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In the title compound, C10H9ClN2O, the benzene ring is twisted with respect to the pyrazole plane, with a dihedral angle of 15.81 (11)°. The centroid-to-centroid separation of 3.721 (4) Å indicates π–π stacking between parallel benzene rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013699/xu2016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013699/xu2016Isup2.hkl
Contains datablock I

CCDC reference: 608531

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.038
  • wR factor = 0.111
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

2-(4-Chlorophenyl)-5-methyl-1H-pyrazol-3(2H)-one top
Crystal data top
C10H9ClN2OZ = 2
Mr = 208.64F(000) = 216
Triclinic, P1Dx = 1.439 Mg m3
Hall symbol: -P 1Melting point: 441 K
a = 5.885 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.704 (7) ÅCell parameters from 1622 reflections
c = 11.38 (1) Åθ = 2.8–26.5°
α = 105.980 (13)°µ = 0.36 mm1
β = 94.719 (14)°T = 294 K
γ = 101.250 (13)°Block, colourless
V = 481.4 (7) Å30.30 × 0.26 × 0.22 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1669 independent reflections
Radiation source: fine-focus sealed tube1421 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 56
Tmin = 0.899, Tmax = 0.925k = 99
2397 measured reflectionsl = 1310
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.054P)2 + 0.1893P]
where P = (Fo2 + 2Fc2)/3
1669 reflections(Δ/σ)max = 0.003
132 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.26 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
Cl10.46931 (12)0.04642 (9)0.14776 (5)0.0653 (3)
O10.1306 (2)0.3563 (2)0.70412 (13)0.0514 (4)
N10.5211 (2)0.3831 (2)0.67330 (13)0.0340 (4)
N20.7367 (3)0.4918 (2)0.73944 (15)0.0397 (4)
C10.5052 (3)0.2847 (2)0.54670 (16)0.0324 (4)
C20.6975 (3)0.3122 (3)0.48463 (18)0.0414 (5)
H20.83390.39900.52530.050*
C30.6851 (4)0.2103 (3)0.36256 (18)0.0457 (5)
H30.81390.22730.32140.055*
C40.4813 (4)0.0834 (3)0.30197 (17)0.0416 (5)
C50.2884 (4)0.0560 (3)0.36099 (19)0.0470 (5)
H50.15140.02880.31880.056*
C60.2997 (3)0.1562 (3)0.48417 (19)0.0423 (5)
H60.17050.13770.52490.051*
C70.3443 (3)0.4248 (3)0.74289 (17)0.0362 (4)
C80.4626 (3)0.5550 (3)0.85669 (17)0.0418 (5)
H80.39160.60820.92330.050*
C90.6962 (3)0.5883 (3)0.85163 (17)0.0400 (5)
C100.8974 (4)0.7108 (3)0.9465 (2)0.0594 (6)
H10A0.99310.63590.97160.089*
H10B0.83840.77861.01690.089*
H10C0.98950.79610.91170.089*
H2A0.857 (4)0.450 (3)0.730 (2)0.058 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0860 (5)0.0646 (4)0.0351 (3)0.0180 (3)0.0105 (3)0.0028 (3)
O10.0266 (8)0.0645 (10)0.0507 (9)0.0087 (6)0.0096 (6)0.0027 (7)
N10.0236 (8)0.0403 (8)0.0329 (8)0.0058 (6)0.0050 (6)0.0034 (7)
N20.0267 (9)0.0469 (9)0.0382 (9)0.0085 (7)0.0051 (7)0.0005 (7)
C10.0320 (10)0.0351 (9)0.0309 (9)0.0114 (7)0.0062 (7)0.0080 (7)
C20.0341 (10)0.0503 (11)0.0354 (10)0.0018 (8)0.0079 (8)0.0102 (9)
C30.0446 (12)0.0589 (13)0.0343 (10)0.0094 (10)0.0143 (9)0.0140 (9)
C40.0518 (12)0.0409 (10)0.0311 (10)0.0150 (9)0.0052 (8)0.0063 (8)
C50.0426 (12)0.0437 (11)0.0431 (11)0.0037 (9)0.0004 (9)0.0002 (9)
C60.0326 (10)0.0441 (11)0.0431 (11)0.0053 (8)0.0090 (8)0.0030 (9)
C70.0287 (10)0.0431 (10)0.0367 (10)0.0115 (8)0.0095 (7)0.0081 (8)
C80.0361 (10)0.0502 (11)0.0350 (10)0.0143 (9)0.0098 (8)0.0014 (8)
C90.0376 (11)0.0431 (11)0.0351 (10)0.0124 (8)0.0049 (8)0.0025 (8)
C100.0396 (12)0.0672 (15)0.0509 (13)0.0088 (10)0.0002 (9)0.0110 (11)
Geometric parameters (Å, º) top
Cl1—C41.753 (2)C3—H30.9300
O1—C71.256 (2)C4—C51.377 (3)
N1—N21.400 (2)C5—C61.391 (3)
N1—C11.417 (2)C5—H50.9300
N1—C71.392 (2)C6—H60.9300
N2—C91.355 (3)C7—C81.426 (3)
N2—H2A0.84 (3)C8—C91.357 (3)
C1—C21.394 (3)C8—H80.9300
C1—C61.397 (3)C9—C101.500 (3)
C2—C31.383 (3)C10—H10A0.9600
C2—H20.9300C10—H10B0.9600
C3—C41.380 (3)C10—H10C0.9600
C7—N1—N2108.91 (15)C6—C5—H5120.2
C7—N1—C1129.69 (15)C5—C6—C1119.97 (18)
N2—N1—C1119.94 (15)C5—C6—H6120.0
C9—N2—N1107.48 (16)C1—C6—H6120.0
C9—N2—H2A122.4 (17)O1—C7—N1123.28 (17)
N1—N2—H2A119.3 (17)O1—C7—C8131.64 (17)
C2—C1—C6119.58 (18)N1—C7—C8105.07 (16)
C2—C1—N1120.00 (16)C9—C8—C7108.60 (17)
C6—C1—N1120.40 (16)C9—C8—H8125.7
C3—C2—C1119.96 (18)C7—C8—H8125.7
C3—C2—H2120.0N2—C9—C8109.75 (17)
C1—C2—H2120.0N2—C9—C10119.95 (19)
C4—C3—C2119.89 (18)C8—C9—C10130.30 (19)
C4—C3—H3120.1C9—C10—H10A109.5
C2—C3—H3120.1C9—C10—H10B109.5
C5—C4—C3121.09 (18)H10A—C10—H10B109.5
C5—C4—Cl1119.55 (16)C9—C10—H10C109.5
C3—C4—Cl1119.36 (16)H10A—C10—H10C109.5
C4—C5—C6119.51 (19)H10B—C10—H10C109.5
C4—C5—H5120.2
C7—N1—N2—C94.5 (2)C4—C5—C6—C10.6 (3)
C1—N1—N2—C9172.07 (16)C2—C1—C6—C50.4 (3)
C7—N1—C1—C2157.37 (19)N1—C1—C6—C5177.99 (17)
N2—N1—C1—C27.2 (3)N2—N1—C7—O1175.83 (18)
C7—N1—C1—C624.3 (3)C1—N1—C7—O19.9 (3)
N2—N1—C1—C6171.14 (17)N2—N1—C7—C83.3 (2)
C6—C1—C2—C31.1 (3)C1—N1—C7—C8169.20 (17)
N1—C1—C2—C3177.26 (17)O1—C7—C8—C9178.1 (2)
C1—C2—C3—C40.9 (3)N1—C7—C8—C90.9 (2)
C2—C3—C4—C50.1 (3)N1—N2—C9—C84.0 (2)
C2—C3—C4—Cl1179.35 (16)N1—N2—C9—C10176.84 (19)
C3—C4—C5—C60.8 (3)C7—C8—C9—N22.0 (2)
Cl1—C4—C5—C6178.61 (15)C7—C8—C9—C10179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.84 (3)1.90 (3)2.737 (3)179 (2)
Symmetry code: (i) x+1, y, z.
 

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