Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055274/nc2071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055274/nc2071Isup2.hkl |
CCDC reference: 672627
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
For general background, see: Xiao et al. (2005). For related structures, see: An et al. (2005).
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.
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)
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).
Fig. 1. Crystal structure of (I) with labeling and displacement ellipsoids drawn at the 50% probability level. Symmetry code: i = -x,-y + 1,-z |
[Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2O | Z = 1 |
Mr = 1293.75 | F(000) = 668 |
Triclinic, P1 | Dx = 1.631 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.296 (2) Å | Cell parameters from 13057 reflections |
b = 11.764 (2) Å | θ = 3.1–27.5° |
c = 12.398 (3) Å | µ = 1.01 mm−1 |
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 |
Bruker APEX CCD area-detector diffractometer | 5989 independent reflections |
Radiation source: fine-focus sealed tube | 5274 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.744, Tmax = 0.831 | k = −13→15 |
13057 measured reflections | l = −15→16 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-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 parameters | Δρmax = 0.46 e Å−3 |
9 restraints | Δρmin = −0.31 e Å−3 |
[Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2O | γ = 61.97 (3)° |
Mr = 1293.75 | V = 1317.3 (5) Å3 |
Triclinic, P1 | Z = 1 |
a = 11.296 (2) Å | Mo Kα radiation |
b = 11.764 (2) Å | µ = 1.01 mm−1 |
c = 12.398 (3) Å | T = 298 K |
α = 66.95 (3)° | 0.31 × 0.25 × 0.19 mm |
β = 87.62 (3)° |
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 = 0.831 | Rint = 0.029 |
13057 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 9 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.46 e Å−3 |
5989 reflections | Δρmin = −0.31 e Å−3 |
379 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | −0.11988 (5) | 0.52096 (5) | 0.08633 (4) | 0.01963 (17) | |
F1 | 0.3341 (3) | −0.0548 (3) | 0.5724 (2) | 0.0315 (6) | |
O1 | −0.0390 (4) | 0.8105 (4) | 0.0927 (3) | 0.0382 (9) | |
O2 | −0.1451 (3) | 0.6892 (3) | 0.1040 (3) | 0.0269 (7) | |
O3 | 0.0951 (3) | 0.4928 (3) | 0.0671 (3) | 0.0252 (6) | |
O4 | 0.2887 (4) | 0.2983 (4) | 0.1743 (3) | 0.0340 (8) | |
O5 | 0.4119 (4) | 0.1723 (4) | 0.5979 (3) | 0.0443 (10) | |
O6 | 0.3091 (6) | 0.3438 (5) | 0.6612 (4) | 0.0649 (15) | |
H6B | 0.3732 | 0.2937 | 0.7171 | 0.078* | |
O7 | −0.3011 (3) | 0.5376 (3) | 0.1017 (3) | 0.0272 (7) | |
O8 | −0.4599 (3) | 0.5006 (4) | 0.1932 (3) | 0.0307 (7) | |
O9 | −0.0314 (3) | 0.3377 (3) | 0.2322 (2) | 0.0227 (6) | |
N1 | −0.2222 (3) | 0.2296 (4) | 0.5123 (3) | 0.0204 (7) | |
N2 | 0.2171 (4) | −0.1024 (4) | 0.7755 (3) | 0.0209 (7) | |
N3 | 0.3583 (4) | −0.2514 (4) | 1.0164 (3) | 0.0232 (7) | |
H3B | 0.4190 | −0.3326 | 1.0768 | 0.028* | |
H3C | 0.3249 | −0.1821 | 1.0419 | 0.028* | |
C1 | 0.0529 (4) | 0.5859 (4) | 0.2505 (4) | 0.0212 (8) | |
C2 | 0.1611 (4) | 0.4548 (4) | 0.2613 (3) | 0.0195 (8) | |
C3 | 0.2508 (4) | 0.3620 (4) | 0.3700 (4) | 0.0221 (8) | |
H3A | 0.3238 | 0.2758 | 0.3775 | 0.027* | |
C4 | 0.2330 (5) | 0.3960 (5) | 0.4663 (4) | 0.0246 (9) | |
C5 | 0.1253 (5) | 0.5263 (5) | 0.4544 (4) | 0.0291 (10) | |
H5A | 0.1127 | 0.5501 | 0.5188 | 0.035* | |
C6 | 0.0375 (5) | 0.6198 (5) | 0.3478 (4) | 0.0273 (9) | |
H6A | −0.0334 | 0.7072 | 0.3404 | 0.033* | |
C7 | 0.1867 (4) | 0.4086 (4) | 0.1619 (4) | 0.0203 (8) | |
C8 | −0.0487 (4) | 0.7019 (4) | 0.1383 (4) | 0.0232 (8) | |
C9 | 0.3269 (5) | 0.2930 (5) | 0.5819 (4) | 0.0282 (9) | |
C10 | −0.2389 (4) | 0.3663 (4) | 0.3046 (3) | 0.0187 (8) | |
C11 | −0.2937 (4) | 0.3236 (4) | 0.4033 (4) | 0.0210 (8) | |
H11A | −0.3879 | 0.3632 | 0.3935 | 0.025* | |
C12 | −0.0811 (4) | 0.1636 (4) | 0.5312 (3) | 0.0174 (7) | |
C13 | −0.0176 (4) | 0.1976 (4) | 0.4332 (3) | 0.0171 (7) | |
C14 | −0.0954 (4) | 0.3054 (4) | 0.3155 (3) | 0.0170 (7) | |
C15 | −0.0041 (4) | 0.0677 (4) | 0.6455 (3) | 0.0189 (8) | |
H15A | −0.0486 | 0.0519 | 0.7101 | 0.023* | |
C16 | 0.1367 (4) | −0.0038 (4) | 0.6641 (3) | 0.0193 (8) | |
C17 | 0.1978 (4) | 0.0240 (4) | 0.5611 (4) | 0.0201 (8) | |
C18 | 0.1255 (4) | 0.1228 (4) | 0.4512 (4) | 0.0200 (8) | |
H18A | 0.1706 | 0.1413 | 0.3875 | 0.024* | |
C19 | 0.1459 (4) | −0.1380 (5) | 0.8740 (4) | 0.0233 (9) | |
H19A | 0.0787 | −0.1562 | 0.8492 | 0.028* | |
H19B | 0.0987 | −0.0583 | 0.8950 | 0.028* | |
C20 | 0.2463 (4) | −0.2687 (5) | 0.9821 (4) | 0.0247 (9) | |
H20A | 0.1986 | −0.2852 | 1.0485 | 0.030* | |
H20B | 0.2838 | −0.3510 | 0.9643 | 0.030* | |
C21 | 0.4275 (5) | −0.2153 (5) | 0.9146 (4) | 0.0287 (10) | |
H21A | 0.4691 | −0.2926 | 0.8903 | 0.034* | |
H21B | 0.4987 | −0.2014 | 0.9383 | 0.034* | |
C22 | 0.3252 (5) | −0.0811 (5) | 0.8118 (4) | 0.0278 (10) | |
H22A | 0.2854 | −0.0032 | 0.8354 | 0.033* | |
H22B | 0.3705 | −0.0571 | 0.7452 | 0.033* | |
C23 | −0.3403 (4) | 0.4758 (4) | 0.1921 (3) | 0.0201 (8) | |
C24 | −0.3002 (5) | 0.2042 (5) | 0.6093 (4) | 0.0296 (10) | |
H24A | −0.2451 | 0.1091 | 0.6712 | 0.035* | |
H24B | −0.3814 | 0.2101 | 0.5785 | 0.035* | |
C25 | −0.3403 (7) | 0.3091 (7) | 0.6615 (5) | 0.0502 (15) | |
H25A | −0.3902 | 0.2891 | 0.7242 | 0.075* | |
H25B | −0.3966 | 0.4032 | 0.6008 | 0.075* | |
H25C | −0.2601 | 0.3026 | 0.6931 | 0.075* | |
O1W | 0.3947 (4) | 0.0289 (4) | 0.1959 (3) | 0.0403 (9) | |
H1 | 0.3596 | 0.1155 | 0.1839 | 0.060* | |
H2 | 0.4260 | −0.0044 | 0.2692 | 0.060* | |
O2W | −0.7730 (4) | 0.9659 (4) | 0.0955 (3) | 0.0421 (9) | |
H3 | −0.8331 | 1.0442 | 0.0418 | 0.063* | |
H4 | −0.7165 | 0.9879 | 0.1117 | 0.063* | |
O3W | −0.4213 (4) | 0.8368 (5) | 0.1153 (4) | 0.0521 (11) | |
H6 | −0.3461 | 0.8208 | 0.0908 | 0.078* | |
H5 | −0.4603 | 0.9196 | 0.1161 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0200 (3) | 0.0207 (3) | 0.0132 (2) | −0.0084 (2) | 0.00266 (17) | −0.00461 (19) |
F1 | 0.0135 (12) | 0.0362 (15) | 0.0273 (13) | −0.0031 (11) | −0.0007 (10) | −0.0082 (12) |
O1 | 0.036 (2) | 0.0218 (17) | 0.041 (2) | −0.0139 (15) | −0.0076 (16) | 0.0022 (15) |
O2 | 0.0198 (15) | 0.0249 (15) | 0.0318 (16) | −0.0061 (12) | 0.0001 (12) | −0.0137 (14) |
O3 | 0.0205 (15) | 0.0325 (17) | 0.0163 (13) | −0.0084 (13) | 0.0016 (11) | −0.0103 (13) |
O4 | 0.0289 (18) | 0.0305 (18) | 0.0294 (17) | −0.0016 (14) | 0.0006 (14) | −0.0163 (15) |
O5 | 0.042 (2) | 0.037 (2) | 0.0328 (19) | −0.0095 (17) | −0.0129 (16) | −0.0050 (17) |
O6 | 0.093 (4) | 0.056 (3) | 0.029 (2) | −0.021 (3) | −0.016 (2) | −0.020 (2) |
O7 | 0.0211 (15) | 0.0306 (17) | 0.0157 (13) | −0.0104 (13) | −0.0008 (11) | 0.0006 (13) |
O8 | 0.0156 (14) | 0.0338 (18) | 0.0228 (15) | −0.0083 (13) | −0.0024 (12) | 0.0022 (14) |
O9 | 0.0174 (14) | 0.0249 (15) | 0.0166 (13) | −0.0080 (12) | 0.0038 (11) | −0.0033 (12) |
N1 | 0.0155 (16) | 0.0231 (17) | 0.0154 (15) | −0.0083 (14) | 0.0021 (12) | −0.0030 (14) |
N2 | 0.0184 (17) | 0.0223 (17) | 0.0149 (15) | −0.0094 (14) | −0.0032 (13) | −0.0014 (14) |
N3 | 0.0201 (17) | 0.0212 (17) | 0.0164 (15) | −0.0055 (14) | −0.0045 (13) | −0.0021 (14) |
C1 | 0.020 (2) | 0.0194 (19) | 0.0216 (19) | −0.0093 (16) | 0.0017 (16) | −0.0069 (17) |
C2 | 0.0190 (19) | 0.0211 (19) | 0.0173 (18) | −0.0092 (16) | 0.0021 (15) | −0.0078 (16) |
C3 | 0.0198 (19) | 0.021 (2) | 0.0211 (19) | −0.0081 (16) | 0.0000 (15) | −0.0065 (17) |
C4 | 0.028 (2) | 0.025 (2) | 0.0188 (19) | −0.0138 (18) | 0.0004 (16) | −0.0059 (17) |
C5 | 0.039 (3) | 0.031 (2) | 0.023 (2) | −0.018 (2) | 0.0070 (19) | −0.0163 (19) |
C6 | 0.029 (2) | 0.023 (2) | 0.030 (2) | −0.0105 (18) | 0.0052 (18) | −0.0145 (19) |
C7 | 0.0189 (19) | 0.022 (2) | 0.0175 (18) | −0.0086 (16) | 0.0025 (15) | −0.0077 (16) |
C8 | 0.019 (2) | 0.020 (2) | 0.024 (2) | −0.0046 (16) | 0.0023 (16) | −0.0088 (17) |
C9 | 0.033 (2) | 0.033 (2) | 0.021 (2) | −0.019 (2) | −0.0004 (18) | −0.0093 (19) |
C10 | 0.0173 (18) | 0.0180 (18) | 0.0143 (17) | −0.0060 (15) | −0.0013 (14) | −0.0039 (15) |
C11 | 0.0150 (18) | 0.021 (2) | 0.0184 (18) | −0.0056 (15) | 0.0006 (14) | −0.0044 (16) |
C12 | 0.0166 (18) | 0.0159 (18) | 0.0164 (17) | −0.0067 (15) | 0.0000 (14) | −0.0052 (15) |
C13 | 0.0158 (18) | 0.0170 (18) | 0.0149 (17) | −0.0069 (15) | −0.0001 (14) | −0.0045 (15) |
C14 | 0.0189 (19) | 0.0163 (18) | 0.0138 (17) | −0.0075 (15) | 0.0014 (14) | −0.0059 (15) |
C15 | 0.0179 (19) | 0.0188 (19) | 0.0148 (17) | −0.0083 (15) | −0.0002 (14) | −0.0030 (16) |
C16 | 0.0190 (19) | 0.0171 (18) | 0.0169 (18) | −0.0079 (15) | −0.0026 (15) | −0.0033 (16) |
C17 | 0.0137 (18) | 0.022 (2) | 0.0219 (19) | −0.0067 (15) | 0.0010 (15) | −0.0091 (17) |
C18 | 0.0178 (19) | 0.021 (2) | 0.0178 (18) | −0.0089 (16) | 0.0025 (15) | −0.0061 (16) |
C19 | 0.0181 (19) | 0.025 (2) | 0.0191 (18) | −0.0100 (17) | −0.0027 (15) | −0.0019 (17) |
C20 | 0.024 (2) | 0.023 (2) | 0.0174 (18) | −0.0107 (17) | −0.0022 (16) | −0.0010 (17) |
C21 | 0.020 (2) | 0.038 (3) | 0.0194 (19) | −0.0142 (19) | −0.0037 (16) | −0.0041 (19) |
C22 | 0.026 (2) | 0.033 (2) | 0.0197 (19) | −0.0184 (19) | −0.0054 (17) | −0.0001 (18) |
C23 | 0.0168 (19) | 0.0189 (19) | 0.0176 (18) | −0.0053 (15) | −0.0012 (15) | −0.0052 (16) |
C24 | 0.019 (2) | 0.035 (2) | 0.0193 (19) | −0.0109 (18) | 0.0050 (16) | −0.0003 (19) |
C25 | 0.049 (3) | 0.045 (3) | 0.036 (3) | −0.012 (3) | 0.023 (3) | −0.013 (3) |
O1W | 0.041 (2) | 0.0298 (18) | 0.044 (2) | −0.0130 (16) | −0.0025 (17) | −0.0144 (17) |
O2W | 0.047 (2) | 0.0273 (18) | 0.0373 (19) | −0.0107 (16) | −0.0111 (17) | −0.0079 (16) |
O3W | 0.032 (2) | 0.063 (3) | 0.049 (2) | −0.0019 (19) | −0.0005 (17) | −0.039 (2) |
Zn1—O2 | 1.962 (3) | C5—H5A | 0.9300 |
Zn1—O3i | 1.969 (3) | C6—H6A | 0.9300 |
Zn1—O7 | 1.970 (3) | C10—C11 | 1.371 (6) |
Zn1—O9 | 1.998 (3) | C10—C14 | 1.417 (6) |
Zn1—O3 | 2.307 (3) | C10—C23 | 1.501 (5) |
F1—C17 | 1.351 (5) | C11—H11A | 0.9300 |
O1—C8 | 1.236 (6) | C12—C15 | 1.402 (5) |
O2—C8 | 1.277 (5) | C12—C13 | 1.403 (5) |
O3—C7 | 1.289 (5) | C13—C18 | 1.406 (6) |
O3—Zn1i | 1.969 (3) | C13—C14 | 1.456 (5) |
O4—C7 | 1.219 (5) | C15—C16 | 1.383 (6) |
O5—C9 | 1.221 (6) | C15—H15A | 0.9300 |
O6—C9 | 1.302 (6) | C16—C17 | 1.423 (6) |
O6—H6B | 0.8200 | C17—C18 | 1.355 (6) |
O7—C23 | 1.267 (5) | C18—H18A | 0.9300 |
O8—C23 | 1.242 (5) | C19—C20 | 1.523 (6) |
O9—C14 | 1.274 (5) | C19—H19A | 0.9700 |
N1—C11 | 1.335 (5) | C19—H19B | 0.9700 |
N1—C12 | 1.387 (5) | C20—H20A | 0.9700 |
N1—C24 | 1.480 (5) | C20—H20B | 0.9700 |
N2—C16 | 1.392 (5) | C21—C22 | 1.511 (6) |
N2—C19 | 1.466 (5) | C21—H21A | 0.9700 |
N2—C22 | 1.474 (5) | C21—H21B | 0.9700 |
N3—C20 | 1.475 (6) | C22—H22A | 0.9700 |
N3—C21 | 1.481 (6) | C22—H22B | 0.9700 |
N3—H3B | 0.9000 | C24—C25 | 1.492 (8) |
N3—H3C | 0.9000 | C24—H24A | 0.9700 |
C1—C6 | 1.392 (6) | C24—H24B | 0.9700 |
C1—C2 | 1.404 (6) | C25—H25A | 0.9600 |
C1—C8 | 1.513 (6) | C25—H25B | 0.9600 |
C2—C3 | 1.397 (6) | C25—H25C | 0.9600 |
C2—C7 | 1.498 (6) | O1W—H1 | 0.8503 |
C3—C4 | 1.380 (6) | O1W—H2 | 0.8500 |
C3—H3A | 0.9300 | O2W—H3 | 0.8500 |
C4—C5 | 1.392 (7) | O2W—H4 | 0.8499 |
C4—C9 | 1.485 (6) | O3W—H6 | 0.8500 |
C5—C6 | 1.373 (7) | O3W—H5 | 0.8643 |
O2—Zn1—O3i | 121.12 (14) | N1—C12—C13 | 118.1 (3) |
O2—Zn1—O7 | 101.54 (14) | C15—C12—C13 | 120.9 (4) |
O3i—Zn1—O7 | 101.61 (14) | C12—C13—C18 | 117.9 (3) |
O2—Zn1—O9 | 116.22 (13) | C12—C13—C14 | 122.0 (4) |
O3i—Zn1—O9 | 116.25 (13) | C18—C13—C14 | 120.1 (4) |
O7—Zn1—O9 | 91.84 (13) | O9—C14—C10 | 125.6 (4) |
O2—Zn1—O3 | 80.92 (13) | O9—C14—C13 | 118.7 (4) |
O3i—Zn1—O3 | 76.93 (13) | C10—C14—C13 | 115.7 (3) |
O7—Zn1—O3 | 177.54 (13) | C16—C15—C12 | 121.2 (4) |
O9—Zn1—O3 | 87.08 (12) | C16—C15—H15A | 119.4 |
C8—O2—Zn1 | 124.5 (3) | C12—C15—H15A | 119.4 |
C7—O3—Zn1i | 123.5 (3) | C15—C16—N2 | 123.1 (4) |
C7—O3—Zn1 | 116.3 (3) | C15—C16—C17 | 116.3 (4) |
Zn1i—O3—Zn1 | 103.07 (13) | N2—C16—C17 | 120.5 (4) |
C9—O6—H6B | 112.1 | F1—C17—C18 | 118.1 (4) |
C23—O7—Zn1 | 128.9 (3) | F1—C17—C16 | 118.6 (3) |
C14—O9—Zn1 | 122.5 (3) | C18—C17—C16 | 123.2 (4) |
C11—N1—C12 | 120.0 (3) | C17—C18—C13 | 120.0 (4) |
C11—N1—C24 | 117.2 (3) | C17—C18—H18A | 120.0 |
C12—N1—C24 | 122.9 (3) | C13—C18—H18A | 120.0 |
C16—N2—C19 | 116.8 (3) | N2—C19—C20 | 110.6 (3) |
C16—N2—C22 | 116.0 (3) | N2—C19—H19A | 109.5 |
C19—N2—C22 | 111.1 (3) | C20—C19—H19A | 109.5 |
C20—N3—C21 | 111.0 (3) | N2—C19—H19B | 109.5 |
C20—N3—H3B | 109.4 | C20—C19—H19B | 109.5 |
C21—N3—H3B | 109.4 | H19A—C19—H19B | 108.1 |
C20—N3—H3C | 109.4 | N3—C20—C19 | 111.6 (3) |
C21—N3—H3C | 109.4 | N3—C20—H20A | 109.3 |
H3B—N3—H3C | 108.0 | C19—C20—H20A | 109.3 |
C6—C1—C2 | 119.4 (4) | N3—C20—H20B | 109.3 |
C6—C1—C8 | 114.7 (4) | C19—C20—H20B | 109.3 |
C2—C1—C8 | 125.9 (4) | H20A—C20—H20B | 108.0 |
C3—C2—C1 | 118.8 (4) | N3—C21—C22 | 109.6 (4) |
C3—C2—C7 | 117.8 (4) | N3—C21—H21A | 109.7 |
C1—C2—C7 | 123.4 (4) | C22—C21—H21A | 109.7 |
C4—C3—C2 | 121.3 (4) | N3—C21—H21B | 109.7 |
C4—C3—H3A | 119.3 | C22—C21—H21B | 109.7 |
C2—C3—H3A | 119.3 | H21A—C21—H21B | 108.2 |
C3—C4—C5 | 119.4 (4) | N2—C22—C21 | 109.8 (4) |
C3—C4—C9 | 120.1 (4) | N2—C22—H22A | 109.7 |
C5—C4—C9 | 120.6 (4) | C21—C22—H22A | 109.7 |
C6—C5—C4 | 120.2 (4) | N2—C22—H22B | 109.7 |
C6—C5—H5A | 119.9 | C21—C22—H22B | 109.7 |
C4—C5—H5A | 119.9 | H22A—C22—H22B | 108.2 |
C5—C6—C1 | 121.0 (4) | O8—C23—O7 | 123.3 (4) |
C5—C6—H6A | 119.5 | O8—C23—C10 | 117.3 (4) |
C1—C6—H6A | 119.5 | O7—C23—C10 | 119.4 (4) |
O4—C7—O3 | 124.8 (4) | N1—C24—C25 | 111.8 (4) |
O4—C7—C2 | 120.0 (4) | N1—C24—H24A | 109.2 |
O3—C7—C2 | 115.2 (4) | C25—C24—H24A | 109.2 |
O1—C8—O2 | 124.3 (4) | N1—C24—H24B | 109.2 |
O1—C8—C1 | 115.6 (4) | C25—C24—H24B | 109.2 |
O2—C8—C1 | 119.7 (4) | H24A—C24—H24B | 107.9 |
O5—C9—O6 | 124.7 (4) | C24—C25—H25A | 109.5 |
O5—C9—C4 | 121.3 (4) | C24—C25—H25B | 109.5 |
O6—C9—C4 | 113.9 (4) | H25A—C25—H25B | 109.5 |
C11—C10—C14 | 119.0 (4) | C24—C25—H25C | 109.5 |
C11—C10—C23 | 115.3 (4) | H25A—C25—H25C | 109.5 |
C14—C10—C23 | 125.7 (4) | H25B—C25—H25C | 109.5 |
N1—C11—C10 | 125.0 (4) | H1—O1W—H2 | 95.1 |
N1—C11—H11A | 117.5 | H3—O2W—H4 | 102.2 |
C10—C11—H11A | 117.5 | H6—O3W—H5 | 109.3 |
N1—C12—C15 | 120.9 (4) |
Symmetry code: (i) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1···O4 | 0.85 | 1.86 | 2.711 (5) | 174 |
O3W—H6···O2 | 0.85 | 2.03 | 2.799 (5) | 151 |
O1W—H2···O5ii | 0.85 | 2.07 | 2.789 (5) | 142 |
O2W—H3···O1iii | 0.85 | 1.85 | 2.688 (5) | 167 |
N3—H3B···O8iv | 0.90 | 1.80 | 2.696 (5) | 177 |
N3—H3C···O2Wiv | 0.90 | 1.93 | 2.824 (6) | 171 |
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) −x−1, −y+2, −z; (iv) x+1, y−1, z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn2(C16H18FN3O3)2(C9H4O6)2]·6H2O |
Mr | 1293.75 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1317.3 (5) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.01 |
Crystal size (mm) | 0.31 × 0.25 × 0.19 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.744, 0.831 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13057, 5989, 5274 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.104, 1.02 |
No. of reflections | 5989 |
No. of parameters | 379 |
No. of restraints | 9 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.31 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1···O4 | 0.85 | 1.86 | 2.711 (5) | 174.1 |
O3W—H6···O2 | 0.85 | 2.03 | 2.799 (5) | 150.6 |
O1W—H2···O5i | 0.85 | 2.07 | 2.789 (5) | 142.4 |
O2W—H3···O1ii | 0.85 | 1.85 | 2.688 (5) | 166.9 |
N3—H3B···O8iii | 0.90 | 1.80 | 2.696 (5) | 177.2 |
N3—H3C···O2Wiii | 0.90 | 1.93 | 2.824 (6) | 171.1 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1, −y+2, −z; (iii) x+1, y−1, z+1. |
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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).