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The title compound hydroxy­ethyl­ammonium enrofloxacinate [systematic name: 2-hydroxy­ethanaminium 1-cyclo­propyl-7-(4-ethyl­piperazin-1-yl)-6-fluoro-4-oxo-1,4-di­hydro­quinoline-3-carboxyl­ate], C2H8NO+·C19H21FN3O3-, contains enrofloxacinate anions and 2-hydroxy­ethanaminium cations. The quinoline ring system in the anions is essentially planar. The piperazine moiety adopts a chair conformation. The cations lie parallel to each other about inversion centers. The structure is stabilized by strong intermolecular hydrogen bonds involving the carbonyl, carboxyl and terminal piperazine N groups of the anion and the hydroxyl and ammonium groups of the cation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021233/wk6021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021233/wk6021Isup2.hkl
Contains datablock I

CCDC reference: 252970

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.102
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C2 H8 N O
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C21 H29 F1 N4 O4 Atom count from _chemical_formula_moiety:C21 H28 F1 N4 O4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-hydroxyethanaminium 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline- 3-carboxylate top
Crystal data top
C2H8NO+·C19H21FN3O3Z = 2
Mr = 420.48F(000) = 448
Triclinic, P1Dx = 1.307 Mg m3
a = 9.791 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.858 (1) ÅCell parameters from 34 reflections
c = 12.274 (2) Åθ = 4.3–15.9°
α = 69.12 (1)°µ = 0.10 mm1
β = 75.74 (1)°T = 298 K
γ = 89.54 (1)°Prism, colourless
V = 1068.5 (3) Å30.54 × 0.32 × 0.24 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.009
Radiation source: normal-focus sealed tubeθmax = 25.5°, θmin = 1.8°
Graphite monochromatorh = 011
ω scansk = 1111
4509 measured reflectionsl = 1414
3932 independent reflections3 standard reflections every 97 reflections
2733 reflections with I > 2σ(I) intensity decay: 5.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.06P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
3932 reflectionsΔρmax = 0.20 e Å3
309 parametersΔρmin = 0.15 e Å3
3 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.041 (3)
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
F0.12637 (9)0.86744 (12)0.54017 (9)0.0505 (3)
O10.36721 (12)0.67145 (14)0.23093 (11)0.0471 (3)
O20.56004 (12)0.51011 (15)0.12676 (11)0.0501 (4)
O30.77943 (13)0.55956 (15)0.12782 (11)0.0523 (4)
N10.64753 (12)0.66343 (14)0.43101 (10)0.0294 (3)
N20.30620 (13)0.86371 (14)0.68422 (11)0.0334 (3)
N30.24206 (13)0.89893 (14)0.91446 (11)0.0333 (3)
C10.67977 (16)0.61612 (17)0.33756 (13)0.0310 (4)
H10.76830.58180.32070.037*
C20.59316 (16)0.61457 (16)0.26589 (13)0.0295 (3)
C30.45509 (16)0.66592 (17)0.28962 (13)0.0306 (4)
C40.41992 (15)0.71469 (16)0.39266 (13)0.0289 (3)
C50.28787 (16)0.76665 (18)0.42289 (14)0.0343 (4)
H50.22330.77020.37780.041*
C60.25381 (16)0.81187 (18)0.51763 (14)0.0343 (4)
C70.34529 (16)0.80887 (17)0.59066 (13)0.0312 (4)
C80.47568 (16)0.75818 (17)0.56029 (13)0.0313 (4)
H80.53920.75400.60640.038*
C90.51481 (15)0.71278 (16)0.46154 (13)0.0276 (3)
C100.74810 (17)0.65515 (19)0.50256 (15)0.0347 (4)
C110.81819 (19)0.7930 (2)0.49433 (19)0.0456 (5)
C120.90070 (19)0.6947 (2)0.44053 (19)0.0475 (5)
C130.64817 (18)0.55797 (18)0.16547 (14)0.0360 (4)
C140.17424 (16)0.79522 (19)0.77874 (14)0.0370 (4)
H14A0.18860.69700.82740.044*
H14B0.09940.78910.74110.044*
C150.13091 (16)0.88291 (18)0.85853 (14)0.0368 (4)
H15A0.10960.97860.81070.044*
H15B0.04570.83500.92110.044*
C160.36874 (17)0.97171 (19)0.81746 (14)0.0370 (4)
H16A0.44370.98550.85250.044*
H16B0.34801.06700.76840.044*
C170.41834 (16)0.88398 (19)0.73853 (14)0.0359 (4)
H17A0.50230.93440.67540.043*
H17B0.44250.78980.78660.043*
C180.19244 (19)0.9873 (2)0.98965 (16)0.0439 (4)
H18A0.10550.93871.04950.053*
H18B0.17061.08090.93860.053*
C190.2967 (2)1.0131 (3)1.05369 (19)0.0627 (6)
H19A0.33030.92211.09480.075*
H19B0.25131.05521.11130.075*
H19C0.37511.07850.99580.075*
O41.01557 (14)0.65443 (15)0.15994 (12)0.0562 (4)
N41.29740 (15)0.58467 (17)0.05639 (12)0.0371 (4)
C201.07615 (19)0.5288 (2)0.22023 (16)0.0490 (5)
H20A1.00150.45240.27120.059*
H20B1.12630.55060.27180.059*
C211.17689 (19)0.4754 (2)0.13325 (16)0.0498 (5)
H21A1.21260.38650.17830.060*
H21B1.12640.45270.08220.060*
H4O0.930 (3)0.624 (3)0.144 (2)0.112 (9)*
H100.7227 (17)0.5763 (18)0.5803 (16)0.045 (5)*
H11A0.8312 (18)0.7950 (18)0.5708 (16)0.050 (5)*
H11B0.7895 (18)0.882 (2)0.4427 (16)0.052 (5)*
H12A0.9271 (19)0.7278 (19)0.3526 (18)0.055 (5)*
H12B0.968 (2)0.636 (2)0.4803 (17)0.061 (6)*
H4A1.268 (2)0.6747 (13)0.0226 (17)0.068 (7)*
H4B1.3444 (17)0.5546 (18)0.0032 (12)0.050 (5)*
H4C1.3569 (16)0.5968 (19)0.0984 (14)0.051 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F0.0336 (5)0.0815 (8)0.0585 (6)0.0223 (5)0.0184 (5)0.0477 (6)
O10.0402 (7)0.0768 (9)0.0494 (7)0.0181 (6)0.0237 (6)0.0448 (7)
O20.0446 (7)0.0761 (9)0.0569 (8)0.0168 (6)0.0220 (6)0.0508 (7)
O30.0383 (7)0.0853 (10)0.0550 (8)0.0190 (7)0.0150 (6)0.0495 (8)
N10.0276 (7)0.0395 (8)0.0276 (7)0.0054 (6)0.0102 (5)0.0180 (6)
N20.0267 (7)0.0472 (8)0.0317 (7)0.0002 (6)0.0031 (6)0.0237 (6)
N30.0322 (7)0.0435 (8)0.0290 (7)0.0055 (6)0.0032 (6)0.0223 (6)
C10.0305 (8)0.0361 (9)0.0313 (8)0.0071 (7)0.0075 (7)0.0185 (7)
C20.0326 (8)0.0322 (9)0.0288 (8)0.0044 (7)0.0085 (7)0.0168 (7)
C30.0338 (9)0.0346 (9)0.0282 (8)0.0007 (7)0.0095 (7)0.0160 (7)
C40.0275 (8)0.0339 (9)0.0275 (8)0.0004 (7)0.0063 (6)0.0143 (7)
C50.0267 (8)0.0483 (10)0.0360 (9)0.0028 (7)0.0111 (7)0.0229 (8)
C60.0262 (8)0.0449 (10)0.0373 (9)0.0055 (7)0.0064 (7)0.0227 (8)
C70.0295 (8)0.0370 (9)0.0299 (8)0.0011 (7)0.0041 (7)0.0180 (7)
C80.0308 (8)0.0404 (9)0.0282 (8)0.0017 (7)0.0093 (7)0.0179 (7)
C90.0258 (8)0.0323 (8)0.0257 (8)0.0005 (6)0.0050 (6)0.0130 (7)
C100.0318 (9)0.0463 (10)0.0318 (9)0.0061 (8)0.0140 (7)0.0171 (8)
C110.0428 (11)0.0546 (13)0.0508 (11)0.0023 (9)0.0192 (9)0.0278 (10)
C120.0321 (10)0.0716 (14)0.0507 (12)0.0094 (9)0.0148 (9)0.0339 (11)
C130.0398 (10)0.0433 (10)0.0353 (9)0.0134 (8)0.0150 (8)0.0232 (8)
C140.0289 (8)0.0497 (10)0.0360 (9)0.0007 (7)0.0038 (7)0.0232 (8)
C150.0303 (9)0.0484 (10)0.0337 (9)0.0055 (8)0.0041 (7)0.0203 (8)
C160.0349 (9)0.0461 (10)0.0350 (9)0.0002 (8)0.0055 (7)0.0231 (8)
C170.0292 (8)0.0500 (10)0.0318 (8)0.0014 (7)0.0029 (7)0.0221 (8)
C180.0461 (10)0.0533 (11)0.0406 (10)0.0121 (9)0.0070 (8)0.0298 (9)
C190.0708 (14)0.0846 (16)0.0564 (12)0.0200 (12)0.0211 (11)0.0510 (12)
O40.0400 (8)0.0660 (9)0.0591 (8)0.0031 (7)0.0062 (7)0.0232 (7)
N40.0339 (8)0.0562 (10)0.0329 (8)0.0113 (7)0.0123 (6)0.0278 (8)
C200.0404 (10)0.0697 (13)0.0383 (10)0.0010 (9)0.0073 (8)0.0233 (10)
C210.0482 (11)0.0584 (12)0.0473 (11)0.0012 (9)0.0088 (9)0.0270 (10)
Geometric parameters (Å, º) top
F—C61.3639 (17)C11—H11B0.971 (18)
O1—C31.2405 (18)C12—H12A0.975 (19)
O2—C131.2495 (18)C12—H12B0.98 (2)
O3—C131.2522 (19)C14—C151.510 (2)
N1—C11.3539 (18)C14—H14A0.9700
N1—C91.3948 (18)C14—H14B0.9700
N1—C101.4564 (18)C15—H15A0.9700
N2—C71.4071 (18)C15—H15B0.9700
N2—C171.4659 (19)C16—C171.510 (2)
N2—C141.4792 (19)C16—H16A0.9700
N3—C151.4589 (19)C16—H16B0.9700
N3—C161.466 (2)C17—H17A0.9700
N3—C181.4805 (18)C17—H17B0.9700
C1—C21.368 (2)C18—C191.506 (2)
C1—H10.9300C18—H18A0.9700
C2—C31.438 (2)C18—H18B0.9700
C2—C131.510 (2)C19—H19A0.9600
C3—C41.471 (2)C19—H19B0.9600
C4—C91.398 (2)C19—H19C0.9600
C4—C51.400 (2)O4—C201.408 (2)
C5—C61.356 (2)O4—H4O0.98 (3)
C5—H50.9300N4—C211.480 (2)
C6—C71.408 (2)N4—H4A0.915 (9)
C7—C81.381 (2)N4—H4B0.906 (9)
C8—C91.404 (2)N4—H4C0.901 (9)
C8—H80.9300C20—C211.505 (2)
C10—C121.484 (2)C20—H20A0.9700
C10—C111.486 (2)C20—H20B0.9700
C10—H100.966 (17)C21—H21A0.9700
C11—C121.486 (3)C21—H21B0.9700
C11—H11A0.985 (18)
C1—N1—C9119.35 (12)O3—C13—C2117.77 (14)
C1—N1—C10119.96 (12)N2—C14—C15110.52 (13)
C9—N1—C10120.60 (12)N2—C14—H14A109.5
C7—N2—C17116.34 (12)C15—C14—H14A109.5
C7—N2—C14116.55 (12)N2—C14—H14B109.5
C17—N2—C14110.64 (12)C15—C14—H14B109.5
C15—N3—C16107.78 (12)H14A—C14—H14B108.1
C15—N3—C18108.34 (12)N3—C15—C14111.62 (13)
C16—N3—C18111.05 (13)N3—C15—H15A109.3
N1—C1—C2125.49 (14)C14—C15—H15A109.3
N1—C1—H1117.3N3—C15—H15B109.3
C2—C1—H1117.3C14—C15—H15B109.3
C1—C2—C3118.91 (13)H15A—C15—H15B108.0
C1—C2—C13117.77 (14)N3—C16—C17111.47 (13)
C3—C2—C13123.32 (13)N3—C16—H16A109.3
O1—C3—C2125.29 (13)C17—C16—H16A109.3
O1—C3—C4119.46 (14)N3—C16—H16B109.3
C2—C3—C4115.25 (13)C17—C16—H16B109.3
C9—C4—C5118.24 (13)H16A—C16—H16B108.0
C9—C4—C3122.26 (13)N2—C17—C16109.77 (13)
C5—C4—C3119.50 (13)N2—C17—H17A109.7
C6—C5—C4120.22 (14)C16—C17—H17A109.7
C6—C5—H5119.9N2—C17—H17B109.7
C4—C5—H5119.9C16—C17—H17B109.7
C5—C6—F117.96 (14)H17A—C17—H17B108.2
C5—C6—C7123.24 (14)N3—C18—C19114.46 (14)
F—C6—C7118.76 (13)N3—C18—H18A108.6
C8—C7—N2123.06 (14)C19—C18—H18A108.6
C8—C7—C6116.39 (13)N3—C18—H18B108.6
N2—C7—C6120.44 (14)C19—C18—H18B108.6
C7—C8—C9121.66 (14)H18A—C18—H18B107.6
C7—C8—H8119.2C18—C19—H19A109.5
C9—C8—H8119.2C18—C19—H19B109.5
N1—C9—C4118.71 (12)H19A—C19—H19B109.5
N1—C9—C8121.06 (13)C18—C19—H19C109.5
C4—C9—C8120.23 (14)H19A—C19—H19C109.5
N1—C10—C12119.24 (14)H19B—C19—H19C109.5
N1—C10—C11118.67 (15)C20—O4—H4O108.6 (16)
C12—C10—C1160.02 (12)C21—N4—H4A111.7 (13)
N1—C10—H10113.3 (10)C21—N4—H4B108.0 (11)
C12—C10—H10117.9 (10)H4A—N4—H4B109.1 (17)
C11—C10—H10117.9 (10)C21—N4—H4C112.4 (11)
C12—C11—C1059.90 (12)H4A—N4—H4C105.7 (16)
C12—C11—H11A118.6 (10)H4B—N4—H4C109.9 (16)
C10—C11—H11A115.5 (10)O4—C20—C21111.92 (15)
C12—C11—H11B120.1 (11)O4—C20—H20A109.2
C10—C11—H11B116.0 (10)C21—C20—H20A109.2
H11A—C11—H11B115.1 (15)O4—C20—H20B109.2
C10—C12—C1160.08 (12)C21—C20—H20B109.2
C10—C12—H12A116.9 (11)H20A—C20—H20B107.9
C11—C12—H12A116.4 (11)N4—C21—C20112.03 (15)
C10—C12—H12B117.1 (11)N4—C21—H21A109.2
C11—C12—H12B119.7 (11)C20—C21—H21A109.2
H12A—C12—H12B115.4 (16)N4—C21—H21B109.2
O2—C13—O3124.18 (14)C20—C21—H21B109.2
O2—C13—C2118.03 (14)H21A—C21—H21B107.9
C9—N1—C1—C21.5 (2)C5—C4—C9—N1178.98 (14)
C10—N1—C1—C2178.18 (15)C3—C4—C9—N10.3 (2)
N1—C1—C2—C30.4 (2)C5—C4—C9—C81.8 (2)
N1—C1—C2—C13179.81 (14)C3—C4—C9—C8178.97 (14)
C1—C2—C3—O1179.32 (15)C7—C8—C9—N1179.24 (14)
C13—C2—C3—O10.9 (3)C7—C8—C9—C41.6 (2)
C1—C2—C3—C40.7 (2)C1—N1—C10—C1241.7 (2)
C13—C2—C3—C4179.10 (14)C9—N1—C10—C12141.65 (16)
O1—C3—C4—C9179.27 (15)C1—N1—C10—C11111.40 (17)
C2—C3—C4—C90.7 (2)C9—N1—C10—C1171.92 (19)
O1—C3—C4—C50.0 (2)N1—C10—C11—C12109.11 (17)
C2—C3—C4—C5179.98 (14)N1—C10—C12—C11108.16 (18)
C9—C4—C5—C60.8 (2)C1—C2—C13—O2156.37 (15)
C3—C4—C5—C6179.94 (15)C3—C2—C13—O223.4 (2)
C4—C5—C6—F177.21 (14)C1—C2—C13—O322.3 (2)
C4—C5—C6—C70.5 (3)C3—C2—C13—O3157.88 (16)
C17—N2—C7—C88.3 (2)C7—N2—C14—C15169.01 (14)
C14—N2—C7—C8125.15 (17)C17—N2—C14—C1555.08 (17)
C17—N2—C7—C6167.74 (14)C16—N3—C15—C1459.05 (17)
C14—N2—C7—C658.9 (2)C18—N3—C15—C14179.30 (13)
C5—C6—C7—C80.8 (2)N2—C14—C15—N357.49 (18)
F—C6—C7—C8176.93 (14)C15—N3—C16—C1760.22 (17)
C5—C6—C7—N2177.03 (15)C18—N3—C16—C17178.74 (13)
F—C6—C7—N20.7 (2)C7—N2—C17—C16168.14 (13)
N2—C7—C8—C9175.88 (14)C14—N2—C17—C1655.84 (17)
C6—C7—C8—C90.3 (2)N3—C16—C17—N259.56 (18)
C1—N1—C9—C41.3 (2)C15—N3—C18—C19179.95 (16)
C10—N1—C9—C4178.03 (14)C16—N3—C18—C1961.9 (2)
C1—N1—C9—C8177.88 (14)O4—C20—C21—N461.6 (2)
C10—N1—C9—C81.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O30.98 (3)1.69 (3)2.6687 (19)175 (2)
N4—H4C···O1i0.90 (1)2.03 (1)2.7973 (17)142 (2)
N4—H4C···O2i0.90 (1)2.22 (1)2.9171 (19)134 (1)
N4—H4B···O2ii0.91 (1)1.89 (1)2.7937 (18)179 (2)
N4—H4A···N3iii0.92 (1)2.19 (1)3.085 (2)168 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z; (iii) x+1, y, z1.
 

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