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The antibiotic norfloxacin recrystallizes from aceto­nitrile as a dihydrate with the norfloxacin mol­ecule in a zwitterionic form, i.e. 1-ethyl-6-fluoro-1,4-di­hydro-4-oxo-7-(1-piperazin-4-io)-3-quinoline­carboxyl­ate dihydrate, C16­H18­F­N3­O3·­2H2O.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010933/bm1423sup1.cif
Contains datablocks I, norfloxacindihydrate

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010933/bm1423Isup2.hkl
Contains datablock I

CCDC reference: 153910

Computing details top

Data collection: MSC/Rigaku Diffractometer Control (Molecular Structure Corporation, 1985); cell refinement: MSC/Rigaku Diffractometer Control; data reduction: TEXSAN (Molecular Structure Corporation, 1993); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1994); software used to prepare material for publication: SHELXL97.

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7(1-piperzinyl)-3-quinolinecarboxylic acid top
Crystal data top
C16H18FN3O3·2H2OF(000) = 752
Mr = 355.37Dx = 1.478 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
a = 8.265 (3) ÅCell parameters from 18 reflections
b = 21.698 (4) Åθ = 9.2–12.0°
c = 9.5250 (17) ŵ = 0.12 mm1
β = 110.794 (19)°T = 123 K
V = 1596.9 (6) Å3Tabular, colourless
Z = 40.40 × 0.30 × 0.15 mm
Data collection top
Rigaku AFC7S
diffractometer
Rint = 0.058
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 2.6°
Graphite monochromatorh = 010
ω/2θ scansk = 028
3918 measured reflectionsl = 1211
3676 independent reflections3 standard reflections every 150 reflections
1701 reflections with I > 2σ(I) intensity decay: 1.7%
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 0.96Calculated w = 1/[σ2(Fo2) + (0.0782P)2]
where P = (Fo2 + 2Fc2)/3
3676 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.32 e Å3
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.

H atoms on O and N were refined isotropically. All other H atoms were placed in calculated positions and in a riding mode.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.1855 (2)0.00803 (8)0.5884 (2)0.0201 (5)
O10.4995 (4)0.14193 (11)1.3917 (3)0.0291 (6)
O20.3427 (3)0.20785 (10)1.2160 (3)0.0175 (5)
O30.0763 (3)0.14837 (10)0.9802 (3)0.0188 (5)
O40.5523 (3)0.20095 (12)1.0520 (3)0.0245 (6)
O50.2650 (3)0.22229 (14)0.4583 (3)0.0252 (6)
N10.3804 (3)0.00629 (12)1.1158 (3)0.0137 (6)
N20.0045 (4)0.11643 (11)0.6723 (3)0.0136 (6)
N30.0451 (4)0.22589 (12)0.4946 (3)0.0140 (6)
C10.4158 (4)0.04593 (14)1.1983 (4)0.0146 (7)
H10.50900.04511.28870.018*
C20.3249 (4)0.10050 (14)1.1592 (4)0.0139 (7)
C30.3928 (4)0.15402 (15)1.2637 (4)0.0157 (7)
C40.1743 (4)0.10302 (14)1.0238 (4)0.0134 (7)
C50.1392 (4)0.04578 (14)0.9351 (3)0.0119 (7)
C60.0015 (4)0.04432 (14)0.7986 (4)0.0141 (7)
H60.06840.07950.76480.017*
C70.0404 (4)0.00792 (15)0.7158 (3)0.0140 (7)
C80.0572 (4)0.06269 (14)0.7571 (4)0.0133 (7)
C90.1995 (4)0.06069 (14)0.8910 (3)0.0132 (7)
H90.26940.09540.92150.016*
C100.2396 (4)0.00757 (14)0.9807 (3)0.0125 (7)
C110.0228 (5)0.11325 (14)0.5115 (4)0.0166 (7)
H11A0.07940.07480.47010.020*
H11B0.08800.11450.49770.020*
C120.1338 (5)0.16706 (14)0.4297 (4)0.0175 (7)
H12A0.15140.16510.32350.021*
H12B0.24610.16520.44050.021*
C130.0096 (4)0.22847 (15)0.6587 (4)0.0164 (7)
H13A0.11840.23000.67590.020*
H13B0.05410.26580.69960.020*
C140.0934 (4)0.17335 (14)0.7391 (4)0.0147 (7)
H14A0.20750.17420.73180.018*
H14B0.10740.17490.84450.018*
C150.4885 (4)0.06167 (14)1.1738 (4)0.0155 (7)
H15A0.51170.08151.09160.019*
H15B0.59850.04891.24720.019*
C160.4054 (5)0.10789 (16)1.2456 (4)0.0215 (8)
H16A0.29380.11931.17530.026*
H16B0.47730.14391.27420.026*
H16C0.39220.08991.33300.026*
H170.051 (6)0.2282 (19)0.464 (5)0.045 (13)*
H180.096 (6)0.261 (2)0.453 (5)0.042 (13)*
H190.584 (5)0.2274 (18)1.121 (5)0.025 (11)*
H200.609 (6)0.2049 (17)0.987 (5)0.032 (12)*
H210.328 (5)0.1955 (17)0.500 (4)0.013 (10)*
H220.322 (6)0.254 (2)0.463 (5)0.047 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0188 (11)0.0180 (10)0.0162 (10)0.0028 (8)0.0029 (9)0.0011 (8)
O10.0401 (16)0.0170 (13)0.0165 (13)0.0045 (12)0.0067 (12)0.0020 (10)
O20.0195 (12)0.0117 (11)0.0200 (12)0.0001 (10)0.0057 (10)0.0018 (9)
O30.0205 (13)0.0112 (11)0.0196 (13)0.0018 (10)0.0011 (10)0.0002 (10)
O40.0267 (15)0.0199 (14)0.0295 (16)0.0034 (11)0.0130 (13)0.0071 (12)
O50.0158 (13)0.0232 (15)0.0340 (16)0.0051 (12)0.0058 (12)0.0122 (13)
N10.0123 (14)0.0132 (14)0.0127 (14)0.0029 (11)0.0009 (11)0.0014 (11)
N20.0181 (15)0.0077 (13)0.0131 (14)0.0015 (11)0.0035 (12)0.0020 (11)
N30.0161 (15)0.0100 (14)0.0155 (14)0.0014 (12)0.0051 (12)0.0027 (12)
C10.0162 (17)0.0136 (16)0.0114 (16)0.0011 (13)0.0017 (14)0.0008 (12)
C20.0151 (16)0.0133 (16)0.0146 (17)0.0037 (13)0.0068 (14)0.0002 (13)
C30.0188 (18)0.0141 (17)0.0168 (18)0.0036 (13)0.0093 (15)0.0020 (13)
C40.0135 (16)0.0127 (16)0.0148 (17)0.0036 (13)0.0060 (14)0.0004 (13)
C50.0097 (16)0.0114 (15)0.0148 (17)0.0004 (12)0.0046 (14)0.0001 (12)
C60.0126 (16)0.0128 (16)0.0179 (18)0.0002 (13)0.0065 (14)0.0021 (13)
C70.0095 (16)0.0177 (17)0.0117 (16)0.0007 (13)0.0002 (13)0.0034 (13)
C80.0146 (17)0.0133 (16)0.0140 (16)0.0009 (12)0.0077 (14)0.0004 (12)
C90.0149 (17)0.0114 (15)0.0126 (17)0.0048 (13)0.0039 (14)0.0017 (12)
C100.0104 (16)0.0135 (16)0.0144 (16)0.0008 (12)0.0053 (13)0.0009 (13)
C110.0233 (18)0.0121 (16)0.0125 (16)0.0024 (14)0.0039 (14)0.0005 (13)
C120.0205 (17)0.0183 (17)0.0102 (16)0.0039 (14)0.0011 (14)0.0000 (13)
C130.0195 (18)0.0109 (16)0.0184 (18)0.0012 (13)0.0063 (15)0.0005 (13)
C140.0189 (17)0.0092 (15)0.0133 (16)0.0018 (13)0.0026 (14)0.0007 (13)
C150.0146 (17)0.0117 (16)0.0183 (17)0.0033 (13)0.0032 (15)0.0030 (13)
C160.0209 (18)0.0217 (19)0.0203 (19)0.0062 (15)0.0052 (15)0.0042 (15)
Geometric parameters (Å, º) top
F1—C71.370 (4)C2—C41.441 (5)
O1—C31.253 (4)C2—C31.502 (4)
O2—C31.268 (4)C4—C51.472 (4)
O3—C41.248 (4)C5—C101.401 (4)
N1—C11.350 (4)C5—C61.404 (4)
N1—C101.396 (4)C6—C71.353 (4)
N1—C151.482 (4)C7—C81.412 (4)
N2—C81.397 (4)C8—C91.396 (4)
N2—C141.462 (4)C9—C101.402 (4)
N2—C111.469 (4)C11—C121.518 (4)
N3—C131.486 (4)C13—C141.510 (4)
N3—C121.492 (4)C15—C161.510 (5)
C1—C21.380 (4)
C1—N1—C10119.4 (3)C10—C5—C4123.0 (3)
C1—N1—C15119.1 (3)C6—C5—C4118.7 (3)
C10—N1—C15121.5 (3)C7—C6—C5120.4 (3)
C8—N2—C14116.6 (3)C6—C7—F1118.0 (3)
C8—N2—C11117.7 (2)C6—C7—C8123.3 (3)
C14—N2—C11111.1 (2)F1—C7—C8118.6 (3)
C13—N3—C12110.7 (3)C9—C8—N2122.9 (3)
N1—C1—C2125.3 (3)C9—C8—C7116.2 (3)
C1—C2—C4119.2 (3)N2—C8—C7120.8 (3)
C1—C2—C3116.4 (3)C8—C9—C10121.5 (3)
C4—C2—C3124.3 (3)N1—C10—C5118.5 (3)
O1—C3—O2124.7 (3)N1—C10—C9121.1 (3)
O1—C3—C2116.8 (3)C5—C10—C9120.3 (3)
O2—C3—C2118.5 (3)N2—C11—C12109.9 (3)
O3—C4—C2125.5 (3)N3—C12—C11109.1 (3)
O3—C4—C5120.1 (3)N3—C13—C14111.6 (3)
C2—C4—C5114.4 (3)N2—C14—C13110.1 (3)
C10—C5—C6118.2 (3)N1—C15—C16113.4 (3)
C10—N1—C1—C21.3 (5)F1—C7—C8—C9177.4 (3)
C15—N1—C1—C2179.1 (3)C6—C7—C8—N2175.8 (3)
N1—C1—C2—C43.1 (5)F1—C7—C8—N21.8 (4)
N1—C1—C2—C3176.7 (3)N2—C8—C9—C10174.0 (3)
C1—C2—C3—O115.5 (4)C7—C8—C9—C101.6 (5)
C4—C2—C3—O1164.7 (3)C1—N1—C10—C50.0 (4)
C1—C2—C3—O2162.6 (3)C15—N1—C10—C5177.7 (3)
C4—C2—C3—O217.2 (5)C1—N1—C10—C9179.4 (3)
C1—C2—C4—O3176.1 (3)C15—N1—C10—C92.9 (5)
C3—C2—C4—O34.0 (5)C6—C5—C10—N1179.5 (3)
C1—C2—C4—C53.3 (4)C4—C5—C10—N10.6 (4)
C3—C2—C4—C5176.5 (3)C6—C5—C10—C90.2 (4)
O3—C4—C5—C10177.3 (3)C4—C5—C10—C9179.9 (3)
C2—C4—C5—C102.2 (4)C8—C9—C10—N1178.9 (3)
O3—C4—C5—C62.6 (4)C8—C9—C10—C51.7 (5)
C2—C4—C5—C6177.9 (3)C8—N2—C11—C12161.2 (3)
C10—C5—C6—C71.5 (5)C14—N2—C11—C1260.6 (3)
C4—C5—C6—C7178.4 (3)C13—N3—C12—C1156.9 (4)
C5—C6—C7—F1175.9 (3)N2—C11—C12—N359.3 (3)
C5—C6—C7—C81.7 (5)C12—N3—C13—C1455.6 (4)
C14—N2—C8—C97.0 (4)C8—N2—C14—C13163.4 (3)
C11—N2—C8—C9128.9 (3)C11—N2—C14—C1357.9 (3)
C14—N2—C8—C7168.3 (3)N3—C13—C14—N255.3 (4)
C11—N2—C8—C755.7 (4)C1—N1—C15—C16100.1 (4)
C6—C7—C8—C90.1 (5)C10—N1—C15—C1677.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H17···O50.94 (5)1.79 (5)2.706 (4)163 (4)
N3—H18···O2i0.89 (4)2.21 (5)2.939 (4)139 (4)
N3—H18···O3i0.89 (4)2.06 (4)2.759 (4)135 (4)
O4—H19···O2ii0.84 (4)2.02 (4)2.862 (4)179 (4)
O4—H20···O2iii0.90 (5)2.11 (5)2.977 (4)161 (4)
O5—H21···O1iii0.79 (4)1.84 (4)2.626 (4)171 (4)
O5—H22···O4iv0.83 (5)2.04 (5)2.776 (4)149 (4)
C13—H13A···O2v0.972.473.397 (5)161
C13—H13B···O5vi0.972.483.136 (5)125
C13—H13B···O3i0.972.502.946 (4)108
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x+1, y+1/2, z+5/2; (iii) x+1, y, z+2; (iv) x, y+1/2, z1/2; (v) x, y, z+2; (vi) x, y+1/2, z+1/2.
 

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