Literature DB >> 22058766

Ethyl 1-(4-methyl-phen-yl)-5-phenyl-4-phenyl-sulfon-yl-1H-pyrazole-3-carboxyl-ate.

Hatem A Abdel-Aziz, Khalid A Al-Rashood, Seik Weng Ng, Edward R T Tiekink.   

Abstract

The title compound, C(25)H(22)N(2)O(4)S, features a tetra-substituted pyrazole ring. The dihedral angles formed between the five-membered ring (r.m.s. deviation = 0.007 Å) and the N- and C-bound phenyl rings are 48.10 (7) and 72.01 (7) °, respectively, indicating that the planes through the residues are significantly twisted from the plane through the heterocycle. The ester-CO(2) group is also twisted out of this plane, with an O-C-C-N torsion angle of -29.04 (11)°. The sulfonyl-O atoms lie to one side of the pyrazole plane and the sulfonyl-phenyl ring to the other. The dihedral angle between the two ring planes is 70.63 (7) °. Supra-molecular arrays are formed in the crystal structure sustained by C-H⋯O and C-H⋯π(pyrazole) inter-actions and methyl-C-H⋯π(N-bound benzene) contacts.

Entities:  

Year:  2011        PMID: 22058766      PMCID: PMC3201465          DOI: 10.1107/S1600536811036580

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


Related literature

For background to the chemistry and biological activity of pyrazole derivatives, see: Abdel-Wahab et al. (2009 ▶); Abdel-Aziz et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C25H22N2O4S M = 446.51 Triclinic, a = 7.2440 (3) Å b = 11.0798 (5) Å c = 14.8247 (5) Å α = 68.818 (4)° β = 87.773 (3)° γ = 81.241 (4)° V = 1096.36 (8) Å3 Z = 2 Cu Kα radiation μ = 1.60 mm−1 T = 100 K 0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.566, T max = 0.740 7378 measured reflections 4304 independent reflections 4106 reflections with I > 2σ(I) R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.091 S = 0.85 4304 reflections 290 parameters H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.42 e Å−3 Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036580/bt5639sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036580/bt5639Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811036580/bt5639Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H22N2O4SZ = 2
Mr = 446.51F(000) = 468
Triclinic, P1Dx = 1.353 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 7.2440 (3) ÅCell parameters from 5331 reflections
b = 11.0798 (5) Åθ = 3.2–74.1°
c = 14.8247 (5) ŵ = 1.60 mm1
α = 68.818 (4)°T = 100 K
β = 87.773 (3)°Block, yellow
γ = 81.241 (4)°0.40 × 0.30 × 0.20 mm
V = 1096.36 (8) Å3
Agilent SuperNova Dual diffractometer with Atlas detector4304 independent reflections
Radiation source: SuperNova (Cu) X-ray Source4106 reflections with I > 2σ(I)
mirrorRint = 0.014
Detector resolution: 10.4041 pixels mm-1θmax = 74.3°, θmin = 3.2°
ω scanh = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)k = −12→13
Tmin = 0.566, Tmax = 0.740l = −18→15
7378 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 0.85w = 1/[σ2(Fo2) + (0.060P)2 + 0.8665P] where P = (Fo2 + 2Fc2)/3
4304 reflections(Δ/σ)max < 0.001
290 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.42 e Å3
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
S10.44173 (4)0.70984 (3)0.10567 (2)0.01551 (10)
O10.24561 (13)0.75817 (9)0.09106 (7)0.0201 (2)
O20.54033 (14)0.66162 (9)0.03658 (7)0.0202 (2)
O30.08177 (14)0.59487 (10)0.38398 (9)0.0275 (2)
O40.19467 (16)0.77438 (10)0.28475 (8)0.0280 (2)
N10.40421 (15)0.44865 (11)0.36938 (8)0.0161 (2)
N20.55383 (15)0.39169 (10)0.33340 (8)0.0150 (2)
C1−0.2495 (2)0.66923 (19)0.37793 (12)0.0333 (4)
H1A−0.34810.72380.39900.050*
H1B−0.27430.57850.40230.050*
H1C−0.24700.70160.30710.050*
C2−0.0656 (2)0.67488 (16)0.41664 (13)0.0286 (3)
H2A−0.04130.76660.39350.034*
H2B−0.06720.64180.48820.034*
C30.20136 (18)0.65804 (13)0.31954 (9)0.0171 (3)
C40.35304 (18)0.56389 (12)0.30001 (9)0.0156 (3)
C50.46821 (18)0.58099 (12)0.21819 (9)0.0152 (3)
C60.59874 (18)0.46782 (12)0.24248 (9)0.0148 (3)
C70.55863 (19)0.83215 (12)0.11696 (9)0.0171 (3)
C80.7518 (2)0.82100 (14)0.10621 (10)0.0225 (3)
H80.81890.74900.09270.027*
C90.8443 (2)0.91673 (15)0.11553 (12)0.0272 (3)
H90.97600.91060.10860.033*
C100.7444 (2)1.02163 (14)0.13504 (11)0.0271 (3)
H100.80831.08680.14170.033*
C110.5522 (2)1.03192 (14)0.14486 (11)0.0247 (3)
H110.48511.10450.15770.030*
C120.4571 (2)0.93691 (13)0.13606 (10)0.0206 (3)
H120.32540.94340.14290.025*
C130.76709 (18)0.42800 (12)0.19410 (9)0.0149 (3)
C140.94252 (19)0.42706 (13)0.23053 (10)0.0182 (3)
H140.95200.45300.28450.022*
C151.10313 (19)0.38814 (13)0.18770 (10)0.0207 (3)
H151.22240.38850.21200.025*
C161.0902 (2)0.34872 (13)0.10965 (10)0.0209 (3)
H161.20040.32160.08080.025*
C170.9159 (2)0.34899 (13)0.07374 (10)0.0204 (3)
H170.90710.32160.02050.025*
C180.75398 (19)0.38910 (13)0.11527 (9)0.0179 (3)
H180.63500.39000.09010.022*
C190.63396 (17)0.26085 (12)0.39171 (9)0.0155 (3)
C200.66215 (19)0.16297 (13)0.35283 (10)0.0184 (3)
H200.64000.18310.28590.022*
C210.72330 (19)0.03502 (13)0.41333 (10)0.0203 (3)
H210.7447−0.03210.38690.024*
C220.75393 (19)0.00307 (13)0.51205 (10)0.0185 (3)
C230.72672 (19)0.10390 (13)0.54866 (10)0.0188 (3)
H230.74900.08430.61550.023*
C240.66765 (18)0.23258 (13)0.48902 (10)0.0173 (3)
H240.65060.30050.51480.021*
C250.8151 (2)−0.13619 (13)0.57784 (11)0.0236 (3)
H25A0.7437−0.19430.56180.035*
H25B0.7929−0.14400.64520.035*
H25C0.9485−0.16100.56940.035*
U11U22U33U12U13U23
S10.01730 (17)0.01487 (16)0.01383 (16)−0.00005 (12)−0.00058 (11)−0.00538 (12)
O10.0178 (5)0.0213 (5)0.0204 (5)0.0010 (4)−0.0032 (4)−0.0078 (4)
O20.0245 (5)0.0202 (5)0.0160 (5)0.0000 (4)0.0020 (4)−0.0081 (4)
O30.0186 (5)0.0235 (5)0.0454 (7)−0.0040 (4)0.0133 (4)−0.0193 (5)
O40.0408 (6)0.0168 (5)0.0235 (5)0.0020 (4)0.0076 (4)−0.0071 (4)
N10.0138 (5)0.0168 (5)0.0186 (5)−0.0007 (4)0.0022 (4)−0.0082 (4)
N20.0137 (5)0.0147 (5)0.0161 (5)0.0000 (4)0.0019 (4)−0.0059 (4)
C10.0208 (8)0.0498 (10)0.0336 (9)0.0035 (7)0.0001 (6)−0.0237 (8)
C20.0190 (7)0.0290 (8)0.0450 (9)−0.0018 (6)0.0104 (6)−0.0237 (7)
C30.0162 (6)0.0197 (6)0.0172 (6)−0.0001 (5)−0.0026 (5)−0.0096 (5)
C40.0145 (6)0.0162 (6)0.0174 (6)−0.0017 (5)−0.0006 (5)−0.0079 (5)
C50.0158 (6)0.0146 (6)0.0159 (6)−0.0019 (5)−0.0003 (5)−0.0065 (5)
C60.0153 (6)0.0156 (6)0.0151 (6)−0.0035 (5)−0.0003 (5)−0.0068 (5)
C70.0204 (7)0.0145 (6)0.0143 (6)−0.0021 (5)−0.0003 (5)−0.0029 (5)
C80.0215 (7)0.0195 (7)0.0240 (7)−0.0006 (5)0.0022 (5)−0.0062 (6)
C90.0211 (7)0.0243 (7)0.0330 (8)−0.0051 (6)0.0006 (6)−0.0059 (6)
C100.0314 (8)0.0199 (7)0.0294 (8)−0.0087 (6)−0.0025 (6)−0.0059 (6)
C110.0310 (8)0.0150 (6)0.0271 (7)−0.0011 (6)−0.0006 (6)−0.0072 (6)
C120.0212 (7)0.0172 (6)0.0208 (7)0.0002 (5)−0.0005 (5)−0.0050 (5)
C130.0164 (6)0.0118 (6)0.0152 (6)−0.0012 (5)0.0020 (5)−0.0037 (5)
C140.0192 (7)0.0178 (6)0.0193 (6)−0.0036 (5)0.0011 (5)−0.0083 (5)
C150.0160 (7)0.0202 (7)0.0249 (7)−0.0030 (5)0.0014 (5)−0.0070 (5)
C160.0209 (7)0.0169 (6)0.0223 (7)−0.0007 (5)0.0075 (5)−0.0055 (5)
C170.0264 (7)0.0179 (6)0.0171 (6)−0.0013 (5)0.0033 (5)−0.0075 (5)
C180.0195 (7)0.0173 (6)0.0173 (6)−0.0020 (5)−0.0006 (5)−0.0068 (5)
C190.0122 (6)0.0137 (6)0.0188 (6)−0.0014 (5)0.0018 (5)−0.0040 (5)
C200.0184 (7)0.0191 (6)0.0183 (6)−0.0026 (5)0.0015 (5)−0.0077 (5)
C210.0200 (7)0.0167 (6)0.0258 (7)−0.0025 (5)0.0037 (5)−0.0099 (5)
C220.0134 (6)0.0166 (6)0.0233 (7)−0.0025 (5)0.0029 (5)−0.0046 (5)
C230.0169 (6)0.0199 (7)0.0177 (6)−0.0028 (5)0.0013 (5)−0.0046 (5)
C240.0165 (6)0.0168 (6)0.0192 (6)−0.0022 (5)0.0020 (5)−0.0073 (5)
C250.0216 (7)0.0168 (7)0.0278 (7)−0.0017 (5)0.0031 (6)−0.0033 (6)
S1—O11.4354 (10)C11—C121.388 (2)
S1—O21.4378 (10)C11—H110.9500
S1—C51.7544 (13)C12—H120.9500
S1—C71.7624 (14)C13—C181.3947 (18)
O3—C31.3380 (17)C13—C141.3971 (19)
O3—C21.4635 (16)C14—C151.3894 (19)
O4—C31.1968 (17)C14—H140.9500
N1—C41.3274 (17)C15—C161.387 (2)
N1—N21.3592 (15)C15—H150.9500
N2—C61.3646 (17)C16—C171.389 (2)
N2—C191.4362 (16)C16—H160.9500
C1—C21.489 (2)C17—C181.3909 (19)
C1—H1A0.9800C17—H170.9500
C1—H1B0.9800C18—H180.9500
C1—H1C0.9800C19—C241.3843 (19)
C2—H2A0.9900C19—C201.3875 (18)
C2—H2B0.9900C20—C211.3897 (19)
C3—C41.4913 (17)C20—H200.9500
C4—C51.4165 (18)C21—C221.394 (2)
C5—C61.3911 (18)C21—H210.9500
C6—C131.4809 (17)C22—C231.3942 (19)
C7—C121.3891 (19)C22—C251.5054 (18)
C7—C81.394 (2)C23—C241.3893 (19)
C8—C91.387 (2)C23—H230.9500
C8—H80.9500C24—H240.9500
C9—C101.389 (2)C25—H25A0.9800
C9—H90.9500C25—H25B0.9800
C10—C111.386 (2)C25—H25C0.9800
C10—H100.9500
O1—S1—O2119.33 (6)C12—C11—H11119.8
O1—S1—C5106.92 (6)C10—C11—H11119.8
O2—S1—C5106.93 (6)C11—C12—C7118.58 (13)
O1—S1—C7109.11 (6)C11—C12—H12120.7
O2—S1—C7107.81 (6)C7—C12—H12120.7
C5—S1—C7105.98 (6)C18—C13—C14119.85 (12)
C3—O3—C2117.09 (11)C18—C13—C6121.66 (12)
C4—N1—N2104.77 (10)C14—C13—C6118.48 (11)
N1—N2—C6113.13 (10)C15—C14—C13119.85 (12)
N1—N2—C19117.27 (10)C15—C14—H14120.1
C6—N2—C19129.49 (11)C13—C14—H14120.1
C2—C1—H1A109.5C16—C15—C14120.34 (13)
C2—C1—H1B109.5C16—C15—H15119.8
H1A—C1—H1B109.5C14—C15—H15119.8
C2—C1—H1C109.5C15—C16—C17119.82 (12)
H1A—C1—H1C109.5C15—C16—H16120.1
H1B—C1—H1C109.5C17—C16—H16120.1
O3—C2—C1109.39 (12)C16—C17—C18120.42 (13)
O3—C2—H2A109.8C16—C17—H17119.8
C1—C2—H2A109.8C18—C17—H17119.8
O3—C2—H2B109.8C17—C18—C13119.72 (13)
C1—C2—H2B109.8C17—C18—H18120.1
H2A—C2—H2B108.2C13—C18—H18120.1
O4—C3—O3125.36 (12)C24—C19—C20120.89 (12)
O4—C3—C4123.58 (13)C24—C19—N2118.50 (11)
O3—C3—C4110.98 (11)C20—C19—N2120.40 (12)
N1—C4—C5111.39 (11)C21—C20—C19119.00 (12)
N1—C4—C3118.83 (11)C21—C20—H20120.5
C5—C4—C3129.57 (12)C19—C20—H20120.5
C6—C5—C4105.42 (11)C20—C21—C22121.40 (13)
C6—C5—S1126.52 (10)C20—C21—H21119.3
C4—C5—S1127.84 (10)C22—C21—H21119.3
N2—C6—C5105.29 (11)C23—C22—C21118.19 (12)
N2—C6—C13121.29 (11)C23—C22—C25120.56 (13)
C5—C6—C13133.20 (12)C21—C22—C25121.25 (13)
C12—C7—C8121.65 (13)C24—C23—C22121.16 (13)
C12—C7—S1119.59 (11)C24—C23—H23119.4
C8—C7—S1118.76 (10)C22—C23—H23119.4
C9—C8—C7118.91 (13)C19—C24—C23119.33 (12)
C9—C8—H8120.5C19—C24—H24120.3
C7—C8—H8120.5C23—C24—H24120.3
C10—C9—C8119.93 (14)C22—C25—H25A109.5
C10—C9—H9120.0C22—C25—H25B109.5
C8—C9—H9120.0H25A—C25—H25B109.5
C9—C10—C11120.51 (14)C22—C25—H25C109.5
C9—C10—H10119.7H25A—C25—H25C109.5
C11—C10—H10119.7H25B—C25—H25C109.5
C12—C11—C10120.40 (13)
C4—N1—N2—C6−0.25 (14)C12—C7—C8—C90.4 (2)
C4—N1—N2—C19−176.77 (11)S1—C7—C8—C9−179.68 (11)
C3—O3—C2—C1110.72 (15)C7—C8—C9—C10−0.2 (2)
C2—O3—C3—O4−2.0 (2)C8—C9—C10—C11−0.3 (2)
C2—O3—C3—C4174.84 (12)C9—C10—C11—C120.5 (2)
N2—N1—C4—C50.83 (14)C10—C11—C12—C7−0.2 (2)
N2—N1—C4—C3−174.42 (11)C8—C7—C12—C11−0.3 (2)
O4—C3—C4—N1147.76 (14)S1—C7—C12—C11179.87 (11)
O3—C3—C4—N1−29.15 (17)N2—C6—C13—C18109.94 (15)
O4—C3—C4—C5−26.5 (2)C5—C6—C13—C18−76.46 (19)
O3—C3—C4—C5156.60 (13)N2—C6—C13—C14−68.59 (16)
N1—C4—C5—C6−1.11 (15)C5—C6—C13—C14105.00 (17)
C3—C4—C5—C6173.49 (13)C18—C13—C14—C150.40 (19)
N1—C4—C5—S1173.74 (10)C6—C13—C14—C15178.96 (12)
C3—C4—C5—S1−11.7 (2)C13—C14—C15—C16−0.8 (2)
O1—S1—C5—C6145.06 (11)C14—C15—C16—C170.4 (2)
O2—S1—C5—C616.17 (13)C15—C16—C17—C180.3 (2)
C7—S1—C5—C6−98.65 (12)C16—C17—C18—C13−0.6 (2)
O1—S1—C5—C4−28.76 (13)C14—C13—C18—C170.31 (19)
O2—S1—C5—C4−157.65 (12)C6—C13—C18—C17−178.21 (12)
C7—S1—C5—C487.53 (13)N1—N2—C19—C24−46.78 (16)
N1—N2—C6—C5−0.43 (14)C6—N2—C19—C24137.37 (14)
C19—N2—C6—C5175.56 (12)N1—N2—C19—C20127.96 (13)
N1—N2—C6—C13174.73 (11)C6—N2—C19—C20−47.90 (19)
C19—N2—C6—C13−9.3 (2)C24—C19—C20—C210.6 (2)
C4—C5—C6—N20.88 (14)N2—C19—C20—C21−173.97 (12)
S1—C5—C6—N2−174.06 (10)C19—C20—C21—C221.0 (2)
C4—C5—C6—C13−173.44 (13)C20—C21—C22—C23−1.8 (2)
S1—C5—C6—C1311.6 (2)C20—C21—C22—C25178.30 (13)
O1—S1—C7—C1216.54 (13)C21—C22—C23—C241.1 (2)
O2—S1—C7—C12147.52 (11)C25—C22—C23—C24−179.04 (12)
C5—S1—C7—C12−98.27 (11)C20—C19—C24—C23−1.4 (2)
O1—S1—C7—C8−163.34 (10)N2—C19—C24—C23173.35 (11)
O2—S1—C7—C8−32.36 (12)C22—C23—C24—C190.5 (2)
C5—S1—C7—C881.85 (12)
Cg1 and Cg2 are the centroids of the N1,N2,C4–C6 and C19–C24 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C9—H9···O1i0.952.453.2392 (19)140
C16—H16···O2ii0.952.493.3928 (18)158
C17—H17···O1iii0.952.503.3895 (18)157
C18—H18···O2iii0.952.583.4031 (17)145
C23—H23···O4iv0.952.593.3155 (18)133
C15—H15···Cg1i0.952.803.6781 (15)154
C25—H25c···Cg2v0.982.643.5649 (16)157
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1,N2,C4–C6 and C19–C24 rings, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
C9—H9⋯O1i0.952.453.2392 (19)140
C16—H16⋯O2ii0.952.493.3928 (18)158
C17—H17⋯O1iii0.952.503.3895 (18)157
C18—H18⋯O2iii0.952.583.4031 (17)145
C23—H23⋯O4iv0.952.593.3155 (18)133
C15—H15⋯Cg1i0.952.803.6781 (15)154
C25—H25c⋯Cg2v0.982.643.5649 (16)157

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

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Microwave-assisted synthesis and in-vitro anti-tumor activity of 1,3,4-triaryl-5-N-arylpyrazole-carboxamides.

Authors:  Hatem A Abdel-Aziz; Heba S A El-Zahabi; Kamal M Dawood
Journal:  Eur J Med Chem       Date:  2010-02-16       Impact factor: 6.514

3.  Immunomodulatory and anticancer activities of some novel 2-substituted-6-bromo-3-methylthiazolo[3,2-a]benzimidazole derivatives.

Authors:  Hatem A Abdel-Aziz; Amira M Gamal-Eldeen; Nehal A Hamdy; Issa M I Fakhr
Journal:  Arch Pharm (Weinheim)       Date:  2009-04       Impact factor: 3.751

  3 in total
  1 in total

1.  3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile.

Authors:  Hatem A Abdel-Aziz; Hazem A Ghabbour; Suchada Chantrapromma; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-17
  1 in total

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