Literature DB >> 21587501

1-{5-[4-(Hex-yloxy)phen-yl]-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl}ethanone.

Asghar Abbas, Safdar Hussain, Noureen Hafeez, Kong Mun Lo, Aurangzeb Hasan.   

Abstract

The crystal structure of the title compound, C(23)H(28)N(2)O(2), is composed of discrete mol-ecules with bond lengths and angles quite typical for pyrazoline derivatives of this class. The plane containing the pyrazoline unit is nearly planar with the mean plane of the phenyl ring at the 3-position, making a dihedral angle of 1.96 (3)°. The crystal packing is stabilized by weak C-H⋯π inter-actions involving both of the aromatic rings.

Entities:  

Year:  2010        PMID： 21587501      PMCID： PMC2983223          DOI： 10.1107/S1600536810033970

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


Related literature

For the biological activity and pharmacological properties of 2-pyrazoline derivatives, see: Cottineau et al. (2002 ▶); Dhal et al. (1975 ▶); Regaila et al. (1979 ▶); Rathish et al. (2009 ▶); Subbaramaiah et al. (2002 ▶); Manna et al. (2002 ▶). For the syntheses and crystal structures of 2-pyrazoline derivatives, see: Bai et al. (2009 ▶); Lu et al. (2008 ▶); Fahrni et al. (2003 ▶); Jian et al. (2008 ▶).

Experimental

Crystal data

C23H28N2O2 M = 364.47 Monoclinic, a = 5.3937 (8) Å b = 20.237 (3) Å c = 18.163 (3) Å β = 95.144 (2)° V = 1974.6 (5) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 100 K 0.3 × 0.2 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.675, T max = 0.746 18731 measured reflections 4517 independent reflections 3430 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.103 S = 1.03 4517 reflections 246 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.21 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033970/zq2055sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033970/zq2055Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H28N2O2F(000) = 784
Mr = 364.47Dx = 1.226 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3895 reflections
a = 5.3937 (8) Åθ = 2.3–28.1°
b = 20.237 (3) ŵ = 0.08 mm−1
c = 18.163 (3) ÅT = 100 K
β = 95.144 (2)°Block, white
V = 1974.6 (5) Å30.3 × 0.2 × 0.18 mm
Z = 4
Bruker APEXII CCD area-detector diffractometer4517 independent reflections
Radiation source: fine-focus sealed tube3430 reflections with I > 2σ(I)
graphiteRint = 0.042
ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→6
Tmin = 0.675, Tmax = 0.746k = −25→26
18731 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0466P)2 + 0.4272P] where P = (Fo2 + 2Fc2)/3
4517 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
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
O10.18742 (16)0.45980 (5)−0.05993 (5)0.0179 (2)
O20.32678 (19)0.17097 (5)0.05044 (5)0.0271 (2)
N10.1119 (2)0.20218 (6)0.14456 (6)0.0191 (3)
N2−0.0638 (2)0.18796 (6)0.19341 (6)0.0179 (2)
C10.5550 (4)0.54544 (9)−0.39381 (9)0.0418 (4)
H1A0.40640.5562−0.42450.063*
H1B0.67000.5234−0.42290.063*
H1C0.62970.5852−0.37340.063*
C20.4902 (3)0.50039 (7)−0.33153 (7)0.0249 (3)
H2A0.64190.4891−0.30140.030*
H2B0.41950.4598−0.35260.030*
C30.3071 (3)0.53097 (7)−0.28225 (7)0.0249 (3)
H3A0.37740.5716−0.26130.030*
H3B0.15510.5421−0.31230.030*
C40.2433 (3)0.48570 (7)−0.21971 (7)0.0225 (3)
H4A0.39430.4769−0.18810.027*
H4B0.18450.4439−0.24080.027*
C50.0473 (3)0.51279 (7)−0.17220 (7)0.0209 (3)
H5A0.11000.5529−0.14800.025*
H5B−0.10100.5241−0.20390.025*
C6−0.0217 (2)0.46428 (7)−0.11418 (7)0.0187 (3)
H6A−0.16750.4796−0.09160.022*
H6B−0.05840.4214−0.13630.022*
C70.1846 (2)0.41158 (6)−0.00717 (6)0.0151 (3)
C8−0.0066 (2)0.36643 (7)−0.00220 (7)0.0165 (3)
H8−0.14870.3685−0.03510.020*
C90.0156 (2)0.31812 (7)0.05236 (7)0.0167 (3)
H9−0.11320.28800.05580.020*
C100.2267 (2)0.31401 (6)0.10170 (6)0.0152 (3)
C110.4149 (2)0.36037 (7)0.09649 (7)0.0168 (3)
H110.55620.35860.12980.020*
C120.3957 (2)0.40882 (7)0.04292 (7)0.0165 (3)
H120.52300.43950.04020.020*
C130.2542 (2)0.26318 (7)0.16271 (7)0.0173 (3)
H130.43060.25240.17420.021*
C140.1407 (2)0.28567 (7)0.23384 (7)0.0174 (3)
H14A0.26580.28710.27560.021*
H14B0.06340.32880.22740.021*
C15−0.0501 (2)0.23286 (7)0.24369 (7)0.0160 (3)
C16−0.2154 (2)0.23144 (7)0.30378 (7)0.0163 (3)
C17−0.3931 (2)0.18129 (7)0.30687 (7)0.0177 (3)
H17−0.40520.14820.27120.021*
C18−0.5505 (2)0.18075 (7)0.36271 (7)0.0194 (3)
H18−0.66790.14730.36440.023*
C19−0.5348 (2)0.22987 (7)0.41648 (7)0.0193 (3)
H19−0.64200.22950.45380.023*
C21−0.1990 (2)0.28018 (7)0.35816 (7)0.0193 (3)
H21−0.08060.31350.35710.023*
C20−0.3591 (3)0.27924 (7)0.41409 (7)0.0199 (3)
H20−0.34780.31210.45010.024*
C220.1542 (3)0.16031 (7)0.08809 (7)0.0209 (3)
C23−0.0247 (3)0.10362 (7)0.07542 (8)0.0259 (3)
H23A0.01720.07840.03350.039*
H23B−0.19110.12040.06620.039*
H23C−0.01450.07580.11840.039*
U11U22U33U12U13U23
O10.0188 (5)0.0165 (5)0.0177 (4)−0.0025 (4)−0.0017 (3)0.0030 (4)
O20.0332 (6)0.0255 (6)0.0248 (5)0.0035 (5)0.0155 (4)0.0011 (4)
N10.0223 (6)0.0178 (6)0.0185 (5)−0.0017 (5)0.0093 (4)0.0004 (4)
N20.0189 (6)0.0197 (6)0.0160 (5)0.0009 (5)0.0067 (4)0.0018 (4)
C10.0560 (12)0.0388 (11)0.0334 (8)0.0093 (9)0.0187 (8)0.0104 (8)
C20.0299 (8)0.0235 (8)0.0209 (7)−0.0010 (6)0.0005 (6)0.0014 (6)
C30.0329 (8)0.0212 (8)0.0205 (6)−0.0001 (6)0.0010 (6)0.0028 (6)
C40.0271 (8)0.0209 (8)0.0194 (6)0.0007 (6)0.0005 (5)0.0018 (5)
C50.0247 (7)0.0179 (7)0.0191 (6)0.0021 (6)−0.0026 (5)0.0009 (5)
C60.0179 (7)0.0187 (7)0.0187 (6)0.0010 (5)−0.0024 (5)−0.0003 (5)
C70.0168 (6)0.0146 (7)0.0145 (6)0.0021 (5)0.0038 (5)−0.0007 (5)
C80.0138 (6)0.0193 (7)0.0163 (6)0.0009 (5)0.0021 (5)−0.0024 (5)
C90.0147 (6)0.0187 (7)0.0175 (6)−0.0023 (5)0.0060 (5)−0.0016 (5)
C100.0163 (6)0.0156 (7)0.0145 (6)0.0012 (5)0.0061 (5)−0.0005 (5)
C110.0145 (6)0.0217 (7)0.0144 (6)0.0013 (5)0.0023 (5)−0.0015 (5)
C120.0142 (6)0.0179 (7)0.0179 (6)−0.0027 (5)0.0041 (5)−0.0012 (5)
C130.0167 (7)0.0189 (7)0.0168 (6)0.0010 (5)0.0040 (5)0.0015 (5)
C140.0186 (7)0.0184 (7)0.0156 (6)−0.0004 (5)0.0041 (5)0.0017 (5)
C150.0155 (6)0.0169 (7)0.0159 (6)0.0022 (5)0.0017 (5)0.0028 (5)
C160.0158 (6)0.0190 (7)0.0144 (6)0.0026 (5)0.0022 (5)0.0031 (5)
C170.0188 (7)0.0178 (7)0.0165 (6)0.0014 (5)0.0012 (5)−0.0006 (5)
C180.0190 (7)0.0207 (7)0.0190 (6)−0.0014 (6)0.0036 (5)0.0035 (5)
C190.0185 (7)0.0240 (8)0.0160 (6)0.0039 (6)0.0057 (5)0.0042 (5)
C210.0191 (7)0.0188 (7)0.0201 (6)−0.0018 (6)0.0026 (5)0.0013 (5)
C200.0241 (7)0.0205 (7)0.0154 (6)0.0021 (6)0.0038 (5)−0.0006 (5)
C220.0270 (8)0.0194 (8)0.0172 (6)0.0053 (6)0.0066 (5)0.0024 (5)
C230.0345 (8)0.0225 (8)0.0214 (7)0.0005 (6)0.0066 (6)−0.0027 (6)
O1—C71.3688 (15)C9—C101.3867 (17)
O1—C61.4325 (14)C9—H90.9300
O2—C221.2226 (17)C10—C111.3918 (18)
N1—C221.3652 (17)C10—C131.5094 (17)
N1—N21.3853 (15)C11—C121.3786 (18)
N1—C131.4753 (17)C11—H110.9300
N2—C151.2856 (17)C12—H120.9300
C1—C21.518 (2)C13—C141.5471 (17)
C1—H1A0.9600C13—H130.9800
C1—H1B0.9600C14—C151.5054 (18)
C1—H1C0.9600C14—H14A0.9700
C2—C31.523 (2)C14—H14B0.9700
C2—H2A0.9700C15—C161.4701 (17)
C2—H2B0.9700C16—C211.3932 (18)
C3—C41.5225 (19)C16—C171.4008 (19)
C3—H3A0.9700C17—C181.3795 (18)
C3—H3B0.9700C17—H170.9300
C4—C51.525 (2)C18—C191.3906 (19)
C4—H4A0.9700C18—H180.9300
C4—H4B0.9700C19—C201.380 (2)
C5—C61.5109 (19)C19—H190.9300
C5—H5A0.9700C21—C201.3912 (18)
C5—H5B0.9700C21—H210.9300
C6—H6A0.9700C20—H200.9300
C6—H6B0.9700C22—C231.504 (2)
C7—C81.3868 (18)C23—H23A0.9600
C7—C121.3934 (17)C23—H23B0.9600
C8—C91.3896 (18)C23—H23C0.9600
C8—H80.9300
C7—O1—C6117.98 (10)C9—C10—C13122.44 (12)
C22—N1—N2121.49 (11)C11—C10—C13119.01 (11)
C22—N1—C13124.64 (11)C12—C11—C10121.22 (12)
N2—N1—C13113.75 (10)C12—C11—H11119.4
C15—N2—N1108.01 (11)C10—C11—H11119.4
C2—C1—H1A109.5C11—C12—C7119.64 (12)
C2—C1—H1B109.5C11—C12—H12120.2
H1A—C1—H1B109.5C7—C12—H12120.2
C2—C1—H1C109.5N1—C13—C10113.03 (10)
H1A—C1—H1C109.5N1—C13—C14101.29 (10)
H1B—C1—H1C109.5C10—C13—C14113.09 (11)
C1—C2—C3113.51 (13)N1—C13—H13109.7
C1—C2—H2A108.9C10—C13—H13109.7
C3—C2—H2A108.9C14—C13—H13109.7
C1—C2—H2B108.9C15—C14—C13102.50 (10)
C3—C2—H2B108.9C15—C14—H14A111.3
H2A—C2—H2B107.7C13—C14—H14A111.3
C4—C3—C2113.33 (12)C15—C14—H14B111.3
C4—C3—H3A108.9C13—C14—H14B111.3
C2—C3—H3A108.9H14A—C14—H14B109.2
C4—C3—H3B108.9N2—C15—C16120.89 (12)
C2—C3—H3B108.9N2—C15—C14114.44 (11)
H3A—C3—H3B107.7C16—C15—C14124.65 (11)
C3—C4—C5114.86 (12)C21—C16—C17118.99 (12)
C3—C4—H4A108.6C21—C16—C15120.56 (12)
C5—C4—H4A108.6C17—C16—C15120.45 (12)
C3—C4—H4B108.6C18—C17—C16120.23 (12)
C5—C4—H4B108.6C18—C17—H17119.9
H4A—C4—H4B107.5C16—C17—H17119.9
C6—C5—C4112.80 (12)C17—C18—C19120.54 (13)
C6—C5—H5A109.0C17—C18—H18119.7
C4—C5—H5A109.0C19—C18—H18119.7
C6—C5—H5B109.0C20—C19—C18119.61 (12)
C4—C5—H5B109.0C20—C19—H19120.2
H5A—C5—H5B107.8C18—C19—H19120.2
O1—C6—C5107.04 (10)C20—C21—C16120.27 (13)
O1—C6—H6A110.3C20—C21—H21119.9
C5—C6—H6A110.3C16—C21—H21119.9
O1—C6—H6B110.3C19—C20—C21120.37 (13)
C5—C6—H6B110.3C19—C20—H20119.8
H6A—C6—H6B108.6C21—C20—H20119.8
O1—C7—C8124.77 (11)O2—C22—N1119.85 (13)
O1—C7—C12115.21 (11)O2—C22—C23124.01 (12)
C8—C7—C12120.00 (12)N1—C22—C23116.12 (12)
C7—C8—C9119.52 (12)C22—C23—H23A109.5
C7—C8—H8120.2C22—C23—H23B109.5
C9—C8—H8120.2H23A—C23—H23B109.5
C10—C9—C8121.11 (12)C22—C23—H23C109.5
C10—C9—H9119.4H23A—C23—H23C109.5
C8—C9—H9119.4H23B—C23—H23C109.5
C9—C10—C11118.49 (12)
C22—N1—N2—C15175.04 (12)C9—C10—C13—C14−86.17 (15)
C13—N1—N2—C15−1.30 (14)C11—C10—C13—C1491.00 (14)
C1—C2—C3—C4−179.80 (13)N1—C13—C14—C15−0.22 (12)
C2—C3—C4—C5−176.14 (12)C10—C13—C14—C15121.03 (11)
C3—C4—C5—C6176.22 (11)N1—N2—C15—C16179.74 (11)
C7—O1—C6—C5−170.59 (10)N1—N2—C15—C141.13 (15)
C4—C5—C6—O170.78 (14)C13—C14—C15—N2−0.55 (14)
C6—O1—C7—C8−0.01 (18)C13—C14—C15—C16−179.10 (11)
C6—O1—C7—C12178.57 (11)N2—C15—C16—C21179.85 (12)
O1—C7—C8—C9177.70 (12)C14—C15—C16—C21−1.68 (19)
C12—C7—C8—C9−0.81 (19)N2—C15—C16—C17−0.64 (18)
C7—C8—C9—C10−0.41 (19)C14—C15—C16—C17177.82 (12)
C8—C9—C10—C111.34 (19)C21—C16—C17—C180.53 (19)
C8—C9—C10—C13178.52 (12)C15—C16—C17—C18−178.98 (12)
C9—C10—C11—C12−1.08 (19)C16—C17—C18—C190.04 (19)
C13—C10—C11—C12−178.36 (12)C17—C18—C19—C20−0.43 (19)
C10—C11—C12—C7−0.12 (19)C17—C16—C21—C20−0.71 (19)
O1—C7—C12—C11−177.58 (11)C15—C16—C21—C20178.80 (12)
C8—C7—C12—C111.07 (19)C18—C19—C20—C210.2 (2)
C22—N1—C13—C1063.40 (16)C16—C21—C20—C190.3 (2)
N2—N1—C13—C10−120.39 (12)N2—N1—C22—O2−172.82 (12)
C22—N1—C13—C14−175.30 (12)C13—N1—C22—O23.1 (2)
N2—N1—C13—C140.90 (13)N2—N1—C22—C238.60 (18)
C9—C10—C13—N128.19 (17)C13—N1—C22—C23−175.47 (12)
C11—C10—C13—N1−154.64 (11)
Cg1 and Cg2 are the centroids of the C7–C12 and C16–C21 aromatic rings, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg2i0.932.953.6252 (15)131
C14—H14A···Cg2ii0.972.633.5024 (14)151
C19—H19···Cg1iii0.932.713.4299 (15)135
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7–C12 and C16–C21 aromatic rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C8—H8⋯Cg2i0.932.953.6252 (15)131
C14—H14A⋯Cg2ii0.972.633.5024 (14)151
C19—H19⋯Cg1iii0.932.713.4299 (15)135

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

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Authors:  Christoph J Fahrni; Liuchun Yang; Donald G VanDerveer
Journal:  J Am Chem Soc       Date:  2003-04-02       Impact factor: 15.419

8.  4-[1-Acetyl-3-(4-methoxy-phen-yl)-2-pyrazolin-5-yl]phenol.

Authors:  Xue Bai; Hua-Feng Chen; Kuan Zhang; Ying Li; Shu-Fan Yin
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-28

9.  1-[5-(3,4-Dichlorophenyl)-3-(2-naphthyl)-4,5-dihydropyrazol-1-yl]ethanone.

Authors:  Zhi-Ke Lu; Shen Li; Yan Feng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-08-23
  9 in total
  1 in total

1.  1-[5-(4-Meth-oxy-phen-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

Authors:  Asghar Abbas; Safdar Hussain; Noureen Hafeez; Kong Mun Lo; Aurangzeb Hasan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-13
  1 in total

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