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]

Kang, X.-P.; An, Z.; Kasimu, R.

doi:10.1107/S160053681004328X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages m1490-m1491

https://doi.org/10.1107/S160053681004328X

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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]

Xin-Ping Kang,^a,^b Zhe An ^b and Rena Kasimu ^a ^*

^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 Cd^II 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 ).

Experimental

Crystal data

[Cd(C₁₇H₁₈F₂N₃O₃)(C₈H₄O₄)]·3H₂O
M_r = 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 ) 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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.135
S = 1.11
4624 reflections
372 parameters
H-atom parameters constrained
Δρ_max = 1.76 e Å⁻³
Δρ_min = −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	D⋯A	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⋯O10^iv	0.85	1.84	2.687 (14)	178
O9—H9A⋯O5^v	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 ); 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/S160053681004328X/hb5699sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004328X/hb5699Isup2.hkl

checkCIF report

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.

Structure description top

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

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.

For background on the medicinal uses of lomefloxacin, 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 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).

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)]·3H₂O	Z = 2
M_r = 680.90	F(000) = 690
Triclinic, P1	D_x = 1.704 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7924 (7) Å	Cell parameters from 6498 reflections
b = 11.9788 (8) Å	θ = 1.8–25.0°
c = 13.3981 (9) Å	µ = 0.90 mm⁻¹
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 tube	4108 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.762, T_max = 0.855	k = −14→13
6581 measured reflections	l = −15→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.077P)² + 3.3034P] where P = (F_o² + 2F_c²)/3
4624 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 1.76 e Å⁻³
0 restraints	Δρ_min = −0.81 e Å⁻³

Crystal data top

[Cd(C₁₇H₁₈F₂N₃O₃)(C₈H₄O₄)]·3H₂O	γ = 100.295 (1)°
M_r = 680.90	V = 1327.00 (16) Å³
Triclinic, P1	Z = 2
a = 9.7924 (7) Å	Mo Kα radiation
b = 11.9788 (8) Å	µ = 0.90 mm⁻¹
c = 13.3981 (9) Å	T = 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)
T_min = 0.762, T_max = 0.855	R_int = 0.014
6581 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.11	Δρ_max = 1.76 e Å⁻³
4624 reflections	Δρ_min = −0.81 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cd1	0.60296 (4)	0.51272 (3)	0.66873 (3)	0.02772 (15)
F1	0.7760 (5)	0.0511 (4)	0.2452 (3)	0.0572 (10)
F2	0.7085 (5)	−0.1943 (3)	0.4378 (3)	0.0528 (9)
N1	0.6840 (5)	0.0195 (4)	0.6257 (4)	0.0319 (9)
N2	0.7709 (6)	−0.1778 (5)	0.2569 (4)	0.0469 (12)
N3	0.7833 (7)	−0.4099 (5)	0.0884 (5)	0.0608 (16)
H3A	0.8174	−0.4574	0.0387	0.073*
O1	0.5949 (5)	0.4247 (4)	0.7917 (3)	0.0419 (9)
O2	0.6845 (5)	0.3373 (4)	0.8987 (3)	0.0499 (11)
O3	0.6497 (5)	0.3294 (3)	0.5729 (3)	0.0384 (9)
O4	0.8541 (4)	0.6499 (4)	0.8163 (4)	0.0457 (10)
O5	0.6668 (4)	0.7265 (4)	0.8070 (4)	0.0501 (11)
O6	0.3731 (4)	0.5173 (4)	0.6448 (4)	0.0480 (10)
O7	0.3361 (4)	0.4186 (4)	0.4565 (3)	0.0381 (9)
O8	1.0201 (6)	−0.3309 (6)	0.0299 (5)	0.0805 (17)
H8A	1.1082	−0.3335	0.0399	0.121*
H8B	0.9839	−0.3370	−0.0370	0.121*
O9	0.4490 (9)	−0.1577 (9)	0.8478 (8)	0.147 (4)
H9A	0.5155	−0.1934	0.8367	0.220*
H9B	0.4402	−0.1481	0.9123	0.220*
O10	0.5836 (11)	0.1231 (9)	0.9489 (9)	0.142 (3)
H5O	0.6181	0.1897	0.9428	0.213*
H6O	0.5537	0.0588	0.8811	0.213*
C1	0.6442 (6)	0.3397 (5)	0.8035 (4)	0.0346 (12)
C2	0.6576 (6)	0.2330 (5)	0.6991 (4)	0.0303 (11)
C3	0.6622 (6)	0.2386 (5)	0.5956 (4)	0.0302 (11)
C4	0.6902 (6)	0.1292 (5)	0.5103 (4)	0.0294 (10)
C5	0.7112 (6)	0.1352 (5)	0.4121 (5)	0.0360 (12)
H5	0.7033	0.2059	0.4011	0.043*
C6	0.7428 (7)	0.0384 (6)	0.3335 (5)	0.0396 (13)
C7	0.7459 (6)	−0.0757 (5)	0.3398 (4)	0.0363 (12)
C8	0.7193 (6)	−0.0807 (5)	0.4357 (4)	0.0344 (12)
C9	0.6984 (6)	0.0206 (5)	0.5248 (4)	0.0298 (10)
C10	0.6692 (6)	0.1241 (5)	0.7075 (4)	0.0324 (11)
H10	0.6666	0.1227	0.7760	0.039*
C11	0.7087 (7)	−0.0836 (5)	0.6569 (5)	0.0432 (14)
H11A	0.6522	−0.1672	0.5909	0.052*
H11B	0.6741	−0.0756	0.7210	0.052*
C12	0.8695 (7)	−0.0743 (6)	0.6911 (6)	0.0514 (16)
H12A	0.9038	−0.0823	0.6276	0.077*
H12B	0.8822	−0.1420	0.7096	0.077*
H12C	0.9252	0.0075	0.7578	0.077*
C13	0.7198 (10)	−0.2110 (8)	0.1326 (5)	0.075 (3)
H13A	0.6421	−0.1739	0.1176	0.090*
H13B	0.8009	−0.1747	0.1139	0.090*
C14	0.6651 (10)	−0.3490 (8)	0.0593 (6)	0.077 (2)
H14A	0.6393	−0.3686	−0.0218	0.092*
H14B	0.5769	−0.3844	0.0712	0.092*
C15	0.8317 (11)	−0.3763 (7)	0.2137 (7)	0.072 (2)
H15	0.7487	−0.4155	0.2302	0.086*
C16	0.8786 (9)	−0.2384 (7)	0.2861 (6)	0.065 (2)
H16A	0.9699	−0.2010	0.2789	0.078*
H16B	0.8990	−0.2196	0.3666	0.078*
C17	0.9593 (11)	−0.4326 (8)	0.2388 (8)	0.076 (3)
H17A	1.0309	−0.4109	0.2061	0.113*
H17B	0.9204	−0.5244	0.2044	0.113*
H17C	1.0053	−0.3972	0.3213	0.113*
C18	0.8017 (6)	0.7408 (5)	0.8452 (4)	0.0354 (12)
C19	0.9057 (6)	0.8760 (5)	0.9286 (4)	0.0316 (11)
C20	0.8504 (6)	0.9742 (5)	0.9815 (5)	0.0378 (12)
H20	0.7497	0.9570	0.9688	0.045*
C21	0.9451 (6)	1.0990 (5)	1.0537 (5)	0.0368 (12)
H21	0.9081	1.1652	1.0898	0.044*
C22	0.2939 (5)	0.4741 (5)	0.5409 (5)	0.0325 (11)
C23	0.1424 (5)	0.4880 (5)	0.5192 (4)	0.0282 (10)
C24	0.1114 (6)	0.5848 (5)	0.6051 (5)	0.0343 (11)
H24	0.1860	0.6422	0.6753	0.041*
C25	−0.0300 (5)	0.5958 (5)	0.5861 (5)	0.0332 (11)
H25	−0.0498	0.6596	0.6442	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0276 (2)	0.0200 (2)	0.0276 (2)	0.00944 (14)	0.00617 (15)	0.00477 (15)
F1	0.098 (3)	0.053 (2)	0.045 (2)	0.041 (2)	0.045 (2)	0.0264 (18)
F2	0.089 (3)	0.0242 (16)	0.0424 (19)	0.0259 (17)	0.0203 (18)	0.0111 (15)
N1	0.041 (2)	0.025 (2)	0.029 (2)	0.0112 (18)	0.0114 (19)	0.0126 (18)
N2	0.069 (3)	0.038 (3)	0.029 (2)	0.032 (3)	0.015 (2)	0.006 (2)
N3	0.093 (5)	0.036 (3)	0.052 (3)	0.032 (3)	0.040 (3)	0.005 (3)
O1	0.062 (3)	0.035 (2)	0.035 (2)	0.0243 (19)	0.0226 (19)	0.0142 (17)
O2	0.077 (3)	0.047 (2)	0.025 (2)	0.030 (2)	0.017 (2)	0.0125 (18)
O3	0.063 (3)	0.0288 (19)	0.035 (2)	0.0267 (18)	0.0252 (19)	0.0163 (17)
O4	0.047 (2)	0.0251 (19)	0.044 (2)	0.0065 (17)	0.0060 (19)	0.0040 (17)
O5	0.035 (2)	0.030 (2)	0.052 (3)	0.0015 (17)	−0.0012 (19)	0.0012 (19)
O6	0.031 (2)	0.063 (3)	0.044 (2)	0.0183 (19)	0.0057 (18)	0.022 (2)
O7	0.036 (2)	0.038 (2)	0.052 (2)	0.0202 (17)	0.0229 (18)	0.0239 (19)
O8	0.065 (3)	0.116 (5)	0.087 (4)	0.031 (3)	0.023 (3)	0.072 (4)
O9	0.108 (6)	0.150 (8)	0.122 (7)	0.065 (6)	0.011 (5)	0.014 (6)
O10	0.150 (8)	0.133 (8)	0.190 (10)	0.070 (6)	0.079 (7)	0.095 (8)
C1	0.041 (3)	0.027 (3)	0.030 (3)	0.011 (2)	0.013 (2)	0.007 (2)
C2	0.035 (3)	0.027 (3)	0.024 (2)	0.011 (2)	0.009 (2)	0.006 (2)
C3	0.035 (3)	0.023 (2)	0.028 (3)	0.012 (2)	0.010 (2)	0.007 (2)
C4	0.036 (3)	0.022 (2)	0.026 (2)	0.012 (2)	0.009 (2)	0.006 (2)
C5	0.052 (3)	0.029 (3)	0.036 (3)	0.022 (2)	0.021 (3)	0.017 (2)
C6	0.055 (3)	0.041 (3)	0.028 (3)	0.023 (3)	0.020 (2)	0.014 (2)
C7	0.046 (3)	0.028 (3)	0.024 (3)	0.018 (2)	0.006 (2)	0.002 (2)
C8	0.046 (3)	0.020 (2)	0.030 (3)	0.015 (2)	0.008 (2)	0.007 (2)
C9	0.036 (3)	0.023 (2)	0.026 (2)	0.011 (2)	0.007 (2)	0.009 (2)
C10	0.044 (3)	0.025 (3)	0.023 (2)	0.011 (2)	0.010 (2)	0.008 (2)
C11	0.072 (4)	0.026 (3)	0.039 (3)	0.019 (3)	0.020 (3)	0.019 (2)
C12	0.064 (4)	0.047 (4)	0.050 (4)	0.029 (3)	0.014 (3)	0.028 (3)
C13	0.100 (6)	0.076 (5)	0.027 (3)	0.057 (5)	0.005 (3)	0.002 (3)
C14	0.101 (6)	0.071 (5)	0.045 (4)	0.048 (5)	0.023 (4)	0.008 (4)
C15	0.109 (7)	0.055 (4)	0.081 (5)	0.047 (5)	0.057 (5)	0.037 (4)
C16	0.084 (5)	0.058 (4)	0.040 (3)	0.050 (4)	0.008 (3)	0.005 (3)
C17	0.127 (7)	0.062 (5)	0.089 (6)	0.069 (5)	0.069 (6)	0.049 (5)
C18	0.043 (3)	0.028 (3)	0.025 (3)	0.004 (2)	0.008 (2)	0.008 (2)
C19	0.036 (3)	0.026 (3)	0.022 (2)	0.003 (2)	0.003 (2)	0.007 (2)
C20	0.032 (3)	0.032 (3)	0.035 (3)	0.003 (2)	0.005 (2)	0.009 (2)
C21	0.041 (3)	0.026 (3)	0.032 (3)	0.010 (2)	0.009 (2)	0.006 (2)
C22	0.027 (3)	0.029 (3)	0.043 (3)	0.007 (2)	0.008 (2)	0.021 (2)
C23	0.025 (2)	0.029 (2)	0.034 (3)	0.010 (2)	0.011 (2)	0.016 (2)
C24	0.027 (3)	0.034 (3)	0.031 (3)	0.005 (2)	0.006 (2)	0.009 (2)
C25	0.029 (3)	0.032 (3)	0.033 (3)	0.013 (2)	0.011 (2)	0.010 (2)

Geometric parameters (Å, º) top

Cd1—O6	2.213 (4)	C5—H5	0.9300
Cd1—O3	2.238 (3)	C6—C7	1.408 (8)
Cd1—O7ⁱ	2.295 (4)	C7—C8	1.391 (8)
Cd1—O1	2.299 (4)	C8—C9	1.398 (7)
Cd1—O5	2.322 (4)	C10—H10	0.9300
Cd1—O4	2.510 (4)	C11—C12	1.504 (9)
F1—C6	1.356 (6)	C11—H11A	0.9700
F2—C8	1.358 (6)	C11—H11B	0.9700
N1—C10	1.345 (6)	C12—H12A	0.9600
N1—C9	1.397 (7)	C12—H12B	0.9600
N1—C11	1.496 (6)	C12—H12C	0.9600
N2—C7	1.383 (7)	C13—C14	1.447 (11)
N2—C16	1.451 (8)	C13—H13A	0.9700
N2—C13	1.477 (8)	C13—H13B	0.9700
N3—C15	1.489 (10)	C14—H14A	0.9700
N3—C14	1.534 (10)	C14—H14B	0.9700
N3—H3A	0.8600	C15—C16	1.447 (10)
O1—C1	1.251 (6)	C15—C17	1.555 (11)
O2—C1	1.258 (7)	C15—H15	0.9800
O3—C3	1.261 (6)	C16—H16A	0.9700
O4—C18	1.243 (7)	C16—H16B	0.9700
O5—C18	1.253 (7)	C17—H17A	0.9600
O6—C22	1.255 (7)	C17—H17B	0.9600
O7—C22	1.261 (6)	C17—H17C	0.9600
O7—Cd1ⁱ	2.295 (4)	C18—C19	1.520 (7)
O8—H8A	0.8500	C19—C20	1.380 (8)
O8—H8B	0.8501	C19—C21ⁱⁱ	1.380 (8)
O9—H9A	0.8501	C20—C21	1.391 (8)
O9—H9B	0.8500	C20—H20	0.9300
O10—H5O	0.8523	C21—C19ⁱⁱ	1.380 (8)
O10—H6O	0.8530	C21—H21	0.9300
C1—C2	1.513 (7)	C22—C23	1.497 (7)
C2—C10	1.377 (7)	C23—C25ⁱⁱⁱ	1.391 (7)
C2—C3	1.427 (7)	C23—C24	1.399 (7)
C3—C4	1.466 (7)	C24—C25	1.389 (7)
C4—C9	1.405 (7)	C24—H24	0.9300
C4—C5	1.406 (7)	C25—C23ⁱⁱⁱ	1.391 (7)
C5—C6	1.353 (7)	C25—H25	0.9300

O6—Cd1—O3	120.64 (16)	N1—C11—H11B	109.4
O6—Cd1—O7ⁱ	102.79 (15)	C12—C11—H11B	109.4
O3—Cd1—O7ⁱ	89.23 (13)	H11A—C11—H11B	108.0
O6—Cd1—O1	91.71 (16)	C11—C12—H12A	109.5
O3—Cd1—O1	79.38 (13)	C11—C12—H12B	109.5
O7ⁱ—Cd1—O1	164.82 (13)	H12A—C12—H12B	109.5
O6—Cd1—O5	84.71 (16)	C11—C12—H12C	109.5
O3—Cd1—O5	154.35 (15)	H12A—C12—H12C	109.5
O7ⁱ—Cd1—O5	88.65 (16)	H12B—C12—H12C	109.5
O1—Cd1—O5	97.27 (15)	C14—C13—N2	111.1 (7)
O6—Cd1—O4	136.90 (15)	C14—C13—H13A	109.4
O3—Cd1—O4	100.57 (14)	N2—C13—H13A	109.4
O7ⁱ—Cd1—O4	88.88 (14)	C14—C13—H13B	109.4
O1—Cd1—O4	83.45 (15)	N2—C13—H13B	109.4
O5—Cd1—O4	53.83 (14)	H13A—C13—H13B	108.0
C10—N1—C9	119.0 (4)	C13—C14—N3	109.9 (7)
C10—N1—C11	117.2 (4)	C13—C14—H14A	109.7
C9—N1—C11	123.0 (4)	N3—C14—H14A	109.7
C7—N2—C16	122.9 (5)	C13—C14—H14B	109.7
C7—N2—C13	121.7 (5)	N3—C14—H14B	109.7
C16—N2—C13	113.6 (5)	H14A—C14—H14B	108.2
C15—N3—C14	111.3 (5)	C16—C15—N3	110.6 (6)
C15—N3—H3A	124.3	C16—C15—C17	110.9 (8)
C14—N3—H3A	124.3	N3—C15—C17	108.5 (6)
C1—O1—Cd1	132.5 (3)	C16—C15—H15	108.9
C3—O3—Cd1	132.3 (3)	N3—C15—H15	108.9
C18—O4—Cd1	87.0 (3)	C17—C15—H15	108.9
C18—O5—Cd1	95.5 (3)	C15—C16—N2	113.7 (6)
C22—O6—Cd1	114.2 (4)	C15—C16—H16A	108.8
C22—O7—Cd1ⁱ	129.7 (3)	N2—C16—H16A	108.8
H8A—O8—H8B	108.7	C15—C16—H16B	108.8
H9A—O9—H9B	108.4	N2—C16—H16B	108.8
H5O—O10—H6O	107.2	H16A—C16—H16B	107.7
O1—C1—O2	123.6 (5)	C15—C17—H17A	109.5
O1—C1—C2	119.5 (5)	C15—C17—H17B	109.5
O2—C1—C2	117.0 (5)	H17A—C17—H17B	109.5
C10—C2—C3	118.5 (4)	C15—C17—H17C	109.5
C10—C2—C1	116.5 (4)	H17A—C17—H17C	109.5
C3—C2—C1	125.0 (5)	H17B—C17—H17C	109.5
O3—C3—C2	126.5 (4)	O4—C18—O5	123.0 (5)
O3—C3—C4	117.8 (4)	O4—C18—C19	118.8 (5)
C2—C3—C4	115.6 (4)	O5—C18—C19	118.2 (5)
C9—C4—C5	119.6 (4)	O4—C18—Cd1	66.0 (3)
C9—C4—C3	122.0 (5)	O5—C18—Cd1	57.4 (3)
C5—C4—C3	118.3 (4)	C19—C18—Cd1	170.3 (4)
C6—C5—C4	120.1 (5)	C20—C19—C21ⁱⁱ	120.3 (5)
C6—C5—H5	119.9	C20—C19—C18	120.2 (5)
C4—C5—H5	119.9	C21ⁱⁱ—C19—C18	119.5 (5)
C5—C6—F1	119.3 (5)	C19—C20—C21	120.1 (5)
C5—C6—C7	123.1 (5)	C19—C20—H20	120.0
F1—C6—C7	117.6 (5)	C21—C20—H20	120.0
N2—C7—C8	121.2 (5)	C19ⁱⁱ—C21—C20	119.6 (5)
N2—C7—C6	123.6 (5)	C19ⁱⁱ—C21—H21	120.2
C8—C7—C6	115.2 (5)	C20—C21—H21	120.2
F2—C8—C7	116.0 (4)	O6—C22—O7	122.8 (5)
F2—C8—C9	119.7 (5)	O6—C22—C23	117.1 (5)
C7—C8—C9	124.2 (5)	O7—C22—C23	120.1 (5)
N1—C9—C8	124.1 (5)	C25ⁱⁱⁱ—C23—C24	119.0 (5)
N1—C9—C4	118.6 (4)	C25ⁱⁱⁱ—C23—C22	120.5 (5)
C8—C9—C4	117.3 (5)	C24—C23—C22	120.5 (5)
N1—C10—C2	125.9 (5)	C25—C24—C23	120.5 (5)
N1—C10—H10	117.0	C25—C24—H24	119.8
C2—C10—H10	117.0	C23—C24—H24	119.8
N1—C11—C12	111.1 (5)	C24—C25—C23ⁱⁱⁱ	120.5 (5)
N1—C11—H11A	109.4	C24—C25—H25	119.7
C12—C11—H11A	109.4	C23ⁱⁱⁱ—C25—H25	119.7

O6—Cd1—O1—C1	140.3 (5)	F2—C8—C9—N1	8.1 (8)
O3—Cd1—O1—C1	19.4 (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—C4	6.2 (8)
O4—Cd1—O1—C1	−82.7 (5)	C5—C4—C9—N1	177.0 (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—C3	168.9 (5)	C3—C4—C9—C8	177.3 (5)
O1—Cd1—O3—C3	−1.0 (5)	C9—N1—C10—C2	4.2 (8)
O5—Cd1—O3—C3	83.6 (6)	C11—N1—C10—C2	174.6 (5)
O4—Cd1—O3—C3	80.2 (5)	C3—C2—C10—N1	−0.4 (8)
C18—Cd1—O3—C3	83.7 (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—C18	173.7 (3)	C9—N1—C11—C12	70.5 (7)
O7ⁱ—Cd1—O4—C18	84.7 (3)	C7—N2—C13—C14	−140.9 (7)
O1—Cd1—O4—C18	−108.4 (3)	C16—N2—C13—C14	54.0 (10)
O5—Cd1—O4—C18	−4.4 (3)	N2—C13—C14—N3	−55.0 (9)
O6—Cd1—O5—C18	171.8 (4)	C15—N3—C14—C13	56.4 (9)
O3—Cd1—O5—C18	0.2 (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—C18	80.8 (4)	N3—C15—C16—N2	52.3 (9)
O4—Cd1—O5—C18	4.4 (3)	C17—C15—C16—N2	172.7 (6)
O3—Cd1—O6—C22	−54.1 (4)	C7—N2—C16—C15	142.6 (7)
O7ⁱ—Cd1—O6—C22	42.7 (4)	C13—N2—C16—C15	−52.6 (10)
O1—Cd1—O6—C22	−132.8 (4)	Cd1—O4—C18—O5	7.9 (6)
O5—Cd1—O6—C22	130.1 (4)	Cd1—O4—C18—C19	−170.6 (4)
O4—Cd1—O6—C22	145.0 (3)	Cd1—O5—C18—O4	−8.6 (6)
C18—Cd1—O6—C22	134.0 (4)	Cd1—O5—C18—C19	170.0 (4)
Cd1—O1—C1—O2	149.8 (5)	O6—Cd1—C18—O4	163.4 (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—C10	18.9 (7)	O1—Cd1—C18—O4	70.6 (3)
O1—C1—C2—C3	20.2 (8)	O5—Cd1—C18—O4	172.1 (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—C4	178.5 (3)	O7ⁱ—Cd1—C18—O5	93.7 (4)
C10—C2—C3—O3	178.2 (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—C4	174.2 (5)	O3—Cd1—C18—C19	114 (2)
O3—C3—C4—C9	−176.7 (5)	O7ⁱ—Cd1—C18—C19	28 (2)
C2—C3—C4—C9	5.6 (7)	O1—Cd1—C18—C19	−167 (2)
O3—C3—C4—C5	4.1 (7)	O5—Cd1—C18—C19	−66 (2)
C2—C3—C4—C5	−173.5 (5)	O4—Cd1—C18—C19	122 (2)
C9—C4—C5—C6	−1.7 (8)	O4—C18—C19—C20	−166.3 (5)
C3—C4—C5—C6	177.5 (5)	O5—C18—C19—C20	15.0 (8)
C4—C5—C6—F1	−174.0 (5)	Cd1—C18—C19—C20	76 (2)
C4—C5—C6—C7	4.7 (9)	O4—C18—C19—C21ⁱⁱ	17.0 (8)
C16—N2—C7—C8	−50.8 (9)	O5—C18—C19—C21ⁱⁱ	−161.7 (5)
C13—N2—C7—C8	145.6 (7)	Cd1—C18—C19—C21ⁱⁱ	−101 (2)
C16—N2—C7—C6	130.3 (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—N2	176.7 (6)	C19—C20—C21—C19ⁱⁱ	0.5 (9)
F1—C6—C7—N2	−4.5 (9)	Cd1—O6—C22—O7	8.1 (7)
C5—C6—C7—C8	−2.3 (9)	Cd1—O6—C22—C23	−173.2 (3)
F1—C6—C7—C8	176.5 (5)	Cd1ⁱ—O7—C22—O6	−109.6 (5)
N2—C7—C8—F2	−4.8 (8)	Cd1ⁱ—O7—C22—C23	71.8 (6)
C6—C7—C8—F2	174.2 (5)	O6—C22—C23—C25ⁱⁱⁱ	−155.0 (5)
N2—C7—C8—C9	177.6 (5)	O7—C22—C23—C25ⁱⁱⁱ	23.7 (7)
C6—C7—C8—C9	−3.4 (8)	O6—C22—C23—C24	24.4 (7)
C10—N1—C9—C8	177.8 (5)	O7—C22—C23—C24	−156.9 (5)
C11—N1—C9—C8	8.1 (8)	C25ⁱⁱⁱ—C23—C24—C25	1.0 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O8	0.86	2.33	2.749 (8)	110
O8—H8A···O2^iv	0.85	2.02	2.854 (7)	166
O8—H8B···O4^v	0.85	2.01	2.837 (7)	166
O9—H9B···O10^vi	0.85	1.84	2.687 (14)	178
O9—H9A···O5^vii	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: (iv) −x+2, −y, −z+1; (v) x, y−1, z−1; (vi) −x+1, −y, −z+2; (vii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₇H₁₈F₂N₃O₃)(C₈H₄O₄)]·3H₂O
M_r	680.90
Crystal system, space group	Triclinic, 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)
V (Å³)	1327.00 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.32 × 0.24 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.762, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	6581, 4624, 4108
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.135, 1.11
No. of reflections	4624
No. of parameters	372
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—O6	2.213 (4)	Cd1—O1	2.299 (4)
Cd1—O3	2.238 (3)	Cd1—O5	2.322 (4)
Cd1—O7ⁱ	2.295 (4)	Cd1—O4	2.510 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···O10^iv	0.85	1.84	2.687 (14)	178
O9—H9A···O5^v	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.

Acknowledgements

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

References

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
Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 (Suppl. A), 41–45. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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