Literature DB >> 21588975

1-(3,5-Dimethyl-phen-yl)-4,5-dimethyl-2-phenyl-1H-imidazole hemihydrate.

P Gayathri, A Thiruvalluvar, N Srinivasan, J Jayabharathi, R J Butcher.   

Abstract

In the title compound, C(19)H(20)N(2)·0.5H(2)O, the imidazole ring is essentially planar [maximum deviation = 0.005 (1) Å]. The imidazole ring makes dihedral angles of 67.46 (10) and 23.10 (11)° with the attached benzene and phenyl rings, respectively. The dihedral angle between the benzene and phenyl rings is 68.22 (10)°. Inter-molecular O-H⋯N and C-H⋯N hydrogen bonds are found in the crystal structure.

Entities:  

Year:  2010        PMID： 21588975      PMCID： PMC3009269          DOI： 10.1107/S1600536810039784

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


Related literature

For pharmacological properties of imidazole compounds, see: Lombardino & Wiseman (1974 ▶); For the applications of substituted imidazoles, see: Maier et al. (1989a ▶,b ▶). For the synthesis of imidazoles, see: Welton (1999 ▶); Hermann & Kocher (1997 ▶). For imidazole derivatives as anti­cancer agents, see: Krezel (1998 ▶). For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010a ▶,b ▶,c ▶,d ▶).

Experimental

Crystal data

C19H20N2·0.5H2O M = 285.38 Orthorhombic, a = 16.7611 (2) Å b = 11.5467 (2) Å c = 16.6563 (2) Å V = 3223.58 (8) Å3 Z = 8 Cu Kα radiation μ = 0.55 mm−1 T = 123 K 0.47 × 0.38 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.818, T max = 1.000 7791 measured reflections 3193 independent reflections 2630 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.062 wR(F 2) = 0.171 S = 1.08 3193 reflections 203 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.56 e Å−3 Δρmin = −0.33 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039784/hg2722sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039784/hg2722Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H20N2·0.5H2ODx = 1.176 Mg m−3
Mr = 285.38Melting point: 415 K
Orthorhombic, PbcnCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2n 2abCell parameters from 5434 reflections
a = 16.7611 (2) Åθ = 5.2–28.5°
b = 11.5467 (2) ŵ = 0.55 mm−1
c = 16.6563 (2) ÅT = 123 K
V = 3223.58 (8) Å3Prism, colourless
Z = 80.47 × 0.38 × 0.18 mm
F(000) = 1224
Oxford Diffraction Xcalibur Ruby Gemini diffractometer3193 independent reflections
Radiation source: Enhance (Cu) X-ray Source2630 reflections with I > 2σ(I)
graphiteRint = 0.020
Detector resolution: 10.5081 pixels mm-1θmax = 74.2°, θmin = 5.3°
ω scansh = −20→20
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −13→8
Tmin = 0.818, Tmax = 1.000l = −20→18
7791 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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0758P)2 + 2.1555P] where P = (Fo2 + 2Fc2)/3
3193 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.56 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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 > 2σ(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
N10.06312 (10)0.58209 (13)0.08298 (9)0.0337 (5)
N30.02135 (14)0.41115 (14)0.12586 (9)0.0486 (6)
C20.00259 (13)0.52288 (16)0.11985 (10)0.0373 (6)
C40.09630 (17)0.39935 (18)0.09289 (12)0.0478 (7)
C50.12333 (13)0.50362 (17)0.06558 (11)0.0405 (6)
C110.07375 (11)0.70592 (16)0.07891 (12)0.0320 (5)
C120.07941 (11)0.75929 (17)0.00507 (13)0.0366 (6)
C130.09222 (12)0.87905 (18)0.00254 (15)0.0457 (7)
C140.09830 (12)0.93880 (18)0.07557 (17)0.0513 (8)
C150.09275 (11)0.88545 (18)0.14936 (15)0.0437 (7)
C160.08061 (11)0.76691 (17)0.15073 (13)0.0378 (6)
C170.09981 (16)0.9395 (2)−0.07700 (17)0.0618 (9)
C180.10108 (15)0.9525 (2)0.22687 (18)0.0622 (9)
C21−0.07307 (12)0.57105 (19)0.14706 (11)0.0394 (6)
C22−0.10598 (12)0.67293 (19)0.11567 (12)0.0410 (6)
C23−0.17918 (13)0.7120 (3)0.14236 (13)0.0529 (8)
C24−0.22085 (14)0.6511 (3)0.20103 (14)0.0654 (11)
C25−0.18898 (15)0.5512 (3)0.23230 (14)0.0682 (12)
C26−0.11644 (14)0.5112 (2)0.20583 (13)0.0540 (8)
C410.1384 (2)0.2843 (2)0.09236 (15)0.0750 (12)
C510.19881 (14)0.5369 (2)0.02610 (16)0.0526 (8)
O1W0.000000.2332 (2)0.250000.126 (2)
H120.074710.71571−0.043080.0439*
H140.106661.020150.074110.0616*
H160.076960.727220.200560.0453*
H17A0.068670.89766−0.117500.0927*
H17B0.079681.01885−0.072210.0927*
H17C0.156010.94126−0.093150.0927*
H18A0.085201.033160.218030.0933*
H18B0.066720.917830.267970.0933*
H18C0.156720.949890.244850.0933*
H22−0.077820.715340.075850.0492*
H23−0.201270.780870.120530.0635*
H24−0.271100.678410.219350.0785*
H25−0.217250.509660.272460.0818*
H26−0.095300.441700.227740.0648*
H41A0.191540.293510.068790.1122*
H41B0.143400.255670.147510.1122*
H41C0.107500.228850.060440.1122*
H51A0.188150.55867−0.029750.0789*
H51B0.222450.602820.054530.0789*
H51C0.235920.471350.027310.0789*
H1W0.009 (3)0.280 (4)0.291 (3)0.138 (17)*
U11U22U33U12U13U23
N10.0457 (9)0.0230 (8)0.0325 (8)−0.0005 (6)−0.0068 (7)−0.0043 (6)
N30.0938 (15)0.0256 (8)0.0263 (8)−0.0062 (9)−0.0095 (9)−0.0004 (6)
C20.0581 (12)0.0287 (10)0.0251 (8)−0.0106 (9)−0.0087 (8)−0.0003 (7)
C40.0891 (18)0.0264 (10)0.0280 (9)0.0084 (10)−0.0105 (10)−0.0056 (7)
C50.0575 (12)0.0305 (10)0.0334 (10)0.0089 (9)−0.0118 (9)−0.0095 (8)
C110.0301 (9)0.0211 (9)0.0447 (10)−0.0013 (7)−0.0033 (8)−0.0052 (7)
C120.0339 (9)0.0286 (10)0.0472 (11)0.0000 (7)0.0032 (8)−0.0027 (8)
C130.0348 (10)0.0308 (10)0.0716 (15)0.0026 (8)0.0136 (10)0.0091 (10)
C140.0373 (11)0.0228 (10)0.0939 (19)−0.0027 (8)0.0135 (11)−0.0146 (11)
C150.0325 (10)0.0304 (10)0.0682 (14)−0.0029 (8)0.0044 (9)−0.0163 (10)
C160.0318 (9)0.0329 (10)0.0486 (11)0.0011 (8)−0.0046 (8)−0.0120 (8)
C170.0595 (15)0.0423 (13)0.0835 (19)0.0066 (11)0.0225 (13)0.0217 (12)
C180.0514 (13)0.0480 (14)0.0872 (19)−0.0053 (11)0.0009 (13)−0.0374 (13)
C210.0488 (11)0.0423 (11)0.0270 (9)−0.0163 (9)−0.0087 (8)0.0002 (8)
C220.0420 (10)0.0500 (12)0.0311 (9)−0.0106 (9)−0.0029 (8)−0.0017 (9)
C230.0415 (11)0.0765 (17)0.0407 (11)−0.0037 (11)−0.0059 (9)−0.0032 (11)
C240.0373 (11)0.118 (3)0.0409 (12)−0.0158 (14)0.0000 (10)−0.0047 (14)
C250.0509 (14)0.117 (3)0.0366 (12)−0.0310 (15)−0.0069 (10)0.0178 (14)
C260.0594 (14)0.0665 (16)0.0361 (11)−0.0281 (12)−0.0119 (10)0.0113 (10)
C410.147 (3)0.0334 (12)0.0445 (13)0.0293 (16)−0.0177 (16)−0.0015 (10)
C510.0514 (13)0.0427 (12)0.0637 (14)0.0120 (10)−0.0073 (11)−0.0182 (11)
O1W0.300 (7)0.0283 (13)0.0503 (16)0.00000.041 (3)0.0000
O1W—H1Wi0.88 (5)C24—C251.374 (5)
O1W—H1W0.88 (5)C25—C261.373 (4)
N1—C51.387 (3)C12—H120.9500
N1—C21.369 (3)C14—H140.9500
N1—C111.443 (2)C16—H160.9500
N3—C41.378 (4)C17—H17B0.9800
N3—C21.332 (3)C17—H17A0.9800
C2—C211.457 (3)C17—H17C0.9800
C4—C411.504 (3)C18—H18C0.9800
C4—C51.365 (3)C18—H18B0.9800
C5—C511.477 (3)C18—H18A0.9800
C11—C121.379 (3)C22—H220.9500
C11—C161.393 (3)C23—H230.9500
C12—C131.400 (3)C24—H240.9500
C13—C171.503 (4)C25—H250.9500
C13—C141.402 (4)C26—H260.9500
C14—C151.378 (4)C41—H41B0.9800
C15—C181.512 (4)C41—H41C0.9800
C15—C161.384 (3)C41—H41A0.9800
C21—C221.401 (3)C51—H51C0.9800
C21—C261.402 (3)C51—H51A0.9800
C22—C231.381 (3)C51—H51B0.9800
C23—C241.392 (4)
O1W···N3i2.937 (2)C26···H16i3.0200
O1W···N32.937 (2)C41···H22ii2.9800
O1W···H262.9100C41···H51C2.9200
O1W···H26i2.9100C51···H41A2.9000
O1W···H17Aii2.9100H1W···N3i2.11 (5)
O1W···H18Aiii2.7700H1W···C4i2.96 (5)
O1W···H18Aiv2.7700H1W···H26i2.3800
O1W···H17Av2.9100H12···H17A2.4400
N3···O1W2.937 (2)H12···N3ii2.5800
N3···O1W2.937 (2)H14···H41Cxii2.4200
N3···C26i3.426 (3)H14···H17B2.4800
N3···C12ii3.388 (3)H14···H18A2.4300
N1···H222.8200H16···C22.9900
N3···H262.6100H16···H18B2.4800
N3···H1Wi2.11 (5)H16···C24i3.0500
N3···H26i2.7600H16···C25i2.9800
N3···H12ii2.5800H16···C26i3.0200
C2···C26i3.477 (3)H17A···O1Wxiii2.9100
C4···C22ii3.576 (3)H17A···H122.4400
C5···C25i3.584 (3)H17A···O1Wii2.9100
C11···C223.098 (3)H17B···C14ix3.0200
C12···N3ii3.388 (3)H17B···H142.4800
C12···C513.274 (3)H17C···C24xiv2.9400
C16···C223.362 (3)H18A···O1Wxii2.7700
C16···C213.428 (3)H18A···O1Wxv2.7700
C17···C18vi3.497 (4)H18A···H142.4300
C18···C18i3.475 (4)H18B···C15i3.0300
C18···C17vii3.497 (4)H18B···H162.4800
C21···C163.428 (3)H18B···C18i2.8400
C22···C41ii3.542 (3)H18B···H18Bi2.3200
C22···C4ii3.576 (3)H18C···C25xvi2.8600
C22···C163.362 (3)H18C···H25xvi2.2400
C22···C113.098 (3)H22···C162.9900
C25···C5i3.584 (3)H22···C41ii2.9800
C26···N3i3.426 (3)H22···N12.8200
C26···C2i3.477 (3)H22···C112.5400
C41···C22ii3.542 (3)H22···H41Cii2.4100
C51···C123.274 (3)H22···C122.9300
C2···H162.9900H25···H18Cxi2.2400
C4···H1Wi2.96 (5)H26···O1W2.9100
C4···H26i3.0300H26···C4i3.0300
C11···H51B2.7900H26···H1Wi2.3800
C11···H222.5400H26···O1W2.9100
C12···H51A3.0000H26···N3i2.7600
C12···H222.9300H26···N32.6100
C13···H51Cviii3.1000H41A···C512.9000
C14···H51Cviii2.9200H41A···H51C2.2900
C14···H17Bix3.0200H41C···H14iv2.4200
C15···H18Bi3.0300H41C···H22ii2.4100
C16···H222.9900H51A···C123.0000
C18···H18Bi2.8400H51B···C112.7900
C24···H17Cx2.9400H51C···H41A2.2900
C24···H16i3.0500H51C···C13xvii3.1000
C25···H18Cxi2.8600H51C···C14xvii2.9200
C25···H16i2.9800H51C···C412.9200
H1W—O1W—H1Wi105 (4)C13—C14—H14118.00
C2—N1—C11127.42 (16)C11—C16—H16120.00
C5—N1—C11123.22 (16)C15—C16—H16120.00
C2—N1—C5107.86 (15)C13—C17—H17B109.00
C2—N3—C4106.33 (18)C13—C17—H17C109.00
N1—C2—C21126.44 (17)C13—C17—H17A109.00
N3—C2—C21123.50 (19)H17A—C17—H17C109.00
N1—C2—N3110.03 (18)H17B—C17—H17C110.00
N3—C4—C41121.2 (2)H17A—C17—H17B109.00
C5—C4—C41128.4 (2)C15—C18—H18B109.00
N3—C4—C5110.39 (19)C15—C18—H18C109.00
N1—C5—C51123.13 (18)C15—C18—H18A109.00
C4—C5—C51131.5 (2)H18A—C18—H18C109.00
N1—C5—C4105.38 (19)H18B—C18—H18C109.00
N1—C11—C16118.10 (17)H18A—C18—H18B109.00
C12—C11—C16122.30 (18)C23—C22—H22120.00
N1—C11—C12119.56 (17)C21—C22—H22120.00
C11—C12—C13118.6 (2)C22—C23—H23120.00
C12—C13—C17119.9 (2)C24—C23—H23120.00
C14—C13—C17122.0 (2)C25—C24—H24120.00
C12—C13—C14118.1 (2)C23—C24—H24120.00
C13—C14—C15123.3 (2)C24—C25—H25120.00
C14—C15—C18121.8 (2)C26—C25—H25120.00
C16—C15—C18120.4 (2)C25—C26—H26119.00
C14—C15—C16117.8 (2)C21—C26—H26119.00
C11—C16—C15119.9 (2)C4—C41—H41A109.00
C2—C21—C22123.18 (18)C4—C41—H41B109.00
C2—C21—C26118.72 (19)H41A—C41—H41B110.00
C22—C21—C26118.08 (19)H41A—C41—H41C110.00
C21—C22—C23120.3 (2)C4—C41—H41C109.00
C22—C23—C24120.5 (3)H41B—C41—H41C109.00
C23—C24—C25119.7 (2)C5—C51—H51B109.00
C24—C25—C26120.3 (2)C5—C51—H51C109.00
C21—C26—C25121.2 (2)C5—C51—H51A109.00
C11—C12—H12121.00H51A—C51—H51C109.00
C13—C12—H12121.00H51B—C51—H51C109.00
C15—C14—H14118.00H51A—C51—H51B109.00
C5—N1—C2—N3−0.6 (2)C41—C4—C5—N1−177.7 (2)
C5—N1—C2—C21−178.74 (17)C41—C4—C5—C511.8 (4)
C11—N1—C2—N3−166.83 (17)N1—C11—C12—C13−178.02 (17)
C11—N1—C2—C2115.0 (3)C16—C11—C12—C13−0.2 (3)
C2—N1—C5—C40.1 (2)N1—C11—C16—C15178.49 (17)
C2—N1—C5—C51−179.45 (19)C12—C11—C16—C150.7 (3)
C11—N1—C5—C4167.03 (17)C11—C12—C13—C14−0.3 (3)
C11—N1—C5—C51−12.5 (3)C11—C12—C13—C17179.14 (19)
C2—N1—C11—C12−122.8 (2)C12—C13—C14—C150.4 (3)
C2—N1—C11—C1659.3 (3)C17—C13—C14—C15−179.0 (2)
C5—N1—C11—C1272.8 (2)C13—C14—C15—C160.0 (3)
C5—N1—C11—C16−105.1 (2)C13—C14—C15—C18178.9 (2)
C4—N3—C2—N10.8 (2)C14—C15—C16—C11−0.6 (3)
C4—N3—C2—C21179.07 (18)C18—C15—C16—C11−179.42 (18)
C2—N3—C4—C5−0.8 (2)C2—C21—C22—C23178.0 (2)
C2—N3—C4—C41177.5 (2)C26—C21—C22—C23−0.1 (3)
N1—C2—C21—C2222.9 (3)C2—C21—C26—C25−178.5 (2)
N1—C2—C21—C26−158.99 (19)C22—C21—C26—C25−0.3 (3)
N3—C2—C21—C22−155.0 (2)C21—C22—C23—C240.4 (4)
N3—C2—C21—C2623.1 (3)C22—C23—C24—C25−0.3 (4)
N3—C4—C5—N10.5 (2)C23—C24—C25—C26−0.1 (4)
N3—C4—C5—C51179.9 (2)C24—C25—C26—C210.4 (4)
D—H···AD—HH···AD···AD—H···A
O1W—H1W···N3i0.88 (5)2.11 (5)2.937 (2)155 (4)
C12—H12···N3ii0.952.583.388 (3)144
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1W—H1W⋯N3i0.88 (5)2.11 (5)2.937 (2)155 (4)
C12—H12⋯N3ii0.952.583.388 (3)144

Symmetry codes: (i) ; (ii) .

  9 in total

1.  Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis.

Authors:  Thomas Welton
Journal:  Chem Rev       Date:  1999-08-11       Impact factor: 60.622

2.  A short history of SHELX.

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

3.  Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles.

Authors:  J G Lombardino; E H Wiseman
Journal:  J Med Chem       Date:  1974-11       Impact factor: 7.446

4.  New derivatives of imidazole as potential anticancer agents.

Authors:  I Krezel
Journal:  Farmaco       Date:  1998-05-30

5.  2-(4-Fluoro-phen-yl)-1-(4-meth-oxy-phen-yl)-4,5-dimethyl-1H-imidazole.

Authors:  P Gayathri; J Jayabharathi; K Saravanan; A Thiruvalluvar; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-26

6.  2-(4-Fluoro-phen-yl)-1,4,5-triphenyl-1H-imidazole.

Authors:  P Gayathri; A Thiruvalluvar; N Srinivasan; J Jayabharathi; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-08

7.  2-(4-Fluoro-phen-yl)-4,5-dimethyl-1-(4-methyl-phen-yl)-1H-imidazole.

Authors:  P Gayathri; J Jayabharathi; N Srinivasan; A Thiruvalluvar; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-18

8.  4,5-Dimethyl-1,2-diphenyl-1H-imidazole monohydrate.

Authors:  P Gayathri; A Thiruvalluvar; K Saravanan; J Jayabharathi; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-08-04

9.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  9 in total
  1 in total

1.  1-(3,5-Dimethyl-phenyl)-2-(4-fluoro-phenyl)-4,5-dimethyl-1H-imidazole.

Authors:  S Rosepriya; A Thiruvalluvar; J Jayabharathi; N Srinivasan; R J Butcher; J P Jasinski; J A Golen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-07
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.