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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1490–m1491.
Published online 2010 October 31. doi:  10.1107/S160053681004328X
PMCID: PMC3009166

Poly[[[[1-ethyl-6,8-difluoro-7-(3-methyl­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ato]cadmium]-μ-benzene-1,4-dicarboxyl­ato] trihydrate]

Abstract

In the title layered coordination polymer, {[Cd(C17H18F2N3O3)(C8H4O4)]·3H2O}n, the CdII atom exhibits a very distorted CdO6 octa­hedral geometry defined by one O 3,O 4-bidentate 1-ethyl-6,8-difluoro-7-(3-methyl­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ate (lome) ligand, one O,O′-bidentate benzene-1,4-dicarboxyl­ate (bdc) dianion and two O-monodentate bdc dianions. Both the bdc species in the asymmetric unit are completed by crystallographic inversion symmetry. The bridging bdc dianions link the cadmium nodes into a recta­ngular grid lying parallel to (01An external file that holds a picture, illustration, etc.
Object name is e-66-m1490-efi1.jpg). A network of N—H(...)O and O—H(...)O hydrogen bonds helps to establish the packing.

Related literature

For background on the medicinal uses of lomefloxacin, see: Mizuki et al. (1996 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1490-scheme1.jpg

Experimental

Crystal data

  • [Cd(C17H18F2N3O3)(C8H4O4)]·3H2O
  • M r = 680.90
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1490-efi2.jpg
  • a = 9.7924 (7) Å
  • b = 11.9788 (8) Å
  • c = 13.3981 (9) Å
  • α = 114.138 (1)°
  • β = 103.430 (1)°
  • γ = 100.295 (1)°
  • V = 1327.00 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.90 mm−1
  • T = 295 K
  • 0.32 × 0.24 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.762, T max = 0.855
  • 6581 measured reflections
  • 4624 independent reflections
  • 4108 reflections with I > 2σ(I)
  • R int = 0.014

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.135
  • S = 1.11
  • 4624 reflections
  • 372 parameters
  • H-atom parameters constrained
  • Δρmax = 1.76 e Å−3
  • Δρmin = −0.81 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004328X/hb5699sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004328X/hb5699Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from Xinjiang Medical University and Guangdong University of Petrochemical Technology.

supplementary crystallographic information

Comment

Lomefloxacin (H-Lome,1,4-dihydro-6,8-difluoro-1-ethyl-7- (3-methyl-1-piperazinyl)-4-oxo-3-quinoline carboxylic acid) is a new member of the class of quinolones that is used to treat infections (Mizuki et al., 1996). The metal complexes of lomefloxacin have not been reported.

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

The structure of (I) is built up from Cd2+ cations, lome ligands, 1,4-benzenedicarboxylate anions, three uncoordinated water molecules (Fig. 1). The Cd atom exhibits a distorted CdO6 octahedral geometry, two O atom come from one bidentate O,O-bonded 1,4-dihydro-6,8-difluoro-1-ethyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinoline carboxylic (lome) and four O atom come from three 1,4-benzenedicarboxylic acid molecules.

In title compound (I) form a square grid propagating in (Fig. 2) which 1,4-benzenedicarboxylic acid is bridged ligands.

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.

Experimental

A mixture of Cd(NO3)2.2H2O (0.5 mmol), lomefloxacin (0.6 mmol), 1,4-benzenedicarboxylic acid (0.25 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. Colourless single crystals of (I) suitable for X-ray analysis were obtained from the reaction mixture.

Refinement

The H on the C atoms and N atoms were positioned geometrically (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(C or N). The H atoms on water molecules were placed at chemically sensible positions on the basis of hydrogen bonds, but these were not refined, O—H = 0.85 Å and U(H) = 1.5Ueq(O).

Figures

Fig. 1.
The asymmetric unit of (I), expanded to show the Cd coordination, showing 50% displacement ellipsoids. Symmetry code: (i) x, y, z.
Fig. 2.
A view of part of a two-dimensional polymeric sheet in (I) showing the square-grid connectivity (lomefloxacin molecule, H atoms and water molecule have been omitted for clarity).

Crystal data

[Cd(C17H18F2N3O3)(C8H4O4)]·3H2OZ = 2
Mr = 680.90F(000) = 690
Triclinic, P1Dx = 1.704 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7924 (7) ÅCell parameters from 6498 reflections
b = 11.9788 (8) Åθ = 1.8–25.0°
c = 13.3981 (9) ŵ = 0.90 mm1
α = 114.138 (1)°T = 295 K
β = 103.430 (1)°Prism, colourless
γ = 100.295 (1)°0.32 × 0.24 × 0.18 mm
V = 1327.00 (16) Å3

Data collection

Bruker SMART CCD diffractometer4624 independent reflections
Radiation source: fine-focus sealed tube4108 reflections with I > 2σ(I)
graphiteRint = 0.014
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −11→11
Tmin = 0.762, Tmax = 0.855k = −14→13
6581 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.077P)2 + 3.3034P] where P = (Fo2 + 2Fc2)/3
4624 reflections(Δ/σ)max = 0.001
372 parametersΔρmax = 1.76 e Å3
0 restraintsΔρmin = −0.81 e Å3

Special details

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)

xyzUiso*/Ueq
Cd10.60296 (4)0.51272 (3)0.66873 (3)0.02772 (15)
F10.7760 (5)0.0511 (4)0.2452 (3)0.0572 (10)
F20.7085 (5)−0.1943 (3)0.4378 (3)0.0528 (9)
N10.6840 (5)0.0195 (4)0.6257 (4)0.0319 (9)
N20.7709 (6)−0.1778 (5)0.2569 (4)0.0469 (12)
N30.7833 (7)−0.4099 (5)0.0884 (5)0.0608 (16)
H3A0.8174−0.45740.03870.073*
O10.5949 (5)0.4247 (4)0.7917 (3)0.0419 (9)
O20.6845 (5)0.3373 (4)0.8987 (3)0.0499 (11)
O30.6497 (5)0.3294 (3)0.5729 (3)0.0384 (9)
O40.8541 (4)0.6499 (4)0.8163 (4)0.0457 (10)
O50.6668 (4)0.7265 (4)0.8070 (4)0.0501 (11)
O60.3731 (4)0.5173 (4)0.6448 (4)0.0480 (10)
O70.3361 (4)0.4186 (4)0.4565 (3)0.0381 (9)
O81.0201 (6)−0.3309 (6)0.0299 (5)0.0805 (17)
H8A1.1082−0.33350.03990.121*
H8B0.9839−0.3370−0.03700.121*
O90.4490 (9)−0.1577 (9)0.8478 (8)0.147 (4)
H9A0.5155−0.19340.83670.220*
H9B0.4402−0.14810.91230.220*
O100.5836 (11)0.1231 (9)0.9489 (9)0.142 (3)
H5O0.61810.18970.94280.213*
H6O0.55370.05880.88110.213*
C10.6442 (6)0.3397 (5)0.8035 (4)0.0346 (12)
C20.6576 (6)0.2330 (5)0.6991 (4)0.0303 (11)
C30.6622 (6)0.2386 (5)0.5956 (4)0.0302 (11)
C40.6902 (6)0.1292 (5)0.5103 (4)0.0294 (10)
C50.7112 (6)0.1352 (5)0.4121 (5)0.0360 (12)
H50.70330.20590.40110.043*
C60.7428 (7)0.0384 (6)0.3335 (5)0.0396 (13)
C70.7459 (6)−0.0757 (5)0.3398 (4)0.0363 (12)
C80.7193 (6)−0.0807 (5)0.4357 (4)0.0344 (12)
C90.6984 (6)0.0206 (5)0.5248 (4)0.0298 (10)
C100.6692 (6)0.1241 (5)0.7075 (4)0.0324 (11)
H100.66660.12270.77600.039*
C110.7087 (7)−0.0836 (5)0.6569 (5)0.0432 (14)
H11A0.6522−0.16720.59090.052*
H11B0.6741−0.07560.72100.052*
C120.8695 (7)−0.0743 (6)0.6911 (6)0.0514 (16)
H12A0.9038−0.08230.62760.077*
H12B0.8822−0.14200.70960.077*
H12C0.92520.00750.75780.077*
C130.7198 (10)−0.2110 (8)0.1326 (5)0.075 (3)
H13A0.6421−0.17390.11760.090*
H13B0.8009−0.17470.11390.090*
C140.6651 (10)−0.3490 (8)0.0593 (6)0.077 (2)
H14A0.6393−0.3686−0.02180.092*
H14B0.5769−0.38440.07120.092*
C150.8317 (11)−0.3763 (7)0.2137 (7)0.072 (2)
H150.7487−0.41550.23020.086*
C160.8786 (9)−0.2384 (7)0.2861 (6)0.065 (2)
H16A0.9699−0.20100.27890.078*
H16B0.8990−0.21960.36660.078*
C170.9593 (11)−0.4326 (8)0.2388 (8)0.076 (3)
H17A1.0309−0.41090.20610.113*
H17B0.9204−0.52440.20440.113*
H17C1.0053−0.39720.32130.113*
C180.8017 (6)0.7408 (5)0.8452 (4)0.0354 (12)
C190.9057 (6)0.8760 (5)0.9286 (4)0.0316 (11)
C200.8504 (6)0.9742 (5)0.9815 (5)0.0378 (12)
H200.74970.95700.96880.045*
C210.9451 (6)1.0990 (5)1.0537 (5)0.0368 (12)
H210.90811.16521.08980.044*
C220.2939 (5)0.4741 (5)0.5409 (5)0.0325 (11)
C230.1424 (5)0.4880 (5)0.5192 (4)0.0282 (10)
C240.1114 (6)0.5848 (5)0.6051 (5)0.0343 (11)
H240.18600.64220.67530.041*
C25−0.0300 (5)0.5958 (5)0.5861 (5)0.0332 (11)
H25−0.04980.65960.64420.040*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.0276 (2)0.0200 (2)0.0276 (2)0.00944 (14)0.00617 (15)0.00477 (15)
F10.098 (3)0.053 (2)0.045 (2)0.041 (2)0.045 (2)0.0264 (18)
F20.089 (3)0.0242 (16)0.0424 (19)0.0259 (17)0.0203 (18)0.0111 (15)
N10.041 (2)0.025 (2)0.029 (2)0.0112 (18)0.0114 (19)0.0126 (18)
N20.069 (3)0.038 (3)0.029 (2)0.032 (3)0.015 (2)0.006 (2)
N30.093 (5)0.036 (3)0.052 (3)0.032 (3)0.040 (3)0.005 (3)
O10.062 (3)0.035 (2)0.035 (2)0.0243 (19)0.0226 (19)0.0142 (17)
O20.077 (3)0.047 (2)0.025 (2)0.030 (2)0.017 (2)0.0125 (18)
O30.063 (3)0.0288 (19)0.035 (2)0.0267 (18)0.0252 (19)0.0163 (17)
O40.047 (2)0.0251 (19)0.044 (2)0.0065 (17)0.0060 (19)0.0040 (17)
O50.035 (2)0.030 (2)0.052 (3)0.0015 (17)−0.0012 (19)0.0012 (19)
O60.031 (2)0.063 (3)0.044 (2)0.0183 (19)0.0057 (18)0.022 (2)
O70.036 (2)0.038 (2)0.052 (2)0.0202 (17)0.0229 (18)0.0239 (19)
O80.065 (3)0.116 (5)0.087 (4)0.031 (3)0.023 (3)0.072 (4)
O90.108 (6)0.150 (8)0.122 (7)0.065 (6)0.011 (5)0.014 (6)
O100.150 (8)0.133 (8)0.190 (10)0.070 (6)0.079 (7)0.095 (8)
C10.041 (3)0.027 (3)0.030 (3)0.011 (2)0.013 (2)0.007 (2)
C20.035 (3)0.027 (3)0.024 (2)0.011 (2)0.009 (2)0.006 (2)
C30.035 (3)0.023 (2)0.028 (3)0.012 (2)0.010 (2)0.007 (2)
C40.036 (3)0.022 (2)0.026 (2)0.012 (2)0.009 (2)0.006 (2)
C50.052 (3)0.029 (3)0.036 (3)0.022 (2)0.021 (3)0.017 (2)
C60.055 (3)0.041 (3)0.028 (3)0.023 (3)0.020 (2)0.014 (2)
C70.046 (3)0.028 (3)0.024 (3)0.018 (2)0.006 (2)0.002 (2)
C80.046 (3)0.020 (2)0.030 (3)0.015 (2)0.008 (2)0.007 (2)
C90.036 (3)0.023 (2)0.026 (2)0.011 (2)0.007 (2)0.009 (2)
C100.044 (3)0.025 (3)0.023 (2)0.011 (2)0.010 (2)0.008 (2)
C110.072 (4)0.026 (3)0.039 (3)0.019 (3)0.020 (3)0.019 (2)
C120.064 (4)0.047 (4)0.050 (4)0.029 (3)0.014 (3)0.028 (3)
C130.100 (6)0.076 (5)0.027 (3)0.057 (5)0.005 (3)0.002 (3)
C140.101 (6)0.071 (5)0.045 (4)0.048 (5)0.023 (4)0.008 (4)
C150.109 (7)0.055 (4)0.081 (5)0.047 (5)0.057 (5)0.037 (4)
C160.084 (5)0.058 (4)0.040 (3)0.050 (4)0.008 (3)0.005 (3)
C170.127 (7)0.062 (5)0.089 (6)0.069 (5)0.069 (6)0.049 (5)
C180.043 (3)0.028 (3)0.025 (3)0.004 (2)0.008 (2)0.008 (2)
C190.036 (3)0.026 (3)0.022 (2)0.003 (2)0.003 (2)0.007 (2)
C200.032 (3)0.032 (3)0.035 (3)0.003 (2)0.005 (2)0.009 (2)
C210.041 (3)0.026 (3)0.032 (3)0.010 (2)0.009 (2)0.006 (2)
C220.027 (3)0.029 (3)0.043 (3)0.007 (2)0.008 (2)0.021 (2)
C230.025 (2)0.029 (2)0.034 (3)0.010 (2)0.011 (2)0.016 (2)
C240.027 (3)0.034 (3)0.031 (3)0.005 (2)0.006 (2)0.009 (2)
C250.029 (3)0.032 (3)0.033 (3)0.013 (2)0.011 (2)0.010 (2)

Geometric parameters (Å, °)

Cd1—O62.213 (4)C5—H50.9300
Cd1—O32.238 (3)C6—C71.408 (8)
Cd1—O7i2.295 (4)C7—C81.391 (8)
Cd1—O12.299 (4)C8—C91.398 (7)
Cd1—O52.322 (4)C10—H100.9300
Cd1—O42.510 (4)C11—C121.504 (9)
F1—C61.356 (6)C11—H11A0.9700
F2—C81.358 (6)C11—H11B0.9700
N1—C101.345 (6)C12—H12A0.9600
N1—C91.397 (7)C12—H12B0.9600
N1—C111.496 (6)C12—H12C0.9600
N2—C71.383 (7)C13—C141.447 (11)
N2—C161.451 (8)C13—H13A0.9700
N2—C131.477 (8)C13—H13B0.9700
N3—C151.489 (10)C14—H14A0.9700
N3—C141.534 (10)C14—H14B0.9700
N3—H3A0.8600C15—C161.447 (10)
O1—C11.251 (6)C15—C171.555 (11)
O2—C11.258 (7)C15—H150.9800
O3—C31.261 (6)C16—H16A0.9700
O4—C181.243 (7)C16—H16B0.9700
O5—C181.253 (7)C17—H17A0.9600
O6—C221.255 (7)C17—H17B0.9600
O7—C221.261 (6)C17—H17C0.9600
O7—Cd1i2.295 (4)C18—C191.520 (7)
O8—H8A0.8500C19—C201.380 (8)
O8—H8B0.8501C19—C21ii1.380 (8)
O9—H9A0.8501C20—C211.391 (8)
O9—H9B0.8500C20—H200.9300
O10—H5O0.8523C21—C19ii1.380 (8)
O10—H6O0.8530C21—H210.9300
C1—C21.513 (7)C22—C231.497 (7)
C2—C101.377 (7)C23—C25iii1.391 (7)
C2—C31.427 (7)C23—C241.399 (7)
C3—C41.466 (7)C24—C251.389 (7)
C4—C91.405 (7)C24—H240.9300
C4—C51.406 (7)C25—C23iii1.391 (7)
C5—C61.353 (7)C25—H250.9300
O6—Cd1—O3120.64 (16)N1—C11—H11B109.4
O6—Cd1—O7i102.79 (15)C12—C11—H11B109.4
O3—Cd1—O7i89.23 (13)H11A—C11—H11B108.0
O6—Cd1—O191.71 (16)C11—C12—H12A109.5
O3—Cd1—O179.38 (13)C11—C12—H12B109.5
O7i—Cd1—O1164.82 (13)H12A—C12—H12B109.5
O6—Cd1—O584.71 (16)C11—C12—H12C109.5
O3—Cd1—O5154.35 (15)H12A—C12—H12C109.5
O7i—Cd1—O588.65 (16)H12B—C12—H12C109.5
O1—Cd1—O597.27 (15)C14—C13—N2111.1 (7)
O6—Cd1—O4136.90 (15)C14—C13—H13A109.4
O3—Cd1—O4100.57 (14)N2—C13—H13A109.4
O7i—Cd1—O488.88 (14)C14—C13—H13B109.4
O1—Cd1—O483.45 (15)N2—C13—H13B109.4
O5—Cd1—O453.83 (14)H13A—C13—H13B108.0
C10—N1—C9119.0 (4)C13—C14—N3109.9 (7)
C10—N1—C11117.2 (4)C13—C14—H14A109.7
C9—N1—C11123.0 (4)N3—C14—H14A109.7
C7—N2—C16122.9 (5)C13—C14—H14B109.7
C7—N2—C13121.7 (5)N3—C14—H14B109.7
C16—N2—C13113.6 (5)H14A—C14—H14B108.2
C15—N3—C14111.3 (5)C16—C15—N3110.6 (6)
C15—N3—H3A124.3C16—C15—C17110.9 (8)
C14—N3—H3A124.3N3—C15—C17108.5 (6)
C1—O1—Cd1132.5 (3)C16—C15—H15108.9
C3—O3—Cd1132.3 (3)N3—C15—H15108.9
C18—O4—Cd187.0 (3)C17—C15—H15108.9
C18—O5—Cd195.5 (3)C15—C16—N2113.7 (6)
C22—O6—Cd1114.2 (4)C15—C16—H16A108.8
C22—O7—Cd1i129.7 (3)N2—C16—H16A108.8
H8A—O8—H8B108.7C15—C16—H16B108.8
H9A—O9—H9B108.4N2—C16—H16B108.8
H5O—O10—H6O107.2H16A—C16—H16B107.7
O1—C1—O2123.6 (5)C15—C17—H17A109.5
O1—C1—C2119.5 (5)C15—C17—H17B109.5
O2—C1—C2117.0 (5)H17A—C17—H17B109.5
C10—C2—C3118.5 (4)C15—C17—H17C109.5
C10—C2—C1116.5 (4)H17A—C17—H17C109.5
C3—C2—C1125.0 (5)H17B—C17—H17C109.5
O3—C3—C2126.5 (4)O4—C18—O5123.0 (5)
O3—C3—C4117.8 (4)O4—C18—C19118.8 (5)
C2—C3—C4115.6 (4)O5—C18—C19118.2 (5)
C9—C4—C5119.6 (4)O4—C18—Cd166.0 (3)
C9—C4—C3122.0 (5)O5—C18—Cd157.4 (3)
C5—C4—C3118.3 (4)C19—C18—Cd1170.3 (4)
C6—C5—C4120.1 (5)C20—C19—C21ii120.3 (5)
C6—C5—H5119.9C20—C19—C18120.2 (5)
C4—C5—H5119.9C21ii—C19—C18119.5 (5)
C5—C6—F1119.3 (5)C19—C20—C21120.1 (5)
C5—C6—C7123.1 (5)C19—C20—H20120.0
F1—C6—C7117.6 (5)C21—C20—H20120.0
N2—C7—C8121.2 (5)C19ii—C21—C20119.6 (5)
N2—C7—C6123.6 (5)C19ii—C21—H21120.2
C8—C7—C6115.2 (5)C20—C21—H21120.2
F2—C8—C7116.0 (4)O6—C22—O7122.8 (5)
F2—C8—C9119.7 (5)O6—C22—C23117.1 (5)
C7—C8—C9124.2 (5)O7—C22—C23120.1 (5)
N1—C9—C8124.1 (5)C25iii—C23—C24119.0 (5)
N1—C9—C4118.6 (4)C25iii—C23—C22120.5 (5)
C8—C9—C4117.3 (5)C24—C23—C22120.5 (5)
N1—C10—C2125.9 (5)C25—C24—C23120.5 (5)
N1—C10—H10117.0C25—C24—H24119.8
C2—C10—H10117.0C23—C24—H24119.8
N1—C11—C12111.1 (5)C24—C25—C23iii120.5 (5)
N1—C11—H11A109.4C24—C25—H25119.7
C12—C11—H11A109.4C23iii—C25—H25119.7
O6—Cd1—O1—C1140.3 (5)F2—C8—C9—N18.1 (8)
O3—Cd1—O1—C119.4 (5)C7—C8—C9—N1−174.4 (5)
O7i—Cd1—O1—C1−22.5 (9)F2—C8—C9—C4−171.3 (5)
O5—Cd1—O1—C1−134.8 (5)C7—C8—C9—C46.2 (8)
O4—Cd1—O1—C1−82.7 (5)C5—C4—C9—N1177.0 (5)
C18—Cd1—O1—C1−108.1 (5)C3—C4—C9—N1−2.1 (7)
O6—Cd1—O3—C3−86.7 (5)C5—C4—C9—C8−3.5 (8)
O7i—Cd1—O3—C3168.9 (5)C3—C4—C9—C8177.3 (5)
O1—Cd1—O3—C3−1.0 (5)C9—N1—C10—C24.2 (8)
O5—Cd1—O3—C383.6 (6)C11—N1—C10—C2174.6 (5)
O4—Cd1—O3—C380.2 (5)C3—C2—C10—N1−0.4 (8)
C18—Cd1—O3—C383.7 (5)C1—C2—C10—N1−179.1 (5)
O6—Cd1—O4—C18−22.9 (4)C10—N1—C11—C12−99.4 (6)
O3—Cd1—O4—C18173.7 (3)C9—N1—C11—C1270.5 (7)
O7i—Cd1—O4—C1884.7 (3)C7—N2—C13—C14−140.9 (7)
O1—Cd1—O4—C18−108.4 (3)C16—N2—C13—C1454.0 (10)
O5—Cd1—O4—C18−4.4 (3)N2—C13—C14—N3−55.0 (9)
O6—Cd1—O5—C18171.8 (4)C15—N3—C14—C1356.4 (9)
O3—Cd1—O5—C180.2 (6)C14—N3—C15—C16−54.0 (9)
O7i—Cd1—O5—C18−85.2 (4)C14—N3—C15—C17−175.8 (7)
O1—Cd1—O5—C1880.8 (4)N3—C15—C16—N252.3 (9)
O4—Cd1—O5—C184.4 (3)C17—C15—C16—N2172.7 (6)
O3—Cd1—O6—C22−54.1 (4)C7—N2—C16—C15142.6 (7)
O7i—Cd1—O6—C2242.7 (4)C13—N2—C16—C15−52.6 (10)
O1—Cd1—O6—C22−132.8 (4)Cd1—O4—C18—O57.9 (6)
O5—Cd1—O6—C22130.1 (4)Cd1—O4—C18—C19−170.6 (4)
O4—Cd1—O6—C22145.0 (3)Cd1—O5—C18—O4−8.6 (6)
C18—Cd1—O6—C22134.0 (4)Cd1—O5—C18—C19170.0 (4)
Cd1—O1—C1—O2149.8 (5)O6—Cd1—C18—O4163.4 (3)
Cd1—O1—C1—C2−30.0 (8)O3—Cd1—C18—O4−7.8 (4)
O1—C1—C2—C10−161.2 (5)O7i—Cd1—C18—O4−94.2 (3)
O2—C1—C2—C1018.9 (7)O1—Cd1—C18—O470.6 (3)
O1—C1—C2—C320.2 (8)O5—Cd1—C18—O4172.1 (6)
O2—C1—C2—C3−159.6 (5)O6—Cd1—C18—O5−8.7 (4)
Cd1—O3—C3—C2−4.1 (8)O3—Cd1—C18—O5−179.9 (3)
Cd1—O3—C3—C4178.5 (3)O7i—Cd1—C18—O593.7 (4)
C10—C2—C3—O3178.2 (5)O1—Cd1—C18—O5−101.5 (4)
C1—C2—C3—O3−3.2 (9)O4—Cd1—C18—O5−172.1 (6)
C10—C2—C3—C4−4.3 (7)O6—Cd1—C18—C19−74 (2)
C1—C2—C3—C4174.2 (5)O3—Cd1—C18—C19114 (2)
O3—C3—C4—C9−176.7 (5)O7i—Cd1—C18—C1928 (2)
C2—C3—C4—C95.6 (7)O1—Cd1—C18—C19−167 (2)
O3—C3—C4—C54.1 (7)O5—Cd1—C18—C19−66 (2)
C2—C3—C4—C5−173.5 (5)O4—Cd1—C18—C19122 (2)
C9—C4—C5—C6−1.7 (8)O4—C18—C19—C20−166.3 (5)
C3—C4—C5—C6177.5 (5)O5—C18—C19—C2015.0 (8)
C4—C5—C6—F1−174.0 (5)Cd1—C18—C19—C2076 (2)
C4—C5—C6—C74.7 (9)O4—C18—C19—C21ii17.0 (8)
C16—N2—C7—C8−50.8 (9)O5—C18—C19—C21ii−161.7 (5)
C13—N2—C7—C8145.6 (7)Cd1—C18—C19—C21ii−101 (2)
C16—N2—C7—C6130.3 (7)C21ii—C19—C20—C21−0.5 (9)
C13—N2—C7—C6−33.4 (10)C18—C19—C20—C21−177.1 (5)
C5—C6—C7—N2176.7 (6)C19—C20—C21—C19ii0.5 (9)
F1—C6—C7—N2−4.5 (9)Cd1—O6—C22—O78.1 (7)
C5—C6—C7—C8−2.3 (9)Cd1—O6—C22—C23−173.2 (3)
F1—C6—C7—C8176.5 (5)Cd1i—O7—C22—O6−109.6 (5)
N2—C7—C8—F2−4.8 (8)Cd1i—O7—C22—C2371.8 (6)
C6—C7—C8—F2174.2 (5)O6—C22—C23—C25iii−155.0 (5)
N2—C7—C8—C9177.6 (5)O7—C22—C23—C25iii23.7 (7)
C6—C7—C8—C9−3.4 (8)O6—C22—C23—C2424.4 (7)
C10—N1—C9—C8177.8 (5)O7—C22—C23—C24−156.9 (5)
C11—N1—C9—C88.1 (8)C25iii—C23—C24—C251.0 (9)
C10—N1—C9—C4−2.8 (7)C22—C23—C24—C25−178.4 (5)
C11—N1—C9—C4−172.5 (5)C23—C24—C25—C23iii−1.0 (9)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z+2; (iii) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···O80.862.332.749 (8)110
O8—H8A···O2iv0.852.022.854 (7)166
O8—H8B···O4v0.852.012.837 (7)166
O9—H9B···O10vi0.851.842.687 (14)178
O9—H9A···O5vii0.851.932.784 (9)178
O10—H5O···O20.852.132.971 (10)171
O10—H6O···O90.852.422.957 (14)121

Symmetry codes: (iv) −x+2, −y, −z+1; (v) x, y−1, z−1; (vi) −x+1, −y, −z+2; (vii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5699).

References

  • Bruker (2001). SAINT-Plus and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother.37 (Suppl. A), 41–45. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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