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The title compound, C13H9ClFNO3, was synthesized from ethyl 2,4-di­chloro-5-fluoro­benzoyl­acetate.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004477/ww6159sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004477/ww6159Isup2.hkl
Contains datablock I

CCDC reference: 238763

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.094
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.791 0.939 Tmin' and Tmax expected: 0.931 0.939 RR' = 0.850 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT431_ALERT_2_C Short Inter HL..A Contact F1 .. O3 .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. CL1 .. 2.87 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid top
Crystal data top
C13H9ClFNO3F(000) = 576
Mr = 281.66Dx = 1.631 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 821 reflections
a = 9.194 (4) Åθ = 2.6–25.9°
b = 7.515 (4) ŵ = 0.35 mm1
c = 16.635 (8) ÅT = 293 K
β = 93.784 (7)°Plate, colourless
V = 1146.9 (9) Å30.20 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2345 independent reflections
Radiation source: fine-focus sealed tube1753 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan
SADABS (Bruker, 1997)
h = 1111
Tmin = 0.791, Tmax = 0.939k = 97
6311 measured reflectionsl = 2020
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.214P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.19 e Å3
2345 reflectionsΔρmin = 0.27 e Å3
173 parameters
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
Cl10.36322 (5)0.04973 (9)0.34750 (3)0.0538 (2)
F10.39000 (13)0.1174 (2)0.51629 (8)0.0611 (4)
N10.16020 (15)0.2551 (2)0.42142 (8)0.0290 (3)
O10.06637 (16)0.3536 (2)0.65430 (8)0.0501 (4)
O20.33404 (17)0.4370 (3)0.68548 (9)0.0564 (5)
H20.24730.41830.69060.085*
O30.48451 (17)0.4271 (2)0.58869 (9)0.0584 (5)
C10.26346 (19)0.3120 (2)0.47639 (10)0.0304 (4)
H10.35740.32780.46010.037*
C20.23837 (19)0.3480 (3)0.55496 (10)0.0319 (4)
C30.0969 (2)0.3240 (3)0.58335 (11)0.0322 (4)
C40.01446 (18)0.2586 (2)0.52393 (10)0.0290 (4)
C50.01861 (18)0.2253 (2)0.44408 (10)0.0277 (4)
C60.09057 (19)0.1603 (3)0.38843 (11)0.0326 (4)
H60.07030.13930.33520.039*
C70.2268 (2)0.1286 (3)0.41347 (12)0.0356 (5)
C80.2578 (2)0.1585 (3)0.49335 (12)0.0381 (5)
C90.1548 (2)0.2244 (3)0.54756 (11)0.0358 (5)
H90.17750.24680.60030.043*
C100.3636 (2)0.4079 (3)0.60968 (12)0.0391 (5)
C110.1978 (2)0.2062 (3)0.34043 (10)0.0320 (4)
H110.20290.07820.32970.038*
C120.1426 (2)0.3186 (3)0.27074 (11)0.0390 (5)
H12A0.08580.42340.28210.047*
H12B0.11350.25900.22050.047*
C130.3014 (2)0.3187 (3)0.29786 (11)0.0410 (5)
H13A0.36820.25930.26390.049*
H13B0.34050.42370.32550.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0344 (3)0.0759 (4)0.0491 (3)0.0174 (3)0.0127 (2)0.0052 (3)
F10.0310 (6)0.0849 (10)0.0688 (9)0.0160 (7)0.0150 (6)0.0076 (8)
N10.0266 (7)0.0368 (9)0.0235 (7)0.0044 (7)0.0001 (6)0.0002 (6)
O10.0446 (8)0.0766 (11)0.0291 (7)0.0002 (8)0.0032 (6)0.0113 (7)
O20.0483 (9)0.0865 (13)0.0331 (8)0.0102 (9)0.0070 (7)0.0146 (8)
O30.0442 (9)0.0870 (13)0.0429 (9)0.0278 (9)0.0058 (7)0.0046 (8)
C10.0253 (9)0.0364 (11)0.0293 (9)0.0056 (8)0.0010 (7)0.0033 (8)
C20.0325 (10)0.0336 (10)0.0286 (9)0.0034 (8)0.0051 (7)0.0014 (8)
C30.0357 (10)0.0333 (10)0.0272 (9)0.0017 (8)0.0010 (7)0.0019 (8)
C40.0291 (9)0.0284 (9)0.0293 (9)0.0021 (8)0.0005 (7)0.0036 (8)
C50.0258 (9)0.0285 (9)0.0285 (9)0.0015 (7)0.0008 (7)0.0032 (7)
C60.0308 (9)0.0384 (11)0.0280 (9)0.0056 (8)0.0020 (7)0.0038 (8)
C70.0303 (10)0.0358 (11)0.0393 (11)0.0042 (8)0.0081 (8)0.0051 (8)
C80.0255 (9)0.0419 (12)0.0473 (12)0.0032 (9)0.0055 (8)0.0034 (9)
C90.0350 (10)0.0404 (12)0.0327 (10)0.0008 (9)0.0072 (8)0.0018 (8)
C100.0391 (11)0.0438 (12)0.0330 (11)0.0092 (10)0.0065 (8)0.0002 (9)
C110.0328 (9)0.0377 (11)0.0255 (9)0.0015 (8)0.0026 (7)0.0018 (8)
C120.0382 (10)0.0511 (13)0.0274 (9)0.0004 (9)0.0002 (8)0.0014 (9)
C130.0337 (10)0.0605 (14)0.0288 (10)0.0078 (10)0.0035 (8)0.0004 (9)
Geometric parameters (Å, º) top
Cl1—C71.7170 (19)C4—C51.404 (2)
F1—C81.334 (2)C5—C61.407 (2)
N1—C11.344 (2)C6—C71.366 (3)
N1—C51.397 (2)C6—H60.9300
N1—C111.460 (2)C7—C81.396 (3)
O1—C31.251 (2)C8—C91.358 (3)
O2—C101.325 (3)C9—H90.9300
O2—H20.8200C11—C131.487 (3)
O3—C101.196 (2)C11—C121.496 (3)
C1—C21.369 (3)C11—H110.9800
C1—H10.9300C12—C131.500 (3)
C2—C31.424 (3)C12—H12A0.9700
C2—C101.490 (3)C12—H12B0.9700
C3—C41.461 (2)C13—H13A0.9700
C4—C91.397 (3)C13—H13B0.9700
C1—N1—C5119.76 (15)F1—C8—C7118.85 (17)
C1—N1—C11120.56 (15)C9—C8—C7120.90 (18)
C5—N1—C11119.36 (14)C8—C9—C4119.80 (18)
C10—O2—H2109.5C8—C9—H9120.1
N1—C1—C2123.82 (17)C4—C9—H9120.1
N1—C1—H1118.1O3—C10—O2120.73 (18)
C2—C1—H1118.1O3—C10—C2123.66 (19)
C1—C2—C3120.44 (16)O2—C10—C2115.61 (18)
C1—C2—C10118.09 (17)N1—C11—C13119.62 (16)
C3—C2—C10121.45 (17)N1—C11—C12118.95 (17)
O1—C3—C2123.86 (17)C13—C11—C1260.35 (13)
O1—C3—C4120.46 (17)N1—C11—H11115.6
C2—C3—C4115.67 (16)C13—C11—H11115.6
C9—C4—C5119.67 (16)C12—C11—H11115.6
C9—C4—C3119.39 (16)C11—C12—C1359.54 (12)
C5—C4—C3120.92 (16)C11—C12—H12A117.8
N1—C5—C4119.37 (15)C13—C12—H12A117.8
N1—C5—C6121.00 (16)C11—C12—H12B117.8
C4—C5—C6119.63 (16)C13—C12—H12B117.8
C7—C6—C5119.23 (17)H12A—C12—H12B115.0
C7—C6—H6120.4C11—C13—C1260.11 (12)
C5—C6—H6120.4C11—C13—H13A117.8
C6—C7—C8120.74 (17)C12—C13—H13A117.8
C6—C7—Cl1120.74 (15)C11—C13—H13B117.8
C8—C7—Cl1118.51 (15)C12—C13—H13B117.8
F1—C8—C9120.24 (18)H13A—C13—H13B114.9
C5—N1—C1—C21.6 (3)C4—C5—C6—C70.8 (3)
C11—N1—C1—C2175.17 (18)C5—C6—C7—C80.5 (3)
N1—C1—C2—C30.8 (3)C5—C6—C7—Cl1179.88 (15)
N1—C1—C2—C10179.19 (18)C6—C7—C8—F1176.66 (18)
C1—C2—C3—O1179.74 (19)Cl1—C7—C8—F13.0 (3)
C10—C2—C3—O11.4 (3)C6—C7—C8—C91.8 (3)
C1—C2—C3—C40.5 (3)Cl1—C7—C8—C9178.58 (16)
C10—C2—C3—C4177.85 (17)F1—C8—C9—C4176.74 (18)
O1—C3—C4—C91.8 (3)C7—C8—C9—C41.7 (3)
C2—C3—C4—C9177.42 (17)C5—C4—C9—C80.3 (3)
O1—C3—C4—C5179.83 (18)C3—C4—C9—C8178.03 (18)
C2—C3—C4—C50.9 (3)C1—C2—C10—O30.4 (3)
C1—N1—C5—C41.2 (3)C3—C2—C10—O3178.8 (2)
C11—N1—C5—C4174.77 (16)C1—C2—C10—O2178.50 (19)
C1—N1—C5—C6177.97 (18)C3—C2—C10—O20.1 (3)
C11—N1—C5—C64.4 (3)C1—N1—C11—C1342.2 (3)
C9—C4—C5—N1178.24 (16)C5—N1—C11—C13144.20 (17)
C3—C4—C5—N10.1 (3)C1—N1—C11—C12112.6 (2)
C9—C4—C5—C60.9 (3)C5—N1—C11—C1273.8 (2)
C3—C4—C5—C6179.26 (17)N1—C11—C12—C13109.58 (19)
N1—C5—C6—C7178.31 (17)N1—C11—C13—C12108.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.821.802.559 (2)154
O2—H2···Cl1i0.822.873.348 (2)119
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

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