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In the crystal structure of the title compound, [Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2O, the ZnII atoms are each coordinated by five O atoms within a distorted trigonal biyramid. The two ZnII atoms are connected by two symmetry-related carboxyl­ate O atoms into dimers, which are located on centres of inversion. These dimers are linked by N—H...O and O—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055274/nc2071sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055274/nc2071Isup2.hkl
Contains datablock I

CCDC reference: 672627

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.035
  • wR factor = 0.104
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 7.44 Cell volume su given = 5.00 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.96 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.39 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 2.12 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

Norfloxacin [1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid] 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 Zn atoms are coordinated by two oxygen atoms of one 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7- (piperazin-1-yl)quinoline-3-carboxylato-O,O')anion and three oxygen atoms of two 4-carboxybenzene-1,2-dicarboxylato-O,O' dianions within a distorted trigonal biyramid geometry (Fig. 1). Two of these octahedra are connected via common edges into dimers, which are located on centres of inversion. These dinuclear dimers are connected by N—H···O and O—H···O hydrogen bonding into a three-dimensional network (Table 1).

Related literature top

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

Experimental top

A mixture of ZnNO3.6H2O (0.5 mmol), norfloxacin (0.5 mmol), benzene-1,2,4-tricarboxylic acid (0.8 mmol) were stirred for 20 min in 10 ml of water) and then transferred into a 23 ml Teflon reactor. The reactor was kept at 433 K for 120 h under autogenous pressure. Single crystals of (I) were obtained after cooling to room temperature.

Refinement top

H atoms were placed in calculated positions with C—H = 0.93, 0.96 and 0.97 Å, N—H = 0.9 Å, and O—H = 0.82 Å and refined in riding mode with Uiso(H) = 1.2Ueq(C,N), H atoms of water molecule were located in difference maps and refined isotropically with O—H = 0.85 Å and Uiso(H) = 1.5Ueq(O)

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
[Figure 1] Fig. 1. Crystal structure of (I) with labeling and displacement ellipsoids drawn at the 50% probability level. Symmetry code: i = -x,-y + 1,-z
Bis(µ-4-carboxybenzene-1,2-dicarboxylato)- 1:2κ3O3,O4:O3;1:2κ3O3:O3,O4– bis[1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3- carboxylato-κ2O,O'] dizinc(II) hexahydrate top
Crystal data top
[Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2OZ = 1
Mr = 1293.75F(000) = 668
Triclinic, P1Dx = 1.631 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.296 (2) ÅCell parameters from 13057 reflections
b = 11.764 (2) Åθ = 3.1–27.5°
c = 12.398 (3) ŵ = 1.01 mm1
α = 66.95 (3)°T = 298 K
β = 87.62 (3)°Block, colourless
γ = 61.97 (3)°0.31 × 0.25 × 0.19 mm
V = 1317.3 (5) Å3
Data collection top
Bruker APEX CCD area-detector
diffractometer
5989 independent reflections
Radiation source: fine-focus sealed tube5274 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.744, Tmax = 0.831k = 1315
13057 measured reflectionsl = 1516
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0604P)2 + 0.9168P]
where P = (Fo2 + 2Fc2)/3
5989 reflections(Δ/σ)max = 0.007
379 parametersΔρmax = 0.46 e Å3
9 restraintsΔρmin = 0.31 e Å3
Crystal data top
[Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2Oγ = 61.97 (3)°
Mr = 1293.75V = 1317.3 (5) Å3
Triclinic, P1Z = 1
a = 11.296 (2) ÅMo Kα radiation
b = 11.764 (2) ŵ = 1.01 mm1
c = 12.398 (3) ÅT = 298 K
α = 66.95 (3)°0.31 × 0.25 × 0.19 mm
β = 87.62 (3)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
5989 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5274 reflections with I > 2σ(I)
Tmin = 0.744, Tmax = 0.831Rint = 0.029
13057 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0359 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.02Δρmax = 0.46 e Å3
5989 reflectionsΔρmin = 0.31 e Å3
379 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
Zn10.11988 (5)0.52096 (5)0.08633 (4)0.01963 (17)
F10.3341 (3)0.0548 (3)0.5724 (2)0.0315 (6)
O10.0390 (4)0.8105 (4)0.0927 (3)0.0382 (9)
O20.1451 (3)0.6892 (3)0.1040 (3)0.0269 (7)
O30.0951 (3)0.4928 (3)0.0671 (3)0.0252 (6)
O40.2887 (4)0.2983 (4)0.1743 (3)0.0340 (8)
O50.4119 (4)0.1723 (4)0.5979 (3)0.0443 (10)
O60.3091 (6)0.3438 (5)0.6612 (4)0.0649 (15)
H6B0.37320.29370.71710.078*
O70.3011 (3)0.5376 (3)0.1017 (3)0.0272 (7)
O80.4599 (3)0.5006 (4)0.1932 (3)0.0307 (7)
O90.0314 (3)0.3377 (3)0.2322 (2)0.0227 (6)
N10.2222 (3)0.2296 (4)0.5123 (3)0.0204 (7)
N20.2171 (4)0.1024 (4)0.7755 (3)0.0209 (7)
N30.3583 (4)0.2514 (4)1.0164 (3)0.0232 (7)
H3B0.41900.33261.07680.028*
H3C0.32490.18211.04190.028*
C10.0529 (4)0.5859 (4)0.2505 (4)0.0212 (8)
C20.1611 (4)0.4548 (4)0.2613 (3)0.0195 (8)
C30.2508 (4)0.3620 (4)0.3700 (4)0.0221 (8)
H3A0.32380.27580.37750.027*
C40.2330 (5)0.3960 (5)0.4663 (4)0.0246 (9)
C50.1253 (5)0.5263 (5)0.4544 (4)0.0291 (10)
H5A0.11270.55010.51880.035*
C60.0375 (5)0.6198 (5)0.3478 (4)0.0273 (9)
H6A0.03340.70720.34040.033*
C70.1867 (4)0.4086 (4)0.1619 (4)0.0203 (8)
C80.0487 (4)0.7019 (4)0.1383 (4)0.0232 (8)
C90.3269 (5)0.2930 (5)0.5819 (4)0.0282 (9)
C100.2389 (4)0.3663 (4)0.3046 (3)0.0187 (8)
C110.2937 (4)0.3236 (4)0.4033 (4)0.0210 (8)
H11A0.38790.36320.39350.025*
C120.0811 (4)0.1636 (4)0.5312 (3)0.0174 (7)
C130.0176 (4)0.1976 (4)0.4332 (3)0.0171 (7)
C140.0954 (4)0.3054 (4)0.3155 (3)0.0170 (7)
C150.0041 (4)0.0677 (4)0.6455 (3)0.0189 (8)
H15A0.04860.05190.71010.023*
C160.1367 (4)0.0038 (4)0.6641 (3)0.0193 (8)
C170.1978 (4)0.0240 (4)0.5611 (4)0.0201 (8)
C180.1255 (4)0.1228 (4)0.4512 (4)0.0200 (8)
H18A0.17060.14130.38750.024*
C190.1459 (4)0.1380 (5)0.8740 (4)0.0233 (9)
H19A0.07870.15620.84920.028*
H19B0.09870.05830.89500.028*
C200.2463 (4)0.2687 (5)0.9821 (4)0.0247 (9)
H20A0.19860.28521.04850.030*
H20B0.28380.35100.96430.030*
C210.4275 (5)0.2153 (5)0.9146 (4)0.0287 (10)
H21A0.46910.29260.89030.034*
H21B0.49870.20140.93830.034*
C220.3252 (5)0.0811 (5)0.8118 (4)0.0278 (10)
H22A0.28540.00320.83540.033*
H22B0.37050.05710.74520.033*
C230.3403 (4)0.4758 (4)0.1921 (3)0.0201 (8)
C240.3002 (5)0.2042 (5)0.6093 (4)0.0296 (10)
H24A0.24510.10910.67120.035*
H24B0.38140.21010.57850.035*
C250.3403 (7)0.3091 (7)0.6615 (5)0.0502 (15)
H25A0.39020.28910.72420.075*
H25B0.39660.40320.60080.075*
H25C0.26010.30260.69310.075*
O1W0.3947 (4)0.0289 (4)0.1959 (3)0.0403 (9)
H10.35960.11550.18390.060*
H20.42600.00440.26920.060*
O2W0.7730 (4)0.9659 (4)0.0955 (3)0.0421 (9)
H30.83311.04420.04180.063*
H40.71650.98790.11170.063*
O3W0.4213 (4)0.8368 (5)0.1153 (4)0.0521 (11)
H60.34610.82080.09080.078*
H50.46030.91960.11610.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0200 (3)0.0207 (3)0.0132 (2)0.0084 (2)0.00266 (17)0.00461 (19)
F10.0135 (12)0.0362 (15)0.0273 (13)0.0031 (11)0.0007 (10)0.0082 (12)
O10.036 (2)0.0218 (17)0.041 (2)0.0139 (15)0.0076 (16)0.0022 (15)
O20.0198 (15)0.0249 (15)0.0318 (16)0.0061 (12)0.0001 (12)0.0137 (14)
O30.0205 (15)0.0325 (17)0.0163 (13)0.0084 (13)0.0016 (11)0.0103 (13)
O40.0289 (18)0.0305 (18)0.0294 (17)0.0016 (14)0.0006 (14)0.0163 (15)
O50.042 (2)0.037 (2)0.0328 (19)0.0095 (17)0.0129 (16)0.0050 (17)
O60.093 (4)0.056 (3)0.029 (2)0.021 (3)0.016 (2)0.020 (2)
O70.0211 (15)0.0306 (17)0.0157 (13)0.0104 (13)0.0008 (11)0.0006 (13)
O80.0156 (14)0.0338 (18)0.0228 (15)0.0083 (13)0.0024 (12)0.0022 (14)
O90.0174 (14)0.0249 (15)0.0166 (13)0.0080 (12)0.0038 (11)0.0033 (12)
N10.0155 (16)0.0231 (17)0.0154 (15)0.0083 (14)0.0021 (12)0.0030 (14)
N20.0184 (17)0.0223 (17)0.0149 (15)0.0094 (14)0.0032 (13)0.0014 (14)
N30.0201 (17)0.0212 (17)0.0164 (15)0.0055 (14)0.0045 (13)0.0021 (14)
C10.020 (2)0.0194 (19)0.0216 (19)0.0093 (16)0.0017 (16)0.0069 (17)
C20.0190 (19)0.0211 (19)0.0173 (18)0.0092 (16)0.0021 (15)0.0078 (16)
C30.0198 (19)0.021 (2)0.0211 (19)0.0081 (16)0.0000 (15)0.0065 (17)
C40.028 (2)0.025 (2)0.0188 (19)0.0138 (18)0.0004 (16)0.0059 (17)
C50.039 (3)0.031 (2)0.023 (2)0.018 (2)0.0070 (19)0.0163 (19)
C60.029 (2)0.023 (2)0.030 (2)0.0105 (18)0.0052 (18)0.0145 (19)
C70.0189 (19)0.022 (2)0.0175 (18)0.0086 (16)0.0025 (15)0.0077 (16)
C80.019 (2)0.020 (2)0.024 (2)0.0046 (16)0.0023 (16)0.0088 (17)
C90.033 (2)0.033 (2)0.021 (2)0.019 (2)0.0004 (18)0.0093 (19)
C100.0173 (18)0.0180 (18)0.0143 (17)0.0060 (15)0.0013 (14)0.0039 (15)
C110.0150 (18)0.021 (2)0.0184 (18)0.0056 (15)0.0006 (14)0.0044 (16)
C120.0166 (18)0.0159 (18)0.0164 (17)0.0067 (15)0.0000 (14)0.0052 (15)
C130.0158 (18)0.0170 (18)0.0149 (17)0.0069 (15)0.0001 (14)0.0045 (15)
C140.0189 (19)0.0163 (18)0.0138 (17)0.0075 (15)0.0014 (14)0.0059 (15)
C150.0179 (19)0.0188 (19)0.0148 (17)0.0083 (15)0.0002 (14)0.0030 (16)
C160.0190 (19)0.0171 (18)0.0169 (18)0.0079 (15)0.0026 (15)0.0033 (16)
C170.0137 (18)0.022 (2)0.0219 (19)0.0067 (15)0.0010 (15)0.0091 (17)
C180.0178 (19)0.021 (2)0.0178 (18)0.0089 (16)0.0025 (15)0.0061 (16)
C190.0181 (19)0.025 (2)0.0191 (18)0.0100 (17)0.0027 (15)0.0019 (17)
C200.024 (2)0.023 (2)0.0174 (18)0.0107 (17)0.0022 (16)0.0010 (17)
C210.020 (2)0.038 (3)0.0194 (19)0.0142 (19)0.0037 (16)0.0041 (19)
C220.026 (2)0.033 (2)0.0197 (19)0.0184 (19)0.0054 (17)0.0001 (18)
C230.0168 (19)0.0189 (19)0.0176 (18)0.0053 (15)0.0012 (15)0.0052 (16)
C240.019 (2)0.035 (2)0.0193 (19)0.0109 (18)0.0050 (16)0.0003 (19)
C250.049 (3)0.045 (3)0.036 (3)0.012 (3)0.023 (3)0.013 (3)
O1W0.041 (2)0.0298 (18)0.044 (2)0.0130 (16)0.0025 (17)0.0144 (17)
O2W0.047 (2)0.0273 (18)0.0373 (19)0.0107 (16)0.0111 (17)0.0079 (16)
O3W0.032 (2)0.063 (3)0.049 (2)0.0019 (19)0.0005 (17)0.039 (2)
Geometric parameters (Å, º) top
Zn1—O21.962 (3)C5—H5A0.9300
Zn1—O3i1.969 (3)C6—H6A0.9300
Zn1—O71.970 (3)C10—C111.371 (6)
Zn1—O91.998 (3)C10—C141.417 (6)
Zn1—O32.307 (3)C10—C231.501 (5)
F1—C171.351 (5)C11—H11A0.9300
O1—C81.236 (6)C12—C151.402 (5)
O2—C81.277 (5)C12—C131.403 (5)
O3—C71.289 (5)C13—C181.406 (6)
O3—Zn1i1.969 (3)C13—C141.456 (5)
O4—C71.219 (5)C15—C161.383 (6)
O5—C91.221 (6)C15—H15A0.9300
O6—C91.302 (6)C16—C171.423 (6)
O6—H6B0.8200C17—C181.355 (6)
O7—C231.267 (5)C18—H18A0.9300
O8—C231.242 (5)C19—C201.523 (6)
O9—C141.274 (5)C19—H19A0.9700
N1—C111.335 (5)C19—H19B0.9700
N1—C121.387 (5)C20—H20A0.9700
N1—C241.480 (5)C20—H20B0.9700
N2—C161.392 (5)C21—C221.511 (6)
N2—C191.466 (5)C21—H21A0.9700
N2—C221.474 (5)C21—H21B0.9700
N3—C201.475 (6)C22—H22A0.9700
N3—C211.481 (6)C22—H22B0.9700
N3—H3B0.9000C24—C251.492 (8)
N3—H3C0.9000C24—H24A0.9700
C1—C61.392 (6)C24—H24B0.9700
C1—C21.404 (6)C25—H25A0.9600
C1—C81.513 (6)C25—H25B0.9600
C2—C31.397 (6)C25—H25C0.9600
C2—C71.498 (6)O1W—H10.8503
C3—C41.380 (6)O1W—H20.8500
C3—H3A0.9300O2W—H30.8500
C4—C51.392 (7)O2W—H40.8499
C4—C91.485 (6)O3W—H60.8500
C5—C61.373 (7)O3W—H50.8643
O2—Zn1—O3i121.12 (14)N1—C12—C13118.1 (3)
O2—Zn1—O7101.54 (14)C15—C12—C13120.9 (4)
O3i—Zn1—O7101.61 (14)C12—C13—C18117.9 (3)
O2—Zn1—O9116.22 (13)C12—C13—C14122.0 (4)
O3i—Zn1—O9116.25 (13)C18—C13—C14120.1 (4)
O7—Zn1—O991.84 (13)O9—C14—C10125.6 (4)
O2—Zn1—O380.92 (13)O9—C14—C13118.7 (4)
O3i—Zn1—O376.93 (13)C10—C14—C13115.7 (3)
O7—Zn1—O3177.54 (13)C16—C15—C12121.2 (4)
O9—Zn1—O387.08 (12)C16—C15—H15A119.4
C8—O2—Zn1124.5 (3)C12—C15—H15A119.4
C7—O3—Zn1i123.5 (3)C15—C16—N2123.1 (4)
C7—O3—Zn1116.3 (3)C15—C16—C17116.3 (4)
Zn1i—O3—Zn1103.07 (13)N2—C16—C17120.5 (4)
C9—O6—H6B112.1F1—C17—C18118.1 (4)
C23—O7—Zn1128.9 (3)F1—C17—C16118.6 (3)
C14—O9—Zn1122.5 (3)C18—C17—C16123.2 (4)
C11—N1—C12120.0 (3)C17—C18—C13120.0 (4)
C11—N1—C24117.2 (3)C17—C18—H18A120.0
C12—N1—C24122.9 (3)C13—C18—H18A120.0
C16—N2—C19116.8 (3)N2—C19—C20110.6 (3)
C16—N2—C22116.0 (3)N2—C19—H19A109.5
C19—N2—C22111.1 (3)C20—C19—H19A109.5
C20—N3—C21111.0 (3)N2—C19—H19B109.5
C20—N3—H3B109.4C20—C19—H19B109.5
C21—N3—H3B109.4H19A—C19—H19B108.1
C20—N3—H3C109.4N3—C20—C19111.6 (3)
C21—N3—H3C109.4N3—C20—H20A109.3
H3B—N3—H3C108.0C19—C20—H20A109.3
C6—C1—C2119.4 (4)N3—C20—H20B109.3
C6—C1—C8114.7 (4)C19—C20—H20B109.3
C2—C1—C8125.9 (4)H20A—C20—H20B108.0
C3—C2—C1118.8 (4)N3—C21—C22109.6 (4)
C3—C2—C7117.8 (4)N3—C21—H21A109.7
C1—C2—C7123.4 (4)C22—C21—H21A109.7
C4—C3—C2121.3 (4)N3—C21—H21B109.7
C4—C3—H3A119.3C22—C21—H21B109.7
C2—C3—H3A119.3H21A—C21—H21B108.2
C3—C4—C5119.4 (4)N2—C22—C21109.8 (4)
C3—C4—C9120.1 (4)N2—C22—H22A109.7
C5—C4—C9120.6 (4)C21—C22—H22A109.7
C6—C5—C4120.2 (4)N2—C22—H22B109.7
C6—C5—H5A119.9C21—C22—H22B109.7
C4—C5—H5A119.9H22A—C22—H22B108.2
C5—C6—C1121.0 (4)O8—C23—O7123.3 (4)
C5—C6—H6A119.5O8—C23—C10117.3 (4)
C1—C6—H6A119.5O7—C23—C10119.4 (4)
O4—C7—O3124.8 (4)N1—C24—C25111.8 (4)
O4—C7—C2120.0 (4)N1—C24—H24A109.2
O3—C7—C2115.2 (4)C25—C24—H24A109.2
O1—C8—O2124.3 (4)N1—C24—H24B109.2
O1—C8—C1115.6 (4)C25—C24—H24B109.2
O2—C8—C1119.7 (4)H24A—C24—H24B107.9
O5—C9—O6124.7 (4)C24—C25—H25A109.5
O5—C9—C4121.3 (4)C24—C25—H25B109.5
O6—C9—C4113.9 (4)H25A—C25—H25B109.5
C11—C10—C14119.0 (4)C24—C25—H25C109.5
C11—C10—C23115.3 (4)H25A—C25—H25C109.5
C14—C10—C23125.7 (4)H25B—C25—H25C109.5
N1—C11—C10125.0 (4)H1—O1W—H295.1
N1—C11—H11A117.5H3—O2W—H4102.2
C10—C11—H11A117.5H6—O3W—H5109.3
N1—C12—C15120.9 (4)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1···O40.851.862.711 (5)174
O3W—H6···O20.852.032.799 (5)151
O1W—H2···O5ii0.852.072.789 (5)142
O2W—H3···O1iii0.851.852.688 (5)167
N3—H3B···O8iv0.901.802.696 (5)177
N3—H3C···O2Wiv0.901.932.824 (6)171
Symmetry codes: (ii) x+1, y, z+1; (iii) x1, y+2, z; (iv) x+1, y1, z+1.

Experimental details

Crystal data
Chemical formula[Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2O
Mr1293.75
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)11.296 (2), 11.764 (2), 12.398 (3)
α, β, γ (°)66.95 (3), 87.62 (3), 61.97 (3)
V3)1317.3 (5)
Z1
Radiation typeMo Kα
µ (mm1)1.01
Crystal size (mm)0.31 × 0.25 × 0.19
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.744, 0.831
No. of measured, independent and
observed [I > 2σ(I)] reflections
13057, 5989, 5274
Rint0.029
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.104, 1.02
No. of reflections5989
No. of parameters379
No. of restraints9
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.31

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···AD—HH···AD···AD—H···A
O1W—H1···O40.851.862.711 (5)174.1
O3W—H6···O20.852.032.799 (5)150.6
O1W—H2···O5i0.852.072.789 (5)142.4
O2W—H3···O1ii0.851.852.688 (5)166.9
N3—H3B···O8iii0.901.802.696 (5)177.2
N3—H3C···O2Wiii0.901.932.824 (6)171.1
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y+2, z; (iii) x+1, y1, z+1.
 

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