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
CCDC reference: 608531
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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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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-1
H-pyrazol-3(2
H)-one
top
Crystal data top
C10H9ClN2O | Z = 2 |
Mr = 208.64 | F(000) = 216 |
Triclinic, P1 | Dx = 1.439 Mg m−3 |
Hall symbol: -P 1 | Melting point: 441 K |
a = 5.885 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.704 (7) Å | Cell parameters from 1622 reflections |
c = 11.38 (1) Å | θ = 2.8–26.5° |
α = 105.980 (13)° | µ = 0.36 mm−1 |
β = 94.719 (14)° | T = 294 K |
γ = 101.250 (13)° | Block, colourless |
V = 481.4 (7) Å3 | 0.30 × 0.26 × 0.22 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1669 independent reflections |
Radiation source: fine-focus sealed tube | 1421 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→6 |
Tmin = 0.899, Tmax = 0.925 | k = −9→9 |
2397 measured reflections | l = −13→10 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H 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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.46931 (12) | −0.04642 (9) | 0.14776 (5) | 0.0653 (3) | |
O1 | 0.1306 (2) | 0.3563 (2) | 0.70412 (13) | 0.0514 (4) | |
N1 | 0.5211 (2) | 0.3831 (2) | 0.67330 (13) | 0.0340 (4) | |
N2 | 0.7367 (3) | 0.4918 (2) | 0.73944 (15) | 0.0397 (4) | |
C1 | 0.5052 (3) | 0.2847 (2) | 0.54670 (16) | 0.0324 (4) | |
C2 | 0.6975 (3) | 0.3122 (3) | 0.48463 (18) | 0.0414 (5) | |
H2 | 0.8339 | 0.3990 | 0.5253 | 0.050* | |
C3 | 0.6851 (4) | 0.2103 (3) | 0.36256 (18) | 0.0457 (5) | |
H3 | 0.8139 | 0.2273 | 0.3214 | 0.055* | |
C4 | 0.4813 (4) | 0.0834 (3) | 0.30197 (17) | 0.0416 (5) | |
C5 | 0.2884 (4) | 0.0560 (3) | 0.36099 (19) | 0.0470 (5) | |
H5 | 0.1514 | −0.0288 | 0.3188 | 0.056* | |
C6 | 0.2997 (3) | 0.1562 (3) | 0.48417 (19) | 0.0423 (5) | |
H6 | 0.1705 | 0.1377 | 0.5249 | 0.051* | |
C7 | 0.3443 (3) | 0.4248 (3) | 0.74289 (17) | 0.0362 (4) | |
C8 | 0.4626 (3) | 0.5550 (3) | 0.85669 (17) | 0.0418 (5) | |
H8 | 0.3916 | 0.6082 | 0.9233 | 0.050* | |
C9 | 0.6962 (3) | 0.5883 (3) | 0.85163 (17) | 0.0400 (5) | |
C10 | 0.8974 (4) | 0.7108 (3) | 0.9465 (2) | 0.0594 (6) | |
H10A | 0.9931 | 0.6359 | 0.9716 | 0.089* | |
H10B | 0.8384 | 0.7786 | 1.0169 | 0.089* | |
H10C | 0.9895 | 0.7961 | 0.9117 | 0.089* | |
H2A | 0.857 (4) | 0.450 (3) | 0.730 (2) | 0.058 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0860 (5) | 0.0646 (4) | 0.0351 (3) | 0.0180 (3) | 0.0105 (3) | −0.0028 (3) |
O1 | 0.0266 (8) | 0.0645 (10) | 0.0507 (9) | 0.0087 (6) | 0.0096 (6) | −0.0027 (7) |
N1 | 0.0236 (8) | 0.0403 (8) | 0.0329 (8) | 0.0058 (6) | 0.0050 (6) | 0.0034 (7) |
N2 | 0.0267 (9) | 0.0469 (9) | 0.0382 (9) | 0.0085 (7) | 0.0051 (7) | 0.0005 (7) |
C1 | 0.0320 (10) | 0.0351 (9) | 0.0309 (9) | 0.0114 (7) | 0.0062 (7) | 0.0080 (7) |
C2 | 0.0341 (10) | 0.0503 (11) | 0.0354 (10) | 0.0018 (8) | 0.0079 (8) | 0.0102 (9) |
C3 | 0.0446 (12) | 0.0589 (13) | 0.0343 (10) | 0.0094 (10) | 0.0143 (9) | 0.0140 (9) |
C4 | 0.0518 (12) | 0.0409 (10) | 0.0311 (10) | 0.0150 (9) | 0.0052 (8) | 0.0063 (8) |
C5 | 0.0426 (12) | 0.0437 (11) | 0.0431 (11) | 0.0037 (9) | 0.0004 (9) | 0.0002 (9) |
C6 | 0.0326 (10) | 0.0441 (11) | 0.0431 (11) | 0.0053 (8) | 0.0090 (8) | 0.0030 (9) |
C7 | 0.0287 (10) | 0.0431 (10) | 0.0367 (10) | 0.0115 (8) | 0.0095 (7) | 0.0081 (8) |
C8 | 0.0361 (10) | 0.0502 (11) | 0.0350 (10) | 0.0143 (9) | 0.0098 (8) | 0.0014 (8) |
C9 | 0.0376 (11) | 0.0431 (11) | 0.0351 (10) | 0.0124 (8) | 0.0049 (8) | 0.0025 (8) |
C10 | 0.0396 (12) | 0.0672 (15) | 0.0509 (13) | 0.0088 (10) | −0.0002 (9) | −0.0110 (11) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.753 (2) | C3—H3 | 0.9300 |
O1—C7 | 1.256 (2) | C4—C5 | 1.377 (3) |
N1—N2 | 1.400 (2) | C5—C6 | 1.391 (3) |
N1—C1 | 1.417 (2) | C5—H5 | 0.9300 |
N1—C7 | 1.392 (2) | C6—H6 | 0.9300 |
N2—C9 | 1.355 (3) | C7—C8 | 1.426 (3) |
N2—H2A | 0.84 (3) | C8—C9 | 1.357 (3) |
C1—C2 | 1.394 (3) | C8—H8 | 0.9300 |
C1—C6 | 1.397 (3) | C9—C10 | 1.500 (3) |
C2—C3 | 1.383 (3) | C10—H10A | 0.9600 |
C2—H2 | 0.9300 | C10—H10B | 0.9600 |
C3—C4 | 1.380 (3) | C10—H10C | 0.9600 |
| | | |
C7—N1—N2 | 108.91 (15) | C6—C5—H5 | 120.2 |
C7—N1—C1 | 129.69 (15) | C5—C6—C1 | 119.97 (18) |
N2—N1—C1 | 119.94 (15) | C5—C6—H6 | 120.0 |
C9—N2—N1 | 107.48 (16) | C1—C6—H6 | 120.0 |
C9—N2—H2A | 122.4 (17) | O1—C7—N1 | 123.28 (17) |
N1—N2—H2A | 119.3 (17) | O1—C7—C8 | 131.64 (17) |
C2—C1—C6 | 119.58 (18) | N1—C7—C8 | 105.07 (16) |
C2—C1—N1 | 120.00 (16) | C9—C8—C7 | 108.60 (17) |
C6—C1—N1 | 120.40 (16) | C9—C8—H8 | 125.7 |
C3—C2—C1 | 119.96 (18) | C7—C8—H8 | 125.7 |
C3—C2—H2 | 120.0 | N2—C9—C8 | 109.75 (17) |
C1—C2—H2 | 120.0 | N2—C9—C10 | 119.95 (19) |
C4—C3—C2 | 119.89 (18) | C8—C9—C10 | 130.30 (19) |
C4—C3—H3 | 120.1 | C9—C10—H10A | 109.5 |
C2—C3—H3 | 120.1 | C9—C10—H10B | 109.5 |
C5—C4—C3 | 121.09 (18) | H10A—C10—H10B | 109.5 |
C5—C4—Cl1 | 119.55 (16) | C9—C10—H10C | 109.5 |
C3—C4—Cl1 | 119.36 (16) | H10A—C10—H10C | 109.5 |
C4—C5—C6 | 119.51 (19) | H10B—C10—H10C | 109.5 |
C4—C5—H5 | 120.2 | | |
| | | |
C7—N1—N2—C9 | 4.5 (2) | C4—C5—C6—C1 | 0.6 (3) |
C1—N1—N2—C9 | 172.07 (16) | C2—C1—C6—C5 | 0.4 (3) |
C7—N1—C1—C2 | 157.37 (19) | N1—C1—C6—C5 | −177.99 (17) |
N2—N1—C1—C2 | −7.2 (3) | N2—N1—C7—O1 | 175.83 (18) |
C7—N1—C1—C6 | −24.3 (3) | C1—N1—C7—O1 | 9.9 (3) |
N2—N1—C1—C6 | 171.14 (17) | N2—N1—C7—C8 | −3.3 (2) |
C6—C1—C2—C3 | −1.1 (3) | C1—N1—C7—C8 | −169.20 (17) |
N1—C1—C2—C3 | 177.26 (17) | O1—C7—C8—C9 | −178.1 (2) |
C1—C2—C3—C4 | 0.9 (3) | N1—C7—C8—C9 | 0.9 (2) |
C2—C3—C4—C5 | 0.1 (3) | N1—N2—C9—C8 | −4.0 (2) |
C2—C3—C4—Cl1 | −179.35 (16) | N1—N2—C9—C10 | 176.84 (19) |
C3—C4—C5—C6 | −0.8 (3) | C7—C8—C9—N2 | 2.0 (2) |
Cl1—C4—C5—C6 | 178.61 (15) | C7—C8—C9—C10 | −179.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.84 (3) | 1.90 (3) | 2.737 (3) | 179 (2) |
Symmetry code: (i) x+1, y, z. |