catena-Poly[[diaqua­[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ato-κ2O,O′]nickel(II)]-μ-4,4′-oxydibenzoato-κ2O:O′]

Hong, J.

doi:10.1107/S1600536807062216

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m17

https://doi.org/10.1107/S1600536807062216

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catena-Poly[[diaqua[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylato-κ²O,O′]nickel(II)]-μ-4,4′-oxydibenzoato-κ²O:O′]

Jun Hong ^a ^*

^aDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
^*Correspondence e-mail: junhong000@hotmail.com

(Received 6 November 2007; accepted 22 November 2007; online 6 December 2007)

In the title compound, [Ni(C₁₆H₁₈FN₃O₃)(C₁₄H₈O₅)(H₂O)₂]_n, the Ni^II atom exhibits a distorted octahedral geometry that is defined by four O atoms and two water molecules. Ni atoms are connected via the 4,4′-oxydibenzoate anions into a one-dimensional chain running along the crystallographic [ $[\overline2]$ 30] direction. In the crystal structure, the one-dimensional chains are connected via N—H⋯O and O—H⋯O hydrogen bonding to form a three-dimensional supramolecular network.

Related literature

For general background, see: Xiao et al. (2005 ). For a related structure, see: An et al. (2005 ).

Experimental

Crystal data

[Ni(C₁₆H₁₈FN₃O₃)(C₁₄H₈O₅)(H₂O)₂]
M_r = 670.28
Triclinic, $[P \overline 1]$
a = 10.105 (2) Å
b = 12.230 (2) Å
c = 13.052 (3) Å
α = 72.50 (3)°
β = 73.13 (3)°
γ = 77.57 (3)°
V = 1457.7 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 298 (2) K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.798, T_max = 0.855
11571 measured reflections
5134 independent reflections
4210 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.02
5134 reflections
406 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H4⋯O2	0.85	1.93	2.695 (3)	149
O2W—H4⋯O1	0.85	2.55	2.965 (3)	111
N3—H3B⋯O2ⁱ	0.90	1.82	2.714 (3)	170
N3—H3C⋯O8ⁱⁱ	0.90	1.85	2.719 (3)	162
O1W—H1⋯O1ⁱⁱⁱ	0.85	2.03	2.761 (3)	144
O1W—H2⋯O4^iv	0.85	1.99	2.834 (3)	173
O2W—H3⋯O5^v	0.85	1.82	2.615 (3)	155
Symmetry codes: (i) x, y+1, z; (ii) x-1, y+1, z; (iii) -x+1, -y, -z+1; (iv) -x, -y+1, -z+1; (v) x+1, y-1, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062216/im2047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062216/im2047Isup2.hkl

checkCIF report

Comment top

Norfloxacin [1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid, Hcf] is a member of a class of quinolones that is used to treat infections (Xiao et al. 2005; An et al. 2005), As a part of our ongoing investigations in this field we report here the crystal structure of the title compound. In the crystal structure of the title compound, the Ni atoms are coordinated by three oxygen atoms of two Hcf ligand and one 4,4'-oxy-bisbenzoate, one oxygen atom from one symmetry related 4,4'-oxy-bisbenzoate and two water molecules within a distorted octahedral geometry (Figure 1). The nickel atoms are linked by the 4,4'-oxy-bisbenzoate anions into a one-dimensional chain running along crystallographic [-1, 1.5, 0] direction. The adjacent chains are further extended into a two-dimensional supramolecular network by N—H···O and O—H···O hydrogen bonds(Tab. 1).

Related literature top

For general background, see: Xiao et al. (2005). For related structures, see: An et al. (2005).

Experimental top

Compound (I) was prepared by a hydrothermal method. A mixture of Ni(NO₃)₂.6H₂O (0.15 g 0.5 mmol), norfloxacin (0.16 g 0.5 mmol), 4,4'-oxy-bisbenzoic acid (0.13 g 0.5 mmol) and water (10 ml) was stirred for 20 min and then transferred to a 23 ml Teflon reactor. The reactor was kept at 433 K for 72 h under autogenous pressure. Single crystals of (I) were obtained after cooling to room temperature.

Structure description top

For general background, see: Xiao et al. (2005). For related structures, see: An et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. Crystal structure of (I) with labeling and displacement ellipsoids drawn at the 50% probability level. Symmetry code: i = x + 1,y - 1,z

catena-Poly[[diaqua[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4- dihydroquinoline-3-carboxylato-κ²O,O']nickel(II)]-µ-4,4'-oxydibenzoato- κ²O:O'] top

Crystal data top

[Ni(C₁₆H₁₈FN₃O₃)(C₁₄H₈O₅)(H₂O)₂]	Z = 2
M_r = 670.28	F(000) = 696
Triclinic, P1	D_x = 1.527 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.105 (2) Å	Cell parameters from 11571 reflections
b = 12.230 (2) Å	θ = 3.0–25.0°
c = 13.052 (3) Å	µ = 0.74 mm⁻¹
α = 72.50 (3)°	T = 298 K
β = 73.13 (3)°	Block, green
γ = 77.57 (3)°	0.32 × 0.24 × 0.22 mm
V = 1457.7 (5) Å³

Data collection top

Bruker APEX CCD area-detector diffractometer	5134 independent reflections
Radiation source: fine-focus sealed tube	4210 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.798, T_max = 0.855	k = −14→14
11571 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0674P)² + 0.5873P] where P = (F_o² + 2F_c²)/3
5134 reflections	(Δ/σ)_max = 0.001
406 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Ni(C₁₆H₁₈FN₃O₃)(C₁₄H₈O₅)(H₂O)₂]	γ = 77.57 (3)°
M_r = 670.28	V = 1457.7 (5) Å³
Triclinic, P1	Z = 2
a = 10.105 (2) Å	Mo Kα radiation
b = 12.230 (2) Å	µ = 0.74 mm⁻¹
c = 13.052 (3) Å	T = 298 K
α = 72.50 (3)°	0.32 × 0.24 × 0.22 mm
β = 73.13 (3)°

Data collection top

Bruker APEX CCD area-detector diffractometer	5134 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4210 reflections with I > 2σ(I)
T_min = 0.798, T_max = 0.855	R_int = 0.027
11571 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.73 e Å⁻³
5134 reflections	Δρ_min = −0.42 e Å⁻³
406 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
Ni1	0.55118 (3)	0.06895 (3)	0.29346 (3)	0.02717 (12)
F1	0.11227 (19)	0.57062 (15)	0.2085 (2)	0.0690 (7)
C1	0.1138 (3)	0.1404 (2)	0.3988 (2)	0.0293 (6)
C2	−0.0181 (3)	0.1367 (3)	0.3899 (3)	0.0407 (7)
H2A	−0.0297	0.0864	0.3532	0.049*
C3	−0.1329 (3)	0.2070 (3)	0.4349 (3)	0.0409 (7)
H3A	−0.2216	0.2037	0.4295	0.049*
C4	−0.1139 (3)	0.2818 (2)	0.4879 (2)	0.0339 (6)
C5	0.0162 (3)	0.2876 (2)	0.4971 (3)	0.0390 (7)
H5A	0.0276	0.3396	0.5322	0.047*
C6	0.1296 (3)	0.2156 (2)	0.4539 (2)	0.0351 (6)
H6A	0.2175	0.2175	0.4618	0.042*
C7	0.2412 (3)	0.0689 (2)	0.3475 (2)	0.0296 (6)
C8	−0.2530 (3)	0.4649 (2)	0.4784 (2)	0.0314 (6)
C9	−0.3601 (3)	0.5352 (2)	0.5311 (2)	0.0362 (7)
H9AA	−0.4120	0.5051	0.6021	0.043*
C10	−0.3900 (3)	0.6506 (2)	0.4779 (3)	0.0376 (7)
H10A	−0.4615	0.6979	0.5139	0.045*
C11	−0.3143 (3)	0.6967 (2)	0.3712 (2)	0.0311 (6)
C12	−0.2076 (3)	0.6244 (2)	0.3210 (2)	0.0370 (7)
H12A	−0.1554	0.6541	0.2500	0.044*
C13	−0.1759 (3)	0.5093 (2)	0.3730 (3)	0.0401 (7)
H13A	−0.1035	0.4622	0.3375	0.048*
C14	−0.3468 (3)	0.8187 (2)	0.3084 (2)	0.0338 (6)
C15	0.7543 (3)	0.4092 (2)	0.1121 (3)	0.0388 (7)
H15A	0.8511	0.4014	0.0884	0.047*
C16	0.6950 (3)	0.3094 (2)	0.1539 (2)	0.0302 (6)
C17	0.5467 (3)	0.3187 (2)	0.1938 (2)	0.0285 (6)
C18	0.4717 (3)	0.4358 (2)	0.1767 (2)	0.0299 (6)
C19	0.5390 (3)	0.5341 (2)	0.1316 (2)	0.0317 (6)
C20	0.7920 (3)	0.1960 (2)	0.1557 (2)	0.0291 (6)
C21	0.3258 (3)	0.4520 (2)	0.2061 (3)	0.0380 (7)
H21A	0.2780	0.3882	0.2377	0.046*
C22	0.2540 (3)	0.5596 (2)	0.1887 (3)	0.0406 (7)
C23	0.3163 (3)	0.6614 (2)	0.1475 (2)	0.0317 (6)
C24	0.4612 (3)	0.6458 (2)	0.1191 (2)	0.0340 (6)
H24A	0.5080	0.7102	0.0914	0.041*
C25	0.1290 (3)	0.7917 (2)	0.2333 (2)	0.0378 (7)
H25A	0.1751	0.8083	0.2815	0.045*
H25B	0.0842	0.7233	0.2734	0.045*
C26	0.0199 (3)	0.8933 (2)	0.2016 (3)	0.0389 (7)
H26A	−0.0283	0.8761	0.1552	0.047*
H26B	−0.0483	0.9074	0.2676	0.047*
C27	0.1966 (3)	0.9750 (2)	0.0411 (2)	0.0391 (7)
H27A	0.2439	1.0425	0.0034	0.047*
H27B	0.1515	0.9616	−0.0095	0.047*
C28	0.3032 (3)	0.8699 (2)	0.0731 (2)	0.0363 (7)
H28A	0.3698	0.8545	0.0069	0.044*
H28B	0.3539	0.8856	0.1186	0.044*
C29	0.7665 (4)	0.6173 (3)	0.0620 (3)	0.0503 (9)
H29A	0.7179	0.6750	0.1024	0.060*
H29B	0.8569	0.5905	0.0795	0.060*
C30	0.7883 (5)	0.6721 (4)	−0.0552 (4)	0.0830 (14)
H30A	0.8412	0.7348	−0.0738	0.124*
H30B	0.6996	0.7015	−0.0733	0.124*
H30C	0.8385	0.6165	−0.0963	0.124*
N1	0.6856 (3)	0.51763 (19)	0.1020 (2)	0.0386 (6)
N2	0.2331 (2)	0.76972 (18)	0.13355 (19)	0.0316 (5)
N3	0.0891 (2)	0.99712 (18)	0.14108 (18)	0.0300 (5)
H3B	0.1298	1.0151	0.1856	0.036*
H3C	0.0252	1.0575	0.1207	0.036*
O1	0.34733 (19)	0.05291 (16)	0.38500 (15)	0.0317 (4)
O2	0.2384 (2)	0.0318 (2)	0.26830 (19)	0.0491 (6)
O3	−0.2308 (2)	0.35044 (16)	0.53603 (17)	0.0446 (5)
O4	−0.3916 (2)	0.89556 (15)	0.36257 (16)	0.0332 (4)
O5	−0.3263 (3)	0.83834 (18)	0.20552 (17)	0.0509 (6)
O6	0.4769 (2)	0.23599 (15)	0.23930 (18)	0.0385 (5)
O7	0.7459 (2)	0.10163 (15)	0.20642 (17)	0.0360 (5)
O8	0.9162 (2)	0.20092 (16)	0.10377 (18)	0.0407 (5)
O1W	0.5830 (2)	0.10404 (15)	0.43009 (15)	0.0325 (4)
H1	0.6392	0.0565	0.4655	0.049*
H2	0.5204	0.1036	0.4899	0.049*
O2W	0.5096 (2)	0.03404 (17)	0.16040 (15)	0.0380 (5)
H3	0.5639	−0.0287	0.1553	0.057*
H4	0.4342	0.0066	0.1966	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0245 (2)	0.01742 (18)	0.0365 (2)	0.00159 (13)	−0.00766 (14)	−0.00538 (14)
F1	0.0262 (10)	0.0311 (10)	0.138 (2)	0.0047 (8)	−0.0149 (11)	−0.0157 (12)
C1	0.0265 (14)	0.0263 (13)	0.0341 (14)	0.0016 (11)	−0.0103 (11)	−0.0071 (12)
C2	0.0313 (16)	0.0398 (17)	0.0594 (19)	0.0024 (13)	−0.0171 (14)	−0.0244 (15)
C3	0.0245 (15)	0.0416 (17)	0.0572 (19)	0.0005 (13)	−0.0128 (14)	−0.0143 (15)
C4	0.0314 (16)	0.0246 (13)	0.0334 (14)	0.0030 (11)	−0.0005 (12)	−0.0012 (12)
C5	0.0419 (18)	0.0313 (15)	0.0444 (16)	−0.0016 (13)	−0.0073 (14)	−0.0162 (13)
C6	0.0284 (15)	0.0361 (15)	0.0440 (16)	−0.0022 (12)	−0.0107 (13)	−0.0149 (13)
C7	0.0252 (14)	0.0247 (13)	0.0373 (14)	−0.0033 (11)	−0.0074 (12)	−0.0061 (12)
C8	0.0299 (15)	0.0236 (13)	0.0380 (15)	0.0003 (11)	−0.0072 (12)	−0.0080 (12)
C9	0.0347 (16)	0.0298 (14)	0.0351 (15)	−0.0009 (12)	0.0019 (12)	−0.0078 (12)
C10	0.0341 (16)	0.0254 (14)	0.0486 (17)	0.0035 (12)	−0.0003 (13)	−0.0172 (13)
C11	0.0313 (15)	0.0215 (13)	0.0414 (15)	−0.0003 (11)	−0.0100 (12)	−0.0104 (12)
C12	0.0378 (16)	0.0288 (14)	0.0343 (15)	0.0023 (12)	−0.0025 (13)	−0.0044 (12)
C13	0.0377 (17)	0.0283 (14)	0.0440 (17)	0.0081 (12)	−0.0015 (13)	−0.0112 (13)
C14	0.0296 (15)	0.0248 (13)	0.0421 (16)	0.0007 (11)	−0.0047 (12)	−0.0084 (13)
C15	0.0280 (15)	0.0281 (14)	0.0558 (18)	0.0033 (12)	−0.0069 (13)	−0.0125 (14)
C16	0.0296 (14)	0.0203 (13)	0.0385 (14)	0.0036 (11)	−0.0100 (12)	−0.0076 (11)
C17	0.0298 (15)	0.0220 (13)	0.0315 (13)	0.0013 (11)	−0.0093 (11)	−0.0051 (11)
C18	0.0297 (15)	0.0196 (13)	0.0366 (14)	0.0027 (11)	−0.0086 (12)	−0.0056 (11)
C19	0.0293 (15)	0.0236 (13)	0.0378 (15)	0.0043 (11)	−0.0062 (12)	−0.0091 (12)
C20	0.0275 (15)	0.0218 (13)	0.0384 (14)	0.0050 (11)	−0.0124 (12)	−0.0098 (12)
C21	0.0292 (16)	0.0205 (13)	0.0578 (18)	0.0000 (11)	−0.0088 (14)	−0.0046 (13)
C22	0.0243 (15)	0.0273 (15)	0.065 (2)	0.0028 (12)	−0.0099 (14)	−0.0092 (14)
C23	0.0355 (16)	0.0207 (13)	0.0325 (14)	0.0049 (11)	−0.0063 (12)	−0.0058 (11)
C24	0.0320 (16)	0.0210 (13)	0.0423 (15)	0.0006 (11)	−0.0040 (12)	−0.0062 (12)
C25	0.0360 (16)	0.0260 (14)	0.0393 (15)	0.0028 (12)	−0.0004 (13)	−0.0042 (13)
C26	0.0301 (16)	0.0286 (15)	0.0543 (18)	0.0039 (12)	−0.0087 (14)	−0.0123 (14)
C27	0.0502 (19)	0.0229 (14)	0.0338 (15)	0.0068 (13)	−0.0050 (13)	−0.0053 (12)
C28	0.0371 (16)	0.0234 (14)	0.0365 (15)	0.0039 (12)	0.0016 (13)	−0.0064 (12)
C29	0.0393 (18)	0.0307 (16)	0.074 (2)	−0.0037 (13)	−0.0025 (17)	−0.0153 (16)
C30	0.088 (3)	0.074 (3)	0.079 (3)	−0.038 (3)	−0.003 (3)	−0.006 (2)
N1	0.0310 (13)	0.0212 (11)	0.0551 (15)	0.0002 (10)	−0.0009 (11)	−0.0092 (11)
N2	0.0316 (13)	0.0190 (11)	0.0361 (12)	0.0060 (9)	−0.0057 (10)	−0.0046 (10)
N3	0.0279 (12)	0.0234 (11)	0.0384 (12)	0.0072 (9)	−0.0133 (10)	−0.0096 (10)
O1	0.0242 (10)	0.0338 (10)	0.0353 (10)	0.0003 (8)	−0.0091 (8)	−0.0073 (8)
O2	0.0320 (11)	0.0685 (15)	0.0625 (14)	0.0049 (11)	−0.0154 (10)	−0.0441 (13)
O3	0.0400 (12)	0.0256 (10)	0.0474 (12)	0.0098 (9)	0.0040 (10)	−0.0032 (9)
O4	0.0358 (11)	0.0200 (9)	0.0412 (10)	0.0031 (8)	−0.0084 (9)	−0.0097 (8)
O5	0.0719 (16)	0.0305 (11)	0.0384 (12)	0.0122 (11)	−0.0074 (11)	−0.0107 (10)
O6	0.0259 (10)	0.0200 (9)	0.0609 (13)	0.0017 (8)	−0.0084 (9)	−0.0030 (9)
O7	0.0287 (10)	0.0183 (9)	0.0529 (12)	0.0031 (8)	−0.0060 (9)	−0.0054 (9)
O8	0.0239 (11)	0.0249 (10)	0.0624 (13)	0.0040 (8)	−0.0038 (10)	−0.0069 (10)
O1W	0.0312 (10)	0.0279 (10)	0.0402 (10)	−0.0021 (8)	−0.0123 (9)	−0.0095 (9)
O2W	0.0382 (12)	0.0347 (11)	0.0350 (10)	−0.0016 (9)	−0.0046 (9)	−0.0067 (9)

Geometric parameters (Å, º) top

Ni1—O6	2.0039 (19)	C17—C18	1.455 (3)
Ni1—O7	2.022 (2)	C18—C19	1.396 (4)
Ni1—O4ⁱ	2.0663 (19)	C18—C21	1.397 (4)
Ni1—O1	2.077 (2)	C19—N1	1.404 (4)
Ni1—O1W	2.0786 (19)	C19—C24	1.410 (4)
Ni1—O2W	2.079 (2)	C20—O8	1.246 (3)
F1—C22	1.363 (3)	C20—O7	1.257 (3)
C1—C2	1.382 (4)	C21—C22	1.347 (4)
C1—C6	1.384 (4)	C21—H21A	0.9300
C1—C7	1.496 (4)	C22—C23	1.406 (4)
C2—C3	1.381 (4)	C23—C24	1.387 (4)
C2—H2A	0.9300	C23—N2	1.400 (3)
C3—C4	1.372 (4)	C24—H24A	0.9300
C3—H3A	0.9300	C25—N2	1.473 (3)
C4—C5	1.373 (4)	C25—C26	1.516 (4)
C4—O3	1.398 (3)	C25—H25A	0.9700
C5—C6	1.377 (4)	C25—H25B	0.9700
C5—H5A	0.9300	C26—N3	1.477 (4)
C6—H6A	0.9300	C26—H26A	0.9700
C7—O2	1.257 (3)	C26—H26B	0.9700
C7—O1	1.259 (3)	C27—N3	1.490 (3)
C8—O3	1.381 (3)	C27—C28	1.526 (4)
C8—C13	1.381 (4)	C27—H27A	0.9700
C8—C9	1.381 (4)	C27—H27B	0.9700
C9—C10	1.382 (4)	C28—N2	1.447 (4)
C9—H9AA	0.9300	C28—H28A	0.9700
C10—C11	1.393 (4)	C28—H28B	0.9700
C10—H10A	0.9300	C29—C30	1.446 (6)
C11—C12	1.379 (4)	C29—N1	1.492 (4)
C11—C14	1.488 (4)	C29—H29A	0.9700
C12—C13	1.379 (4)	C29—H29B	0.9700
C12—H12A	0.9300	C30—H30A	0.9600
C13—H13A	0.9300	C30—H30B	0.9600
C14—O5	1.253 (4)	C30—H30C	0.9600
C14—O4	1.273 (3)	N3—H3B	0.9000
C15—N1	1.345 (4)	N3—H3C	0.9000
C15—C16	1.368 (4)	O4—Ni1ⁱⁱ	2.0663 (19)
C15—H15A	0.9300	O1W—H1	0.8500
C16—C17	1.428 (4)	O1W—H2	0.8501
C16—C20	1.515 (3)	O2W—H3	0.8500
C17—O6	1.255 (3)	O2W—H4	0.8499

O6—Ni1—O7	89.94 (8)	O8—C20—C16	117.4 (2)
O6—Ni1—O4ⁱ	173.89 (8)	O7—C20—C16	120.1 (2)
O7—Ni1—O4ⁱ	95.85 (8)	C22—C21—C18	120.3 (3)
O6—Ni1—O1	84.98 (8)	C22—C21—H21A	119.9
O7—Ni1—O1	173.98 (7)	C18—C21—H21A	119.9
O4ⁱ—Ni1—O1	89.13 (8)	C21—C22—F1	118.1 (3)
O6—Ni1—O1W	90.05 (8)	C21—C22—C23	124.1 (3)
O7—Ni1—O1W	90.44 (8)	F1—C22—C23	117.8 (2)
O4ⁱ—Ni1—O1W	87.94 (8)	C24—C23—N2	124.1 (3)
O1—Ni1—O1W	86.35 (8)	C24—C23—C22	115.7 (2)
O6—Ni1—O2W	89.40 (9)	N2—C23—C22	120.1 (3)
O7—Ni1—O2W	92.15 (9)	C23—C24—C19	121.3 (3)
O4ⁱ—Ni1—O2W	92.34 (8)	C23—C24—H24A	119.3
O1—Ni1—O2W	91.02 (8)	C19—C24—H24A	119.3
O1W—Ni1—O2W	177.35 (7)	N2—C25—C26	110.2 (2)
C2—C1—C6	119.0 (2)	N2—C25—H25A	109.6
C2—C1—C7	122.3 (2)	C26—C25—H25A	109.6
C6—C1—C7	118.6 (2)	N2—C25—H25B	109.6
C3—C2—C1	120.8 (3)	C26—C25—H25B	109.6
C3—C2—H2A	119.6	H25A—C25—H25B	108.1
C1—C2—H2A	119.6	N3—C26—C25	109.2 (2)
C2—C3—C4	118.9 (3)	N3—C26—H26A	109.8
C2—C3—H3A	120.5	C25—C26—H26A	109.8
C4—C3—H3A	120.5	N3—C26—H26B	109.8
C5—C4—C3	121.3 (3)	C25—C26—H26B	109.8
C5—C4—O3	119.9 (3)	H26A—C26—H26B	108.3
C3—C4—O3	118.8 (3)	N3—C27—C28	110.7 (2)
C4—C5—C6	119.3 (3)	N3—C27—H27A	109.5
C4—C5—H5A	120.3	C28—C27—H27A	109.5
C6—C5—H5A	120.3	N3—C27—H27B	109.5
C5—C6—C1	120.6 (3)	C28—C27—H27B	109.5
C5—C6—H6A	119.7	H27A—C27—H27B	108.1
C1—C6—H6A	119.7	N2—C28—C27	110.0 (2)
O2—C7—O1	123.9 (2)	N2—C28—H28A	109.7
O2—C7—C1	119.1 (2)	C27—C28—H28A	109.7
O1—C7—C1	116.9 (2)	N2—C28—H28B	109.7
O3—C8—C13	123.3 (2)	C27—C28—H28B	109.7
O3—C8—C9	116.5 (2)	H28A—C28—H28B	108.2
C13—C8—C9	120.3 (3)	C30—C29—N1	114.9 (3)
C8—C9—C10	119.8 (3)	C30—C29—H29A	108.5
C8—C9—H9AA	120.1	N1—C29—H29A	108.5
C10—C9—H9AA	120.1	C30—C29—H29B	108.5
C9—C10—C11	120.8 (2)	N1—C29—H29B	108.5
C9—C10—H10A	119.6	H29A—C29—H29B	107.5
C11—C10—H10A	119.6	C29—C30—H30A	109.5
C12—C11—C10	118.0 (3)	C29—C30—H30B	109.5
C12—C11—C14	119.1 (3)	H30A—C30—H30B	109.5
C10—C11—C14	122.9 (2)	C29—C30—H30C	109.5
C13—C12—C11	122.0 (3)	H30A—C30—H30C	109.5
C13—C12—H12A	119.0	H30B—C30—H30C	109.5
C11—C12—H12A	119.0	C15—N1—C19	119.0 (2)
C12—C13—C8	119.2 (3)	C15—N1—C29	119.4 (3)
C12—C13—H13A	120.4	C19—N1—C29	121.5 (2)
C8—C13—H13A	120.4	C23—N2—C28	117.2 (2)
O5—C14—O4	124.8 (3)	C23—N2—C25	115.8 (2)
O5—C14—C11	117.4 (2)	C28—N2—C25	110.8 (2)
O4—C14—C11	117.9 (2)	C26—N3—C27	110.1 (2)
N1—C15—C16	126.1 (3)	C26—N3—H3B	109.6
N1—C15—H15A	116.9	C27—N3—H3B	109.6
C16—C15—H15A	116.9	C26—N3—H3C	109.6
C15—C16—C17	118.2 (2)	C27—N3—H3C	109.6
C15—C16—C20	117.5 (2)	H3B—N3—H3C	108.2
C17—C16—C20	124.4 (2)	C7—O1—Ni1	126.74 (17)
O6—C17—C16	126.2 (2)	C8—O3—C4	116.6 (2)
O6—C17—C18	118.1 (2)	C14—O4—Ni1ⁱⁱ	124.49 (18)
C16—C17—C18	115.7 (2)	C17—O6—Ni1	126.84 (18)
C19—C18—C21	117.9 (2)	C20—O7—Ni1	130.58 (17)
C19—C18—C17	122.9 (2)	Ni1—O1W—H1	118.9
C21—C18—C17	119.2 (2)	Ni1—O1W—H2	123.4
C18—C19—N1	117.8 (2)	H1—O1W—H2	90.7
C18—C19—C24	120.6 (3)	Ni1—O2W—H3	102.1
N1—C19—C24	121.6 (3)	Ni1—O2W—H4	96.0
O8—C20—O7	122.5 (2)	H3—O2W—H4	99.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H4···O2	0.85	1.93	2.695 (3)	149
O2W—H4···O1	0.85	2.55	2.965 (3)	111
N3—H3B···O2ⁱⁱⁱ	0.90	1.82	2.714 (3)	170
N3—H3C···O8ⁱⁱ	0.90	1.85	2.719 (3)	162
O1W—H1···O1^iv	0.85	2.03	2.761 (3)	144
O1W—H2···O4^v	0.85	1.99	2.834 (3)	173
O2W—H3···O5ⁱ	0.85	1.82	2.615 (3)	155

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₆H₁₈FN₃O₃)(C₁₄H₈O₅)(H₂O)₂]
M_r	670.28
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.105 (2), 12.230 (2), 13.052 (3)
α, β, γ (°)	72.50 (3), 73.13 (3), 77.57 (3)
V (Å³)	1457.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.32 × 0.24 × 0.22

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.798, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	11571, 5134, 4210
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.03
No. of reflections	5134
No. of parameters	406
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.42

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H4···O2	0.85	1.93	2.695 (3)	149.3
O2W—H4···O1	0.85	2.55	2.965 (3)	111.1
N3—H3B···O2ⁱ	0.90	1.82	2.714 (3)	169.6
N3—H3C···O8ⁱⁱ	0.90	1.85	2.719 (3)	162.2
O1W—H1···O1ⁱⁱⁱ	0.85	2.03	2.761 (3)	143.6
O1W—H2···O4^iv	0.85	1.99	2.834 (3)	173.2
O2W—H3···O5^v	0.85	1.82	2.615 (3)	155.0

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

Acknowledgements

The author thanks Jilin Normal University for supporting this work.

References

An, Z., Huang, J. & Qi, W. (2007). Acta Cryst. E63, m2009. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Bruker (1999). SAINT. Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1990). SHELXTL-Plus. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Xiao, D.-R., Wang, E.-B., An, H.-Y., Su, Z.-M., Li, Y.-G., Gao, L., Sun, C.-Y. & Xu, L. (2005). Chem. Eur. J. 11, 6673–6686. Web of Science CSD CrossRef PubMed CAS Google Scholar

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