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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages m1490-m1491

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]

aSchool of Pharmacological Sciences, Xinjiang Medical University, Urumqi 830054, People's Republic of China, and bSchool of Chemistry and Life Science, Guangdong University of Petrochemical Technology, Maoming 525000, People's Republic of China
*Correspondence e-mail: kasimu_xmu@163.com

(Received 21 October 2010; accepted 23 October 2010; online 31 October 2010)

In the title layered coordination polymer, {[Cd(C17H18F2N3O3)(C8H4O4)]·3H2O}n, the CdII atom exhibits a very distorted CdO6 octa­hedral geometry defined by one O3,O4-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 (01[\overline{1}]). 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[Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 (Suppl. A), 41-45.]).

[Scheme 1]

Experimental

Crystal data
  • [Cd(C17H18F2N3O3)(C8H4O4)]·3H2O

  • Mr = 680.90

  • Triclinic, [P \overline 1]

  • 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[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.762, Tmax = 0.855

  • 6581 measured reflections

  • 4624 independent reflections

  • 4108 reflections with I > 2σ(I)

  • Rint = 0.014

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

Cd1—O6 2.213 (4)
Cd1—O3 2.238 (3)
Cd1—O7i 2.295 (4)
Cd1—O1 2.299 (4)
Cd1—O5 2.322 (4)
Cd1—O4 2.510 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯O8 0.86 2.33 2.749 (8) 110
O8—H8A⋯O2ii 0.85 2.02 2.854 (7) 166
O8—H8B⋯O4iii 0.85 2.01 2.837 (7) 166
O9—H9B⋯O10iv 0.85 1.84 2.687 (14) 178
O9—H9A⋯O5v 0.85 1.93 2.784 (9) 178
O10—H5O⋯O2 0.85 2.13 2.971 (10) 171
O10—H6O⋯O9 0.85 2.42 2.957 (14) 121
Symmetry codes: (ii) -x+2, -y, -z+1; (iii) x, y-1, z-1; (iv) -x+1, -y, -z+2; (v) x, y-1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

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
[Figure 1] Fig. 1. The asymmetric unit of (I), expanded to show the Cd coordination, showing 50% displacement ellipsoids. Symmetry code: (i) x, y, z.
[Figure 2] 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).
Poly[[[[1-ethyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4- dihydroquinoline-3-carboxylato]cadmium(II)]-µ-benzene-1,4-dicarboxylato] trihydrate] top
Crystal data top
[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 top
Bruker SMART CCD
diffractometer
4624 independent reflections
Radiation source: fine-focus sealed tube4108 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1111
Tmin = 0.762, Tmax = 0.855k = 1413
6581 measured reflectionsl = 1515
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.11 w = 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
Crystal data top
[Cd(C17H18F2N3O3)(C8H4O4)]·3H2Oγ = 100.295 (1)°
Mr = 680.90V = 1327.00 (16) Å3
Triclinic, P1Z = 2
a = 9.7924 (7) ÅMo Kα radiation
b = 11.9788 (8) ŵ = 0.90 mm1
c = 13.3981 (9) ÅT = 295 K
α = 114.138 (1)°0.32 × 0.24 × 0.18 mm
β = 103.430 (1)°
Data collection top
Bruker SMART CCD
diffractometer
4624 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
4108 reflections with I > 2σ(I)
Tmin = 0.762, Tmax = 0.855Rint = 0.014
6581 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.11Δρmax = 1.76 e Å3
4624 reflectionsΔρmin = 0.81 e Å3
372 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
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)
H3A0.81740.45740.03870.073*
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)
H8A1.10820.33350.03990.121*
H8B0.98390.33700.03700.121*
O90.4490 (9)0.1577 (9)0.8478 (8)0.147 (4)
H9A0.51550.19340.83670.220*
H9B0.44020.14810.91230.220*
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)
H11A0.65220.16720.59090.052*
H11B0.67410.07560.72100.052*
C120.8695 (7)0.0743 (6)0.6911 (6)0.0514 (16)
H12A0.90380.08230.62760.077*
H12B0.88220.14200.70960.077*
H12C0.92520.00750.75780.077*
C130.7198 (10)0.2110 (8)0.1326 (5)0.075 (3)
H13A0.64210.17390.11760.090*
H13B0.80090.17470.11390.090*
C140.6651 (10)0.3490 (8)0.0593 (6)0.077 (2)
H14A0.63930.36860.02180.092*
H14B0.57690.38440.07120.092*
C150.8317 (11)0.3763 (7)0.2137 (7)0.072 (2)
H150.74870.41550.23020.086*
C160.8786 (9)0.2384 (7)0.2861 (6)0.065 (2)
H16A0.96990.20100.27890.078*
H16B0.89900.21960.36660.078*
C170.9593 (11)0.4326 (8)0.2388 (8)0.076 (3)
H17A1.03090.41090.20610.113*
H17B0.92040.52440.20440.113*
H17C1.00530.39720.32130.113*
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*
C250.0300 (5)0.5958 (5)0.5861 (5)0.0332 (11)
H250.04980.65960.64420.040*
Atomic displacement parameters (Å2) top
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, º) top
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—N1174.4 (5)
O7i—Cd1—O1—C122.5 (9)F2—C8—C9—C4171.3 (5)
O5—Cd1—O1—C1134.8 (5)C7—C8—C9—C46.2 (8)
O4—Cd1—O1—C182.7 (5)C5—C4—C9—N1177.0 (5)
C18—Cd1—O1—C1108.1 (5)C3—C4—C9—N12.1 (7)
O6—Cd1—O3—C386.7 (5)C5—C4—C9—C83.5 (8)
O7i—Cd1—O3—C3168.9 (5)C3—C4—C9—C8177.3 (5)
O1—Cd1—O3—C31.0 (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—N10.4 (8)
C18—Cd1—O3—C383.7 (5)C1—C2—C10—N1179.1 (5)
O6—Cd1—O4—C1822.9 (4)C10—N1—C11—C1299.4 (6)
O3—Cd1—O4—C18173.7 (3)C9—N1—C11—C1270.5 (7)
O7i—Cd1—O4—C1884.7 (3)C7—N2—C13—C14140.9 (7)
O1—Cd1—O4—C18108.4 (3)C16—N2—C13—C1454.0 (10)
O5—Cd1—O4—C184.4 (3)N2—C13—C14—N355.0 (9)
O6—Cd1—O5—C18171.8 (4)C15—N3—C14—C1356.4 (9)
O3—Cd1—O5—C180.2 (6)C14—N3—C15—C1654.0 (9)
O7i—Cd1—O5—C1885.2 (4)C14—N3—C15—C17175.8 (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—C2254.1 (4)C7—N2—C16—C15142.6 (7)
O7i—Cd1—O6—C2242.7 (4)C13—N2—C16—C1552.6 (10)
O1—Cd1—O6—C22132.8 (4)Cd1—O4—C18—O57.9 (6)
O5—Cd1—O6—C22130.1 (4)Cd1—O4—C18—C19170.6 (4)
O4—Cd1—O6—C22145.0 (3)Cd1—O5—C18—O48.6 (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—C230.0 (8)O3—Cd1—C18—O47.8 (4)
O1—C1—C2—C10161.2 (5)O7i—Cd1—C18—O494.2 (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—C3159.6 (5)O6—Cd1—C18—O58.7 (4)
Cd1—O3—C3—C24.1 (8)O3—Cd1—C18—O5179.9 (3)
Cd1—O3—C3—C4178.5 (3)O7i—Cd1—C18—O593.7 (4)
C10—C2—C3—O3178.2 (5)O1—Cd1—C18—O5101.5 (4)
C1—C2—C3—O33.2 (9)O4—Cd1—C18—O5172.1 (6)
C10—C2—C3—C44.3 (7)O6—Cd1—C18—C1974 (2)
C1—C2—C3—C4174.2 (5)O3—Cd1—C18—C19114 (2)
O3—C3—C4—C9176.7 (5)O7i—Cd1—C18—C1928 (2)
C2—C3—C4—C95.6 (7)O1—Cd1—C18—C19167 (2)
O3—C3—C4—C54.1 (7)O5—Cd1—C18—C1966 (2)
C2—C3—C4—C5173.5 (5)O4—Cd1—C18—C19122 (2)
C9—C4—C5—C61.7 (8)O4—C18—C19—C20166.3 (5)
C3—C4—C5—C6177.5 (5)O5—C18—C19—C2015.0 (8)
C4—C5—C6—F1174.0 (5)Cd1—C18—C19—C2076 (2)
C4—C5—C6—C74.7 (9)O4—C18—C19—C21ii17.0 (8)
C16—N2—C7—C850.8 (9)O5—C18—C19—C21ii161.7 (5)
C13—N2—C7—C8145.6 (7)Cd1—C18—C19—C21ii101 (2)
C16—N2—C7—C6130.3 (7)C21ii—C19—C20—C210.5 (9)
C13—N2—C7—C633.4 (10)C18—C19—C20—C21177.1 (5)
C5—C6—C7—N2176.7 (6)C19—C20—C21—C19ii0.5 (9)
F1—C6—C7—N24.5 (9)Cd1—O6—C22—O78.1 (7)
C5—C6—C7—C82.3 (9)Cd1—O6—C22—C23173.2 (3)
F1—C6—C7—C8176.5 (5)Cd1i—O7—C22—O6109.6 (5)
N2—C7—C8—F24.8 (8)Cd1i—O7—C22—C2371.8 (6)
C6—C7—C8—F2174.2 (5)O6—C22—C23—C25iii155.0 (5)
N2—C7—C8—C9177.6 (5)O7—C22—C23—C25iii23.7 (7)
C6—C7—C8—C93.4 (8)O6—C22—C23—C2424.4 (7)
C10—N1—C9—C8177.8 (5)O7—C22—C23—C24156.9 (5)
C11—N1—C9—C88.1 (8)C25iii—C23—C24—C251.0 (9)
C10—N1—C9—C42.8 (7)C22—C23—C24—C25178.4 (5)
C11—N1—C9—C4172.5 (5)C23—C24—C25—C23iii1.0 (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, º) top
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, y1, z1; (vi) x+1, y, z+2; (vii) x, y1, z.

Experimental details

Crystal data
Chemical formula[Cd(C17H18F2N3O3)(C8H4O4)]·3H2O
Mr680.90
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)9.7924 (7), 11.9788 (8), 13.3981 (9)
α, β, γ (°)114.138 (1), 103.430 (1), 100.295 (1)
V3)1327.00 (16)
Z2
Radiation typeMo Kα
µ (mm1)0.90
Crystal size (mm)0.32 × 0.24 × 0.18
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.762, 0.855
No. of measured, independent and
observed [I > 2σ(I)] reflections
6581, 4624, 4108
Rint0.014
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.135, 1.11
No. of reflections4624
No. of parameters372
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.76, 0.81

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

Selected bond lengths (Å) top
Cd1—O62.213 (4)Cd1—O12.299 (4)
Cd1—O32.238 (3)Cd1—O52.322 (4)
Cd1—O7i2.295 (4)Cd1—O42.510 (4)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O80.862.332.749 (8)110
O8—H8A···O2ii0.852.022.854 (7)166
O8—H8B···O4iii0.852.012.837 (7)166
O9—H9B···O10iv0.851.842.687 (14)178
O9—H9A···O5v0.851.932.784 (9)178
O10—H5O···O20.852.132.971 (10)171
O10—H6O···O90.852.422.957 (14)121
Symmetry codes: (ii) x+2, y, z+1; (iii) x, y1, z1; (iv) x+1, y, z+2; (v) x, y1, z.
 

Acknowledgements

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

References

First citationBruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationMizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 (Suppl. A), 41–45.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Pages m1490-m1491
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