W2···O7Wvi0.84 (1)1.83 (1)2.662 (2)175 (2)
O2W—H2W1···O60.85 (1)1.92 (1)2.764 (2)172 (3)
O3W—H3W1···O50.85 (1)1.95 (1)2.797 (2)171 (2)
O6W—H6W1···O2Wii0.86 (1)1.93 (1)2.785 (3)174 (2)
O4W—H4W1···F10.85 (1)2.29 (1)2.976 (2)138 (2)
O6W—H6W2···O6iii0.86 (1)2.13 (1)2.972 (2)170 (2)
O5W—H5W1···O2iv0.85 (1)2.20 (1)3.023 (3)164 (2)
O2W—H2W2···O5W0.85 (1)2.07 (1)2.912 (3)175 (2)
O5W—H5W2···O4W0.85 (1)1.92 (1)2.774 (3)178 (3)
O4W—H4W2···O3Wii0.85 (1)1.96 (1)2.801 (3)170 (2)
O3W—H3W2···O5Wviii0.84 (1)1.99 (1)2.802 (3)162 (2)
Symmetry codes: (iii) x+1, y, z; (iv) x, y+1, z; (v) x−1, y, z; (vi) −x+1, −y+1, −z+1; (vii) x+1, y+1, z; (ii) −x+1, −y+1, −z+2; (viii) x, y−1, z.
Table 1
Selected geometric parameters (Å) top
Mn1—O32.1261 (12)Mn1—O42.2223 (15)
Mn1—O12.1569 (13)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H1O···O50.85 (1)1.91 (1)2.7565 (18)173 (2)
N3—H3N···O1Wi0.91 (1)1.71 (1)2.618 (2)174 (2)
O1W—H1W1···O2ii0.84 (1)1.81 (1)2.644 (2)169 (2)
O4—H2O···O6Wiii0.85 (1)1.98 (1)2.787 (2)157 (2)
O7W—H7W1···O6iv0.85 (1)1.98 (1)2.828 (2)173 (2)
O7W—H7W2···O1v0.86 (1)1.95 (1)2.8013 (18)174 (2)
O1W—H1W2···O7Wiv0.84 (1)1.83 (1)2.662 (2)175 (2)
O2W—H2W1···O60.85 (1)1.92 (1)2.764 (2)172 (3)
O3W—H3W1···O50.85 (1)1.95 (1)2.797 (2)171 (2)
O6W—H6W1···O2Wvi0.86 (1)1.93 (1)2.785 (3)174 (2)
O4W—H4W1···F10.85 (1)2.29 (1)2.976 (2)138 (2)
O6W—H6W2···O6i0.86 (1)2.13 (1)2.972 (2)170 (2)
O5W—H5W1···O2ii0.85 (1)2.20 (1)3.023 (3)164 (2)
O2W—H2W2···O5W0.85 (1)2.07 (1)2.912 (3)175 (2)
O5W—H5W2···O4W0.85 (1)1.92 (1)2.774 (3)178 (3)
O4W—H4W2···O3Wvi0.85 (1)1.96 (1)2.801 (3)170 (2)
O3W—H3W2···O5Wvii0.84 (1)1.99 (1)2.802 (3)162 (2)
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+1; (v) x+1, y+1, z; (vi) −x+1, −y+1, −z+2; (vii) x, y−1, z.
Acknowledgements top

The authors thank the Innovation Science Foundation of Harbin Medical University for financial support (grant No.060041).

references
References top

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Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 Suppl. A, 41-45.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.