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The title compound [systematic name: 1-cyclo­propyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ate methanol hemisolvate], C17H18FN3O3·0.5CH4O, is an anti­bacterial fluoro­quinolone. The mol­ecule exists as a zwitterion in the solid state. The methanol mol­ecule is disordered across a twofold rotation axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049087/fl2076sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049087/fl2076Isup2.hkl
Contains datablock I

CCDC reference: 629675

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in solvent or counterion
  • R factor = 0.050
  • wR factor = 0.132
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C H4 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPII (Johnson 1976) and MS Modeling (Accelrys, 2004); software used to prepare material for publication: SHELXTL.

1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3- carboxylate methanol hemisolvate top
Crystal data top
C17H18FN3O3·0.5CH4OF(000) = 1464
Mr = 347.37Dx = 1.389 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 26.036 (11) ÅCell parameters from 918 reflections
b = 12.697 (5) Åθ = 2.8–28.0°
c = 10.235 (4) ŵ = 0.11 mm1
β = 100.941 (7)°T = 193 K
V = 3322 (2) Å3Needle, colourless
Z = 80.4 × 0.1 × 0.1 mm
Data collection top
Bruker APEX CCD
diffractometer
3174 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 28.4°, θmin = 1.6°
ω scansh = 3434
19542 measured reflectionsk = 1616
4067 independent reflectionsl = 1313
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0834P)2]
where P = (Fo2 + 2Fc2)/3
4067 reflections(Δ/σ)max = 0.004
236 parametersΔρmax = 0.42 e Å3
1 restraintΔρmin = 0.27 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F10.31322 (3)0.30371 (7)0.17111 (9)0.0353 (2)
O10.01072 (4)0.22152 (9)0.06628 (13)0.0445 (3)
O20.02182 (4)0.38496 (7)0.08540 (11)0.0319 (3)
O30.12327 (4)0.36614 (8)0.01847 (10)0.0278 (2)
N10.13471 (4)0.12707 (8)0.29290 (11)0.0217 (3)
N20.32619 (4)0.15634 (9)0.36645 (11)0.0241 (3)
N30.42473 (4)0.06580 (9)0.48346 (12)0.0247 (3)
H1A0.45820.07680.52350.030*
H1B0.41920.00420.47820.030*
C10.13796 (5)0.03814 (11)0.38372 (15)0.0287 (3)
H10.14850.02890.34950.034*
C20.10033 (7)0.03035 (15)0.47579 (18)0.0460 (5)
H2A0.08800.03920.49410.055*
H2B0.07480.08620.47320.055*
C30.15640 (7)0.05633 (15)0.52964 (16)0.0435 (4)
H3A0.17800.00240.58020.052*
H3B0.16470.12800.55930.052*
C40.18026 (5)0.17178 (10)0.26491 (13)0.0204 (3)
C50.08739 (5)0.16224 (10)0.22787 (14)0.0228 (3)
H50.05770.12810.24420.027*
C60.08065 (5)0.24431 (10)0.14029 (14)0.0220 (3)
C70.02596 (5)0.28519 (11)0.09177 (15)0.0263 (3)
C80.12511 (5)0.29326 (10)0.10155 (13)0.0212 (3)
C90.17597 (5)0.25132 (10)0.16800 (13)0.0203 (3)
C100.22188 (5)0.29428 (11)0.13676 (14)0.0248 (3)
H100.21970.34650.07220.030*
C110.26926 (5)0.25971 (11)0.20052 (14)0.0250 (3)
C120.27531 (5)0.18160 (11)0.30065 (14)0.0229 (3)
C130.33232 (5)0.10545 (11)0.49636 (14)0.0246 (3)
H13A0.32210.03200.48570.030*
H13B0.31020.13970.55000.030*
C140.38936 (5)0.11393 (11)0.56417 (14)0.0253 (3)
H14A0.39840.18760.57940.030*
H14B0.39420.07910.65000.030*
C150.41588 (5)0.11097 (12)0.34772 (15)0.0282 (3)
H15A0.43690.07320.29430.034*
H15B0.42680.18410.35230.034*
C160.35877 (5)0.10385 (12)0.28255 (15)0.0269 (3)
H16A0.35340.13720.19580.032*
H16B0.34860.03050.27020.032*
C170.23015 (5)0.13762 (11)0.33074 (13)0.0225 (3)
H170.23280.08510.39500.027*
O40.01072 (14)0.0755 (3)0.1677 (4)0.0812 (11)0.50
H40.02090.11140.11100.122*0.50
C180.0001 (11)0.1404 (5)0.2681 (13)0.124 (3)0.50
H18C0.03130.15140.33300.187*0.50
H18A0.02600.10780.30990.187*0.50
H18B0.01290.20690.23090.187*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0189 (4)0.0374 (5)0.0499 (6)0.0029 (3)0.0072 (4)0.0134 (4)
O10.0202 (5)0.0301 (6)0.0782 (9)0.0054 (4)0.0029 (6)0.0093 (6)
O20.0173 (5)0.0229 (5)0.0529 (7)0.0028 (4)0.0002 (4)0.0058 (5)
O30.0246 (5)0.0279 (5)0.0314 (6)0.0060 (4)0.0068 (4)0.0109 (4)
N10.0194 (6)0.0193 (5)0.0273 (6)0.0030 (4)0.0069 (5)0.0050 (4)
N20.0159 (6)0.0291 (6)0.0271 (6)0.0044 (4)0.0034 (5)0.0022 (5)
N30.0143 (5)0.0212 (6)0.0364 (7)0.0000 (4)0.0010 (5)0.0036 (5)
C10.0272 (7)0.0225 (7)0.0385 (8)0.0061 (5)0.0111 (6)0.0115 (6)
C20.0408 (10)0.0454 (10)0.0590 (11)0.0136 (8)0.0275 (8)0.0279 (9)
C30.0515 (11)0.0463 (10)0.0342 (9)0.0086 (8)0.0118 (8)0.0176 (8)
C40.0190 (6)0.0198 (6)0.0229 (7)0.0024 (5)0.0048 (5)0.0003 (5)
C50.0172 (6)0.0213 (7)0.0309 (7)0.0008 (5)0.0068 (5)0.0005 (5)
C60.0178 (6)0.0198 (6)0.0272 (7)0.0015 (5)0.0015 (5)0.0003 (5)
C70.0181 (7)0.0264 (7)0.0332 (8)0.0009 (5)0.0014 (6)0.0059 (6)
C80.0203 (7)0.0202 (6)0.0227 (7)0.0024 (5)0.0034 (5)0.0001 (5)
C90.0176 (6)0.0203 (6)0.0231 (7)0.0021 (5)0.0039 (5)0.0011 (5)
C100.0233 (7)0.0229 (7)0.0285 (7)0.0011 (5)0.0055 (6)0.0070 (6)
C110.0175 (6)0.0262 (7)0.0321 (8)0.0018 (5)0.0064 (5)0.0030 (6)
C120.0182 (6)0.0244 (7)0.0252 (7)0.0033 (5)0.0018 (5)0.0005 (5)
C130.0189 (7)0.0284 (7)0.0260 (7)0.0042 (5)0.0032 (5)0.0013 (6)
C140.0203 (7)0.0261 (7)0.0279 (7)0.0020 (5)0.0002 (5)0.0008 (5)
C150.0197 (7)0.0303 (8)0.0354 (8)0.0012 (5)0.0072 (6)0.0016 (6)
C160.0197 (7)0.0330 (8)0.0281 (7)0.0036 (5)0.0045 (5)0.0014 (6)
C170.0217 (7)0.0219 (7)0.0238 (7)0.0036 (5)0.0041 (5)0.0039 (5)
O40.096 (3)0.085 (3)0.073 (2)0.035 (2)0.042 (2)0.019 (2)
C180.253 (8)0.093 (4)0.034 (7)0.049 (9)0.045 (7)0.011 (4)
Geometric parameters (Å, º) top
F1—C111.3579 (16)C5—H50.9300
O1—C71.2405 (17)C6—C81.4345 (18)
O2—C71.2720 (17)C6—C71.5085 (19)
O3—C81.2514 (16)C8—C91.4689 (18)
N1—C51.3597 (17)C9—C101.4049 (19)
N1—C41.3926 (17)C10—C111.3545 (19)
N1—C11.4548 (17)C10—H100.9300
N2—C121.4046 (17)C11—C121.413 (2)
N2—C131.4596 (18)C12—C171.3880 (19)
N2—C161.4756 (18)C13—C141.5190 (19)
N3—C151.4801 (19)C13—H13A0.9700
N3—C141.4807 (18)C13—H13B0.9700
N3—H1A0.9000C14—H14A0.9700
N3—H1B0.9000C14—H14B0.9700
C1—C21.486 (2)C15—C161.5124 (19)
C1—C31.497 (2)C15—H15A0.9700
C1—H10.9800C15—H15B0.9700
C2—C31.496 (3)C16—H16A0.9700
C2—H2A0.9700C16—H16B0.9700
C2—H2B0.9700C17—H170.9300
C3—H3A0.9700O4—C181.386 (8)
C3—H3B0.9700O4—H40.8200
C4—C91.4051 (19)C18—H18C0.9600
C4—C171.4133 (18)C18—H18A0.9600
C5—C61.3640 (19)C18—H18B0.9600
C5—N1—C4119.55 (11)O3—C8—C9119.85 (12)
C5—N1—C1120.33 (11)C6—C8—C9114.75 (12)
C4—N1—C1119.96 (11)C10—C9—C4118.86 (12)
C12—N2—C13117.90 (11)C10—C9—C8119.02 (12)
C12—N2—C16114.72 (11)C4—C9—C8122.09 (12)
C13—N2—C16110.78 (11)C11—C10—C9120.06 (13)
C15—N3—C14111.17 (11)C11—C10—H10120.0
C15—N3—H1A109.4C9—C10—H10120.0
C14—N3—H1A109.4C10—C11—F1119.26 (12)
C15—N3—H1B109.4C10—C11—C12122.87 (13)
C14—N3—H1B109.4F1—C11—C12117.83 (12)
H1A—N3—H1B108.0C17—C12—N2124.29 (13)
N1—C1—C2119.44 (12)C17—C12—C11117.43 (12)
N1—C1—C3119.10 (13)N2—C12—C11118.23 (12)
C2—C1—C360.20 (12)N2—C13—C14108.25 (11)
N1—C1—H1115.6N2—C13—H13A110.0
C2—C1—H1115.6C14—C13—H13A110.0
C3—C1—H1115.6N2—C13—H13B110.0
C1—C2—C360.28 (11)C14—C13—H13B110.0
C1—C2—H2A117.7H13A—C13—H13B108.4
C3—C2—H2A117.7N3—C14—C13111.93 (11)
C1—C2—H2B117.7N3—C14—H14A109.2
C3—C2—H2B117.7C13—C14—H14A109.2
H2A—C2—H2B114.9N3—C14—H14B109.2
C2—C3—C159.52 (11)C13—C14—H14B109.2
C2—C3—H3A117.8H14A—C14—H14B107.9
C1—C3—H3A117.8N3—C15—C16110.84 (11)
C2—C3—H3B117.8N3—C15—H15A109.5
C1—C3—H3B117.8C16—C15—H15A109.5
H3A—C3—H3B115.0N3—C15—H15B109.5
N1—C4—C9118.78 (11)C16—C15—H15B109.5
N1—C4—C17121.22 (12)H15A—C15—H15B108.1
C9—C4—C17119.99 (12)N2—C16—C15109.99 (12)
N1—C5—C6124.35 (12)N2—C16—H16A109.7
N1—C5—H5117.8C15—C16—H16A109.7
C6—C5—H5117.8N2—C16—H16B109.7
C5—C6—C8120.18 (12)C15—C16—H16B109.7
C5—C6—C7118.36 (12)H16A—C16—H16B108.2
C8—C6—C7121.39 (12)C12—C17—C4120.76 (12)
O1—C7—O2125.74 (13)C12—C17—H17119.6
O1—C7—C6119.07 (13)C4—C17—H17119.6
O2—C7—C6115.15 (12)C18—O4—H4109.5
O3—C8—C6125.40 (12)
C5—N1—C1—C241.7 (2)C6—C8—C9—C10179.93 (12)
C4—N1—C1—C2142.90 (15)O3—C8—C9—C4178.04 (13)
C5—N1—C1—C3111.89 (15)C6—C8—C9—C41.95 (19)
C4—N1—C1—C372.71 (17)C4—C9—C10—C110.6 (2)
N1—C1—C2—C3108.68 (16)C8—C9—C10—C11177.44 (13)
N1—C1—C3—C2109.24 (15)C9—C10—C11—F1178.59 (12)
C5—N1—C4—C91.04 (19)C9—C10—C11—C120.8 (2)
C1—N1—C4—C9174.39 (12)C13—N2—C12—C1718.35 (19)
C5—N1—C4—C17179.78 (12)C16—N2—C12—C17114.94 (15)
C1—N1—C4—C174.79 (19)C13—N2—C12—C11159.17 (13)
C4—N1—C5—C64.0 (2)C16—N2—C12—C1167.54 (17)
C1—N1—C5—C6179.43 (13)C10—C11—C12—C171.7 (2)
N1—C5—C6—C86.0 (2)F1—C11—C12—C17179.54 (12)
N1—C5—C6—C7170.79 (12)C10—C11—C12—N2175.95 (13)
C5—C6—C7—O139.6 (2)F1—C11—C12—N21.8 (2)
C8—C6—C7—O1143.59 (15)C12—N2—C13—C14164.22 (12)
C5—C6—C7—O2137.98 (14)C16—N2—C13—C1460.79 (14)
C8—C6—C7—O238.8 (2)C15—N3—C14—C1354.62 (15)
C5—C6—C8—O3177.16 (13)N2—C13—C14—N357.72 (15)
C7—C6—C8—O36.1 (2)C14—N3—C15—C1653.26 (15)
C5—C6—C8—C92.85 (19)C12—N2—C16—C15162.40 (12)
C7—C6—C8—C9173.88 (12)C13—N2—C16—C1561.08 (15)
N1—C4—C9—C10178.10 (12)N3—C15—C16—N256.20 (16)
C17—C4—C9—C101.1 (2)N2—C12—C17—C4176.32 (12)
N1—C4—C9—C83.9 (2)C11—C12—C17—C41.2 (2)
C17—C4—C9—C8176.89 (12)N1—C4—C17—C12179.02 (12)
O3—C8—C9—C100.1 (2)C9—C4—C17—C120.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O10.822.273.029 (4)155
N3—H1A···O2i0.901.732.6209 (17)171
N3—H1B···O3ii0.901.992.8247 (18)154
N3—H1B···O2ii0.902.272.8422 (17)121
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z+1/2.
 

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