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

In the cation of the title compound, C(21)H(16)N(3)O(2) (+)·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 mol-ecules, forming a chain parallel to the b axis.

Related literature

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

Experimental

Crystal data

C21H16N3O2 +·Cl−

M = 377.82

Monoclinic,

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 ▶) 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 ▶); 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, 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

C21H16N3O2+·Cl−	F(000) = 784
Mr = 377.82	Dx = 1.378 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4160 reflections
a = 15.106 (3) Å	θ = 3.1–27.5°
b = 15.837 (3) Å	µ = 0.23 mm−1
c = 7.8833 (16) Å	T = 298 K
β = 105.10 (3)°	Block, colourless
V = 1820.8 (7) Å3	0.45 × 0.40 × 0.25 mm
Z = 4

Rigaku Mercury2 diffractometer	4165 independent reflections
Radiation source: fine-focus sealed tube	2393 reflections with I > 2σ(I)
graphite	Rint = 0.109
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD profile fitting scans	h = −19→19
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
Tmin = 0.910, Tmax = 1.000	l = −10→10
18591 measured reflections

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

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
Cl1	0.50431 (5)	0.90216 (4)	0.28931 (13)	0.0625 (3)
N1	0.57993 (14)	0.72042 (13)	0.2790 (3)	0.0325 (5)
H1A	0.5620	0.7717	0.2840	0.039*
C7	0.52567 (17)	0.65254 (16)	0.2629 (3)	0.0321 (6)
N2	0.57744 (14)	0.58548 (13)	0.2592 (3)	0.0339 (5)
H2A	0.5581	0.5342	0.2501	0.041*
N3	0.14392 (17)	0.65834 (17)	0.2081 (4)	0.0480 (7)
C6	0.42716 (17)	0.65341 (15)	0.2489 (3)	0.0323 (6)
C2	0.27691 (18)	0.59458 (17)	0.1358 (4)	0.0399 (7)
H2	0.2382	0.5540	0.0700	0.048*
C15	0.66881 (17)	0.69658 (16)	0.2865 (3)	0.0307 (6)
C13	0.73980 (17)	0.54725 (16)	0.2772 (3)	0.0320 (6)
C3	0.24275 (18)	0.65705 (17)	0.2217 (4)	0.0370 (7)
C1	0.37003 (18)	0.59320 (16)	0.1493 (4)	0.0389 (7)
H1	0.3944	0.5517	0.0912	0.047*
C14	0.66699 (17)	0.60935 (16)	0.2719 (3)	0.0308 (6)
C18	0.7947 (2)	0.89632 (18)	0.2438 (4)	0.0449 (8)
H18	0.7821	0.9490	0.1908	0.054*
C4	0.29746 (19)	0.71829 (17)	0.3209 (4)	0.0418 (7)
H4	0.2725	0.7601	0.3773	0.050*
O2	0.11287 (15)	0.71883 (15)	0.2695 (4)	0.0696 (7)
C5	0.39062 (19)	0.71577 (17)	0.3342 (4)	0.0404 (7)
H5	0.4291	0.7562	0.4008	0.049*
O1	0.09771 (15)	0.59864 (15)	0.1374 (4)	0.0740 (8)
C16	0.74249 (18)	0.75918 (15)	0.3069 (3)	0.0315 (6)
C17	0.7250 (2)	0.83847 (16)	0.2293 (4)	0.0374 (7)
H17	0.6657	0.8526	0.1671	0.045*
C9	0.8082 (2)	0.41135 (18)	0.3652 (4)	0.0455 (7)
H9	0.8052	0.3581	0.4132	0.055*
C21	0.83144 (18)	0.74111 (17)	0.4041 (4)	0.0387 (7)
H21	0.8441	0.6893	0.4608	0.046*
C12	0.81528 (19)	0.56718 (17)	0.2152 (4)	0.0390 (7)
H12	0.8172	0.6190	0.1606	0.047*
C8	0.73622 (19)	0.46743 (17)	0.3498 (4)	0.0399 (7)
H8	0.6853	0.4518	0.3881	0.048*
C11	0.8874 (2)	0.51169 (19)	0.2330 (4)	0.0497 (8)
H11	0.9381	0.5266	0.1934	0.060*
C20	0.9012 (2)	0.7994 (2)	0.4172 (4)	0.0480 (8)
H20	0.9605	0.7861	0.4812	0.058*
C19	0.8833 (2)	0.8769 (2)	0.3361 (4)	0.0501 (8)
H19	0.9303	0.9157	0.3435	0.060*
C10	0.8841 (2)	0.4339 (2)	0.3099 (4)	0.0517 (8)
H10	0.9331	0.3967	0.3243	0.062*

	U11	U22	U33	U12	U13	U23
Cl1	0.0444 (5)	0.0305 (4)	0.1135 (8)	0.0066 (3)	0.0224 (5)	0.0007 (4)
N1	0.0281 (13)	0.0225 (11)	0.0463 (14)	−0.0003 (9)	0.0087 (11)	−0.0024 (10)
C7	0.0270 (14)	0.0291 (14)	0.0390 (15)	0.0003 (12)	0.0064 (12)	−0.0005 (12)
N2	0.0293 (13)	0.0238 (11)	0.0482 (14)	−0.0043 (9)	0.0095 (10)	−0.0023 (10)
N3	0.0286 (14)	0.0472 (16)	0.0670 (17)	0.0050 (13)	0.0103 (13)	0.0089 (14)
C6	0.0252 (14)	0.0280 (13)	0.0437 (16)	−0.0024 (11)	0.0086 (12)	0.0015 (12)
C2	0.0272 (15)	0.0368 (16)	0.0520 (18)	−0.0064 (12)	0.0038 (13)	−0.0048 (14)
C15	0.0238 (15)	0.0315 (14)	0.0362 (15)	−0.0007 (11)	0.0068 (12)	−0.0010 (12)
C13	0.0274 (15)	0.0293 (14)	0.0388 (15)	0.0003 (11)	0.0076 (12)	−0.0029 (12)
C3	0.0225 (14)	0.0376 (15)	0.0494 (17)	0.0035 (12)	0.0066 (13)	0.0107 (14)
C1	0.0328 (16)	0.0290 (14)	0.0538 (18)	0.0004 (12)	0.0094 (13)	−0.0066 (13)
C14	0.0251 (14)	0.0293 (14)	0.0381 (15)	−0.0044 (11)	0.0084 (12)	−0.0005 (12)
C18	0.059 (2)	0.0314 (15)	0.0494 (18)	−0.0075 (15)	0.0227 (16)	−0.0027 (14)
C4	0.0341 (17)	0.0382 (16)	0.0564 (19)	0.0021 (13)	0.0175 (14)	−0.0052 (14)
O2	0.0399 (14)	0.0615 (15)	0.112 (2)	0.0115 (12)	0.0282 (14)	−0.0054 (14)
C5	0.0333 (17)	0.0343 (15)	0.0530 (18)	−0.0049 (12)	0.0102 (14)	−0.0111 (14)
O1	0.0313 (13)	0.0674 (16)	0.118 (2)	−0.0119 (12)	0.0094 (13)	−0.0165 (16)
C16	0.0311 (15)	0.0285 (13)	0.0371 (15)	−0.0045 (11)	0.0129 (12)	−0.0038 (12)
C17	0.0371 (17)	0.0324 (14)	0.0428 (16)	−0.0011 (12)	0.0109 (13)	−0.0009 (13)
C9	0.0491 (19)	0.0328 (15)	0.0538 (19)	0.0065 (14)	0.0122 (15)	0.0061 (14)
C21	0.0314 (16)	0.0374 (15)	0.0459 (17)	−0.0038 (13)	0.0072 (13)	−0.0037 (13)
C12	0.0386 (17)	0.0328 (15)	0.0484 (18)	−0.0005 (13)	0.0166 (14)	0.0022 (13)
C8	0.0364 (17)	0.0351 (15)	0.0496 (18)	0.0017 (13)	0.0139 (14)	0.0021 (13)
C11	0.0343 (17)	0.0530 (19)	0.067 (2)	0.0031 (15)	0.0235 (16)	−0.0019 (17)
C20	0.0266 (16)	0.054 (2)	0.060 (2)	−0.0079 (14)	0.0054 (14)	−0.0087 (16)
C19	0.047 (2)	0.0476 (18)	0.063 (2)	−0.0217 (15)	0.0264 (17)	−0.0146 (16)
C10	0.0420 (19)	0.0477 (19)	0.064 (2)	0.0179 (15)	0.0107 (16)	0.0036 (16)

N1—C7	1.338 (3)	C18—C19	1.380 (4)
N1—C15	1.381 (3)	C18—H18	0.93
N1—H1A	0.86	C4—C5	1.384 (4)
C7—N2	1.324 (3)	C4—H4	0.93
C7—C6	1.463 (4)	C5—H5	0.93
N2—C14	1.383 (3)	C16—C17	1.392 (3)
N2—H2A	0.86	C16—C21	1.392 (4)
N3—O1	1.220 (3)	C17—H17	0.9300
N3—O2	1.221 (3)	C9—C10	1.375 (4)
N3—C3	1.469 (4)	C9—C8	1.384 (4)
C6—C1	1.385 (4)	C9—H9	0.93
C6—C5	1.388 (4)	C21—C20	1.384 (4)
C2—C3	1.373 (4)	C21—H21	0.93
C2—C1	1.383 (4)	C12—C11	1.378 (4)
C2—H2	0.93	C12—H12	0.93
C15—C14	1.386 (3)	C8—H8	0.93
C15—C16	1.468 (3)	C11—C10	1.379 (4)
C13—C12	1.389 (4)	C11—H11	0.93
C13—C8	1.395 (4)	C20—C19	1.378 (4)
C13—C14	1.468 (3)	C20—H20	0.93
C3—C4	1.378 (4)	C19—H19	0.93
C1—H1	0.93	C10—H10	0.93
C18—C17	1.378 (4)
C7—N1—C15	110.4 (2)	C3—C4—C5	118.1 (3)
C7—N1—H1A	124.8	C3—C4—H4	121.0
C15—N1—H1A	124.8	C5—C4—H4	121.0
N2—C7—N1	107.2 (2)	C4—C5—C6	120.6 (3)
N2—C7—C6	126.9 (2)	C4—C5—H5	119.7
N1—C7—C6	125.8 (2)	C6—C5—H5	119.7
C7—N2—C14	110.6 (2)	C17—C16—C21	118.2 (2)
C7—N2—H2A	124.7	C17—C16—C15	120.6 (2)
C14—N2—H2A	124.7	C21—C16—C15	121.1 (2)
O1—N3—O2	123.8 (3)	C18—C17—C16	120.6 (3)
O1—N3—C3	118.2 (3)	C18—C17—H17	119.7
O2—N3—C3	118.0 (3)	C16—C17—H17	119.7
C1—C6—C5	119.8 (2)	C10—C9—C8	120.4 (3)
C1—C6—C7	120.5 (2)	C10—C9—H9	119.8
C5—C6—C7	119.7 (2)	C8—C9—H9	119.8
C3—C2—C1	118.6 (2)	C20—C21—C16	120.7 (3)
C3—C2—H2	120.7	C20—C21—H21	119.6
C1—C2—H2	120.7	C16—C21—H21	119.6
N1—C15—C14	105.7 (2)	C11—C12—C13	121.2 (3)
N1—C15—C16	121.4 (2)	C11—C12—H12	119.4
C14—C15—C16	132.9 (2)	C13—C12—H12	119.4
C12—C13—C8	118.3 (2)	C9—C8—C13	120.3 (3)
C12—C13—C14	121.0 (2)	C9—C8—H8	119.9
C8—C13—C14	120.7 (2)	C13—C8—H8	119.9
C2—C3—C4	122.7 (3)	C12—C11—C10	119.8 (3)
C2—C3—N3	118.7 (3)	C12—C11—H11	120.1
C4—C3—N3	118.7 (3)	C10—C11—H11	120.1
C2—C1—C6	120.2 (3)	C19—C20—C21	120.4 (3)
C2—C1—H1	119.9	C19—C20—H20	119.8
C6—C1—H1	119.9	C21—C20—H20	119.8
N2—C14—C15	106.0 (2)	C20—C19—C18	119.3 (3)
N2—C14—C13	122.0 (2)	C20—C19—H19	120.3
C15—C14—C13	131.8 (2)	C18—C19—H19	120.3
C17—C18—C19	120.6 (3)	C9—C10—C11	120.0 (3)
C17—C18—H18	119.7	C9—C10—H10	120.0
C19—C18—H18	119.7	C11—C10—H10	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.86	2.25	3.105 (2)	176
N2—H2A···Cl1i	0.86	2.28	3.139 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	0.86	2.25	3.105 (2)	176
N2—H2A⋯Cl1i	0.86	2.28	3.139 (2)	175

Symmetry code: (i) .