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

Zhang, Y.

doi:10.1107/S1600536809023599

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1675

doi:10.1107/S1600536809023599

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

Yi Zhang ^a ^*

^aDepartment of Physics, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 27 May 2009; accepted 19 June 2009; online 24 June 2009)

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 ); Fu et al. (2008 ); Huang et al. (2008 ).

Experimental

Crystal data

C₂₁H₁₆N₃O₂⁺·NO₃⁻
M_r = 404.38
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.063
wR(F²) = 0.162
S = 1.04
4443 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.86	1.93	2.768 (2)	165
N2—H2A⋯O3	0.86	1.88	2.705 (2)	160
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023599/im2120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023599/im2120Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

	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.

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

Crystal data top

C₂₁H₁₆N₃O₂⁺·NO₃⁻	F(000) = 840
M_r = 404.38	D_x = 1.387 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4443 reflections
a = 5.870 (1) Å	θ = 3.1–27.5°
b = 12.509 (3) Å	µ = 0.10 mm⁻¹
c = 26.476 (5) Å	T = 298 K
β = 95.06 (3)°	Block, colorless
V = 1936.2 (7) Å³	0.45 × 0.40 × 0.25 mm
Z = 4

Data collection top

Rigaku Mercury2 diffractometer	4443 independent reflections
Radiation source: fine-focus sealed tube	2546 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
CCD profile fitting scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
T_min = 0.949, T_max = 1.000	l = −34→34
19751 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0623P)² + 0.3275P] where P = (F_o² + 2F_c²)/3
4443 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₁₆N₃O₂⁺·NO₃⁻	V = 1936.2 (7) Å³
M_r = 404.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.870 (1) Å	µ = 0.10 mm⁻¹
b = 12.509 (3) Å	T = 298 K
c = 26.476 (5) Å	0.45 × 0.40 × 0.25 mm
β = 95.06 (3)°

Data collection top

Rigaku Mercury2 diffractometer	4443 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2546 reflections with I > 2σ(I)
T_min = 0.949, T_max = 1.000	R_int = 0.085
19751 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
4443 reflections	Δρ_min = −0.22 e Å⁻³
271 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
O3	0.2948 (3)	0.82802 (12)	0.22754 (7)	0.0478 (5)
N3	0.5060 (4)	0.84341 (19)	0.22241 (8)	0.0512 (6)
O2	0.6316 (4)	0.76676 (19)	0.21888 (9)	0.0876 (8)
O1	0.5694 (4)	0.93609 (19)	0.22221 (11)	0.0982 (9)
N2	0.1754 (3)	0.64621 (14)	0.27380 (6)	0.0341 (4)
H2A	0.2441	0.6959	0.2586	0.041*
N1	−0.0446 (3)	0.51473 (14)	0.28709 (7)	0.0354 (5)
H1A	−0.1439	0.4645	0.2819	0.043*
C7	0.0303 (4)	0.57674 (17)	0.25109 (8)	0.0332 (5)
C13	0.0275 (4)	0.47970 (17)	0.37962 (8)	0.0356 (5)
C16	0.3635 (4)	0.68723 (17)	0.35972 (8)	0.0347 (5)
C1	0.1235 (4)	0.60288 (18)	0.16282 (9)	0.0416 (6)
H1	0.2548	0.6404	0.1743	0.050*
C18	0.7179 (4)	0.7836 (2)	0.37476 (11)	0.0490 (7)
H18	0.8493	0.8118	0.3627	0.059*
C15	0.2004 (4)	0.62735 (17)	0.32540 (8)	0.0337 (5)
C2	0.0714 (5)	0.5842 (2)	0.11185 (9)	0.0472 (6)
C21	0.3271 (4)	0.70151 (19)	0.41038 (9)	0.0440 (6)
H21	0.1955	0.6741	0.4227	0.053*
C6	−0.0249 (4)	0.56435 (17)	0.19669 (8)	0.0347 (5)
C17	0.5628 (4)	0.72880 (18)	0.34219 (9)	0.0404 (6)
H17	0.5910	0.7195	0.3085	0.049*
C5	−0.2202 (4)	0.5095 (2)	0.17802 (9)	0.0474 (6)
H5	−0.3215	0.4842	0.2003	0.057*
C14	0.0604 (4)	0.54308 (17)	0.33367 (8)	0.0344 (5)
C20	0.4843 (5)	0.7559 (2)	0.44270 (10)	0.0517 (7)
H20	0.4578	0.7649	0.4766	0.062*
O5	0.3866 (4)	0.6812 (2)	0.09223 (9)	0.0871 (7)
C8	−0.1602 (5)	0.4912 (2)	0.40612 (11)	0.0607 (8)
H8	−0.2725	0.5405	0.3953	0.073*
N4	0.2321 (5)	0.6234 (2)	0.07626 (10)	0.0687 (7)
C19	0.6799 (5)	0.7970 (2)	0.42501 (11)	0.0535 (7)
H19	0.7858	0.8335	0.4468	0.064*
C10	−0.0231 (5)	0.3584 (2)	0.46502 (10)	0.0602 (8)
H10	−0.0386	0.3186	0.4942	0.072*
C4	−0.2650 (5)	0.4923 (2)	0.12670 (10)	0.0581 (8)
H4	−0.3965	0.4555	0.1147	0.070*
O4	0.1968 (5)	0.5963 (2)	0.03177 (9)	0.1162 (10)
C12	0.1888 (5)	0.4055 (2)	0.39616 (11)	0.0652 (9)
H12	0.3178	0.3963	0.3786	0.078*
C11	0.1621 (6)	0.3445 (3)	0.43847 (11)	0.0758 (10)
H11	0.2716	0.2934	0.4489	0.091*
C3	−0.1176 (5)	0.5290 (2)	0.09306 (10)	0.0557 (7)
H3	−0.1459	0.5165	0.0585	0.067*
C9	−0.1853 (5)	0.4305 (3)	0.44881 (11)	0.0700 (9)
H9	−0.3141	0.4392	0.4665	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0438 (10)	0.0367 (9)	0.0637 (12)	−0.0033 (8)	0.0099 (9)	0.0069 (8)
N3	0.0560 (15)	0.0527 (14)	0.0477 (13)	0.0027 (12)	0.0209 (11)	0.0054 (11)
O2	0.0859 (17)	0.0920 (16)	0.0904 (17)	0.0467 (14)	0.0390 (14)	0.0154 (14)
O1	0.0733 (16)	0.0666 (15)	0.161 (3)	−0.0267 (12)	0.0439 (15)	0.0050 (16)
N2	0.0397 (11)	0.0327 (10)	0.0304 (10)	−0.0023 (8)	0.0057 (8)	0.0031 (8)
N1	0.0363 (10)	0.0369 (10)	0.0333 (11)	−0.0043 (8)	0.0041 (8)	0.0007 (9)
C7	0.0347 (12)	0.0315 (11)	0.0335 (12)	−0.0001 (10)	0.0037 (10)	−0.0007 (10)
C13	0.0411 (13)	0.0350 (12)	0.0310 (12)	−0.0011 (10)	0.0039 (10)	0.0015 (10)
C16	0.0391 (13)	0.0318 (12)	0.0330 (13)	0.0041 (10)	0.0024 (10)	0.0015 (10)
C1	0.0480 (14)	0.0373 (13)	0.0398 (14)	−0.0034 (11)	0.0054 (11)	0.0010 (11)
C18	0.0384 (14)	0.0482 (15)	0.0594 (18)	−0.0009 (11)	−0.0009 (12)	0.0042 (14)
C15	0.0374 (12)	0.0338 (12)	0.0303 (12)	0.0027 (10)	0.0047 (9)	0.0006 (10)
C2	0.0637 (17)	0.0449 (15)	0.0339 (14)	−0.0004 (13)	0.0091 (12)	0.0055 (12)
C21	0.0441 (14)	0.0497 (15)	0.0380 (14)	0.0005 (11)	0.0017 (11)	0.0000 (12)
C6	0.0398 (13)	0.0318 (12)	0.0321 (13)	0.0014 (10)	0.0017 (10)	0.0023 (10)
C17	0.0407 (14)	0.0415 (13)	0.0388 (13)	0.0027 (11)	0.0019 (11)	0.0017 (11)
C5	0.0505 (15)	0.0481 (15)	0.0434 (15)	−0.0081 (12)	0.0027 (12)	0.0024 (12)
C14	0.0350 (12)	0.0346 (12)	0.0340 (13)	0.0042 (10)	0.0054 (10)	−0.0003 (10)
C20	0.0612 (18)	0.0568 (17)	0.0352 (14)	0.0056 (14)	−0.0066 (13)	−0.0043 (12)
O5	0.0782 (16)	0.115 (2)	0.0699 (15)	−0.0193 (15)	0.0203 (13)	0.0227 (14)
C8	0.0539 (17)	0.0628 (18)	0.0692 (19)	0.0168 (14)	0.0262 (14)	0.0261 (16)
N4	0.092 (2)	0.0691 (17)	0.0481 (16)	0.0050 (16)	0.0231 (14)	0.0119 (14)
C19	0.0531 (17)	0.0487 (16)	0.0546 (17)	0.0003 (13)	−0.0185 (14)	−0.0015 (14)
C10	0.074 (2)	0.0654 (19)	0.0424 (16)	−0.0017 (16)	0.0105 (14)	0.0163 (14)
C4	0.0692 (19)	0.0573 (17)	0.0449 (16)	−0.0155 (14)	−0.0119 (14)	0.0000 (14)
O4	0.189 (3)	0.121 (2)	0.0462 (15)	−0.029 (2)	0.0507 (16)	−0.0077 (14)
C12	0.0593 (18)	0.087 (2)	0.0529 (18)	0.0242 (16)	0.0230 (14)	0.0262 (16)
C11	0.082 (2)	0.089 (2)	0.0580 (19)	0.0300 (19)	0.0143 (17)	0.0364 (18)
C3	0.082 (2)	0.0526 (16)	0.0315 (14)	0.0005 (15)	0.0004 (13)	−0.0021 (13)
C9	0.068 (2)	0.079 (2)	0.068 (2)	0.0061 (17)	0.0356 (16)	0.0236 (18)

Geometric parameters (Å, º) top

O3—N3	1.273 (3)	C2—N4	1.475 (3)
N3—O1	1.218 (3)	C21—C20	1.381 (4)
N3—O2	1.218 (3)	C21—H21	0.9300
N2—C7	1.323 (3)	C6—C5	1.389 (3)
N2—C15	1.381 (3)	C17—H17	0.9300
N2—H2A	0.8600	C5—C4	1.378 (3)
N1—C7	1.333 (3)	C5—H5	0.9300
N1—C14	1.376 (3)	C20—C19	1.377 (4)
N1—H1A	0.8600	C20—H20	0.9300
C7—C6	1.456 (3)	O5—N4	1.206 (3)
C13—C8	1.365 (3)	C8—C9	1.380 (4)
C13—C12	1.370 (3)	C8—H8	0.9300
C13—C14	1.479 (3)	N4—O4	1.226 (3)
C16—C21	1.388 (3)	C19—H19	0.9300
C16—C17	1.396 (3)	C10—C9	1.353 (4)
C16—C15	1.466 (3)	C10—C11	1.357 (4)
C1—C2	1.377 (3)	C10—H10	0.9300
C1—C6	1.390 (3)	C4—C3	1.374 (4)
C1—H1	0.9300	C4—H4	0.9300
C18—C19	1.378 (4)	C12—C11	1.376 (4)
C18—C17	1.380 (3)	C12—H12	0.9300
C18—H18	0.9300	C11—H11	0.9300
C15—C14	1.366 (3)	C3—H3	0.9300
C2—C3	1.363 (4)	C9—H9	0.9300

O1—N3—O2	124.2 (3)	C16—C17—H17	119.9
O1—N3—O3	116.4 (2)	C4—C5—C6	120.5 (2)
O2—N3—O3	119.4 (2)	C4—C5—H5	119.7
C7—N2—C15	110.19 (18)	C6—C5—H5	119.7
C7—N2—H2A	124.9	C15—C14—N1	106.46 (19)
C15—N2—H2A	124.9	C15—C14—C13	132.0 (2)
C7—N1—C14	109.94 (18)	N1—C14—C13	121.24 (19)
C7—N1—H1A	125.0	C19—C20—C21	120.3 (2)
C14—N1—H1A	125.0	C19—C20—H20	119.8
N2—C7—N1	107.27 (19)	C21—C20—H20	119.8
N2—C7—C6	126.7 (2)	C13—C8—C9	120.9 (3)
N1—C7—C6	125.9 (2)	C13—C8—H8	119.6
C8—C13—C12	118.2 (2)	C9—C8—H8	119.6
C8—C13—C14	122.4 (2)	O5—N4—O4	124.1 (3)
C12—C13—C14	119.3 (2)	O5—N4—C2	118.6 (3)
C21—C16—C17	118.6 (2)	O4—N4—C2	117.3 (3)
C21—C16—C15	121.1 (2)	C20—C19—C18	119.6 (2)
C17—C16—C15	120.3 (2)	C20—C19—H19	120.2
C2—C1—C6	118.4 (2)	C18—C19—H19	120.2
C2—C1—H1	120.8	C9—C10—C11	119.6 (3)
C6—C1—H1	120.8	C9—C10—H10	120.2
C19—C18—C17	120.6 (2)	C11—C10—H10	120.2
C19—C18—H18	119.7	C3—C4—C5	120.7 (3)
C17—C18—H18	119.7	C3—C4—H4	119.6
C14—C15—N2	106.10 (19)	C5—C4—H4	119.6
C14—C15—C16	131.6 (2)	C13—C12—C11	120.7 (3)
N2—C15—C16	122.16 (19)	C13—C12—H12	119.6
C3—C2—C1	123.1 (2)	C11—C12—H12	119.6
C3—C2—N4	118.8 (2)	C10—C11—C12	120.3 (3)
C1—C2—N4	118.1 (2)	C10—C11—H11	119.9
C20—C21—C16	120.7 (2)	C12—C11—H11	119.9
C20—C21—H21	119.6	C2—C3—C4	118.1 (2)
C16—C21—H21	119.6	C2—C3—H3	120.9
C5—C6—C1	119.1 (2)	C4—C3—H3	120.9
C5—C6—C7	120.6 (2)	C10—C9—C8	120.2 (3)
C1—C6—C7	120.2 (2)	C10—C9—H9	119.9
C18—C17—C16	120.2 (2)	C8—C9—H9	119.9
C18—C17—H17	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.86	1.93	2.768 (2)	165
N2—H2A···O3	0.86	1.88	2.705 (2)	160

Symmetry code: (i) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₃O₂⁺·NO₃⁻
M_r	404.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	5.870 (1), 12.509 (3), 26.476 (5)
β (°)	95.06 (3)
V (Å³)	1936.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.40 × 0.25

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.949, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	19751, 4443, 2546
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.162, 1.04
No. of reflections	4443
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.86	1.93	2.768 (2)	164.7
N2—H2A···O3	0.86	1.88	2.705 (2)	159.8

Symmetry code: (i) −x, y−1/2, −z+1/2.

Acknowledgements

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

References

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