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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1499.
Published online 2009 June 6. doi:  10.1107/S1600536809020807
PMCID: PMC2969499

2-(4-Nitro­phen­yl)-4,5-diphenyl-1H-imidazol-3-ium chloride

Abstract

In the cation of the title compound, C21H16N3O2 +·Cl, the N atom in the 3-position of the imidazole ring is protonated. The three pendant aromatic rings are twisted from the plane of the imidazolium ring by dihedral angles of 31.69 (14)°, 31.09 (14)° and 34.77 (14)°. In the crystal structure, N—H(...)Cl hydrogen bonds link the mol­ecules, forming a chain parallel to the b axis.

Related literature

For uses of imidazole derivatives, see: Dai & Fu (2008 [triangle]); Fu et al. (2008 [triangle]); Huang et al. (2008 [triangle]).

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Object name is e-65-o1499-scheme1.jpg

Experimental

Crystal data

  • C21H16N3O2 +·Cl
  • M r = 377.82
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1499-efi1.jpg
  • a = 15.106 (3) Å
  • b = 15.837 (3) Å
  • c = 7.8833 (16) Å
  • β = 105.10 (3)°
  • V = 1820.8 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 298 K
  • 0.45 × 0.40 × 0.25 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.910, T max = 1.000 (expected range = 0.859–0.944)
  • 18591 measured reflections
  • 4165 independent reflections
  • 2393 reflections with I > 2σ(I)
  • R int = 0.109

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.157
  • S = 1.03
  • 4165 reflections
  • 245 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809020807/ci2820sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020807/ci2820Isup2.hkl

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

Acknowledgments

This work was supported by a grant from the Outstanding Doctoral Dissertation Fund of Southeast University.

supplementary crystallographic information

Comment

Imidazole derivatives have found wide range of applications in coordination chemistry because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Huang et al. 2008; Fu et al. 2008; Dai & Fu 2008). We report herein the crystal structure of the title compound, 2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazol-3-ium chloride.

The title compound contains an organic cation and a Cl- anion in the asymmetric unit. The imidazole N atom in 3-position is protonated. The C1-C6, C8-C13 and C16-C21 benzene rings are twisted from the imidazolium ring an angle of 31.69 (14)°, 31.09 (14)° and 34.77 (14)°, respectively.

The crystal packing is stabilized by N—H···Cl hydrogen bonds to form a linear chain parallel to the b axis (Table 1 and Fig. 2).

Experimental

Under nitrogen protection, 1,2-diphenyl-ethane-1,2-dione (20 mmol), 4-nitrobenzaldehyde (20 mmol) and amine acetate (50 mmol) were dissolved in 60 ml of HOAc. The mixture was stirred at 383 K for 20 h. The resulting solution was poured into ice water (200 ml) and after neutralizing the mixture with NaOH (6 mol/L) a white solid was obtained. After filtration and washing with distilled water the crude product was recrystallized from a ethanolic solution (150 ml) to which HCl (5 ml) was added to yield colourless block-shaped crystals of the title compound, suitable for X-ray analysis.

Refinement

H atoms attached to C and N atoms were positioned geometrically and treated as riding, with C-H = 0.93 Å, N-H = 0.86 Å and Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The crystal packing of the title compound viewed along the c axis, showing a hydrogen bonded chain. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Crystal data

C21H16N3O2+·ClF(000) = 784
Mr = 377.82Dx = 1.378 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4160 reflections
a = 15.106 (3) Åθ = 3.1–27.5°
b = 15.837 (3) ŵ = 0.23 mm1
c = 7.8833 (16) ÅT = 298 K
β = 105.10 (3)°Block, colourless
V = 1820.8 (7) Å30.45 × 0.40 × 0.25 mm
Z = 4

Data collection

Rigaku Mercury2 diffractometer4165 independent reflections
Radiation source: fine-focus sealed tube2393 reflections with I > 2σ(I)
graphiteRint = 0.109
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
CCD profile fitting scansh = −19→19
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −20→20
Tmin = 0.910, Tmax = 1.000l = −10→10
18591 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.157w = 1/[σ2(Fo2) + (0.0533P)2 + 0.4461P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4165 reflectionsΔρmax = 0.32 e Å3
245 parametersΔρmin = −0.35 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0053 (10)

Special details

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.

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

xyzUiso*/Ueq
Cl10.50431 (5)0.90216 (4)0.28931 (13)0.0625 (3)
N10.57993 (14)0.72042 (13)0.2790 (3)0.0325 (5)
H1A0.56200.77170.28400.039*
C70.52567 (17)0.65254 (16)0.2629 (3)0.0321 (6)
N20.57744 (14)0.58548 (13)0.2592 (3)0.0339 (5)
H2A0.55810.53420.25010.041*
N30.14392 (17)0.65834 (17)0.2081 (4)0.0480 (7)
C60.42716 (17)0.65341 (15)0.2489 (3)0.0323 (6)
C20.27691 (18)0.59458 (17)0.1358 (4)0.0399 (7)
H20.23820.55400.07000.048*
C150.66881 (17)0.69658 (16)0.2865 (3)0.0307 (6)
C130.73980 (17)0.54725 (16)0.2772 (3)0.0320 (6)
C30.24275 (18)0.65705 (17)0.2217 (4)0.0370 (7)
C10.37003 (18)0.59320 (16)0.1493 (4)0.0389 (7)
H10.39440.55170.09120.047*
C140.66699 (17)0.60935 (16)0.2719 (3)0.0308 (6)
C180.7947 (2)0.89632 (18)0.2438 (4)0.0449 (8)
H180.78210.94900.19080.054*
C40.29746 (19)0.71829 (17)0.3209 (4)0.0418 (7)
H40.27250.76010.37730.050*
O20.11287 (15)0.71883 (15)0.2695 (4)0.0696 (7)
C50.39062 (19)0.71577 (17)0.3342 (4)0.0404 (7)
H50.42910.75620.40080.049*
O10.09771 (15)0.59864 (15)0.1374 (4)0.0740 (8)
C160.74249 (18)0.75918 (15)0.3069 (3)0.0315 (6)
C170.7250 (2)0.83847 (16)0.2293 (4)0.0374 (7)
H170.66570.85260.16710.045*
C90.8082 (2)0.41135 (18)0.3652 (4)0.0455 (7)
H90.80520.35810.41320.055*
C210.83144 (18)0.74111 (17)0.4041 (4)0.0387 (7)
H210.84410.68930.46080.046*
C120.81528 (19)0.56718 (17)0.2152 (4)0.0390 (7)
H120.81720.61900.16060.047*
C80.73622 (19)0.46743 (17)0.3498 (4)0.0399 (7)
H80.68530.45180.38810.048*
C110.8874 (2)0.51169 (19)0.2330 (4)0.0497 (8)
H110.93810.52660.19340.060*
C200.9012 (2)0.7994 (2)0.4172 (4)0.0480 (8)
H200.96050.78610.48120.058*
C190.8833 (2)0.8769 (2)0.3361 (4)0.0501 (8)
H190.93030.91570.34350.060*
C100.8841 (2)0.4339 (2)0.3099 (4)0.0517 (8)
H100.93310.39670.32430.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0444 (5)0.0305 (4)0.1135 (8)0.0066 (3)0.0224 (5)0.0007 (4)
N10.0281 (13)0.0225 (11)0.0463 (14)−0.0003 (9)0.0087 (11)−0.0024 (10)
C70.0270 (14)0.0291 (14)0.0390 (15)0.0003 (12)0.0064 (12)−0.0005 (12)
N20.0293 (13)0.0238 (11)0.0482 (14)−0.0043 (9)0.0095 (10)−0.0023 (10)
N30.0286 (14)0.0472 (16)0.0670 (17)0.0050 (13)0.0103 (13)0.0089 (14)
C60.0252 (14)0.0280 (13)0.0437 (16)−0.0024 (11)0.0086 (12)0.0015 (12)
C20.0272 (15)0.0368 (16)0.0520 (18)−0.0064 (12)0.0038 (13)−0.0048 (14)
C150.0238 (15)0.0315 (14)0.0362 (15)−0.0007 (11)0.0068 (12)−0.0010 (12)
C130.0274 (15)0.0293 (14)0.0388 (15)0.0003 (11)0.0076 (12)−0.0029 (12)
C30.0225 (14)0.0376 (15)0.0494 (17)0.0035 (12)0.0066 (13)0.0107 (14)
C10.0328 (16)0.0290 (14)0.0538 (18)0.0004 (12)0.0094 (13)−0.0066 (13)
C140.0251 (14)0.0293 (14)0.0381 (15)−0.0044 (11)0.0084 (12)−0.0005 (12)
C180.059 (2)0.0314 (15)0.0494 (18)−0.0075 (15)0.0227 (16)−0.0027 (14)
C40.0341 (17)0.0382 (16)0.0564 (19)0.0021 (13)0.0175 (14)−0.0052 (14)
O20.0399 (14)0.0615 (15)0.112 (2)0.0115 (12)0.0282 (14)−0.0054 (14)
C50.0333 (17)0.0343 (15)0.0530 (18)−0.0049 (12)0.0102 (14)−0.0111 (14)
O10.0313 (13)0.0674 (16)0.118 (2)−0.0119 (12)0.0094 (13)−0.0165 (16)
C160.0311 (15)0.0285 (13)0.0371 (15)−0.0045 (11)0.0129 (12)−0.0038 (12)
C170.0371 (17)0.0324 (14)0.0428 (16)−0.0011 (12)0.0109 (13)−0.0009 (13)
C90.0491 (19)0.0328 (15)0.0538 (19)0.0065 (14)0.0122 (15)0.0061 (14)
C210.0314 (16)0.0374 (15)0.0459 (17)−0.0038 (13)0.0072 (13)−0.0037 (13)
C120.0386 (17)0.0328 (15)0.0484 (18)−0.0005 (13)0.0166 (14)0.0022 (13)
C80.0364 (17)0.0351 (15)0.0496 (18)0.0017 (13)0.0139 (14)0.0021 (13)
C110.0343 (17)0.0530 (19)0.067 (2)0.0031 (15)0.0235 (16)−0.0019 (17)
C200.0266 (16)0.054 (2)0.060 (2)−0.0079 (14)0.0054 (14)−0.0087 (16)
C190.047 (2)0.0476 (18)0.063 (2)−0.0217 (15)0.0264 (17)−0.0146 (16)
C100.0420 (19)0.0477 (19)0.064 (2)0.0179 (15)0.0107 (16)0.0036 (16)

Geometric parameters (Å, °)

N1—C71.338 (3)C18—C191.380 (4)
N1—C151.381 (3)C18—H180.93
N1—H1A0.86C4—C51.384 (4)
C7—N21.324 (3)C4—H40.93
C7—C61.463 (4)C5—H50.93
N2—C141.383 (3)C16—C171.392 (3)
N2—H2A0.86C16—C211.392 (4)
N3—O11.220 (3)C17—H170.9300
N3—O21.221 (3)C9—C101.375 (4)
N3—C31.469 (4)C9—C81.384 (4)
C6—C11.385 (4)C9—H90.93
C6—C51.388 (4)C21—C201.384 (4)
C2—C31.373 (4)C21—H210.93
C2—C11.383 (4)C12—C111.378 (4)
C2—H20.93C12—H120.93
C15—C141.386 (3)C8—H80.93
C15—C161.468 (3)C11—C101.379 (4)
C13—C121.389 (4)C11—H110.93
C13—C81.395 (4)C20—C191.378 (4)
C13—C141.468 (3)C20—H200.93
C3—C41.378 (4)C19—H190.93
C1—H10.93C10—H100.93
C18—C171.378 (4)
C7—N1—C15110.4 (2)C3—C4—C5118.1 (3)
C7—N1—H1A124.8C3—C4—H4121.0
C15—N1—H1A124.8C5—C4—H4121.0
N2—C7—N1107.2 (2)C4—C5—C6120.6 (3)
N2—C7—C6126.9 (2)C4—C5—H5119.7
N1—C7—C6125.8 (2)C6—C5—H5119.7
C7—N2—C14110.6 (2)C17—C16—C21118.2 (2)
C7—N2—H2A124.7C17—C16—C15120.6 (2)
C14—N2—H2A124.7C21—C16—C15121.1 (2)
O1—N3—O2123.8 (3)C18—C17—C16120.6 (3)
O1—N3—C3118.2 (3)C18—C17—H17119.7
O2—N3—C3118.0 (3)C16—C17—H17119.7
C1—C6—C5119.8 (2)C10—C9—C8120.4 (3)
C1—C6—C7120.5 (2)C10—C9—H9119.8
C5—C6—C7119.7 (2)C8—C9—H9119.8
C3—C2—C1118.6 (2)C20—C21—C16120.7 (3)
C3—C2—H2120.7C20—C21—H21119.6
C1—C2—H2120.7C16—C21—H21119.6
N1—C15—C14105.7 (2)C11—C12—C13121.2 (3)
N1—C15—C16121.4 (2)C11—C12—H12119.4
C14—C15—C16132.9 (2)C13—C12—H12119.4
C12—C13—C8118.3 (2)C9—C8—C13120.3 (3)
C12—C13—C14121.0 (2)C9—C8—H8119.9
C8—C13—C14120.7 (2)C13—C8—H8119.9
C2—C3—C4122.7 (3)C12—C11—C10119.8 (3)
C2—C3—N3118.7 (3)C12—C11—H11120.1
C4—C3—N3118.7 (3)C10—C11—H11120.1
C2—C1—C6120.2 (3)C19—C20—C21120.4 (3)
C2—C1—H1119.9C19—C20—H20119.8
C6—C1—H1119.9C21—C20—H20119.8
N2—C14—C15106.0 (2)C20—C19—C18119.3 (3)
N2—C14—C13122.0 (2)C20—C19—H19120.3
C15—C14—C13131.8 (2)C18—C19—H19120.3
C17—C18—C19120.6 (3)C9—C10—C11120.0 (3)
C17—C18—H18119.7C9—C10—H10120.0
C19—C18—H18119.7C11—C10—H10120.0

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl10.862.253.105 (2)176
N2—H2A···Cl1i0.862.283.139 (2)175

Symmetry codes: (i) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2820).

References

  • Dai, W. & Fu, D.-W. (2008). Acta Cryst. E64, o971. [PMC free article] [PubMed]
  • Fu, D.-W. & Xiong, R.-G. (2008). Dalton Trans. pp. 3946–3948. [PubMed]
  • Huang, X.-F., Fu, D.-W. & Xiong, R.-G. (2008). Cryst. Growth. Des.8, 1795–1797.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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