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The title compound, C14H17ClN2O3, adopts a keto–hydrazo tautomeric form stabilized by an intra­molecular N—H...O hydrogen bond. The mol­ecule is roughly planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602215X/bt2104sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602215X/bt2104Isup2.hkl
Contains datablock I

CCDC reference: 613594

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.126
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm
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 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 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-2-[2-(2,6-dimethylphenyl)hydrazono]-3-oxobutanoate top
Crystal data top
C14H17ClN2O3Z = 2
Mr = 296.75F(000) = 312
Triclinic, P1Dx = 1.340 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0423 (7) ÅCell parameters from 17696 reflections
b = 9.3029 (9) Åθ = 2.3–27.2°
c = 11.8285 (11) ŵ = 0.27 mm1
α = 93.707 (8)°T = 296 K
β = 100.515 (8)°Prismatic rod, yellow
γ = 103.75 (8)°0.68 × 0.36 × 0.20 mm
V = 735.3 (3) Å3
Data collection top
Stoe IPDS-II
diffractometer
2892 independent reflections
Radiation source: fine-focus sealed tube2019 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.7°
rotation method scansh = 88
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 1111
Tmin = 0.880, Tmax = 0.952l = 1414
12526 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.072P)2 + 0.0348P]
where P = (Fo2 + 2Fc2)/3
2892 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.22 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
C10.7203 (3)0.4413 (2)0.42935 (15)0.0527 (4)
C20.6641 (3)0.3125 (3)0.34925 (17)0.0652 (5)
C30.6693 (4)0.3311 (4)0.23329 (19)0.0822 (7)
H30.63280.24760.17880.099*
C40.7263 (4)0.4677 (4)0.1988 (2)0.0897 (8)
H40.72900.47750.12130.108*
C50.7808 (4)0.5930 (3)0.2789 (2)0.0789 (7)
H50.82010.68610.25380.095*
C60.7788 (3)0.5846 (3)0.39475 (17)0.0616 (5)
C70.6001 (4)0.1600 (3)0.3849 (2)0.0814 (7)
H7A0.57060.08730.31850.122*
H7B0.48300.15250.41720.122*
H7C0.70560.14240.44180.122*
C80.8386 (4)0.7281 (3)0.4748 (2)0.0771 (6)
H8A0.94960.72640.53490.116*
H8B0.72800.73870.50870.116*
H8C0.87600.81060.43170.116*
C90.7517 (3)0.4891 (2)0.73605 (14)0.0525 (4)
C100.6833 (3)0.3383 (2)0.76694 (16)0.0582 (5)
C110.6727 (4)0.3167 (2)0.89112 (17)0.0689 (6)
H11A0.59810.38190.91900.083*
H11B0.80680.34500.93810.083*
C120.8195 (3)0.6207 (2)0.82426 (16)0.0599 (5)
C130.9328 (4)0.8815 (2)0.85993 (19)0.0808 (7)
H13A1.04940.87500.91540.097*
H13B0.83030.89370.90180.097*
C140.9846 (5)1.0087 (3)0.7938 (2)0.0899 (8)
H14A1.03331.09890.84590.135*
H14B0.86811.01450.73950.135*
H14C1.08620.99560.75280.135*
Cl10.55836 (12)0.13146 (7)0.90817 (5)0.0901 (3)
N10.7107 (2)0.41531 (19)0.54384 (13)0.0549 (4)
N20.7609 (2)0.51950 (17)0.62949 (12)0.0517 (4)
O10.6337 (3)0.23091 (15)0.69263 (12)0.0754 (5)
O20.8391 (3)0.61467 (17)0.92696 (12)0.0856 (5)
O30.8605 (2)0.74750 (14)0.77844 (11)0.0662 (4)
H10.673 (4)0.326 (3)0.562 (2)0.085 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0447 (10)0.0648 (11)0.0465 (9)0.0150 (8)0.0064 (7)0.0051 (8)
C20.0531 (12)0.0798 (14)0.0584 (11)0.0190 (10)0.0065 (8)0.0169 (10)
C30.0757 (15)0.114 (2)0.0539 (12)0.0286 (14)0.0112 (10)0.0202 (13)
C40.0922 (19)0.131 (3)0.0513 (12)0.0362 (17)0.0201 (11)0.0015 (14)
C50.0776 (16)0.1000 (18)0.0647 (13)0.0258 (13)0.0218 (11)0.0181 (12)
C60.0514 (11)0.0756 (13)0.0572 (10)0.0178 (9)0.0093 (8)0.0024 (9)
C70.0785 (15)0.0688 (14)0.0855 (15)0.0079 (11)0.0145 (12)0.0269 (12)
C80.0876 (16)0.0653 (13)0.0720 (14)0.0111 (11)0.0112 (12)0.0080 (11)
C90.0588 (11)0.0494 (10)0.0446 (9)0.0155 (8)0.0006 (8)0.0029 (7)
C100.0664 (12)0.0518 (11)0.0504 (9)0.0156 (9)0.0014 (8)0.0028 (8)
C110.0907 (16)0.0522 (11)0.0544 (10)0.0124 (10)0.0004 (10)0.0029 (8)
C120.0730 (13)0.0509 (10)0.0494 (10)0.0161 (9)0.0020 (9)0.0013 (8)
C130.1128 (19)0.0482 (11)0.0669 (13)0.0119 (11)0.0015 (12)0.0088 (10)
C140.105 (2)0.0552 (13)0.0973 (17)0.0059 (12)0.0108 (15)0.0015 (12)
Cl10.1230 (6)0.0645 (4)0.0699 (4)0.0003 (3)0.0172 (3)0.0100 (3)
N10.0590 (10)0.0536 (9)0.0471 (8)0.0122 (7)0.0049 (7)0.0061 (7)
N20.0516 (9)0.0521 (8)0.0462 (8)0.0126 (7)0.0018 (6)0.0062 (6)
O10.1122 (12)0.0467 (8)0.0571 (8)0.0125 (7)0.0052 (8)0.0053 (6)
O20.1395 (15)0.0575 (8)0.0438 (7)0.0141 (9)0.0048 (8)0.0033 (6)
O30.0906 (10)0.0455 (7)0.0536 (7)0.0114 (7)0.0032 (7)0.0029 (6)
Geometric parameters (Å, º) top
C1—N11.402 (2)C9—C101.463 (3)
C1—C21.407 (3)C9—C121.480 (3)
C1—C61.409 (3)C10—O11.226 (2)
C2—C31.400 (3)C10—C111.508 (3)
C2—C71.495 (4)C11—Cl11.762 (2)
C3—C41.352 (4)C11—H11A0.9700
C3—H30.9300C11—H11B0.9700
C4—C51.385 (4)C12—O21.204 (2)
C4—H40.9300C12—O31.322 (2)
C5—C61.380 (3)C13—O31.452 (2)
C5—H50.9300C13—C141.470 (3)
C6—C81.510 (3)C13—H13A0.9700
C7—H7A0.9600C13—H13B0.9700
C7—H7B0.9600C14—H14A0.9600
C7—H7C0.9600C14—H14B0.9600
C8—H8A0.9600C14—H14C0.9600
C8—H8B0.9600N1—N21.293 (2)
C8—H8C0.9600N1—H10.86 (3)
C9—N21.319 (2)
N1—C1—C2114.95 (19)N2—C9—C12114.52 (17)
N1—C1—C6123.46 (17)C10—C9—C12121.78 (16)
C2—C1—C6121.58 (19)O1—C10—C9120.40 (18)
C3—C2—C1117.7 (2)O1—C10—C11120.33 (19)
C3—C2—C7120.3 (2)C9—C10—C11119.27 (16)
C1—C2—C7122.0 (2)C10—C11—Cl1112.55 (14)
C4—C3—C2121.5 (2)C10—C11—H11A109.1
C4—C3—H3119.3Cl1—C11—H11A109.1
C2—C3—H3119.3C10—C11—H11B109.1
C3—C4—C5119.9 (2)Cl1—C11—H11B109.1
C3—C4—H4120.1H11A—C11—H11B107.8
C5—C4—H4120.1O2—C12—O3122.89 (18)
C6—C5—C4122.4 (3)O2—C12—C9124.41 (18)
C6—C5—H5118.8O3—C12—C9112.69 (16)
C4—C5—H5118.8O3—C13—C14107.81 (19)
C5—C6—C1117.0 (2)O3—C13—H13A110.1
C5—C6—C8118.2 (2)C14—C13—H13A110.1
C1—C6—C8124.85 (18)O3—C13—H13B110.1
C2—C7—H7A109.5C14—C13—H13B110.1
C2—C7—H7B109.5H13A—C13—H13B108.5
H7A—C7—H7B109.5C13—C14—H14A109.5
C2—C7—H7C109.5C13—C14—H14B109.5
H7A—C7—H7C109.5H14A—C14—H14B109.5
H7B—C7—H7C109.5C13—C14—H14C109.5
C6—C8—H8A109.5H14A—C14—H14C109.5
C6—C8—H8B109.5H14B—C14—H14C109.5
H8A—C8—H8B109.5N2—N1—C1123.73 (18)
C6—C8—H8C109.5N2—N1—H1115.5 (17)
H8A—C8—H8C109.5C1—N1—H1120.7 (17)
H8B—C8—H8C109.5N1—N2—C9121.41 (17)
N2—C9—C10123.70 (16)C12—O3—C13115.88 (16)
N1—C1—C2—C3179.63 (19)N2—C9—C10—C11178.09 (19)
C6—C1—C2—C30.4 (3)C12—C9—C10—C112.8 (3)
N1—C1—C2—C70.3 (3)O1—C10—C11—Cl16.9 (3)
C6—C1—C2—C7179.5 (2)C9—C10—C11—Cl1172.61 (16)
C1—C2—C3—C40.0 (4)N2—C9—C12—O2173.1 (2)
C7—C2—C3—C4179.9 (2)C10—C9—C12—O26.1 (3)
C2—C3—C4—C50.1 (4)N2—C9—C12—O35.7 (3)
C3—C4—C5—C60.2 (4)C10—C9—C12—O3175.06 (17)
C4—C5—C6—C10.7 (3)C2—C1—N1—N2178.39 (17)
C4—C5—C6—C8179.3 (2)C6—C1—N1—N22.4 (3)
N1—C1—C6—C5179.88 (19)C1—N1—N2—C9179.07 (17)
C2—C1—C6—C50.8 (3)C10—C9—N2—N10.7 (3)
N1—C1—C6—C80.0 (3)C12—C9—N2—N1178.44 (16)
C2—C1—C6—C8179.2 (2)O2—C12—O3—C130.3 (3)
N2—C9—C10—O11.4 (3)C9—C12—O3—C13178.53 (19)
C12—C9—C10—O1177.8 (2)C14—C13—O3—C12175.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.86 (3)1.86 (2)2.575 (2)138 (2)
 

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