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The title compound, C12H12ClFN2O3, adopts a keto–hydrazo tautomeric form stabilized by an intra­molecular N—H...O hydrogen bond. The whole mol­ecule is roughly planar, the largest deviation from the mean plane being 0.328 (3) Å for the terminal methyl C atom of the ethyl side chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024153/dn6242sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024153/dn6242Isup2.hkl
Contains datablock I

CCDC reference: 283904

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.099
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for F1 - C2 .. 6.25 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-Ethyl 4-chloro-3-[2-(2-fluorophenyl)hydrazono]butanoate top
Crystal data top
C12H12ClFN2O3Z = 2
Mr = 286.69F(000) = 296
Triclinic, P1Dx = 1.437 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.3633 (5) ÅCell parameters from 9166 reflections
b = 9.2982 (11) Åθ = 2.2–27.9°
c = 16.7339 (17) ŵ = 0.31 mm1
α = 94.781 (9)°T = 296 K
β = 93.394 (9)°Rod, red
γ = 100.822 (9)°0.42 × 0.25 × 0.15 mm
V = 662.57 (13) Å3
Data collection top
Stoe IPDS-II
diffractometer
3155 independent reflections
Radiation source: fine-focus sealed tube1687 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 6.67 pixels mm-1θmax = 27.9°, θmin = 2.2°
rotation method; φ or ω ? scansh = 55
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 1212
Tmin = 0.924, Tmax = 0.968l = 2122
11451 measured reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 0.83 w = 1/[σ2(Fo2) + (0.0562P)2]
where P = (Fo2 + 2Fc2)/3
3155 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.20 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
C10.9942 (4)0.77992 (17)0.26970 (9)0.0534 (4)
C21.1367 (4)0.88880 (19)0.22505 (10)0.0657 (5)
C31.3823 (5)0.9965 (2)0.25614 (14)0.0767 (5)
H31.47411.06800.22460.092*
C41.4902 (5)0.9971 (2)0.33439 (13)0.0794 (6)
H41.65701.06970.35660.095*
C51.3530 (4)0.8907 (2)0.38040 (12)0.0727 (5)
H51.42810.89180.43370.087*
C61.1057 (4)0.78239 (18)0.34853 (10)0.0619 (4)
H61.01430.71110.38020.074*
C70.3544 (4)0.47587 (16)0.24449 (9)0.0509 (4)
C80.2403 (4)0.46242 (19)0.15890 (9)0.0593 (4)
C90.2032 (4)0.38166 (17)0.30365 (9)0.0527 (4)
C100.3722 (4)0.4041 (2)0.38670 (10)0.0692 (5)
H10A0.40610.50750.40620.083*
H10B0.57550.37700.38320.083*
C110.0913 (5)0.3261 (2)0.05152 (10)0.0801 (6)
H11A0.07870.33040.01640.096*
H11B0.20530.40310.04040.096*
C120.3026 (6)0.1798 (2)0.03855 (13)0.1009 (8)
H12A0.18430.10440.04690.151*
H12B0.39780.16510.01550.151*
H12C0.46250.17520.07580.151*
Cl10.16283 (12)0.29970 (6)0.45586 (3)0.0827 (2)
N10.7444 (3)0.67347 (14)0.23296 (7)0.0568 (3)
H10.69100.67230.18260.068*
N20.5928 (3)0.57601 (14)0.27556 (7)0.0518 (3)
O10.3407 (3)0.55327 (14)0.11390 (7)0.0811 (4)
O20.0300 (3)0.34414 (14)0.13553 (6)0.0760 (4)
O30.0404 (3)0.29566 (14)0.28906 (7)0.0753 (4)
F11.0202 (3)0.88529 (13)0.14758 (7)0.0948 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0516 (9)0.0469 (8)0.0595 (9)0.0024 (7)0.0088 (7)0.0058 (7)
C20.0720 (12)0.0609 (10)0.0639 (10)0.0054 (10)0.0122 (9)0.0167 (8)
C30.0718 (13)0.0536 (10)0.1022 (16)0.0036 (10)0.0226 (11)0.0175 (10)
C40.0677 (13)0.0566 (11)0.1045 (16)0.0078 (10)0.0070 (11)0.0026 (10)
C50.0694 (12)0.0673 (12)0.0734 (11)0.0001 (10)0.0030 (9)0.0032 (9)
C60.0622 (11)0.0580 (10)0.0617 (10)0.0006 (9)0.0068 (8)0.0071 (8)
C70.0531 (9)0.0474 (8)0.0497 (8)0.0035 (7)0.0010 (7)0.0063 (6)
C80.0640 (11)0.0571 (10)0.0523 (9)0.0013 (9)0.0009 (7)0.0073 (7)
C90.0540 (10)0.0498 (9)0.0512 (8)0.0022 (8)0.0017 (7)0.0059 (6)
C100.0654 (11)0.0790 (12)0.0551 (9)0.0095 (10)0.0012 (8)0.0164 (8)
C110.0961 (15)0.0811 (13)0.0505 (9)0.0078 (11)0.0136 (9)0.0038 (8)
C120.1180 (18)0.0895 (15)0.0745 (13)0.0198 (14)0.0189 (12)0.0018 (11)
Cl10.0886 (4)0.0951 (4)0.0552 (2)0.0126 (3)0.0051 (2)0.0229 (2)
N10.0609 (8)0.0544 (8)0.0510 (7)0.0022 (7)0.0045 (6)0.0108 (6)
N20.0524 (8)0.0483 (7)0.0527 (7)0.0025 (6)0.0058 (6)0.0083 (6)
O10.0974 (10)0.0786 (9)0.0547 (7)0.0163 (7)0.0089 (6)0.0191 (6)
O20.0946 (9)0.0687 (8)0.0504 (6)0.0154 (7)0.0120 (6)0.0063 (5)
O30.0708 (8)0.0791 (8)0.0614 (7)0.0226 (7)0.0039 (6)0.0129 (6)
F10.1123 (9)0.0938 (8)0.0736 (7)0.0041 (7)0.0095 (6)0.0341 (6)
Geometric parameters (Å, º) top
C1—C61.376 (2)C8—O21.308 (2)
C1—C21.384 (2)C9—O31.2027 (18)
C1—N11.400 (2)C9—C101.514 (2)
C2—F11.360 (2)C10—Cl11.7596 (17)
C2—C31.366 (3)C10—H10A0.9700
C3—C41.364 (3)C10—H10B0.9700
C3—H30.9300C11—O21.457 (2)
C4—C51.375 (3)C11—C121.484 (3)
C4—H40.9300C11—H11A0.9700
C5—C61.377 (2)C11—H11B0.9700
C5—H50.9300C12—H12A0.9600
C6—H60.9300C12—H12B0.9600
C7—N21.3081 (19)C12—H12C0.9600
C7—C81.475 (2)N1—N21.3058 (17)
C7—C91.479 (2)N1—H10.8600
C8—O11.2161 (19)
C6—C1—C2117.93 (15)O3—C9—C10121.20 (14)
C6—C1—N1123.26 (14)C7—C9—C10115.08 (13)
C2—C1—N1118.81 (14)C9—C10—Cl1112.49 (12)
F1—C2—C3120.48 (16)C9—C10—H10A109.1
F1—C2—C1116.94 (15)Cl1—C10—H10A109.1
C3—C2—C1122.58 (16)C9—C10—H10B109.1
C4—C3—C2118.69 (17)Cl1—C10—H10B109.1
C4—C3—H3120.7H10A—C10—H10B107.8
C2—C3—H3120.7O2—C11—C12106.42 (16)
C3—C4—C5120.13 (17)O2—C11—H11A110.4
C3—C4—H4119.9C12—C11—H11A110.4
C5—C4—H4119.9O2—C11—H11B110.4
C4—C5—C6120.79 (18)C12—C11—H11B110.4
C4—C5—H5119.6H11A—C11—H11B108.6
C6—C5—H5119.6C11—C12—H12A109.5
C1—C6—C5119.88 (16)C11—C12—H12B109.5
C1—C6—H6120.1H12A—C12—H12B109.5
C5—C6—H6120.1C11—C12—H12C109.5
N2—C7—C8122.86 (14)H12A—C12—H12C109.5
N2—C7—C9113.78 (13)H12B—C12—H12C109.5
C8—C7—C9123.32 (13)N2—N1—C1119.70 (12)
O1—C8—O2123.27 (14)N2—N1—H1120.1
O1—C8—C7122.05 (15)C1—N1—H1120.1
O2—C8—C7114.66 (14)N1—N2—C7122.12 (13)
O3—C9—C7123.69 (14)C8—O2—C11116.78 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.962.6067 (17)132
N1—H1···F10.862.362.6743 (16)102
C10—H10B···O3i0.972.543.383 (2)145
Symmetry code: (i) x+1, y, z.
 

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