organic compounds
5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde
aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: dr@physics.uni-mysore.ac.in
In the title compound, C17H13ClN2O2, the phenyl and chlorobenzene rings are inclined to the central pyrazole ring at 40.84 (9) and 65.30 (9)°, respectively. In the crystal, pairs of C—H⋯π interactions link the molecules into inversion dimers and C—H⋯O hydrogen bonds link these dimers into columns extended in [010]. The crystal packing exhibits short intermolecular O⋯Cl contacts of 3.0913 (16) Å.
CCDC reference: 996262
Related literature
For biological properties and pharmocological applications of aryloxy pyrazole derivatives, see: Rai et al. (2008); Girisha et al. (2010); Isloor et al. (2009, 2010); Shobhitha et al. (2013). For related structures, see: Shahani, Fun, Ragavan et al. (2011); Shahani, Fun, Shetty et al. (2011); Prasath et al. (2011).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 996262
10.1107/S1600536814007879/cv5447sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814007879/cv5447Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814007879/cv5447Isup3.cml
The title compound was prepared by refluxing a mixture of 5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-carboxaldehyde (0.1 mol) and 4-chloro phenol (0.1 mol) in 10 ml of dimethyl sulfoxide. To this solution, 0.1 mol of potassium hydroxide was added. The reaction mixture was refluxed for 3 hrs and then it was cooled to room temperature and poured to crushed ice. The solid product that separated was filtered and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from slow evaporation of ethanol.
All the H atoms were fixed geometrically (C—H= 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoids. |
C17H13ClN2O2 | F(000) = 648 |
Mr = 312.74 | Dx = 1.373 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 2501 reflections |
a = 9.1016 (7) Å | θ = 4.0–64.4° |
b = 7.5298 (6) Å | µ = 2.31 mm−1 |
c = 22.1242 (16) Å | T = 296 K |
β = 93.908 (3)° | Block, brown |
V = 1512.7 (2) Å3 | 0.23 × 0.22 × 0.21 mm |
Z = 4 |
Bruker X8 Proteum diffractometer | 2501 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 2314 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.041 |
Detector resolution: 18.4 pixels mm-1 | θmax = 64.5°, θmin = 4.0° |
ϕ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −3→8 |
Tmin = 0.619, Tmax = 0.643 | l = −25→25 |
9744 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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.5076P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2501 reflections | Δρmax = 0.25 e Å−3 |
200 parameters | Δρmin = −0.38 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: 0.0171 (10) |
C17H13ClN2O2 | V = 1512.7 (2) Å3 |
Mr = 312.74 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 9.1016 (7) Å | µ = 2.31 mm−1 |
b = 7.5298 (6) Å | T = 296 K |
c = 22.1242 (16) Å | 0.23 × 0.22 × 0.21 mm |
β = 93.908 (3)° |
Bruker X8 Proteum diffractometer | 2501 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 2314 reflections with I > 2σ(I) |
Tmin = 0.619, Tmax = 0.643 | Rint = 0.041 |
9744 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.25 e Å−3 |
2501 reflections | Δρmin = −0.38 e Å−3 |
200 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
Cl1 | 0.33674 (5) | 0.67384 (7) | 0.29951 (2) | 0.0525 (2) | |
O1 | 0.96938 (13) | 0.67414 (15) | 0.37256 (6) | 0.0417 (4) | |
O2 | 0.96678 (16) | 0.16557 (19) | 0.27222 (7) | 0.0579 (5) | |
N1 | 1.15356 (14) | 0.51714 (19) | 0.42604 (6) | 0.0354 (4) | |
N2 | 1.23196 (16) | 0.3599 (2) | 0.42482 (7) | 0.0420 (5) | |
C1 | 0.81860 (18) | 0.6650 (2) | 0.35492 (7) | 0.0335 (5) | |
C2 | 0.72891 (19) | 0.5340 (3) | 0.37544 (8) | 0.0419 (5) | |
C3 | 0.58011 (19) | 0.5360 (3) | 0.35785 (8) | 0.0417 (5) | |
C4 | 0.52407 (19) | 0.6712 (2) | 0.32108 (7) | 0.0378 (5) | |
C5 | 0.6139 (2) | 0.8024 (2) | 0.30129 (8) | 0.0438 (6) | |
C6 | 0.7637 (2) | 0.8000 (2) | 0.31799 (8) | 0.0403 (6) | |
C7 | 1.04684 (16) | 0.5223 (2) | 0.38079 (7) | 0.0332 (5) | |
C8 | 1.05021 (18) | 0.3640 (2) | 0.34914 (7) | 0.0354 (5) | |
C9 | 1.16849 (19) | 0.2680 (2) | 0.37941 (8) | 0.0398 (5) | |
C10 | 0.9588 (2) | 0.3101 (3) | 0.29611 (8) | 0.0407 (6) | |
C11 | 1.20153 (18) | 0.6520 (2) | 0.46814 (7) | 0.0336 (5) | |
C12 | 1.3510 (2) | 0.6767 (2) | 0.47974 (8) | 0.0407 (6) | |
C13 | 1.4008 (2) | 0.8051 (3) | 0.52092 (9) | 0.0488 (6) | |
C14 | 1.3028 (2) | 0.9086 (3) | 0.54945 (9) | 0.0533 (7) | |
C15 | 1.1529 (2) | 0.8822 (3) | 0.53819 (8) | 0.0495 (6) | |
C16 | 1.10095 (19) | 0.7530 (2) | 0.49751 (7) | 0.0404 (5) | |
C17 | 1.2243 (2) | 0.0881 (3) | 0.36473 (11) | 0.0592 (7) | |
H02A | 1.30480 | 0.05740 | 0.39310 | 0.0890* | |
H2 | 0.76800 | 0.44510 | 0.40090 | 0.0500* | |
H02B | 1.25740 | 0.08840 | 0.32440 | 0.0890* | |
H3 | 0.51850 | 0.44700 | 0.37070 | 0.0500* | |
H02C | 1.14670 | 0.00270 | 0.36720 | 0.0890* | |
H5 | 0.57430 | 0.89290 | 0.27670 | 0.0530* | |
H6 | 0.82560 | 0.88770 | 0.30450 | 0.0480* | |
H10 | 0.89020 | 0.39080 | 0.27940 | 0.0490* | |
H12 | 1.41770 | 0.60760 | 0.46010 | 0.0490* | |
H13 | 1.50150 | 0.82140 | 0.52930 | 0.0590* | |
H14 | 1.33690 | 0.99660 | 0.57640 | 0.0640* | |
H15 | 1.08660 | 0.95150 | 0.55800 | 0.0590* | |
H16 | 1.00030 | 0.73440 | 0.49010 | 0.0480* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0314 (3) | 0.0597 (4) | 0.0649 (3) | 0.0089 (2) | −0.0083 (2) | −0.0045 (2) |
O1 | 0.0335 (6) | 0.0355 (7) | 0.0536 (7) | 0.0015 (5) | −0.0141 (5) | 0.0023 (5) |
O2 | 0.0543 (9) | 0.0558 (9) | 0.0619 (9) | −0.0033 (6) | −0.0090 (7) | −0.0195 (7) |
N1 | 0.0304 (7) | 0.0367 (8) | 0.0378 (7) | 0.0046 (6) | −0.0069 (5) | −0.0024 (6) |
N2 | 0.0365 (8) | 0.0382 (8) | 0.0497 (8) | 0.0084 (6) | −0.0094 (6) | −0.0035 (6) |
C1 | 0.0294 (8) | 0.0379 (9) | 0.0321 (8) | 0.0039 (6) | −0.0057 (6) | −0.0005 (6) |
C2 | 0.0382 (9) | 0.0447 (10) | 0.0418 (9) | 0.0044 (8) | −0.0038 (7) | 0.0129 (7) |
C3 | 0.0342 (9) | 0.0454 (10) | 0.0456 (9) | 0.0018 (7) | 0.0038 (7) | 0.0068 (8) |
C4 | 0.0316 (9) | 0.0442 (10) | 0.0368 (8) | 0.0072 (7) | −0.0034 (7) | −0.0030 (7) |
C5 | 0.0423 (10) | 0.0432 (10) | 0.0445 (9) | 0.0091 (8) | −0.0071 (8) | 0.0099 (8) |
C6 | 0.0390 (10) | 0.0379 (10) | 0.0435 (9) | 0.0020 (7) | −0.0014 (7) | 0.0076 (7) |
C7 | 0.0258 (7) | 0.0365 (9) | 0.0364 (8) | 0.0000 (6) | −0.0044 (6) | 0.0037 (7) |
C8 | 0.0302 (8) | 0.0366 (9) | 0.0386 (8) | −0.0034 (7) | −0.0030 (6) | 0.0003 (7) |
C9 | 0.0340 (9) | 0.0393 (10) | 0.0453 (9) | 0.0013 (7) | −0.0021 (7) | −0.0040 (7) |
C10 | 0.0360 (9) | 0.0442 (11) | 0.0409 (9) | −0.0062 (7) | −0.0037 (7) | −0.0020 (8) |
C11 | 0.0350 (9) | 0.0340 (9) | 0.0308 (8) | 0.0012 (6) | −0.0042 (6) | 0.0031 (6) |
C12 | 0.0340 (9) | 0.0490 (11) | 0.0386 (9) | 0.0006 (7) | −0.0020 (7) | −0.0009 (7) |
C13 | 0.0440 (10) | 0.0539 (12) | 0.0468 (10) | −0.0090 (9) | −0.0097 (8) | −0.0019 (8) |
C14 | 0.0658 (13) | 0.0454 (12) | 0.0467 (10) | −0.0040 (9) | −0.0104 (9) | −0.0069 (8) |
C15 | 0.0623 (12) | 0.0430 (11) | 0.0429 (9) | 0.0136 (9) | 0.0021 (8) | −0.0035 (8) |
C16 | 0.0360 (9) | 0.0432 (10) | 0.0412 (9) | 0.0062 (7) | −0.0023 (7) | 0.0021 (8) |
C17 | 0.0530 (12) | 0.0482 (12) | 0.0741 (13) | 0.0116 (10) | −0.0122 (10) | −0.0135 (10) |
Cl1—C4 | 1.7390 (18) | C11—C16 | 1.386 (2) |
O1—C1 | 1.403 (2) | C12—C13 | 1.384 (3) |
O1—C7 | 1.3490 (19) | C13—C14 | 1.370 (3) |
O2—C10 | 1.214 (3) | C14—C15 | 1.384 (3) |
N1—N2 | 1.384 (2) | C15—C16 | 1.386 (3) |
N1—C7 | 1.347 (2) | C2—H2 | 0.9300 |
N1—C11 | 1.426 (2) | C3—H3 | 0.9300 |
N2—C9 | 1.320 (2) | C5—H5 | 0.9300 |
C1—C2 | 1.377 (3) | C6—H6 | 0.9300 |
C1—C6 | 1.377 (2) | C10—H10 | 0.9300 |
C2—C3 | 1.384 (2) | C12—H12 | 0.9300 |
C3—C4 | 1.379 (3) | C13—H13 | 0.9300 |
C4—C5 | 1.373 (2) | C14—H14 | 0.9300 |
C5—C6 | 1.388 (3) | C15—H15 | 0.9300 |
C7—C8 | 1.384 (2) | C16—H16 | 0.9300 |
C8—C9 | 1.425 (2) | C17—H02A | 0.9600 |
C8—C10 | 1.449 (2) | C17—H02B | 0.9600 |
C9—C17 | 1.490 (3) | C17—H02C | 0.9600 |
C11—C12 | 1.380 (2) | ||
C1—O1—C7 | 119.23 (12) | C13—C14—C15 | 119.99 (19) |
N2—N1—C7 | 110.91 (13) | C14—C15—C16 | 120.39 (18) |
N2—N1—C11 | 119.12 (13) | C11—C16—C15 | 118.86 (16) |
C7—N1—C11 | 129.64 (14) | C1—C2—H2 | 120.00 |
N1—N2—C9 | 105.30 (13) | C3—C2—H2 | 120.00 |
O1—C1—C2 | 122.29 (14) | C2—C3—H3 | 120.00 |
O1—C1—C6 | 115.95 (14) | C4—C3—H3 | 120.00 |
C2—C1—C6 | 121.69 (16) | C4—C5—H5 | 120.00 |
C1—C2—C3 | 119.37 (18) | C6—C5—H5 | 120.00 |
C2—C3—C4 | 119.31 (18) | C1—C6—H6 | 121.00 |
Cl1—C4—C3 | 119.12 (13) | C5—C6—H6 | 121.00 |
Cl1—C4—C5 | 119.89 (13) | O2—C10—H10 | 118.00 |
C3—C4—C5 | 121.00 (16) | C8—C10—H10 | 118.00 |
C4—C5—C6 | 120.08 (15) | C11—C12—H12 | 120.00 |
C1—C6—C5 | 118.54 (15) | C13—C12—H12 | 120.00 |
O1—C7—N1 | 117.94 (14) | C12—C13—H13 | 120.00 |
O1—C7—C8 | 133.72 (14) | C14—C13—H13 | 120.00 |
N1—C7—C8 | 108.15 (13) | C13—C14—H14 | 120.00 |
C7—C8—C9 | 103.96 (14) | C15—C14—H14 | 120.00 |
C7—C8—C10 | 128.28 (16) | C14—C15—H15 | 120.00 |
C9—C8—C10 | 127.72 (15) | C16—C15—H15 | 120.00 |
N2—C9—C8 | 111.66 (14) | C11—C16—H16 | 121.00 |
N2—C9—C17 | 120.29 (16) | C15—C16—H16 | 121.00 |
C8—C9—C17 | 128.05 (16) | C9—C17—H02A | 109.00 |
O2—C10—C8 | 123.73 (18) | C9—C17—H02B | 109.00 |
N1—C11—C12 | 118.14 (14) | C9—C17—H02C | 109.00 |
N1—C11—C16 | 120.96 (14) | H02A—C17—H02B | 110.00 |
C12—C11—C16 | 120.89 (15) | H02A—C17—H02C | 109.00 |
C11—C12—C13 | 119.43 (16) | H02B—C17—H02C | 109.00 |
C12—C13—C14 | 120.43 (17) | ||
C7—O1—C1—C2 | 36.1 (2) | C2—C3—C4—C5 | 0.6 (3) |
C7—O1—C1—C6 | −146.92 (15) | Cl1—C4—C5—C6 | −179.47 (13) |
C1—O1—C7—N1 | −143.39 (14) | C3—C4—C5—C6 | 0.3 (3) |
C1—O1—C7—C8 | 42.4 (2) | C4—C5—C6—C1 | −0.6 (2) |
C7—N1—N2—C9 | −1.81 (18) | O1—C7—C8—C9 | 174.01 (17) |
C11—N1—N2—C9 | −175.88 (14) | O1—C7—C8—C10 | −3.9 (3) |
N2—N1—C7—O1 | −174.08 (13) | N1—C7—C8—C9 | −0.60 (17) |
N2—N1—C7—C8 | 1.51 (18) | N1—C7—C8—C10 | −178.50 (16) |
C11—N1—C7—O1 | −0.8 (2) | C7—C8—C9—N2 | −0.55 (19) |
C11—N1—C7—C8 | 174.78 (15) | C7—C8—C9—C17 | −179.41 (17) |
N2—N1—C11—C12 | 37.2 (2) | C10—C8—C9—N2 | 177.37 (17) |
N2—N1—C11—C16 | −141.54 (15) | C10—C8—C9—C17 | −1.5 (3) |
C7—N1—C11—C12 | −135.63 (17) | C7—C8—C10—O2 | −177.79 (18) |
C7—N1—C11—C16 | 45.7 (2) | C9—C8—C10—O2 | 4.8 (3) |
N1—N2—C9—C8 | 1.42 (19) | N1—C11—C12—C13 | −179.23 (16) |
N1—N2—C9—C17 | −179.62 (16) | C16—C11—C12—C13 | −0.5 (2) |
O1—C1—C2—C3 | 177.88 (16) | N1—C11—C16—C15 | 179.80 (15) |
C6—C1—C2—C3 | 1.0 (3) | C12—C11—C16—C15 | 1.1 (2) |
O1—C1—C6—C5 | −177.13 (15) | C11—C12—C13—C14 | −0.8 (3) |
C2—C1—C6—C5 | −0.1 (3) | C12—C13—C14—C15 | 1.5 (3) |
C1—C2—C3—C4 | −1.3 (3) | C13—C14—C15—C16 | −0.9 (3) |
C2—C3—C4—Cl1 | −179.59 (14) | C14—C15—C16—C11 | −0.4 (3) |
Cg is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.93 | 2.58 | 3.503 (2) | 171 |
C2—H2···Cgii | 0.93 | 2.63 | 3.476 (2) | 152 |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z+1. |
Cg is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.93 | 2.58 | 3.503 (2) | 171.00 |
C2—H2···Cgii | 0.93 | 2.63 | 3.476 (2) | 152.00 |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z+1. |
Acknowledgements
The authors are thankful to the IOE and UPE, University of Mysore, for providing the single-crystal X-ray diffraction facility and for the financial support. VN is grateful to the UGC for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41–882/2012 (SR) dated 01/07/2012].
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Aryloxy pyrazoles and their derivatives possess a significant pharmcological activities such as antimicrobial (Rai et al. 2008; Girisha et al., 2010), anti-inflammatory (Isloor et al., 2009) and analgesic activities (Shobhitha et al., 2013). The title compound can serve as an intermediate in the synthesis of various pyrazole derivatives with significant pharmacological activities (Isloor et al., 2010).
In the title compound (Fig.1), all bond lengths and angles are normal and correspond well to those observed in the related compounds (Shahani, Fun, Ragavan et al., 2011; Shahani, Fun, Shetty et al., 2011; Prasath et al., 2011). The pyrazole ring makes dihedral angles of 65.30 (9)° with chlorobenzene ring and 40.84 (9)° with benzene ring. The dihedral angle between the chlorobenzene ring and benzene ring is 76.23 (9)°.
In the crystal, C–H···π interactions (Table 1) link the molecules into inversion dimers, and intermolecular C–H···O hydrogen bonds (Table 1) link these dimers into columns extended in [010]. The crystal packing exhibits short intermolecular O···Cl contacts of 3.0913 (16) Å.