2-(3-Nitro-phen-yl)-4,5-diphenyl-1H-imidazol-3-ium nitrate.

In the cation of the title compound, C(21)H(16)N(3)O(2) (+)·NO(3) (-), 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 mol-ecules, 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 = 404.38

Monoclinic,

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[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 ▶); 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.

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

C21H16N3O2+·NO3−	F(000) = 840
Mr = 404.38	Dx = 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

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

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 = 1.03	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.3275P] where P = (Fo2 + 2Fc2)/3
4443 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .