Crystal structure of 1-[(1-methyl-5-nitro-1H-imidazol-2-yl)meth-yl]pyridinium iodide.

In the title salt, C10H11N4O2 (+)·I(-), the asymmetric unit consists of a pyridinium cation bearning a (1-methyl-5-nitro-1H-imidazol-2-yl)methyl group at the N position and an iodide anion. The imidazole ring is quasiplanar, with a maxiumum deviation of 0.0032 (16) Å, and forms a dihedral angle of 67.39 (6)° with the plane of the pyridinium ring. The crystal packing can be described as alternating zigzag layers of cations parallel to the (001) plane, which are sandwiched by the iodide ions. The structure features two types of hydrogen bonds (C-H⋯O and C-H⋯I), viz. cation-anion and cation-cation, which lead to the form ation of a three-dimensional network.

Related literature

For the synthesis and applications of imidazole derivatives, see: Upcroft & Upcroft (2001 ▸); Çelik & Ateş (2006 ▸); Boyer (1986 ▸); Olender et al. (2009 ▸); Gaonkar et al. (2009 ▸); Larina & Lopyrev (2009 ▸). For our previous work on this type of chemistry, see: Zama et al. (2013 ▸); Alliouche et al. (2014 ▸); Bahnous et al. (2012 ▸). For the synthesis of the title compound, see: Albright & Shepherd (1973 ▸).

Experimental

Crystal data

C10H11N4O2 +·I−

M = 346.13

Monoclinic,

a = 11.035 (7) Å

b = 9.073 (6) Å

c = 12.859 (8) Å

β = 91.69 (2)°

V = 1286.8 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.49 mm−1

T = 295 K

0.14 × 0.12 × 0.11 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▸) T min = 0.615, T max = 0.745

22502 measured reflections

6134 independent reflections

3669 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.067

S = 0.99

6134 reflections

155 parameters

H-atom parameters constrained

Δρmax = 1.14 e Å−3

Δρmin = −0.89 e Å−3

Data collection: APEX2 (Bruker, 2011 ▸); cell refinement: SAINT (Bruker, 2011 ▸); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and DIAMOND (Brandenburg, 2006 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015001541/hg5425sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001541/hg5425Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015001541/hg5425Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015001541/hg5425fig1.tif

(Farrugia, 2012). The mol­ecule structure of the title compound with the atomic labelling scheme. Displacement are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.

Click here for additional data file.

via a . DOI: 10.1107/S2056989015001541/hg5425fig2.tif

(Brandenburg, 2006). Alternating layers parallel to (001) plane of (I) sandwiched by iodide ions viewed via a axis

Click here for additional data file.

via b . DOI: 10.1107/S2056989015001541/hg5425fig3.tif

(Brandenburg, 2006). Crystal packing of (I) viewed via b axis showing hydrogen bond as dashed lines [C—H⋯I in red and C—H⋯O in black]

CCDC reference: 1045139

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H11N4O2+·I−	F(000) = 672
Mr = 346.13	Dx = 1.787 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.035 (7) Å	Cell parameters from 6343 reflections
b = 9.073 (6) Å	θ = 2.8–29.3°
c = 12.859 (8) Å	µ = 2.49 mm−1
β = 91.69 (2)°	T = 295 K
V = 1286.8 (14) Å3	Prism, colorless
Z = 4	0.14 × 0.12 × 0.11 mm

Bruker APEXII diffractometer	6134 independent reflections
Radiation source: Enraf–Nonius FR590	3669 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
CCD rotation images, thick slices scans	θmax = 36.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −18→17
Tmin = 0.615, Tmax = 0.745	k = −14→14
22502 measured reflections	l = −21→21

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0275P)2] where P = (Fo2 + 2Fc2)/3
6134 reflections	(Δ/σ)max = 0.006
155 parameters	Δρmax = 1.14 e Å−3
0 restraints	Δρmin = −0.89 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
C1	0.53170 (14)	−0.02548 (17)	0.12964 (12)	0.0288 (3)
C2	0.75852 (17)	−0.0764 (2)	0.10429 (18)	0.0469 (5)
H2A	0.8317	−0.0235	0.1217	0.07*
H2B	0.755	−0.0965	0.031	0.07*
H2C	0.7577	−0.1676	0.1421	0.07*
C3	0.65440 (15)	0.15859 (18)	0.15888 (12)	0.0299 (3)
C4	0.46650 (16)	0.09581 (18)	0.15569 (14)	0.0361 (4)
H4	0.3826	0.0995	0.1603	0.043*
C5	0.76681 (16)	0.25171 (19)	0.16974 (12)	0.0353 (4)
H5A	0.7584	0.3202	0.227	0.042*
H5B	0.8361	0.189	0.1855	0.042*
C6	0.87603 (16)	0.2915 (2)	0.01029 (14)	0.0458 (4)
H6	0.9214	0.2079	0.0268	0.055*
C7	0.8991 (2)	0.3696 (3)	−0.07726 (17)	0.0563 (5)
H7	0.9604	0.3395	−0.1206	0.068*
C8	0.8319 (3)	0.4928 (3)	−0.10157 (16)	0.0633 (6)
H8	0.8489	0.5479	−0.1603	0.076*
C9	0.7398 (3)	0.5340 (2)	−0.03922 (18)	0.0698 (7)
H9	0.6922	0.6156	−0.0562	0.084*
C10	0.7181 (2)	0.4539 (2)	0.04885 (16)	0.0520 (5)
H10	0.6556	0.481	0.092	0.062*
N1	0.48460 (14)	−0.16821 (16)	0.10430 (11)	0.0361 (3)
N2	0.65316 (11)	0.01303 (14)	0.13202 (9)	0.0278 (3)
N3	0.54387 (13)	0.21140 (15)	0.17398 (11)	0.0377 (3)
N4	0.78797 (12)	0.33517 (15)	0.07265 (10)	0.0323 (3)
O1	0.37309 (12)	−0.17941 (15)	0.09568 (11)	0.0516 (3)
O2	0.55464 (14)	−0.27106 (14)	0.09207 (13)	0.0594 (4)
I1	1.107377 (10)	0.089936 (13)	0.189052 (9)	0.04248 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0291 (8)	0.0313 (8)	0.0262 (7)	−0.0053 (6)	0.0025 (6)	0.0001 (6)
C2	0.0322 (10)	0.0468 (11)	0.0620 (12)	0.0067 (8)	0.0072 (9)	−0.0108 (9)
C3	0.0317 (8)	0.0315 (8)	0.0268 (7)	−0.0030 (6)	0.0042 (6)	0.0000 (6)
C4	0.0269 (8)	0.0405 (9)	0.0412 (9)	−0.0011 (7)	0.0070 (7)	−0.0027 (7)
C5	0.0376 (9)	0.0392 (9)	0.0291 (7)	−0.0098 (7)	0.0012 (7)	0.0012 (7)
C6	0.0322 (9)	0.0637 (12)	0.0416 (10)	−0.0018 (9)	0.0049 (8)	0.0067 (9)
C7	0.0492 (12)	0.0784 (15)	0.0417 (10)	−0.0130 (11)	0.0102 (9)	0.0030 (11)
C8	0.1028 (19)	0.0505 (12)	0.0368 (10)	−0.0304 (13)	0.0066 (11)	0.0034 (10)
C9	0.123 (2)	0.0316 (10)	0.0558 (13)	0.0119 (12)	0.0106 (14)	0.0052 (11)
C10	0.0778 (16)	0.0293 (8)	0.0498 (11)	0.0068 (10)	0.0161 (10)	−0.0007 (9)
N1	0.0418 (9)	0.0356 (7)	0.0311 (7)	−0.0086 (6)	0.0038 (6)	−0.0016 (6)
N2	0.0259 (7)	0.0309 (7)	0.0267 (6)	0.0000 (5)	0.0039 (5)	0.0005 (5)
N3	0.0354 (8)	0.0333 (7)	0.0449 (8)	−0.0005 (6)	0.0095 (6)	−0.0049 (6)
N4	0.0349 (8)	0.0312 (7)	0.0310 (6)	−0.0096 (6)	0.0028 (6)	−0.0037 (6)
O1	0.0413 (8)	0.0544 (8)	0.0589 (8)	−0.0164 (6)	−0.0041 (6)	−0.0063 (7)
O2	0.0606 (9)	0.0336 (7)	0.0847 (11)	−0.0003 (7)	0.0177 (8)	−0.0112 (7)
I1	0.03084 (7)	0.04881 (8)	0.04816 (8)	0.00945 (5)	0.00730 (5)	0.00972 (5)

C1—C4	1.362 (2)	C5—H5B	0.97
C1—N2	1.385 (2)	C6—N4	1.338 (2)
C1—N1	1.429 (2)	C6—C7	1.360 (3)
C2—N2	1.470 (2)	C6—H6	0.93
C2—H2A	0.96	C7—C8	1.373 (3)
C2—H2B	0.96	C7—H7	0.93
C2—H2C	0.96	C8—C9	1.365 (4)
C3—N3	1.330 (2)	C8—H8	0.93
C3—N2	1.365 (2)	C9—C10	1.373 (3)
C3—C5	1.504 (2)	C9—H9	0.93
C4—N3	1.368 (2)	C10—N4	1.355 (2)
C4—H4	0.93	C10—H10	0.93
C5—N4	1.484 (2)	N1—O2	1.225 (2)
C5—H5A	0.97	N1—O1	1.236 (2)
C4—C1—N2	107.98 (14)	C7—C6—H6	120
C4—C1—N1	126.65 (15)	C6—C7—C8	119.9 (2)
N2—C1—N1	125.37 (14)	C6—C7—H7	120
N2—C2—H2A	109.5	C8—C7—H7	120
N2—C2—H2B	109.5	C9—C8—C7	119.7 (2)
H2A—C2—H2B	109.5	C9—C8—H8	120.1
N2—C2—H2C	109.5	C7—C8—H8	120.1
H2A—C2—H2C	109.5	C8—C9—C10	119.4 (2)
H2B—C2—H2C	109.5	C8—C9—H9	120.3
N3—C3—N2	112.53 (14)	C10—C9—H9	120.3
N3—C3—C5	122.78 (15)	N4—C10—C9	119.7 (2)
N2—C3—C5	124.69 (15)	N4—C10—H10	120.2
C1—C4—N3	109.28 (16)	C9—C10—H10	120.2
C1—C4—H4	125.4	O2—N1—O1	123.78 (15)
N3—C4—H4	125.4	O2—N1—C1	119.53 (15)
N4—C5—C3	110.99 (13)	O1—N1—C1	116.69 (15)
N4—C5—H5A	109.4	C3—N2—C1	104.61 (13)
C3—C5—H5A	109.4	C3—N2—C2	126.38 (14)
N4—C5—H5B	109.4	C1—N2—C2	128.85 (14)
C3—C5—H5B	109.4	C3—N3—C4	105.60 (14)
H5A—C5—H5B	108	C6—N4—C10	121.25 (16)
N4—C6—C7	119.9 (2)	C6—N4—C5	119.21 (15)
N4—C6—H6	120	C10—N4—C5	119.53 (15)
N2—C1—C4—N3	0.4 (2)	C5—C3—N2—C2	−3.1 (2)
N1—C1—C4—N3	−179.70 (15)	C4—C1—N2—C3	−0.60 (17)
N3—C3—C5—N4	−83.61 (19)	N1—C1—N2—C3	179.51 (14)
N2—C3—C5—N4	95.79 (18)	C4—C1—N2—C2	−176.19 (17)
N4—C6—C7—C8	−0.1 (3)	N1—C1—N2—C2	3.9 (3)
C6—C7—C8—C9	−1.8 (3)	N2—C3—N3—C4	−0.35 (19)
C7—C8—C9—C10	1.9 (4)	C5—C3—N3—C4	179.12 (15)
C8—C9—C10—N4	−0.1 (4)	C1—C4—N3—C3	−0.1 (2)
C4—C1—N1—O2	−173.00 (17)	C7—C6—N4—C10	2.1 (3)
N2—C1—N1—O2	6.9 (2)	C7—C6—N4—C5	−177.91 (17)
C4—C1—N1—O1	7.2 (2)	C9—C10—N4—C6	−2.0 (3)
N2—C1—N1—O1	−172.89 (15)	C9—C10—N4—C5	178.00 (19)
N3—C3—N2—C1	0.59 (17)	C3—C5—N4—C6	−105.28 (18)
C5—C3—N2—C1	−178.86 (14)	C3—C5—N4—C10	74.8 (2)
N3—C3—N2—C2	176.33 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···O2	0.96	2.50	2.861 (3)	102
C10—H10···O2i	0.93	2.51	3.138 (3)	125
C5—H5A···I1ii	0.97	3.04	3.807 (3)	137
C7—H7···I1iii	0.93	3.04	3.854 (3)	147

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C10H10O2i	0.93	2.51	3.138(3)	125
C5H5AI1ii	0.97	3.04	3.807(3)	137
C7H7I1iii	0.93	3.04	3.854(3)	147

Symmetry codes: (i) ; (ii) ; (iii) .