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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1675.
Published online 2009 June 24. doi:  10.1107/S1600536809023599
PMCID: PMC2969496

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

Abstract

In the cation of the title compound, C21H16N3O2 +·NO3 , 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 22.75 (1), 79.63 (1) and 29.65 (1)°. In the crystal structure, N—H(...)O hydrogen bonds link the mol­ecules, forming an infinite one-dimensional chain parallel to the b axis.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-o1675-scheme1.jpg

Experimental

Crystal data

  • C21H16N3O2 +·NO3
  • M r = 404.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1675-efi1.jpg
  • a = 5.870 (1) Å
  • b = 12.509 (3) Å
  • c = 26.476 (5) Å
  • β = 95.06 (3)°
  • V = 1936.2 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 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 = 0.949, T max = 1.000 (expected range = 0.925–0.975)
  • 19751 measured reflections
  • 4443 independent reflections
  • 2546 reflections with I > 2σ(I)
  • R int = 0.085

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.162
  • S = 1.04
  • 4443 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.22 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, global. DOI: 10.1107/S1600536809023599/im2120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023599/im2120Isup2.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-(3-nitrophenyl)-4,5-diphenyl-1H-imidazol-3-ium nitrate.

The title compound contains an organic cation and a nitrate anion in the asymmetric unit. The imidazole N atom in 3-position is protonated. Benzene and imidazole rings are twisted from each other by dihedral angles of 22.75 (1)°, 79.63 (1)° and 29.65 (1)°. The crystal packing is stabilized by N—H···O hydrogen bonds to form an infinite one-dimensional chain parallel to b axis (Table 1, Fig. 2).

Experimental

Under nitrogen protection, 1,2-diphenyl-ethane-1,2-dione (20 mmol), 3-nitrobenzaldehyde (20 mmol) and amine acetate (50 mmol) were dissolved in 60 ml of HOAc. The mixture was stirred at 110 °C 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 an ethanolic solution (150 ml) to which nitric acid (5 ml) was added to yield colorless block-like crystals of the title compound, suitable for X-ray analysis.

Refinement

All H atoms attached to C and N atoms were fixed geometrically and treated as riding with C–H = 0.93 Å and N–H = 0.86 Å with Uiso(H) = 1.2Ueq(C or N).

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
Fig. 2.
Crystal packing of the title compound viewed down a axis showing the one-dimensional chain made up by hydrogen bonding (dashed lines). Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C21H16N3O2+·NO3F(000) = 840
Mr = 404.38Dx = 1.387 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4443 reflections
a = 5.870 (1) Åθ = 3.1–27.5°
b = 12.509 (3) ŵ = 0.10 mm1
c = 26.476 (5) ÅT = 298 K
β = 95.06 (3)°Block, colorless
V = 1936.2 (7) Å30.45 × 0.40 × 0.25 mm
Z = 4

Data collection

Rigaku Mercury2 diffractometer4443 independent reflections
Radiation source: fine-focus sealed tube2546 reflections with I > 2σ(I)
graphiteRint = 0.085
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
CCD profile fitting scansh = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −16→16
Tmin = 0.949, Tmax = 1.000l = −34→34
19751 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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0623P)2 + 0.3275P] where P = (Fo2 + 2Fc2)/3
4443 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.22 e Å3

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
O30.2948 (3)0.82802 (12)0.22754 (7)0.0478 (5)
N30.5060 (4)0.84341 (19)0.22241 (8)0.0512 (6)
O20.6316 (4)0.76676 (19)0.21888 (9)0.0876 (8)
O10.5694 (4)0.93609 (19)0.22221 (11)0.0982 (9)
N20.1754 (3)0.64621 (14)0.27380 (6)0.0341 (4)
H2A0.24410.69590.25860.041*
N1−0.0446 (3)0.51473 (14)0.28709 (7)0.0354 (5)
H1A−0.14390.46450.28190.043*
C70.0303 (4)0.57674 (17)0.25109 (8)0.0332 (5)
C130.0275 (4)0.47970 (17)0.37962 (8)0.0356 (5)
C160.3635 (4)0.68723 (17)0.35972 (8)0.0347 (5)
C10.1235 (4)0.60288 (18)0.16282 (9)0.0416 (6)
H10.25480.64040.17430.050*
C180.7179 (4)0.7836 (2)0.37476 (11)0.0490 (7)
H180.84930.81180.36270.059*
C150.2004 (4)0.62735 (17)0.32540 (8)0.0337 (5)
C20.0714 (5)0.5842 (2)0.11185 (9)0.0472 (6)
C210.3271 (4)0.70151 (19)0.41038 (9)0.0440 (6)
H210.19550.67410.42270.053*
C6−0.0249 (4)0.56435 (17)0.19669 (8)0.0347 (5)
C170.5628 (4)0.72880 (18)0.34219 (9)0.0404 (6)
H170.59100.71950.30850.049*
C5−0.2202 (4)0.5095 (2)0.17802 (9)0.0474 (6)
H5−0.32150.48420.20030.057*
C140.0604 (4)0.54308 (17)0.33367 (8)0.0344 (5)
C200.4843 (5)0.7559 (2)0.44270 (10)0.0517 (7)
H200.45780.76490.47660.062*
O50.3866 (4)0.6812 (2)0.09223 (9)0.0871 (7)
C8−0.1602 (5)0.4912 (2)0.40612 (11)0.0607 (8)
H8−0.27250.54050.39530.073*
N40.2321 (5)0.6234 (2)0.07626 (10)0.0687 (7)
C190.6799 (5)0.7970 (2)0.42501 (11)0.0535 (7)
H190.78580.83350.44680.064*
C10−0.0231 (5)0.3584 (2)0.46502 (10)0.0602 (8)
H10−0.03860.31860.49420.072*
C4−0.2650 (5)0.4923 (2)0.12670 (10)0.0581 (8)
H4−0.39650.45550.11470.070*
O40.1968 (5)0.5963 (2)0.03177 (9)0.1162 (10)
C120.1888 (5)0.4055 (2)0.39616 (11)0.0652 (9)
H120.31780.39630.37860.078*
C110.1621 (6)0.3445 (3)0.43847 (11)0.0758 (10)
H110.27160.29340.44890.091*
C3−0.1176 (5)0.5290 (2)0.09306 (10)0.0557 (7)
H3−0.14590.51650.05850.067*
C9−0.1853 (5)0.4305 (3)0.44881 (11)0.0700 (9)
H9−0.31410.43920.46650.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O30.0438 (10)0.0367 (9)0.0637 (12)−0.0033 (8)0.0099 (9)0.0069 (8)
N30.0560 (15)0.0527 (14)0.0477 (13)0.0027 (12)0.0209 (11)0.0054 (11)
O20.0859 (17)0.0920 (16)0.0904 (17)0.0467 (14)0.0390 (14)0.0154 (14)
O10.0733 (16)0.0666 (15)0.161 (3)−0.0267 (12)0.0439 (15)0.0050 (16)
N20.0397 (11)0.0327 (10)0.0304 (10)−0.0023 (8)0.0057 (8)0.0031 (8)
N10.0363 (10)0.0369 (10)0.0333 (11)−0.0043 (8)0.0041 (8)0.0007 (9)
C70.0347 (12)0.0315 (11)0.0335 (12)−0.0001 (10)0.0037 (10)−0.0007 (10)
C130.0411 (13)0.0350 (12)0.0310 (12)−0.0011 (10)0.0039 (10)0.0015 (10)
C160.0391 (13)0.0318 (12)0.0330 (13)0.0041 (10)0.0024 (10)0.0015 (10)
C10.0480 (14)0.0373 (13)0.0398 (14)−0.0034 (11)0.0054 (11)0.0010 (11)
C180.0384 (14)0.0482 (15)0.0594 (18)−0.0009 (11)−0.0009 (12)0.0042 (14)
C150.0374 (12)0.0338 (12)0.0303 (12)0.0027 (10)0.0047 (9)0.0006 (10)
C20.0637 (17)0.0449 (15)0.0339 (14)−0.0004 (13)0.0091 (12)0.0055 (12)
C210.0441 (14)0.0497 (15)0.0380 (14)0.0005 (11)0.0017 (11)0.0000 (12)
C60.0398 (13)0.0318 (12)0.0321 (13)0.0014 (10)0.0017 (10)0.0023 (10)
C170.0407 (14)0.0415 (13)0.0388 (13)0.0027 (11)0.0019 (11)0.0017 (11)
C50.0505 (15)0.0481 (15)0.0434 (15)−0.0081 (12)0.0027 (12)0.0024 (12)
C140.0350 (12)0.0346 (12)0.0340 (13)0.0042 (10)0.0054 (10)−0.0003 (10)
C200.0612 (18)0.0568 (17)0.0352 (14)0.0056 (14)−0.0066 (13)−0.0043 (12)
O50.0782 (16)0.115 (2)0.0699 (15)−0.0193 (15)0.0203 (13)0.0227 (14)
C80.0539 (17)0.0628 (18)0.0692 (19)0.0168 (14)0.0262 (14)0.0261 (16)
N40.092 (2)0.0691 (17)0.0481 (16)0.0050 (16)0.0231 (14)0.0119 (14)
C190.0531 (17)0.0487 (16)0.0546 (17)0.0003 (13)−0.0185 (14)−0.0015 (14)
C100.074 (2)0.0654 (19)0.0424 (16)−0.0017 (16)0.0105 (14)0.0163 (14)
C40.0692 (19)0.0573 (17)0.0449 (16)−0.0155 (14)−0.0119 (14)0.0000 (14)
O40.189 (3)0.121 (2)0.0462 (15)−0.029 (2)0.0507 (16)−0.0077 (14)
C120.0593 (18)0.087 (2)0.0529 (18)0.0242 (16)0.0230 (14)0.0262 (16)
C110.082 (2)0.089 (2)0.0580 (19)0.0300 (19)0.0143 (17)0.0364 (18)
C30.082 (2)0.0526 (16)0.0315 (14)0.0005 (15)0.0004 (13)−0.0021 (13)
C90.068 (2)0.079 (2)0.068 (2)0.0061 (17)0.0356 (16)0.0236 (18)

Geometric parameters (Å, °)

O3—N31.273 (3)C2—N41.475 (3)
N3—O11.218 (3)C21—C201.381 (4)
N3—O21.218 (3)C21—H210.9300
N2—C71.323 (3)C6—C51.389 (3)
N2—C151.381 (3)C17—H170.9300
N2—H2A0.8600C5—C41.378 (3)
N1—C71.333 (3)C5—H50.9300
N1—C141.376 (3)C20—C191.377 (4)
N1—H1A0.8600C20—H200.9300
C7—C61.456 (3)O5—N41.206 (3)
C13—C81.365 (3)C8—C91.380 (4)
C13—C121.370 (3)C8—H80.9300
C13—C141.479 (3)N4—O41.226 (3)
C16—C211.388 (3)C19—H190.9300
C16—C171.396 (3)C10—C91.353 (4)
C16—C151.466 (3)C10—C111.357 (4)
C1—C21.377 (3)C10—H100.9300
C1—C61.390 (3)C4—C31.374 (4)
C1—H10.9300C4—H40.9300
C18—C191.378 (4)C12—C111.376 (4)
C18—C171.380 (3)C12—H120.9300
C18—H180.9300C11—H110.9300
C15—C141.366 (3)C3—H30.9300
C2—C31.363 (4)C9—H90.9300
O1—N3—O2124.2 (3)C16—C17—H17119.9
O1—N3—O3116.4 (2)C4—C5—C6120.5 (2)
O2—N3—O3119.4 (2)C4—C5—H5119.7
C7—N2—C15110.19 (18)C6—C5—H5119.7
C7—N2—H2A124.9C15—C14—N1106.46 (19)
C15—N2—H2A124.9C15—C14—C13132.0 (2)
C7—N1—C14109.94 (18)N1—C14—C13121.24 (19)
C7—N1—H1A125.0C19—C20—C21120.3 (2)
C14—N1—H1A125.0C19—C20—H20119.8
N2—C7—N1107.27 (19)C21—C20—H20119.8
N2—C7—C6126.7 (2)C13—C8—C9120.9 (3)
N1—C7—C6125.9 (2)C13—C8—H8119.6
C8—C13—C12118.2 (2)C9—C8—H8119.6
C8—C13—C14122.4 (2)O5—N4—O4124.1 (3)
C12—C13—C14119.3 (2)O5—N4—C2118.6 (3)
C21—C16—C17118.6 (2)O4—N4—C2117.3 (3)
C21—C16—C15121.1 (2)C20—C19—C18119.6 (2)
C17—C16—C15120.3 (2)C20—C19—H19120.2
C2—C1—C6118.4 (2)C18—C19—H19120.2
C2—C1—H1120.8C9—C10—C11119.6 (3)
C6—C1—H1120.8C9—C10—H10120.2
C19—C18—C17120.6 (2)C11—C10—H10120.2
C19—C18—H18119.7C3—C4—C5120.7 (3)
C17—C18—H18119.7C3—C4—H4119.6
C14—C15—N2106.10 (19)C5—C4—H4119.6
C14—C15—C16131.6 (2)C13—C12—C11120.7 (3)
N2—C15—C16122.16 (19)C13—C12—H12119.6
C3—C2—C1123.1 (2)C11—C12—H12119.6
C3—C2—N4118.8 (2)C10—C11—C12120.3 (3)
C1—C2—N4118.1 (2)C10—C11—H11119.9
C20—C21—C16120.7 (2)C12—C11—H11119.9
C20—C21—H21119.6C2—C3—C4118.1 (2)
C16—C21—H21119.6C2—C3—H3120.9
C5—C6—C1119.1 (2)C4—C3—H3120.9
C5—C6—C7120.6 (2)C10—C9—C8120.2 (3)
C1—C6—C7120.2 (2)C10—C9—H9119.9
C18—C17—C16120.2 (2)C8—C9—H9119.9
C18—C17—H17119.9

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O3i0.861.932.768 (2)165
N2—H2A···O30.861.882.705 (2)160

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2120).

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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