organic compounds
Dimethyl 2-[2-(2,4,6-trichlorophenyl)hydrazin-1-ylidene]butanedioate
aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and cPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
*Correspondence e-mail: dr@physics.uni-mysore.ac.in
In the title compound, C12H11Cl3N2O4, the dihedral angle between the aromatic ring and the hydrazine (NH—N=C) grouping is 52.2 (3)°. The butanedioate groups exhibit planar conformations. An intramolecular N—H⋯O hydrogen bond links the N—H group of the hydrazine to one of the methoxy groups of the butanedioate moiety. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and π–π interactions are also observed [centroid–centroid separation = 3.535 (1) Å].
CCDC reference: 967565
Related literature
For the pharmacological activity of halo-substituted derivatives, see: Kees et al. (1996). For the use of the title compound in the synthesis of pyrazoles, see: Palacios et al. (1999). For the biological activity of pyrazoles, see: Palacios et al. (1999); Lee et al. (2003); Nithinchandra et al. (2012); Genin et al. (2000); Reddy et al. (2008); Kees et al. (1996). For a related structure, see: Huang et al. (2011).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 967565
https://doi.org/10.1107/S160053681303242X/sj5364sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681303242X/sj5364Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681303242X/sj5364Isup3.cml
The title compound was prepared by refluxing a mixture of trichlorophenyl hydrazine (0.01 mol) and dimethylacetylene dicarboxylate (0.01 mol) in a 10 ml toluene solution for 4 h. The completion of the reaction was monitored by thin layer
After completion the solvent was evaporated under reduced pressure and the white solid obtained was recrystallized from ethanol.Atom H10 attached to N10 was located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically and were refined as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å; and with Uiso(H) = 1.2Ueq(C), except for the methyl groups where Uiso(H) = 1.5Ueq(C).
It has been reported in the literature that halo substituted derivatives possess significant pharmacological activity (Kees et al., 1996). Also the title compound can be used as an intermediate for the synthesis of pyrazoles (Palacios et al., 1999). Aryl pyrazoles have antimicrobial (Palacios et al., 1999, Lee et al., 2003), anti-inflammatory (Nithinchandra et al., 2012) and non-nucleoside HIV-I reverse transcriptase inhibitor activity (Genin et al., 2000). Furthermore, pyrazoles with a wide array of substituted groups were reported to be selective inhibitors of cyclooxygenase (Reddy et al., 2008) and also exhibit antidiabetic properties (Kees et al., 1996).
In the title compound, C12H11C13N2O4, the trichlorophenyl ring is planar (r.m.s. deviation 0.018 Å); the largest deviation from the mean plane is 0.02 (3) Å for atom C1. The bond distances in the title compound are comparable to those observed in the closely related structure (E)-benzaldehyde (2,4,6-trichlorophenyl) hydrazone (Huang et al., 2011). The C1—N10—N11—C12 torsion angle of the atoms joining the trichlorophenyl ring and the butanedioate group is 175.9 (3). An intramolecular N10–H10···O15 hydrogen bond links the N–H group of the hydrazine to one of the methoxy groups of the butanedioate moiety. In the crystal, molecules are stacked along the a axis by C5—H5..O19 hydrogen bonds and π–π interactions between adjacent trichlorophenyl rings [centroid–centroid separation = 3.535 (1) Å, = 3.494 Å, centroid shift = 0.53 Å, symmetry code: -1/2 + x,y,1/2 - z].
For the pharmacological activity of halo-substituted derivatives , see: Kees et al. (1996). For the use of the title compound in the synthesis of pyrazoles, see: Palacios et al. (1999). For the biological activity of pyrazoles, see: Palacios et al. (1999); Lee et al. (2003); Nithinchandra et al. (2012); Genin et al. (2000); Reddy et al. (2008); Kees et al. (1996). For a related structure, see: Huang et al. (2011).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).C12H11Cl3N2O4 | F(000) = 1440 |
Mr = 353.58 | Dx = 1.562 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1944 reflections |
a = 7.0182 (5) Å | θ = 3.9–27.4° |
b = 16.0165 (12) Å | µ = 0.63 mm−1 |
c = 26.7488 (15) Å | T = 293 K |
V = 3006.8 (4) Å3 | Block, white |
Z = 8 | 0.30 × 0.20 × 0.20 mm |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 2954 independent reflections |
Radiation source: fine-focus sealed tube | 1844 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 16.1049 pixels mm-1 | θmax = 26.0°, θmin = 3.9° |
ω scans | h = −7→8 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | k = −19→11 |
Tmin = 0.716, Tmax = 1.000 | l = −32→30 |
7083 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0358P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.006 |
2954 reflections | Δρmax = 0.26 e Å−3 |
195 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0029 (4) |
C12H11Cl3N2O4 | V = 3006.8 (4) Å3 |
Mr = 353.58 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 7.0182 (5) Å | µ = 0.63 mm−1 |
b = 16.0165 (12) Å | T = 293 K |
c = 26.7488 (15) Å | 0.30 × 0.20 × 0.20 mm |
Oxford Diffraction Xcalibur Sapphire3 diffractometer | 2954 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | 1844 reflections with I > 2σ(I) |
Tmin = 0.716, Tmax = 1.000 | Rint = 0.040 |
7083 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.26 e Å−3 |
2954 reflections | Δρmin = −0.24 e Å−3 |
195 parameters |
Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01–02-2013 CrysAlis171. NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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. |
x | y | z | Uiso*/Ueq | ||
Cl7 | 0.13759 (16) | 0.09353 (6) | 0.31855 (3) | 0.0641 (3) | |
Cl9 | 0.09570 (15) | −0.23591 (5) | 0.27554 (3) | 0.0589 (3) | |
Cl8 | 0.16340 (14) | −0.01155 (7) | 0.12827 (3) | 0.0640 (3) | |
O21 | 0.4517 (4) | −0.22006 (15) | 0.47244 (7) | 0.0604 (7) | |
N11 | 0.2602 (4) | −0.14140 (16) | 0.36258 (8) | 0.0385 (6) | |
N10 | 0.1266 (4) | −0.08714 (18) | 0.34507 (9) | 0.0406 (7) | |
O19 | 0.5314 (3) | −0.24056 (15) | 0.39230 (8) | 0.0572 (7) | |
O15 | 0.2372 (4) | 0.01540 (15) | 0.43653 (8) | 0.0582 (7) | |
C3 | 0.1464 (4) | 0.0307 (2) | 0.22574 (11) | 0.0443 (8) | |
H3 | 0.1510 | 0.0859 | 0.2150 | 0.053* | |
C12 | 0.2654 (4) | −0.15507 (19) | 0.41006 (10) | 0.0385 (8) | |
C1 | 0.1339 (4) | −0.0696 (2) | 0.29355 (10) | 0.0344 (7) | |
O17 | 0.2154 (4) | −0.02745 (18) | 0.51588 (9) | 0.0796 (9) | |
C6 | 0.1257 (4) | −0.13302 (19) | 0.25794 (11) | 0.0385 (8) | |
C5 | 0.1340 (4) | −0.1159 (2) | 0.20686 (11) | 0.0429 (8) | |
H5 | 0.1315 | −0.1589 | 0.1835 | 0.051* | |
C13 | 0.1318 (5) | −0.1207 (2) | 0.44935 (11) | 0.0459 (9) | |
H13A | 0.0081 | −0.1111 | 0.4342 | 0.055* | |
H13B | 0.1158 | −0.1622 | 0.4754 | 0.055* | |
C4 | 0.1460 (4) | −0.0342 (2) | 0.19178 (12) | 0.0459 (9) | |
C2 | 0.1399 (4) | 0.0117 (2) | 0.27610 (11) | 0.0401 (8) | |
C18 | 0.4236 (5) | −0.2085 (2) | 0.42838 (12) | 0.0437 (8) | |
C14 | 0.1996 (5) | −0.0411 (2) | 0.47251 (12) | 0.0508 (9) | |
C16 | 0.3100 (6) | 0.0954 (2) | 0.45282 (14) | 0.0744 (12) | |
H16A | 0.3322 | 0.1303 | 0.4242 | 0.112* | |
H16B | 0.4275 | 0.0874 | 0.4706 | 0.112* | |
H16C | 0.2187 | 0.1217 | 0.4744 | 0.112* | |
C20 | 0.6937 (6) | −0.2892 (3) | 0.40768 (13) | 0.0762 (13) | |
H20A | 0.7602 | −0.3090 | 0.3787 | 0.114* | |
H20B | 0.6515 | −0.3358 | 0.4273 | 0.114* | |
H20C | 0.7775 | −0.2550 | 0.4273 | 0.114* | |
H10 | 0.096 (5) | −0.044 (2) | 0.3640 (11) | 0.050 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl7 | 0.0891 (8) | 0.0417 (5) | 0.0615 (6) | −0.0035 (5) | 0.0025 (5) | −0.0015 (4) |
Cl9 | 0.0786 (7) | 0.0401 (5) | 0.0580 (6) | −0.0024 (5) | −0.0102 (4) | 0.0033 (4) |
Cl8 | 0.0631 (6) | 0.0898 (8) | 0.0393 (5) | −0.0039 (6) | −0.0063 (4) | 0.0186 (5) |
O21 | 0.0808 (18) | 0.0676 (18) | 0.0327 (13) | 0.0156 (15) | −0.0090 (12) | 0.0032 (11) |
N11 | 0.0441 (16) | 0.0355 (15) | 0.0359 (14) | 0.0012 (13) | −0.0024 (11) | 0.0004 (12) |
N10 | 0.0456 (16) | 0.0408 (16) | 0.0353 (16) | 0.0085 (14) | 0.0012 (12) | 0.0040 (14) |
O19 | 0.0691 (16) | 0.0619 (17) | 0.0406 (13) | 0.0275 (14) | 0.0008 (12) | 0.0060 (11) |
O15 | 0.0717 (18) | 0.0510 (16) | 0.0519 (14) | −0.0054 (14) | 0.0097 (13) | −0.0132 (12) |
C3 | 0.0340 (17) | 0.050 (2) | 0.049 (2) | −0.0022 (17) | −0.0002 (14) | 0.0149 (18) |
C12 | 0.0480 (19) | 0.0361 (18) | 0.0314 (16) | −0.0027 (16) | −0.0009 (13) | 0.0017 (13) |
C1 | 0.0289 (16) | 0.0398 (19) | 0.0344 (17) | 0.0020 (15) | 0.0001 (12) | 0.0065 (14) |
O17 | 0.109 (2) | 0.090 (2) | 0.0399 (14) | 0.018 (2) | −0.0080 (14) | −0.0129 (15) |
C6 | 0.0330 (16) | 0.0365 (19) | 0.0461 (19) | 0.0000 (15) | −0.0038 (14) | 0.0096 (15) |
C5 | 0.0390 (18) | 0.055 (2) | 0.0346 (18) | 0.0054 (18) | −0.0061 (14) | −0.0010 (16) |
C13 | 0.055 (2) | 0.050 (2) | 0.0328 (17) | 0.0003 (18) | 0.0049 (14) | −0.0002 (16) |
C4 | 0.0306 (17) | 0.060 (2) | 0.0470 (19) | −0.0008 (18) | −0.0043 (14) | 0.0105 (19) |
C2 | 0.0366 (17) | 0.0421 (19) | 0.0415 (19) | −0.0009 (16) | 0.0009 (14) | 0.0031 (15) |
C18 | 0.058 (2) | 0.0343 (18) | 0.0390 (19) | −0.0038 (17) | −0.0011 (16) | −0.0001 (15) |
C14 | 0.049 (2) | 0.062 (2) | 0.041 (2) | 0.014 (2) | 0.0062 (16) | −0.0017 (18) |
C16 | 0.091 (3) | 0.045 (2) | 0.087 (3) | 0.000 (2) | 0.001 (2) | −0.016 (2) |
C20 | 0.081 (3) | 0.081 (3) | 0.067 (3) | 0.043 (3) | −0.002 (2) | 0.008 (2) |
Cl7—C2 | 1.735 (3) | C12—C13 | 1.512 (4) |
Cl9—C6 | 1.727 (3) | C1—C2 | 1.383 (4) |
Cl8—C4 | 1.741 (3) | C1—C6 | 1.394 (4) |
O21—C18 | 1.209 (3) | O17—C14 | 1.186 (3) |
N11—C12 | 1.289 (3) | C6—C5 | 1.395 (4) |
N11—N10 | 1.362 (3) | C5—C4 | 1.372 (5) |
N10—C1 | 1.407 (4) | C5—H5 | 0.9300 |
N10—H10 | 0.88 (3) | C13—C14 | 1.495 (5) |
O19—C18 | 1.329 (4) | C13—H13A | 0.9700 |
O19—C20 | 1.440 (4) | C13—H13B | 0.9700 |
O15—C14 | 1.348 (4) | C16—H16A | 0.9600 |
O15—C16 | 1.447 (4) | C16—H16B | 0.9600 |
C3—C2 | 1.382 (4) | C16—H16C | 0.9600 |
C3—C4 | 1.380 (5) | C20—H20A | 0.9600 |
C3—H3 | 0.9300 | C20—H20B | 0.9600 |
C12—C18 | 1.485 (4) | C20—H20C | 0.9600 |
C12—N11—N10 | 117.8 (3) | H13A—C13—H13B | 107.7 |
N11—N10—C1 | 116.1 (2) | C5—C4—C3 | 121.7 (3) |
N11—N10—H10 | 118 (2) | C5—C4—Cl8 | 119.3 (3) |
C1—N10—H10 | 115 (2) | C3—C4—Cl8 | 119.0 (3) |
C18—O19—C20 | 116.9 (3) | C3—C2—C1 | 122.5 (3) |
C14—O15—C16 | 116.7 (3) | C3—C2—Cl7 | 118.1 (3) |
C2—C3—C4 | 118.4 (3) | C1—C2—Cl7 | 119.3 (2) |
C2—C3—H3 | 120.8 | O21—C18—O19 | 123.7 (3) |
C4—C3—H3 | 120.8 | O21—C18—C12 | 122.2 (3) |
N11—C12—C18 | 116.4 (3) | O19—C18—C12 | 114.1 (3) |
N11—C12—C13 | 127.3 (3) | O17—C14—O15 | 123.8 (4) |
C18—C12—C13 | 116.3 (3) | O17—C14—C13 | 126.4 (4) |
C2—C1—C6 | 117.1 (3) | O15—C14—C13 | 109.8 (3) |
C2—C1—N10 | 121.3 (3) | O15—C16—H16A | 109.5 |
C6—C1—N10 | 121.5 (3) | O15—C16—H16B | 109.5 |
C1—C6—C5 | 121.6 (3) | H16A—C16—H16B | 109.5 |
C1—C6—Cl9 | 120.9 (2) | O15—C16—H16C | 109.5 |
C5—C6—Cl9 | 117.4 (3) | H16A—C16—H16C | 109.5 |
C4—C5—C6 | 118.5 (3) | H16B—C16—H16C | 109.5 |
C4—C5—H5 | 120.7 | O19—C20—H20A | 109.5 |
C6—C5—H5 | 120.7 | O19—C20—H20B | 109.5 |
C14—C13—C12 | 113.6 (3) | H20A—C20—H20B | 109.5 |
C14—C13—H13A | 108.8 | O19—C20—H20C | 109.5 |
C12—C13—H13A | 108.8 | H20A—C20—H20C | 109.5 |
C14—C13—H13B | 108.8 | H20B—C20—H20C | 109.5 |
C12—C13—H13B | 108.8 | ||
C12—N11—N10—C1 | 175.9 (3) | C4—C3—C2—C1 | 0.3 (5) |
N10—N11—C12—C18 | −174.7 (3) | C4—C3—C2—Cl7 | −179.3 (2) |
N10—N11—C12—C13 | 3.4 (5) | C6—C1—C2—C3 | −2.9 (5) |
N11—N10—C1—C2 | −127.5 (3) | N10—C1—C2—C3 | −179.8 (3) |
N11—N10—C1—C6 | 55.8 (4) | C6—C1—C2—Cl7 | 176.7 (2) |
C2—C1—C6—C5 | 3.5 (4) | N10—C1—C2—Cl7 | −0.2 (4) |
N10—C1—C6—C5 | −179.6 (3) | C20—O19—C18—O21 | −2.2 (5) |
C2—C1—C6—Cl9 | −174.0 (2) | C20—O19—C18—C12 | 176.6 (3) |
N10—C1—C6—Cl9 | 2.9 (4) | N11—C12—C18—O21 | 173.9 (3) |
C1—C6—C5—C4 | −1.6 (4) | C13—C12—C18—O21 | −4.3 (5) |
Cl9—C6—C5—C4 | 176.0 (2) | N11—C12—C18—O19 | −4.9 (4) |
N11—C12—C13—C14 | −92.3 (4) | C13—C12—C18—O19 | 176.8 (3) |
C18—C12—C13—C14 | 85.7 (4) | C16—O15—C14—O17 | 3.2 (5) |
C6—C5—C4—C3 | −1.2 (5) | C16—O15—C14—C13 | −178.2 (3) |
C6—C5—C4—Cl8 | 178.2 (2) | C12—C13—C14—O17 | −127.7 (4) |
C2—C3—C4—C5 | 1.8 (5) | C12—C13—C14—O15 | 53.8 (4) |
C2—C3—C4—Cl8 | −177.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H10···O15 | 0.87 (3) | 2.38 (3) | 3.047 (3) | 133 (3) |
C5—H5···O19i | 0.93 | 2.51 | 3.397 (4) | 159 |
Symmetry code: (i) x−1/2, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H10···O15 | 0.87 (3) | 2.38 (3) | 3.047 (3) | 133 (3) |
C5—H5···O19i | 0.93 | 2.51 | 3.397 (4) | 159 |
Symmetry code: (i) x−1/2, y, −z+1/2. |
Acknowledgements
MKU thanks the Department of Science & Technology (DST), New Delhi, for the award of an INSPIRE Fellowship. DR acknowledges the UGC for financial support under the Major Research Project scheme [No. F.41–882/2012 (SR)]. RK acknowledges the DST, New Delhi, for the single-crystal X-ray diffractometer sanctioned as a National Facility.
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It has been reported in the literature that halo substituted derivatives possess significant pharmacological activity (Kees et al., 1996). Also the title compound can be used as an intermediate for the synthesis of pyrazoles (Palacios et al., 1999). Aryl pyrazoles have antimicrobial (Palacios et al., 1999, Lee et al., 2003), anti-inflammatory (Nithinchandra et al., 2012) and non-nucleoside HIV-I reverse transcriptase inhibitor activity (Genin et al., 2000). Furthermore, pyrazoles with a wide array of substituted groups were reported to be selective inhibitors of cyclooxygenase (Reddy et al., 2008) and also exhibit antidiabetic properties (Kees et al., 1996).
In the title compound, C12H11C13N2O4, the trichlorophenyl ring is planar (r.m.s. deviation 0.018 Å); the largest deviation from the mean plane is 0.02 (3) Å for atom C1. The bond distances in the title compound are comparable to those observed in the closely related structure (E)-benzaldehyde (2,4,6-trichlorophenyl) hydrazone (Huang et al., 2011). The C1—N10—N11—C12 torsion angle of the atoms joining the trichlorophenyl ring and the butanedioate group is 175.9 (3). An intramolecular N10–H10···O15 hydrogen bond links the N–H group of the hydrazine to one of the methoxy groups of the butanedioate moiety. In the crystal, molecules are stacked along the a axis by C5—H5..O19 hydrogen bonds and π–π interactions between adjacent trichlorophenyl rings [centroid–centroid separation = 3.535 (1) Å, interplanar spacing = 3.494 Å, centroid shift = 0.53 Å, symmetry code: -1/2 + x,y,1/2 - z].