1,2-Di­methyl-3-(2-nitro­phenyl)-4,5-di­hydro­imidazolium iodide

In the crystal structure of the title compound, C₁₁H₁₄N₃O₂⁺·I⁻, intermolecular C—H...O and C—H...I hydrogen bonds link the ions into a three-dimensional structure. The imidazolinium ring is planar within 0.0502 (2) Å. The dihedral angle of the imidazolinium plane and the benzene ring plane is 78.45 (7)°.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.021
• wR factor = 0.054
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: SMART (Bruker,2000); cell refinement: SMART; data reduction: SHELXTL (Bruker,2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,2-Dimethyl-3-(2-nitrophenyl)-4,5-dihydroimidazolium iodide

Crystal data

C11H14IN3O2	F(000) = 680
Mr = 347.15	Dx = 1.758 Mg m^−3
Monoclinic, P21/c	Melting point: 517 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.597 (2) Å	Cell parameters from 3981 reflections
b = 10.090 (2) Å	θ = 2.5–27.3°
c = 13.577 (3) Å	µ = 2.44 mm^−1
β = 94.187 (2)°	T = 183 K
V = 1311.3 (5) Å^3	Block, yellow
Z = 4	0.40 × 0.40 × 0.30 mm

Data collection

Bruker CCD area-detector diffractometer	2304 independent reflections
Radiation source: fine-focus sealed tube	2123 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 100x100 microns pixels mm^-1	θmax = 25.0°, θmin = 2.1°
ω scans	h = −11→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −5→12
Tmin = 0.403, Tmax = 0.481	l = −16→15
4370 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.054	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0289P)^2 + 0.5719P] where P = (Fo^2 + 2Fc^2)/3
2304 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.194882 (19)	0.078500 (16)	0.335354 (12)	0.03786 (8)
O1	0.3568 (2)	0.32925 (19)	0.52629 (14)	0.0516 (5)
O2	0.4367 (2)	0.42986 (18)	0.40114 (15)	0.0452 (5)
N1	0.3526 (3)	0.41841 (19)	0.46588 (16)	0.0356 (5)
N2	0.2325 (2)	0.56138 (19)	0.29049 (15)	0.0320 (5)
N3	0.3248 (2)	0.57686 (19)	0.14932 (15)	0.0312 (5)
C1	0.2450 (2)	0.5208 (2)	0.47116 (17)	0.0296 (5)
C2	0.1970 (3)	0.5450 (3)	0.56297 (18)	0.0355 (6)
H2	0.2293	0.4933	0.6185	0.043*
C3	0.1010 (3)	0.6459 (3)	0.57273 (19)	0.0415 (6)
H3	0.0687	0.6648	0.6357	0.050*
C4	0.0522 (3)	0.7188 (3)	0.4920 (2)	0.0433 (6)
H4	−0.0131	0.7882	0.4994	0.052*
C5	0.0982 (3)	0.6913 (3)	0.3994 (2)	0.0392 (6)
H5	0.0625	0.7407	0.3436	0.047*
C6	0.1954 (3)	0.5925 (2)	0.38803 (18)	0.0296 (5)
C7	0.1728 (3)	0.4450 (2)	0.23538 (19)	0.0370 (6)
H7A	0.0694	0.4458	0.2323	0.044*
H7B	0.2074	0.3608	0.2655	0.044*
C8	0.2265 (3)	0.4654 (3)	0.1335 (2)	0.0420 (6)
H8A	0.2746	0.3852	0.1114	0.050*
H8B	0.1493	0.4883	0.0841	0.050*
C9	0.3208 (2)	0.6270 (2)	0.23788 (17)	0.0282 (5)
C10	0.4048 (3)	0.7413 (3)	0.27611 (18)	0.0379 (6)
H10A	0.4842	0.7543	0.2356	0.057*
H10B	0.4394	0.7241	0.3446	0.057*
H10C	0.3466	0.8212	0.2734	0.057*
C11	0.4027 (3)	0.6290 (3)	0.06906 (19)	0.0409 (6)
H11A	0.4036	0.7260	0.0719	0.061*
H11B	0.3578	0.6002	0.0055	0.061*
H11C	0.4988	0.5956	0.0760	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.04885 (14)	0.03393 (12)	0.03047 (11)	0.00265 (7)	0.00072 (8)	−0.00157 (6)
O1	0.0710 (15)	0.0378 (11)	0.0442 (11)	0.0075 (10)	−0.0068 (10)	0.0110 (9)
O2	0.0395 (11)	0.0512 (12)	0.0454 (11)	0.0097 (9)	0.0067 (9)	−0.0020 (8)
N1	0.0451 (14)	0.0286 (11)	0.0325 (12)	0.0023 (9)	−0.0011 (10)	−0.0007 (9)
N2	0.0419 (13)	0.0300 (11)	0.0242 (10)	−0.0057 (9)	0.0036 (9)	−0.0011 (8)
N3	0.0337 (12)	0.0318 (12)	0.0282 (11)	−0.0022 (8)	0.0035 (9)	−0.0039 (8)
C1	0.0305 (13)	0.0291 (12)	0.0291 (12)	−0.0039 (10)	0.0011 (10)	0.0016 (10)
C2	0.0392 (15)	0.0394 (14)	0.0278 (12)	−0.0086 (12)	0.0025 (11)	0.0038 (10)
C3	0.0415 (16)	0.0492 (16)	0.0356 (14)	−0.0094 (13)	0.0145 (12)	−0.0088 (12)
C4	0.0409 (15)	0.0439 (16)	0.0456 (16)	0.0058 (12)	0.0062 (12)	−0.0058 (12)
C5	0.0409 (15)	0.0382 (14)	0.0382 (14)	0.0070 (12)	0.0011 (11)	0.0045 (11)
C6	0.0330 (13)	0.0307 (13)	0.0250 (12)	−0.0040 (10)	0.0025 (10)	0.0006 (9)
C7	0.0471 (16)	0.0294 (13)	0.0345 (14)	−0.0072 (11)	0.0024 (12)	−0.0017 (10)
C8	0.0550 (18)	0.0366 (14)	0.0345 (14)	−0.0096 (13)	0.0036 (12)	−0.0078 (11)
C9	0.0300 (13)	0.0272 (11)	0.0271 (12)	0.0048 (10)	0.0004 (9)	0.0014 (10)
C10	0.0413 (15)	0.0376 (14)	0.0347 (13)	−0.0087 (12)	0.0029 (11)	−0.0034 (11)
C11	0.0415 (15)	0.0508 (16)	0.0320 (13)	−0.0016 (13)	0.0129 (11)	−0.0062 (12)

Geometric parameters (Å, º)

O1—N1	1.216 (3)	C4—H4	0.9500
O2—N1	1.241 (3)	C5—C6	1.381 (4)
N1—C1	1.466 (3)	C5—H5	0.9500
N2—C9	1.325 (3)	C7—C8	1.525 (4)
N2—C6	1.431 (3)	C7—H7A	0.9900
N2—C7	1.485 (3)	C7—H7B	0.9900
N3—C9	1.307 (3)	C8—H8A	0.9900
N3—C11	1.464 (3)	C8—H8B	0.9900
N3—C8	1.473 (3)	C9—C10	1.480 (3)
C1—C2	1.382 (3)	C10—H10A	0.9800
C1—C6	1.395 (3)	C10—H10B	0.9800
C2—C3	1.385 (4)	C10—H10C	0.9800
C2—H2	0.9500	C11—H11A	0.9800
C3—C4	1.374 (4)	C11—H11B	0.9800
C3—H3	0.9500	C11—H11C	0.9800
C4—C5	1.390 (4)
O1—N1—O2	123.7 (2)	N2—C7—C8	101.9 (2)
O1—N1—C1	118.5 (2)	N2—C7—H7A	111.4
O2—N1—C1	117.76 (19)	C8—C7—H7A	111.4
C9—N2—C6	127.0 (2)	N2—C7—H7B	111.4
C9—N2—C7	111.2 (2)	C8—C7—H7B	111.4
C6—N2—C7	121.8 (2)	H7A—C7—H7B	109.2
C9—N3—C11	126.6 (2)	N3—C8—C7	103.1 (2)
C9—N3—C8	111.6 (2)	N3—C8—H8A	111.1
C11—N3—C8	121.5 (2)	C7—C8—H8A	111.1
C2—C1—C6	121.4 (2)	N3—C8—H8B	111.1
C2—C1—N1	116.8 (2)	C7—C8—H8B	111.1
C6—C1—N1	121.7 (2)	H8A—C8—H8B	109.1
C1—C2—C3	118.9 (2)	N3—C9—N2	111.4 (2)
C1—C2—H2	120.5	N3—C9—C10	124.9 (2)
C3—C2—H2	120.5	N2—C9—C10	123.6 (2)
C4—C3—C2	120.5 (2)	C9—C10—H10A	109.5
C4—C3—H3	119.8	C9—C10—H10B	109.5
C2—C3—H3	119.8	H10A—C10—H10B	109.5
C3—C4—C5	120.2 (3)	C9—C10—H10C	109.5
C3—C4—H4	119.9	H10A—C10—H10C	109.5
C5—C4—H4	119.9	H10B—C10—H10C	109.5
C6—C5—C4	120.5 (2)	N3—C11—H11A	109.5
C6—C5—H5	119.8	N3—C11—H11B	109.5
C4—C5—H5	119.8	H11A—C11—H11B	109.5
C5—C6—C1	118.5 (2)	N3—C11—H11C	109.5
C5—C6—N2	118.5 (2)	H11A—C11—H11C	109.5
C1—C6—N2	122.8 (2)	H11B—C11—H11C	109.5
O1—N1—C1—C2	27.5 (3)	C7—N2—C6—C5	−100.5 (3)
O2—N1—C1—C2	−150.7 (2)	C9—N2—C6—C1	−105.2 (3)
O1—N1—C1—C6	−153.9 (2)	C7—N2—C6—C1	74.5 (3)
O2—N1—C1—C6	27.9 (3)	C9—N2—C7—C8	−7.9 (3)
C6—C1—C2—C3	−2.2 (4)	C6—N2—C7—C8	172.4 (2)
N1—C1—C2—C3	176.4 (2)	C9—N3—C8—C7	−6.7 (3)
C1—C2—C3—C4	1.3 (4)	C11—N3—C8—C7	179.3 (2)
C2—C3—C4—C5	0.4 (4)	N2—C7—C8—N3	8.2 (3)
C3—C4—C5—C6	−1.4 (4)	C11—N3—C9—N2	175.5 (2)
C4—C5—C6—C1	0.6 (4)	C8—N3—C9—N2	1.9 (3)
C4—C5—C6—N2	175.7 (2)	C11—N3—C9—C10	−5.2 (4)
C2—C1—C6—C5	1.2 (4)	C8—N3—C9—C10	−178.8 (2)
N1—C1—C6—C5	−177.3 (2)	C6—N2—C9—N3	−176.2 (2)
C2—C1—C6—N2	−173.7 (2)	C7—N2—C9—N3	4.1 (3)
N1—C1—C6—N2	7.7 (4)	C6—N2—C9—C10	4.5 (4)
C9—N2—C6—C5	79.9 (4)	C7—N2—C9—C10	−175.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···I1^i	0.99	2.95	3.833 (3)	148
C11—H11A···O2^ii	0.98	2.58	3.416 (4)	143
C7—H7B···I1	0.99	3.01	3.940 (3)	157

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