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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2219.
Published online 2010 August 4. doi:  10.1107/S1600536810030072
PMCID: PMC3007850

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

Abstract

In the title compound, C17H16N2·H2O, the imidazole ring is essentially planar [maximum deviation = 0.0037 (7) Å]. The imidazole ring makes dihedral angles of 80.74 (7) and 41.62 (7)° with the phenyl rings attached to the N and C atoms, respectively. The dihedral angle between the two phenyl rings is 75.83 (8)°. Inter­molecular O—H(...)N and O—H(...)O hydrogen bonds are found in the crystal structure.

Related literature

For related crystal structures and applications of imidazole derivatives, see: Gayathri et al. (2010a [triangle],b [triangle]).

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Object name is e-66-o2219-scheme1.jpg

Experimental

Crystal data

  • C17H16N2·H2O
  • M r = 266.33
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-66-o2219-efi1.jpg
  • a = 25.5498 (2) Å
  • c = 9.3792 (1) Å
  • V = 6122.67 (9) Å3
  • Z = 16
  • Cu Kα radiation
  • μ = 0.57 mm−1
  • T = 295 K
  • 0.53 × 0.42 × 0.18 mm

Data collection

  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 [triangle]) T min = 0.805, T max = 1.000
  • 8078 measured reflections
  • 3109 independent reflections
  • 2610 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.134
  • S = 1.08
  • 3109 reflections
  • 189 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030072/tk2693sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030072/tk2693Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

JJ is thankful to the Department of Science and Technology (No. SR/S1/IC-07/2007) and the University Grants Commission [F. No. 36–21/2008 (SR)] for providing funds for this research. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

supplementary crystallographic information

Comment

As part of our research (Gayathri et al., 2010a,b), we have synthesized the title compound (I) and report its crystal structure here.

In the title compound (Fig. 1), the imidazole ring is essentially planar [maximum deviation of 0.0037 (7) Å for C5]. The imidazole ring makes dihedral angles of 80.74 (7) and 41.62 (7) ° with the phenyl ring (C11—C16) attached to N1 and the phenyl ring (C21—C26) attached to C2, respectively. The dihedral angle between the two phenyl rings is 75.83 (8) °. Intermolecular O1W—H1W···N3 and O1W—H2W···O1W hydrogen bonds are found in the crystal structure (Table 1, Fig. 2).

Experimental

To pure butane-2,3-dione (1.48 g, 15 mmol), aniline (1.36 g, 15 mmol) and ammonium acetate (1.15 g, 15 mmol) in in ethanol (10 ml) was added benzaldehyde (1.5 g, 15 mmol) over about 1 h with the temperature maintained at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by column chromatography using hexane:ethyl acetate as the eluent. Yield: 1.79 g (48%).

Refinement

H1W and H2W attached to O1W were located in a difference Fourier map and refined freely. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 – 0.96 Å; Uiso(H) = kUeq(C), where k = 1.5 for methyl and 1.2 for all other H atoms. The methyl groups were found to be disordered over two positions. They were each refined as an idealized disordered methyl group.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.
Fig. 2.
The packing of the title compound, viewed down the c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C17H16N2·H2ODx = 1.156 Mg m3
Mr = 266.33Melting point: 375 K
Tetragonal, I41/aCu Kα radiation, λ = 1.54184 Å
Hall symbol: -I 4adCell parameters from 4027 reflections
a = 25.5498 (2) Åθ = 4.9–77.4°
c = 9.3792 (1) ŵ = 0.57 mm1
V = 6122.67 (9) Å3T = 295 K
Z = 16Irregular plate, colourless
F(000) = 22720.53 × 0.42 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer3109 independent reflections
Radiation source: Enhance (Cu) X-ray Source2610 reflections with I > 2σ(I)
graphiteRint = 0.019
Detector resolution: 10.5081 pixels mm-1θmax = 77.6°, θmin = 4.9°
ω scansh = −29→31
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −31→31
Tmin = 0.805, Tmax = 1.000l = −6→11
8078 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0876P)2 + 0.4988P] where P = (Fo2 + 2Fc2)/3
3109 reflections(Δ/σ)max = 0.001
189 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.21 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
N10.00564 (4)0.01347 (4)0.24242 (9)0.0428 (3)
N30.09186 (4)0.00845 (4)0.23202 (10)0.0452 (3)
C20.04817 (4)−0.01899 (5)0.23981 (11)0.0412 (3)
C40.07726 (5)0.06023 (5)0.22951 (13)0.0487 (3)
C50.02420 (5)0.06453 (5)0.23682 (13)0.0488 (3)
C11−0.04871 (4)−0.00047 (5)0.25460 (11)0.0421 (3)
C12−0.07965 (5)−0.00048 (6)0.13375 (13)0.0582 (5)
C13−0.13211 (5)−0.01271 (7)0.14490 (16)0.0649 (5)
C14−0.15362 (5)−0.02441 (7)0.27589 (17)0.0618 (4)
C15−0.12261 (5)−0.02413 (7)0.39614 (15)0.0627 (5)
C16−0.06994 (5)−0.01241 (6)0.38579 (12)0.0526 (4)
C210.04616 (5)−0.07654 (5)0.24358 (12)0.0473 (3)
C220.01046 (6)−0.10535 (6)0.16451 (16)0.0597 (4)
C230.01189 (7)−0.15977 (6)0.1680 (2)0.0778 (6)
C240.04837 (8)−0.18527 (7)0.2490 (2)0.0856 (7)
C250.08410 (8)−0.15716 (7)0.3262 (2)0.0869 (7)
C260.08325 (6)−0.10288 (6)0.32454 (17)0.0662 (5)
C410.11729 (7)0.10273 (6)0.2167 (2)0.0696 (5)
C51−0.01126 (7)0.11082 (6)0.2437 (2)0.0704 (5)
O1W0.24177 (4)0.04630 (4)0.44390 (11)0.0590 (3)
H12−0.065220.007700.045490.0699*
H13−0.15303−0.013070.063750.0779*
H14−0.18902−0.032470.283110.0742*
H15−0.13718−0.031860.484530.0753*
H16−0.04894−0.012570.466800.0631*
H22−0.01446−0.088280.109170.0716*
H23−0.01212−0.178940.114790.0933*
H240.04891−0.221650.251550.1027*
H250.10914−0.174600.380220.1043*
H260.10756−0.084100.377730.0794*
H41A0.151640.087520.213900.1045*0.500
H41B0.114670.125730.297330.1045*0.500
H41C0.111260.122190.130730.1045*0.500
H41D0.100070.136110.214080.1045*0.500
H41E0.137040.097900.130640.1045*0.500
H41F0.140450.101440.297240.1045*0.500
H51A−0.046950.099180.247950.1055*0.500
H51B−0.006340.132050.160320.1055*0.500
H51C−0.003320.131020.327240.1055*0.500
H51D0.009210.142320.242390.1055*0.500
H51E−0.031400.109450.330020.1055*0.500
H51F−0.034420.110480.163100.1055*0.500
H1W0.2423 (7)0.0816 (7)0.4596 (18)0.064 (4)*
H2W0.2563 (9)0.0340 (9)0.520 (2)0.095 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0387 (5)0.0480 (5)0.0416 (5)−0.0005 (4)−0.0003 (3)0.0024 (4)
N30.0396 (5)0.0533 (5)0.0427 (4)−0.0041 (4)0.0026 (4)0.0011 (4)
C20.0382 (5)0.0498 (6)0.0357 (5)−0.0006 (4)0.0019 (4)0.0033 (4)
C40.0484 (6)0.0510 (6)0.0468 (6)−0.0068 (5)0.0022 (5)−0.0010 (5)
C50.0512 (6)0.0466 (6)0.0485 (6)−0.0023 (5)−0.0005 (5)0.0010 (5)
C110.0363 (5)0.0498 (6)0.0403 (5)0.0019 (4)−0.0005 (4)0.0015 (4)
C120.0493 (7)0.0851 (10)0.0402 (6)−0.0004 (6)−0.0044 (5)0.0102 (6)
C130.0463 (7)0.0911 (10)0.0574 (7)0.0015 (6)−0.0156 (6)0.0082 (7)
C140.0370 (6)0.0771 (9)0.0713 (8)−0.0010 (5)−0.0022 (6)0.0031 (7)
C150.0496 (7)0.0881 (10)0.0505 (7)−0.0062 (6)0.0081 (5)0.0060 (7)
C160.0457 (6)0.0745 (8)0.0377 (5)−0.0039 (5)−0.0026 (4)0.0032 (5)
C210.0448 (6)0.0486 (6)0.0486 (6)0.0008 (4)0.0111 (5)0.0060 (5)
C220.0538 (7)0.0548 (7)0.0705 (8)−0.0052 (5)0.0082 (6)−0.0030 (6)
C230.0768 (10)0.0573 (8)0.0992 (12)−0.0150 (7)0.0224 (9)−0.0099 (8)
C240.0900 (12)0.0491 (8)0.1177 (15)0.0020 (8)0.0344 (11)0.0162 (9)
C250.0846 (12)0.0666 (10)0.1096 (14)0.0172 (9)0.0127 (11)0.0349 (10)
C260.0621 (8)0.0636 (8)0.0729 (9)0.0066 (6)0.0011 (7)0.0178 (7)
C410.0635 (8)0.0572 (8)0.0882 (10)−0.0169 (6)0.0119 (8)−0.0054 (7)
C510.0643 (9)0.0542 (8)0.0926 (11)0.0080 (6)−0.0007 (8)−0.0011 (7)
O1W0.0640 (5)0.0518 (6)0.0611 (5)−0.0050 (4)−0.0054 (4)−0.0043 (4)

Geometric parameters (Å, °)

O1W—H2W0.86 (2)C12—H120.9300
O1W—H1W0.914 (18)C13—H130.9300
N1—C51.3891 (16)C14—H140.9300
N1—C21.3672 (15)C15—H150.9300
N1—C111.4381 (15)C16—H160.9300
N3—C41.3748 (16)C22—H220.9300
N3—C21.3202 (15)C23—H230.9300
C2—C211.4717 (18)C24—H240.9300
C4—C411.497 (2)C25—H250.9300
C4—C51.3618 (18)C26—H260.9300
C5—C511.491 (2)C41—H41B0.9600
C11—C121.3819 (16)C41—H41A0.9600
C11—C161.3789 (16)C41—H41E0.9600
C12—C131.3803 (18)C41—H41C0.9600
C13—C141.379 (2)C41—H41D0.9600
C14—C151.378 (2)C41—H41F0.9600
C15—C161.3820 (18)C51—H51B0.9600
C21—C261.388 (2)C51—H51C0.9600
C21—C221.387 (2)C51—H51E0.9600
C22—C231.391 (2)C51—H51F0.9600
C23—C241.368 (3)C51—H51D0.9600
C24—C251.369 (3)C51—H51A0.9600
C25—C261.387 (2)
O1W···O1Wi2.8957 (15)C41···H51D2.9500
O1W···O1Wii2.8957 (15)C51···H41D2.9300
O1W···N3ii2.9111 (14)H1W···N3ii2.010 (18)
O1W···H14iii2.8200H1W···H41Aii2.4700
O1W···H2Wi2.03 (2)H1W···C4ii2.910 (18)
O1W···H13iv2.7900H1W···C2ii3.098 (18)
O1W···H15v2.7800H2W···O1Wii2.03 (2)
O1W···H41Aii2.7900H2W···H14v2.5200
O1W···H14v2.9100H12···N3vi2.7200
N3···O1Wi2.9111 (14)H12···C2vi2.7300
N1···H16v2.9400H13···O1Wviii2.7900
N1···H222.9300H14···O1Wvii2.8200
N3···H262.7600H14···O1Wv2.9100
N3···H1Wi2.010 (18)H14···H2Wv2.5200
N3···H12vi2.7200H15···O1Wv2.7800
C11···C223.191 (2)H16···C2v2.8700
C12···C223.544 (2)H16···N1v2.9400
C12···C513.493 (2)H22···N12.9300
C22···C123.544 (2)H22···C112.7700
C22···C113.191 (2)H22···C122.8000
C23···C25vii3.597 (3)H24···C24iii3.0800
C25···C23iii3.597 (3)H24···H51Ci2.5600
C51···C123.493 (2)H25···C23iii2.9600
C2···H1Wi3.098 (18)H25···C22iii3.0600
C2···H16v2.8700H26···N32.7600
C2···H12vi2.7300H41A···H1Wi2.4700
C4···H1Wi2.910 (18)H41A···O1Wi2.7900
C11···H222.7700H41B···C24ii2.9900
C11···H51A2.5500H41B···C25ii2.8600
C11···H51E2.9300H41B···C26ii2.9200
C11···H51F2.9800H41D···C512.9300
C12···H51F3.0700H41D···H51D2.3400
C12···H222.8000H41F···C26ii3.0900
C12···H51A2.8900H51A···C112.5500
C22···H25vii3.0600H51A···C122.8900
C23···H25vii2.9600H51C···C24ii2.9800
C24···H51Ci2.9800H51C···H24ii2.5600
C24···H41Bi2.9900H51D···C412.9500
C24···H24vii3.0800H51D···H41D2.3400
C25···H41Bi2.8600H51E···C112.9300
C26···H41Fi3.0900H51F···C112.9800
C26···H41Bi2.9200H51F···C123.0700
H1W—O1W—H2W102.7 (18)C26—C25—H25120.00
C2—N1—C11128.22 (10)C24—C25—H25120.00
C5—N1—C11124.42 (10)C25—C26—H26120.00
C2—N1—C5107.32 (10)C21—C26—H26120.00
C2—N3—C4106.41 (10)C4—C41—H41A109.00
N1—C2—N3110.54 (11)C4—C41—H41C109.00
N1—C2—C21125.30 (10)C4—C41—H41D109.00
N3—C2—C21124.15 (10)C4—C41—H41B109.00
N3—C4—C41120.94 (12)C4—C41—H41F109.00
C5—C4—C41128.74 (12)H41A—C41—H41B109.00
N3—C4—C5110.30 (11)H41A—C41—H41C109.00
N1—C5—C51122.40 (12)H41A—C41—H41D141.00
C4—C5—C51132.14 (13)H41A—C41—H41E56.00
N1—C5—C4105.43 (11)H41A—C41—H41F56.00
N1—C11—C16120.37 (10)C4—C41—H41E109.00
C12—C11—C16120.46 (11)H41B—C41—H41D56.00
N1—C11—C12119.16 (10)H41B—C41—H41E141.00
C11—C12—C13119.56 (12)H41B—C41—H41F56.00
C12—C13—C14120.25 (13)H41C—C41—H41D56.00
C13—C14—C15119.93 (12)H41C—C41—H41E56.00
C14—C15—C16120.22 (13)H41C—C41—H41F141.00
C11—C16—C15119.58 (11)H41D—C41—H41E109.00
C2—C21—C26118.27 (11)H41D—C41—H41F109.00
C22—C21—C26118.95 (13)H41E—C41—H41F109.00
C2—C21—C22122.71 (11)H41B—C41—H41C109.00
C21—C22—C23120.04 (14)C5—C51—H51B109.00
C22—C23—C24120.47 (16)C5—C51—H51C109.00
C23—C24—C25119.90 (17)C5—C51—H51A109.00
C24—C25—C26120.55 (17)C5—C51—H51E109.00
C21—C26—C25120.10 (15)C5—C51—H51F109.00
C13—C12—H12120.00C5—C51—H51D109.00
C11—C12—H12120.00H51A—C51—H51C109.00
C14—C13—H13120.00H51A—C51—H51D141.00
C12—C13—H13120.00H51A—C51—H51E56.00
C13—C14—H14120.00H51A—C51—H51F56.00
C15—C14—H14120.00H51B—C51—H51C109.00
C16—C15—H15120.00H51B—C51—H51D56.00
C14—C15—H15120.00H51B—C51—H51E141.00
C11—C16—H16120.00H51B—C51—H51F56.00
C15—C16—H16120.00H51C—C51—H51D56.00
C23—C22—H22120.00H51C—C51—H51E56.00
C21—C22—H22120.00H51C—C51—H51F141.00
C22—C23—H23120.00H51D—C51—H51E109.00
C24—C23—H23120.00H51D—C51—H51F109.00
C23—C24—H24120.00H51E—C51—H51F109.00
C25—C24—H24120.00H51A—C51—H51B109.00
C5—N1—C2—N3−0.41 (12)N3—C4—C5—N1−0.66 (13)
C5—N1—C2—C21−179.82 (10)N3—C4—C5—C51177.15 (14)
C11—N1—C2—N3−178.01 (9)C41—C4—C5—N1177.86 (13)
C11—N1—C2—C212.58 (17)C41—C4—C5—C51−4.3 (2)
C2—N1—C5—C40.65 (12)N1—C11—C12—C13−178.61 (13)
C2—N1—C5—C51−177.43 (12)C16—C11—C12—C13−0.2 (2)
C11—N1—C5—C4178.36 (10)N1—C11—C16—C15177.99 (13)
C11—N1—C5—C510.28 (18)C12—C11—C16—C15−0.4 (2)
C2—N1—C11—C12−101.64 (14)C11—C12—C13—C140.6 (2)
C2—N1—C11—C1679.95 (16)C12—C13—C14—C15−0.3 (3)
C5—N1—C11—C1281.14 (15)C13—C14—C15—C16−0.3 (3)
C5—N1—C11—C16−97.27 (15)C14—C15—C16—C110.7 (2)
C4—N3—C2—N10.00 (13)C2—C21—C22—C23177.34 (13)
C4—N3—C2—C21179.42 (10)C26—C21—C22—C230.5 (2)
C2—N3—C4—C50.42 (13)C2—C21—C26—C25−177.29 (14)
C2—N3—C4—C41−178.24 (12)C22—C21—C26—C25−0.3 (2)
N1—C2—C21—C2242.85 (17)C21—C22—C23—C240.0 (3)
N1—C2—C21—C26−140.30 (12)C22—C23—C24—C25−0.6 (3)
N3—C2—C21—C22−136.48 (13)C23—C24—C25—C260.8 (3)
N3—C2—C21—C2640.36 (17)C24—C25—C26—C21−0.4 (3)

Symmetry codes: (i) −y+1/4, x−1/4, z−1/4; (ii) y+1/4, −x+1/4, z+1/4; (iii) y+1/4, −x−1/4, −z+3/4; (iv) −y+1/4, x+1/4, −z+1/4; (v) −x, −y, −z+1; (vi) −x, −y, −z; (vii) −y−1/4, x−1/4, −z+3/4; (viii) y−1/4, −x+1/4, −z+1/4.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1W···N3ii0.914 (18)2.010 (18)2.9111 (14)168.6 (16)
O1W—H2W···O1Wii0.86 (2)2.03 (2)2.8957 (15)175 (2)

Symmetry codes: (ii) y+1/4, −x+1/4, z+1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2693).

References

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