Literature DB >> 21200928

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-methyl-benzene-sulfonamide.

Luiz Everson da Silva, Paulo Teixeira de Sousa, Evandro Luiz Dall'oglio, Sabine Foro.   

Abstract

In the title compound, C(18)H(19)N(3)O(3)S, the phenyl ring and the pyrazole ring are twisted with respect to each other by an angle of 49.11 (7)°. The C-N-S-C torsion angle is -122.5 (2)°. The methyl group bonded to the N atom of the pyrazole ring has a large deviation from the mean ring plane of 0.603 (3) Å. One inter-molecular N-H⋯O and two non-classical inter-molecular C-H⋯O hydrogen bonds are observed in the crystal structure.

Entities:  

Year:  2007        PMID： 21200928      PMCID： PMC2915010          DOI： 10.1107/S1600536807061594

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Xue et al. (2000 ▶); Alves & Duarte (2002 ▶).

Experimental

Crystal data

C18H19N3O3S M = 357.42 Triclinic, a = 9.202 (1) Å b = 9.892 (1) Å c = 10.067 (1) Å α = 103.688 (9)° β = 90.360 (9)° γ = 104.300 (9)° V = 860.71 (15) Å3 Z = 2 Mo Kα radiation μ = 0.21 mm−1 T = 299 (2) K 0.50 × 0.20 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.902, T max = 0.967 10096 measured reflections 3519 independent reflections 2600 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.109 S = 1.07 3519 reflections 259 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.23 e Å−3 Δρmin = −0.35 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXS97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061594/bt2634sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061594/bt2634Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H19N3O3SZ = 2
Mr = 357.42F000 = 376
Triclinic, P1Dx = 1.379 Mg m−3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.202 (1) ÅCell parameters from 4280 reflections
b = 9.892 (1) Åθ = 2.0–25.6º
c = 10.067 (1) ŵ = 0.21 mm−1
α = 103.688 (9)ºT = 299 (2) K
β = 90.360 (9)ºRod, colorless
γ = 104.300 (9)º0.50 × 0.20 × 0.16 mm
V = 860.71 (15) Å3
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector3519 independent reflections
Radiation source: fine-focus sealed tube2600 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 299(2) Kθmax = 26.4º
Rotation method data acquisition using ω and phi scans.θmin = 2.3º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)h = −11→11
Tmin = 0.902, Tmax = 0.967k = −12→12
10096 measured reflectionsl = −12→12
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109  w = 1/[σ2(Fo2) + (0.0545P)2 + 0.208P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.041
3519 reflectionsΔρmax = 0.23 e Å−3
259 parametersΔρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
C10.15033 (19)0.83574 (19)0.62802 (18)0.0331 (4)
C20.0708 (2)0.8120 (2)0.50358 (19)0.0381 (4)
H20.015 (2)0.875 (2)0.491 (2)0.046*
C30.0712 (2)0.6926 (2)0.4009 (2)0.0416 (5)
H30.016 (2)0.677 (2)0.319 (2)0.050*
C40.1508 (2)0.5953 (2)0.4180 (2)0.0429 (5)
C50.2301 (3)0.6212 (2)0.5424 (2)0.0478 (5)
H50.280 (3)0.554 (3)0.562 (2)0.057*
C60.2306 (2)0.7402 (2)0.6482 (2)0.0429 (5)
H60.285 (2)0.756 (2)0.731 (2)0.051*
C70.1510 (3)0.4657 (2)0.3046 (2)0.0620 (6)
H7A0.23060.49040.24660.074*
H7B0.05630.43400.25170.074*
H7C0.16630.38980.34300.074*
C8−0.12615 (19)1.02665 (19)0.81942 (17)0.0330 (4)
C9−0.2574 (2)0.9894 (2)0.74125 (17)0.0347 (4)
C10−0.11502 (19)1.16193 (19)0.91546 (17)0.0327 (4)
C11−0.3116 (2)1.2945 (2)0.98271 (17)0.0343 (4)
C12−0.4544 (2)1.2434 (2)1.0227 (2)0.0416 (5)
H12−0.510 (2)1.144 (2)0.988 (2)0.050*
C13−0.5179 (3)1.3360 (3)1.1144 (2)0.0525 (6)
H13−0.617 (3)1.300 (3)1.140 (2)0.063*
C14−0.4392 (3)1.4765 (3)1.1678 (2)0.0583 (6)
H14−0.482 (3)1.542 (3)1.228 (2)0.070*
C15−0.2969 (3)1.5266 (3)1.1285 (2)0.0559 (6)
H15−0.247 (3)1.622 (3)1.159 (2)0.067*
C16−0.2324 (2)1.4360 (2)1.0346 (2)0.0446 (5)
H16−0.136 (3)1.466 (2)1.005 (2)0.054*
C17−0.3153 (2)0.8652 (2)0.6214 (2)0.0472 (5)
H17A−0.25890.79500.61830.057*
H17B−0.30510.89800.53860.057*
H17C−0.41940.82260.62990.057*
C18−0.4369 (2)1.1268 (2)0.6960 (2)0.0441 (5)
H18A−0.50811.04120.64560.053*
H18B−0.37861.17360.63320.053*
H18C−0.48961.19080.74980.053*
N1−0.02275 (17)0.94195 (17)0.81689 (15)0.0349 (4)
H1N−0.024 (2)0.889 (2)0.875 (2)0.042*
N2−0.33766 (17)1.08873 (17)0.78608 (15)0.0374 (4)
N3−0.24404 (16)1.20148 (16)0.88633 (15)0.0361 (4)
O10.15031 (16)1.10496 (14)0.70246 (14)0.0467 (4)
O20.25442 (14)0.99605 (15)0.86636 (13)0.0478 (4)
O3−0.01857 (14)1.23296 (14)1.00850 (13)0.0403 (3)
S10.14404 (5)0.98554 (5)0.76144 (4)0.03506 (15)
U11U22U33U12U13U23
C10.0302 (9)0.0337 (9)0.0365 (9)0.0078 (7)0.0056 (7)0.0112 (8)
C20.0388 (10)0.0400 (11)0.0389 (10)0.0138 (9)0.0014 (8)0.0126 (8)
C30.0436 (11)0.0444 (11)0.0353 (10)0.0083 (9)0.0031 (9)0.0100 (9)
C40.0466 (11)0.0370 (11)0.0441 (11)0.0076 (9)0.0160 (9)0.0110 (9)
C50.0524 (13)0.0464 (12)0.0541 (12)0.0253 (10)0.0102 (10)0.0171 (10)
C60.0415 (11)0.0518 (12)0.0402 (10)0.0182 (10)0.0015 (9)0.0139 (9)
C70.0764 (17)0.0471 (13)0.0580 (14)0.0161 (12)0.0197 (12)0.0034 (11)
C80.0306 (9)0.0390 (10)0.0305 (9)0.0090 (8)0.0037 (7)0.0105 (8)
C90.0341 (9)0.0394 (10)0.0303 (9)0.0078 (8)0.0037 (7)0.0094 (8)
C100.0293 (9)0.0380 (10)0.0321 (9)0.0077 (8)0.0026 (7)0.0118 (8)
C110.0326 (9)0.0393 (10)0.0333 (9)0.0133 (8)0.0000 (7)0.0093 (8)
C120.0395 (11)0.0431 (11)0.0424 (10)0.0106 (9)0.0030 (8)0.0107 (9)
C130.0460 (13)0.0643 (15)0.0523 (13)0.0217 (11)0.0136 (10)0.0162 (11)
C140.0621 (15)0.0639 (15)0.0524 (13)0.0344 (13)0.0064 (11)0.0016 (11)
C150.0616 (15)0.0409 (12)0.0602 (14)0.0169 (11)−0.0104 (12)−0.0006 (11)
C160.0380 (11)0.0426 (11)0.0515 (12)0.0084 (9)−0.0009 (9)0.0098 (9)
C170.0458 (12)0.0487 (12)0.0410 (11)0.0091 (10)−0.0031 (9)0.0026 (9)
C180.0345 (10)0.0566 (13)0.0415 (10)0.0104 (9)−0.0033 (8)0.0142 (9)
N10.0347 (8)0.0386 (9)0.0365 (8)0.0131 (7)0.0057 (7)0.0147 (7)
N20.0317 (8)0.0445 (9)0.0344 (8)0.0105 (7)−0.0045 (6)0.0057 (7)
N30.0307 (8)0.0409 (9)0.0345 (8)0.0099 (7)−0.0013 (6)0.0043 (7)
O10.0529 (9)0.0362 (7)0.0511 (8)0.0088 (6)0.0111 (7)0.0138 (6)
O20.0348 (7)0.0570 (9)0.0443 (8)0.0050 (6)−0.0057 (6)0.0059 (7)
O30.0348 (7)0.0408 (7)0.0412 (7)0.0064 (6)−0.0068 (6)0.0058 (6)
S10.0318 (3)0.0350 (3)0.0358 (2)0.00564 (18)0.00188 (18)0.00684 (18)
C1—C61.384 (3)C11—C121.386 (3)
C1—C21.387 (3)C11—N31.429 (2)
C1—S11.7620 (18)C12—C131.380 (3)
C2—C31.375 (3)C12—H120.97 (2)
C2—H20.92 (2)C13—C141.375 (3)
C3—C41.385 (3)C13—H130.96 (2)
C3—H30.93 (2)C14—C151.377 (3)
C4—C51.382 (3)C14—H140.94 (2)
C4—C71.502 (3)C15—C161.384 (3)
C5—C61.387 (3)C15—H150.92 (3)
C5—H50.95 (2)C16—H160.94 (2)
C6—H60.92 (2)C17—H17A0.9600
C7—H7A0.9600C17—H17B0.9600
C7—H7B0.9600C17—H17C0.9600
C7—H7C0.9600C18—N21.456 (2)
C8—C91.358 (2)C18—H18A0.9600
C8—N11.411 (2)C18—H18B0.9600
C8—C101.433 (2)C18—H18C0.9600
C9—N21.367 (2)N1—S11.6281 (16)
C9—C171.488 (3)N1—H1N0.87 (2)
C10—O31.236 (2)N2—N31.409 (2)
C10—N31.389 (2)O1—S11.4318 (14)
C11—C161.381 (3)O2—S11.4284 (14)
C6—C1—C2120.13 (18)C14—C13—C12120.4 (2)
C6—C1—S1120.34 (14)C14—C13—H13121.2 (14)
C2—C1—S1119.51 (14)C12—C13—H13118.3 (14)
C3—C2—C1119.68 (19)C13—C14—C15120.1 (2)
C3—C2—H2120.0 (13)C13—C14—H14121.8 (16)
C1—C2—H2120.3 (13)C15—C14—H14118.0 (16)
C2—C3—C4121.46 (19)C14—C15—C16120.3 (2)
C2—C3—H3118.7 (13)C14—C15—H15120.4 (16)
C4—C3—H3119.8 (13)C16—C15—H15119.2 (16)
C5—C4—C3118.02 (18)C11—C16—C15119.2 (2)
C5—C4—C7121.1 (2)C11—C16—H16117.9 (13)
C3—C4—C7120.87 (19)C15—C16—H16122.8 (14)
C4—C5—C6121.73 (19)C9—C17—H17A109.5
C4—C5—H5121.0 (14)C9—C17—H17B109.5
C6—C5—H5117.0 (14)H17A—C17—H17B109.5
C1—C6—C5118.98 (19)C9—C17—H17C109.5
C1—C6—H6120.6 (14)H17A—C17—H17C109.5
C5—C6—H6120.4 (14)H17B—C17—H17C109.5
C4—C7—H7A109.5N2—C18—H18A109.5
C4—C7—H7B109.5N2—C18—H18B109.5
H7A—C7—H7B109.5H18A—C18—H18B109.5
C4—C7—H7C109.5N2—C18—H18C109.5
H7A—C7—H7C109.5H18A—C18—H18C109.5
H7B—C7—H7C109.5H18B—C18—H18C109.5
C9—C8—N1126.38 (17)C8—N1—S1122.21 (13)
C9—C8—C10108.83 (16)C8—N1—H1N121.7 (13)
N1—C8—C10124.56 (16)S1—N1—H1N110.7 (13)
C8—C9—N2109.58 (16)C9—N2—N3106.85 (14)
C8—C9—C17129.48 (18)C9—N2—C18123.39 (15)
N2—C9—C17120.92 (17)N3—N2—C18117.59 (15)
O3—C10—N3124.10 (17)C10—N3—N2109.26 (14)
O3—C10—C8130.98 (17)C10—N3—C11124.48 (14)
N3—C10—C8104.90 (15)N2—N3—C11118.75 (14)
C16—C11—C12120.73 (18)O2—S1—O1119.94 (9)
C16—C11—N3118.91 (17)O2—S1—N1109.23 (8)
C12—C11—N3120.36 (17)O1—S1—N1107.43 (8)
C13—C12—C11119.2 (2)O2—S1—C1106.91 (9)
C13—C12—H12119.7 (13)O1—S1—C1107.94 (8)
C11—C12—H12121.1 (13)N1—S1—C1104.32 (8)
C6—C1—C2—C30.5 (3)C10—C8—N1—S1−73.9 (2)
S1—C1—C2—C3−177.76 (14)C8—C9—N2—N36.99 (19)
C1—C2—C3—C4−0.7 (3)C17—C9—N2—N3−171.68 (15)
C2—C3—C4—C50.3 (3)C8—C9—N2—C18148.18 (17)
C2—C3—C4—C7−179.63 (18)C17—C9—N2—C18−30.5 (3)
C3—C4—C5—C60.3 (3)O3—C10—N3—N2−172.84 (16)
C7—C4—C5—C6−179.82 (19)C8—C10—N3—N25.62 (18)
C2—C1—C6—C50.0 (3)O3—C10—N3—C11−23.8 (3)
S1—C1—C6—C5178.27 (15)C8—C10—N3—C11154.70 (16)
C4—C5—C6—C1−0.4 (3)C9—N2—N3—C10−7.89 (19)
N1—C8—C9—N2171.06 (16)C18—N2—N3—C10−151.70 (15)
C10—C8—C9—N2−3.6 (2)C9—N2—N3—C11−159.01 (15)
N1—C8—C9—C17−10.4 (3)C18—N2—N3—C1157.2 (2)
C10—C8—C9—C17174.95 (17)C16—C11—N3—C1064.2 (2)
C9—C8—C10—O3176.98 (18)C12—C11—N3—C10−116.1 (2)
N1—C8—C10—O32.2 (3)C16—C11—N3—N2−149.34 (17)
C9—C8—C10—N3−1.34 (18)C12—C11—N3—N230.4 (2)
N1—C8—C10—N3−176.10 (15)C8—N1—S1—O2123.46 (15)
C16—C11—C12—C130.6 (3)C8—N1—S1—O1−8.10 (16)
N3—C11—C12—C13−179.08 (17)C8—N1—S1—C1−122.52 (15)
C11—C12—C13—C14−1.3 (3)C6—C1—S1—O211.34 (18)
C12—C13—C14—C150.9 (4)C2—C1—S1—O2−170.41 (14)
C13—C14—C15—C160.3 (4)C6—C1—S1—O1141.64 (16)
C12—C11—C16—C150.6 (3)C2—C1—S1—O1−40.11 (17)
N3—C11—C16—C15−179.73 (18)C6—C1—S1—N1−104.31 (16)
C14—C15—C16—C11−1.0 (3)C2—C1—S1—N173.94 (16)
C9—C8—N1—S1112.28 (19)
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.87 (2)1.97 (2)2.826 (2)167.1 (18)
C2—H2···O1ii0.92 (2)2.54 (2)3.270 (2)136.4 (16)
C12—H12···O2iii0.97 (2)2.43 (2)3.245 (2)141.9 (17)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1N⋯O3i0.87 (2)1.97 (2)2.826 (2)167.1 (18)
C2—H2⋯O1ii0.92 (2)2.54 (2)3.270 (2)136.4 (16)
C12—H12⋯O2iii0.97 (2)2.43 (2)3.245 (2)141.9 (17)

Symmetry codes: (i) ; (ii) ; (iii) .

  1 in total

1.  Involvement of ATP-sensitive K(+) channels in the peripheral antinociceptive effect induced by dipyrone.

Authors:  Daniela Alves; Igor Duarte
Journal:  Eur J Pharmacol       Date:  2002-05-24       Impact factor: 4.432
  1 in total

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