The title compound, C13H9ClFNO3, was synthesized from ethyl 2,4-dichloro-5-fluorobenzoylacetate.
Supporting information
CCDC reference: 238763
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C13H9ClFNO3 | F(000) = 576 |
Mr = 281.66 | Dx = 1.631 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 821 reflections |
a = 9.194 (4) Å | θ = 2.6–25.9° |
b = 7.515 (4) Å | µ = 0.35 mm−1 |
c = 16.635 (8) Å | T = 293 K |
β = 93.784 (7)° | Plate, colourless |
V = 1146.9 (9) Å3 | 0.20 × 0.20 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2345 independent reflections |
Radiation source: fine-focus sealed tube | 1753 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan SADABS (Bruker, 1997) | h = −11→11 |
Tmin = 0.791, Tmax = 0.939 | k = −9→7 |
6311 measured reflections | l = −20→20 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-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 = 1.04 | Δρmax = 0.19 e Å−3 |
2345 reflections | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | −0.36322 (5) | 0.04973 (9) | 0.34750 (3) | 0.0538 (2) | |
F1 | −0.39000 (13) | 0.1174 (2) | 0.51629 (8) | 0.0611 (4) | |
N1 | 0.16020 (15) | 0.2551 (2) | 0.42142 (8) | 0.0290 (3) | |
O1 | 0.06637 (16) | 0.3536 (2) | 0.65430 (8) | 0.0501 (4) | |
O2 | 0.33404 (17) | 0.4370 (3) | 0.68548 (9) | 0.0564 (5) | |
H2 | 0.2473 | 0.4183 | 0.6906 | 0.085* | |
O3 | 0.48451 (17) | 0.4271 (2) | 0.58869 (9) | 0.0584 (5) | |
C1 | 0.26346 (19) | 0.3120 (2) | 0.47639 (10) | 0.0304 (4) | |
H1 | 0.3574 | 0.3278 | 0.4601 | 0.037* | |
C2 | 0.23837 (19) | 0.3480 (3) | 0.55496 (10) | 0.0319 (4) | |
C3 | 0.0969 (2) | 0.3240 (3) | 0.58335 (11) | 0.0322 (4) | |
C4 | −0.01446 (18) | 0.2586 (2) | 0.52393 (10) | 0.0290 (4) | |
C5 | 0.01861 (18) | 0.2253 (2) | 0.44408 (10) | 0.0277 (4) | |
C6 | −0.09057 (19) | 0.1603 (3) | 0.38843 (11) | 0.0326 (4) | |
H6 | −0.0703 | 0.1393 | 0.3352 | 0.039* | |
C7 | −0.2268 (2) | 0.1286 (3) | 0.41347 (12) | 0.0356 (5) | |
C8 | −0.2578 (2) | 0.1585 (3) | 0.49335 (12) | 0.0381 (5) | |
C9 | −0.1548 (2) | 0.2244 (3) | 0.54756 (11) | 0.0358 (5) | |
H9 | −0.1775 | 0.2468 | 0.6003 | 0.043* | |
C10 | 0.3636 (2) | 0.4079 (3) | 0.60968 (12) | 0.0391 (5) | |
C11 | 0.1978 (2) | 0.2062 (3) | 0.34043 (10) | 0.0320 (4) | |
H11 | 0.2029 | 0.0782 | 0.3297 | 0.038* | |
C12 | 0.1426 (2) | 0.3186 (3) | 0.27074 (11) | 0.0390 (5) | |
H12A | 0.0858 | 0.4234 | 0.2821 | 0.047* | |
H12B | 0.1135 | 0.2590 | 0.2205 | 0.047* | |
C13 | 0.3014 (2) | 0.3187 (3) | 0.29786 (11) | 0.0410 (5) | |
H13A | 0.3682 | 0.2593 | 0.2639 | 0.049* | |
H13B | 0.3405 | 0.4237 | 0.3255 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0344 (3) | 0.0759 (4) | 0.0491 (3) | −0.0174 (3) | −0.0127 (2) | 0.0052 (3) |
F1 | 0.0310 (6) | 0.0849 (10) | 0.0688 (9) | −0.0160 (7) | 0.0150 (6) | −0.0076 (8) |
N1 | 0.0266 (7) | 0.0368 (9) | 0.0235 (7) | −0.0044 (7) | 0.0001 (6) | −0.0002 (6) |
O1 | 0.0446 (8) | 0.0766 (11) | 0.0291 (7) | 0.0002 (8) | 0.0032 (6) | −0.0113 (7) |
O2 | 0.0483 (9) | 0.0865 (13) | 0.0331 (8) | −0.0102 (9) | −0.0070 (7) | −0.0146 (8) |
O3 | 0.0442 (9) | 0.0870 (13) | 0.0429 (9) | −0.0278 (9) | −0.0058 (7) | −0.0046 (8) |
C1 | 0.0253 (9) | 0.0364 (11) | 0.0293 (9) | −0.0056 (8) | −0.0010 (7) | 0.0033 (8) |
C2 | 0.0325 (10) | 0.0336 (10) | 0.0286 (9) | −0.0034 (8) | −0.0051 (7) | 0.0014 (8) |
C3 | 0.0357 (10) | 0.0333 (10) | 0.0272 (9) | 0.0017 (8) | −0.0010 (7) | 0.0019 (8) |
C4 | 0.0291 (9) | 0.0284 (9) | 0.0293 (9) | 0.0021 (8) | 0.0005 (7) | 0.0036 (8) |
C5 | 0.0258 (9) | 0.0285 (9) | 0.0285 (9) | −0.0015 (7) | −0.0008 (7) | 0.0032 (7) |
C6 | 0.0308 (9) | 0.0384 (11) | 0.0280 (9) | −0.0056 (8) | −0.0020 (7) | 0.0038 (8) |
C7 | 0.0303 (10) | 0.0358 (11) | 0.0393 (11) | −0.0042 (8) | −0.0081 (8) | 0.0051 (8) |
C8 | 0.0255 (9) | 0.0419 (12) | 0.0473 (12) | −0.0032 (9) | 0.0055 (8) | 0.0034 (9) |
C9 | 0.0350 (10) | 0.0404 (12) | 0.0327 (10) | 0.0008 (9) | 0.0072 (8) | 0.0018 (8) |
C10 | 0.0391 (11) | 0.0438 (12) | 0.0330 (11) | −0.0092 (10) | −0.0065 (8) | −0.0002 (9) |
C11 | 0.0328 (9) | 0.0377 (11) | 0.0255 (9) | −0.0015 (8) | 0.0026 (7) | −0.0018 (8) |
C12 | 0.0382 (10) | 0.0511 (13) | 0.0274 (9) | 0.0004 (9) | 0.0002 (8) | 0.0014 (9) |
C13 | 0.0337 (10) | 0.0605 (14) | 0.0288 (10) | −0.0078 (10) | 0.0035 (8) | −0.0004 (9) |
Geometric parameters (Å, º) top
Cl1—C7 | 1.7170 (19) | C4—C5 | 1.404 (2) |
F1—C8 | 1.334 (2) | C5—C6 | 1.407 (2) |
N1—C1 | 1.344 (2) | C6—C7 | 1.366 (3) |
N1—C5 | 1.397 (2) | C6—H6 | 0.9300 |
N1—C11 | 1.460 (2) | C7—C8 | 1.396 (3) |
O1—C3 | 1.251 (2) | C8—C9 | 1.358 (3) |
O2—C10 | 1.325 (3) | C9—H9 | 0.9300 |
O2—H2 | 0.8200 | C11—C13 | 1.487 (3) |
O3—C10 | 1.196 (2) | C11—C12 | 1.496 (3) |
C1—C2 | 1.369 (3) | C11—H11 | 0.9800 |
C1—H1 | 0.9300 | C12—C13 | 1.500 (3) |
C2—C3 | 1.424 (3) | C12—H12A | 0.9700 |
C2—C10 | 1.490 (3) | C12—H12B | 0.9700 |
C3—C4 | 1.461 (2) | C13—H13A | 0.9700 |
C4—C9 | 1.397 (3) | C13—H13B | 0.9700 |
| | | |
C1—N1—C5 | 119.76 (15) | F1—C8—C7 | 118.85 (17) |
C1—N1—C11 | 120.56 (15) | C9—C8—C7 | 120.90 (18) |
C5—N1—C11 | 119.36 (14) | C8—C9—C4 | 119.80 (18) |
C10—O2—H2 | 109.5 | C8—C9—H9 | 120.1 |
N1—C1—C2 | 123.82 (17) | C4—C9—H9 | 120.1 |
N1—C1—H1 | 118.1 | O3—C10—O2 | 120.73 (18) |
C2—C1—H1 | 118.1 | O3—C10—C2 | 123.66 (19) |
C1—C2—C3 | 120.44 (16) | O2—C10—C2 | 115.61 (18) |
C1—C2—C10 | 118.09 (17) | N1—C11—C13 | 119.62 (16) |
C3—C2—C10 | 121.45 (17) | N1—C11—C12 | 118.95 (17) |
O1—C3—C2 | 123.86 (17) | C13—C11—C12 | 60.35 (13) |
O1—C3—C4 | 120.46 (17) | N1—C11—H11 | 115.6 |
C2—C3—C4 | 115.67 (16) | C13—C11—H11 | 115.6 |
C9—C4—C5 | 119.67 (16) | C12—C11—H11 | 115.6 |
C9—C4—C3 | 119.39 (16) | C11—C12—C13 | 59.54 (12) |
C5—C4—C3 | 120.92 (16) | C11—C12—H12A | 117.8 |
N1—C5—C4 | 119.37 (15) | C13—C12—H12A | 117.8 |
N1—C5—C6 | 121.00 (16) | C11—C12—H12B | 117.8 |
C4—C5—C6 | 119.63 (16) | C13—C12—H12B | 117.8 |
C7—C6—C5 | 119.23 (17) | H12A—C12—H12B | 115.0 |
C7—C6—H6 | 120.4 | C11—C13—C12 | 60.11 (12) |
C5—C6—H6 | 120.4 | C11—C13—H13A | 117.8 |
C6—C7—C8 | 120.74 (17) | C12—C13—H13A | 117.8 |
C6—C7—Cl1 | 120.74 (15) | C11—C13—H13B | 117.8 |
C8—C7—Cl1 | 118.51 (15) | C12—C13—H13B | 117.8 |
F1—C8—C9 | 120.24 (18) | H13A—C13—H13B | 114.9 |
| | | |
C5—N1—C1—C2 | −1.6 (3) | C4—C5—C6—C7 | −0.8 (3) |
C11—N1—C1—C2 | −175.17 (18) | C5—C6—C7—C8 | −0.5 (3) |
N1—C1—C2—C3 | 0.8 (3) | C5—C6—C7—Cl1 | 179.88 (15) |
N1—C1—C2—C10 | 179.19 (18) | C6—C7—C8—F1 | −176.66 (18) |
C1—C2—C3—O1 | 179.74 (19) | Cl1—C7—C8—F1 | 3.0 (3) |
C10—C2—C3—O1 | 1.4 (3) | C6—C7—C8—C9 | 1.8 (3) |
C1—C2—C3—C4 | 0.5 (3) | Cl1—C7—C8—C9 | −178.58 (16) |
C10—C2—C3—C4 | −177.85 (17) | F1—C8—C9—C4 | 176.74 (18) |
O1—C3—C4—C9 | −1.8 (3) | C7—C8—C9—C4 | −1.7 (3) |
C2—C3—C4—C9 | 177.42 (17) | C5—C4—C9—C8 | 0.3 (3) |
O1—C3—C4—C5 | 179.83 (18) | C3—C4—C9—C8 | −178.03 (18) |
C2—C3—C4—C5 | −0.9 (3) | C1—C2—C10—O3 | 0.4 (3) |
C1—N1—C5—C4 | 1.2 (3) | C3—C2—C10—O3 | 178.8 (2) |
C11—N1—C5—C4 | 174.77 (16) | C1—C2—C10—O2 | −178.50 (19) |
C1—N1—C5—C6 | −177.97 (18) | C3—C2—C10—O2 | −0.1 (3) |
C11—N1—C5—C6 | −4.4 (3) | C1—N1—C11—C13 | −42.2 (3) |
C9—C4—C5—N1 | −178.24 (16) | C5—N1—C11—C13 | 144.20 (17) |
C3—C4—C5—N1 | 0.1 (3) | C1—N1—C11—C12 | −112.6 (2) |
C9—C4—C5—C6 | 0.9 (3) | C5—N1—C11—C12 | 73.8 (2) |
C3—C4—C5—C6 | 179.26 (17) | N1—C11—C12—C13 | 109.58 (19) |
N1—C5—C6—C7 | 178.31 (17) | N1—C11—C13—C12 | −108.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.82 | 1.80 | 2.559 (2) | 154 |
O2—H2···Cl1i | 0.82 | 2.87 | 3.348 (2) | 119 |
Symmetry code: (i) x+1/2, −y+1/2, z+1/2. |