addenda and errata\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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1-Cyclo­propyl-6-fluoro-7-(4-formyl­piperazin-1-yl)-4-oxo-1,4-di­hydro­quinoline-3-carboxylic acid. Corrigendum

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aSchool of Life Sciences, Nanjing University, Nanjing 210093, People's Republic of China, and bDepartment of Biochemistry, Fujian Institute of Education, Fuzhou 350001, Fujian, People's Republic of China
*Correspondence e-mail: hu_yiqiao@yahoo.com.cn

(Received 25 July 2005; accepted 29 July 2005; online 6 August 2005)

The crystal structure of the title compound, C18H18FN3O4, was published [Li et al. (2005[Li, X.-W., Zhi, F., Shen, J.-H. & Hu, Y.-Q. (2005). Acta Cryst. E61, o2235-o2236.]). Acta Cryst. E61, o2235–o2236] with an error in the chemical formula and without location of the carboxyl H atom. This has now been corrected. The missing H atom was located and refined. This H atom is involved in an intra­molecular O—H⋯O hydrogen bond with the carbonyl O atom.

1.

[Scheme 1]

2. Experimental

2.1.1. Crystal data
  • C18H18FN3O4

  • Mr = 359.35

  • Triclinic, [P \overline 1]

  • a = 8.414 (2) Å

  • b = 9.513 (2) Å

  • c = 10.497 (2) Å

  • α = 102.57 (3)°

  • β = 96.58 (3)°

  • γ = 97.08 (3)°

  • V = 805.1 (3) Å3

  • Z = 2

  • Dx = 1.482 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 25 reflections

  • θ = 9–13°

  • μ = 0.11 mm−1

  • T = 293 (2) K

  • Block, yellow

  • 0.48 × 0.21 × 0.19 mm

2.1.2. Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • ω/2θ scans

  • Absorption correction: ψ scan(XCAD4; Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995) XCAD4. University of Marburg, Germany.])Tmin = 0.947, Tmax = 0.979

  • 3379 measured reflections

  • 3154 independent reflections

  • 1822 reflections with I > 2σ(I)

  • Rint = 0.027

  • θmax = 26.0°

  • h = 0 → 10

  • k = −11 → 11

  • l = −12 → 12

  • 3 standard reflections every 200 reflections intensity decay: none

2.1.3. Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.140

  • S = 1.01

  • 3154 reflections

  • 238 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • w = 1/[σ2(Fo2) + (0.06P)2 + 0.035P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.001

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O2 0.90 (1) 1.69 (2) 2.514 (3) 151 (3)

Supporting information


Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

1-Cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3- carboxylic acid top
Crystal data top
C18H18FN3O4Z = 2
Mr = 359.35F(000) = 376
Triclinic, P1Dx = 1.482 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.414 (2) ÅCell parameters from 25 reflections
b = 9.513 (2) Åθ = 9–13°
c = 10.497 (2) ŵ = 0.11 mm1
α = 102.57 (3)°T = 293 K
β = 96.58 (3)°Block, yellow
γ = 97.08 (3)°0.48 × 0.21 × 0.19 mm
V = 805.1 (3) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
1822 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 26.0°, θmin = 2.2°
ω/2θ scansh = 010
Absorption correction: ψ scan
(XCAD4; Harms & Wocadlo, 1995)
k = 1111
Tmin = 0.947, Tmax = 0.979l = 1212
3379 measured reflections3 standard reflections every 200 reflections
3154 independent reflections intensity decay: none
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) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.06P)2 + 0.035P]
where P = (Fo2 + 2Fc2)/3
3154 reflections(Δ/σ)max = 0.001
238 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.23 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*/Ueq
F10.52063 (18)0.74819 (15)0.07309 (14)0.0470 (4)
O10.7511 (3)1.3189 (2)0.4184 (2)0.0826 (8)
O20.0708 (2)0.32798 (18)0.24166 (17)0.0451 (5)
O30.1250 (3)0.1022 (2)0.25234 (19)0.0545 (5)
O40.1734 (2)0.0351 (2)0.06989 (19)0.0544 (5)
N10.7420 (3)1.0744 (2)0.36587 (19)0.0403 (5)
N20.5558 (2)0.8162 (2)0.20153 (19)0.0362 (5)
N30.1515 (2)0.38818 (19)0.16083 (18)0.0316 (5)
C10.7561 (4)1.2033 (3)0.4492 (3)0.0548 (8)
H1A0.77111.20560.53890.066*
C20.7396 (3)0.9372 (3)0.4054 (2)0.0435 (7)
H2B0.74860.95560.50080.052*
H2C0.83220.89290.37900.052*
C30.5846 (3)0.8319 (3)0.3435 (2)0.0440 (7)
H3A0.59320.73750.36230.053*
H3B0.49370.86780.38220.053*
C40.5543 (3)0.9592 (3)0.1686 (3)0.0491 (7)
H4A0.46621.00400.20390.059*
H4B0.53660.94590.07350.059*
C50.7127 (3)1.0574 (3)0.2252 (2)0.0458 (7)
H5A0.80011.01570.18560.055*
H5B0.70931.15190.20510.055*
C60.4412 (3)0.6999 (2)0.1267 (2)0.0329 (6)
C70.4207 (3)0.6684 (2)0.0128 (2)0.0341 (6)
C80.3098 (3)0.5589 (2)0.0912 (2)0.0342 (6)
H8A0.29660.54680.18230.041*
C90.2149 (3)0.4638 (2)0.0344 (2)0.0318 (6)
C100.0981 (3)0.3454 (2)0.1176 (2)0.0335 (6)
C110.0169 (3)0.2494 (2)0.0500 (2)0.0343 (6)
C120.1022 (3)0.1194 (3)0.1222 (3)0.0391 (6)
C130.0465 (3)0.2758 (2)0.0842 (2)0.0340 (6)
H13A0.00940.21200.12510.041*
C140.2387 (3)0.4863 (2)0.1032 (2)0.0298 (5)
C150.3470 (3)0.6054 (2)0.1819 (2)0.0328 (6)
H15A0.35610.62160.27320.039*
C160.1684 (3)0.4125 (3)0.3041 (2)0.0364 (6)
H16A0.12030.49480.34910.044*
C170.1618 (4)0.2866 (3)0.3656 (3)0.0519 (8)
H17A0.14900.19010.30790.062*
H17B0.10880.29220.44350.062*
C180.3182 (3)0.3848 (3)0.3778 (3)0.0487 (7)
H18A0.35990.45000.46310.058*
H18B0.40010.34790.32740.058*
H30.066 (3)0.174 (3)0.277 (3)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0499 (10)0.0444 (9)0.0495 (9)0.0030 (7)0.0129 (7)0.0197 (7)
O10.110 (2)0.0391 (12)0.0880 (18)0.0120 (13)0.0026 (15)0.0020 (11)
O20.0506 (12)0.0433 (10)0.0369 (10)0.0042 (9)0.0016 (9)0.0053 (8)
O30.0563 (13)0.0474 (12)0.0469 (12)0.0068 (10)0.0070 (10)0.0012 (9)
O40.0480 (12)0.0434 (11)0.0616 (13)0.0125 (9)0.0044 (10)0.0075 (10)
N10.0481 (14)0.0320 (11)0.0355 (12)0.0028 (10)0.0015 (10)0.0041 (9)
N20.0397 (13)0.0290 (10)0.0375 (12)0.0045 (9)0.0032 (9)0.0128 (9)
N30.0324 (12)0.0250 (10)0.0346 (11)0.0003 (8)0.0035 (9)0.0046 (8)
C10.0558 (19)0.0458 (17)0.0520 (18)0.0011 (14)0.0053 (15)0.0054 (14)
C20.0512 (17)0.0388 (14)0.0351 (14)0.0024 (13)0.0029 (12)0.0074 (11)
C30.0490 (17)0.0368 (14)0.0435 (16)0.0042 (12)0.0013 (13)0.0127 (11)
C40.0552 (18)0.0328 (14)0.0544 (17)0.0023 (13)0.0128 (14)0.0157 (12)
C50.0565 (18)0.0326 (14)0.0466 (16)0.0039 (13)0.0041 (13)0.0135 (12)
C60.0328 (14)0.0262 (12)0.0392 (14)0.0052 (10)0.0005 (11)0.0085 (10)
C70.0351 (14)0.0297 (12)0.0403 (14)0.0046 (11)0.0058 (11)0.0144 (11)
C80.0423 (15)0.0316 (12)0.0296 (13)0.0092 (11)0.0043 (11)0.0074 (10)
C90.0334 (14)0.0258 (12)0.0359 (13)0.0069 (10)0.0030 (11)0.0064 (10)
C100.0322 (14)0.0293 (12)0.0380 (15)0.0095 (10)0.0022 (11)0.0049 (10)
C110.0296 (13)0.0286 (12)0.0412 (15)0.0056 (10)0.0005 (11)0.0023 (11)
C120.0335 (15)0.0319 (13)0.0469 (16)0.0051 (11)0.0017 (12)0.0024 (11)
C130.0312 (14)0.0258 (12)0.0435 (15)0.0003 (10)0.0040 (11)0.0082 (10)
C140.0308 (13)0.0233 (11)0.0354 (13)0.0056 (10)0.0061 (10)0.0057 (9)
C150.0370 (14)0.0275 (12)0.0330 (13)0.0036 (10)0.0039 (11)0.0065 (10)
C160.0401 (15)0.0322 (13)0.0346 (13)0.0007 (11)0.0058 (11)0.0064 (10)
C170.0624 (19)0.0425 (15)0.0472 (16)0.0100 (14)0.0013 (14)0.0176 (13)
C180.0450 (17)0.0559 (17)0.0414 (15)0.0025 (14)0.0017 (13)0.0102 (13)
Geometric parameters (Å, º) top
F1—C71.363 (3)C5—H5A0.97
O1—C11.216 (3)C5—H5B0.97
O2—C101.267 (3)C6—C151.388 (3)
O3—C121.328 (3)C6—C71.415 (3)
O3—H30.900 (10)C7—C81.359 (3)
O4—C121.206 (3)C8—C91.406 (3)
N1—C11.326 (3)C8—H8A0.93
N1—C51.439 (3)C9—C141.400 (3)
N1—C21.452 (3)C9—C101.449 (3)
N2—C61.398 (3)C10—C111.429 (3)
N2—C31.454 (3)C11—C131.363 (3)
N2—C41.475 (3)C11—C121.490 (3)
N3—C131.341 (3)C13—H13A0.93
N3—C141.398 (3)C14—C151.401 (3)
N3—C161.459 (3)C15—H15A0.93
C1—H1A0.93C16—C171.477 (3)
C2—C31.525 (3)C16—C181.485 (4)
C2—H2B0.97C16—H16A0.98
C2—H2C0.97C17—C181.492 (4)
C3—H3A0.97C17—H17A0.97
C3—H3B0.97C17—H17B0.97
C4—C51.508 (4)C18—H18A0.97
C4—H4A0.97C18—H18B0.97
C4—H4B0.97
C12—O3—H3112 (2)C7—C8—C9119.9 (2)
C1—N1—C5122.0 (2)C7—C8—H8A120.1
C1—N1—C2124.3 (2)C9—C8—H8A120.1
C5—N1—C2113.53 (19)C14—C9—C8118.1 (2)
C6—N2—C3117.8 (2)C14—C9—C10121.8 (2)
C6—N2—C4117.43 (19)C8—C9—C10120.2 (2)
C3—N2—C4111.2 (2)O2—C10—C11122.5 (2)
C13—N3—C14119.8 (2)O2—C10—C9122.2 (2)
C13—N3—C16120.2 (2)C11—C10—C9115.4 (2)
C14—N3—C16119.98 (18)C13—C11—C10120.2 (2)
O1—C1—N1125.5 (3)C13—C11—C12118.1 (2)
O1—C1—H1A117.2C10—C11—C12121.7 (2)
N1—C1—H1A117.2O4—C12—O3121.4 (2)
N1—C2—C3111.7 (2)O4—C12—C11124.3 (2)
N1—C2—H2B109.3O3—C12—C11114.3 (2)
C3—C2—H2B109.3N3—C13—C11124.1 (2)
N1—C2—H2C109.3N3—C13—H13A118.0
C3—C2—H2C109.3C11—C13—H13A118.0
H2B—C2—H2C107.9N3—C14—C9118.8 (2)
N2—C3—C2111.0 (2)N3—C14—C15120.5 (2)
N2—C3—H3A109.4C9—C14—C15120.7 (2)
C2—C3—H3A109.4C6—C15—C14121.6 (2)
N2—C3—H3B109.4C6—C15—H15A119.2
C2—C3—H3B109.4C14—C15—H15A119.2
H3A—C3—H3B108.0N3—C16—C17119.7 (2)
N2—C4—C5110.4 (2)N3—C16—C18119.6 (2)
N2—C4—H4A109.6C17—C16—C1860.49 (18)
C5—C4—H4A109.6N3—C16—H16A115.4
N2—C4—H4B109.6C17—C16—H16A115.4
C5—C4—H4B109.6C18—C16—H16A115.4
H4A—C4—H4B108.1C16—C17—C1860.02 (17)
N1—C5—C4109.9 (2)C16—C17—H17A117.8
N1—C5—H5A109.7C18—C17—H17A117.8
C4—C5—H5A109.7C16—C17—H17B117.8
N1—C5—H5B109.7C18—C17—H17B117.8
C4—C5—H5B109.7H17A—C17—H17B114.9
H5A—C5—H5B108.2C16—C18—C1759.49 (17)
C15—C6—N2123.4 (2)C16—C18—H18A117.8
C15—C6—C7116.0 (2)C17—C18—H18A117.8
N2—C6—C7120.6 (2)C16—C18—H18B117.8
C8—C7—F1117.5 (2)C17—C18—H18B117.8
C8—C7—C6123.6 (2)H18A—C18—H18B115.0
F1—C7—C6118.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.90 (1)1.69 (2)2.514 (3)151 (3)
 

References

First citationHarms, K. & Wocadlo, S. (1995) XCAD4. University of Marburg, Germany.  Google Scholar
First citationLi, X.-W., Zhi, F., Shen, J.-H. & Hu, Y.-Q. (2005). Acta Cryst. E61, o2235–o2236.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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