Iodo­metronidazole

In the title compound, 1-(2-iodo­ethyl)-2-methyl-5-nitro-1H-imidazole, C₆H₈IN₃O₂, the dihedral angle between the imidazole ring and the nitro group attached to it is 7.8 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.039
• wR factor = 0.104
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT230_ALERT_2_B Hirshfeld Test Diff for    I1     -   C6      ..       7.44 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C5      ..       6.28 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.04
PLAT431_ALERT_2_C Short Inter HL..A Contact  I1     ..  O2      ..       3.41 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART'; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1-(2-iodoethyl)-2-methyl-5-nitro-1H-imidazole

Crystal data

C6H8IN3O2	Z = 2
Mr = 281.05	F(000) = 268
Triclinic, P1	Dx = 2.039 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.192 (3) Å	Cell parameters from 1310 reflections
b = 7.740 (3) Å	θ = 6.1–25.8°
c = 10.001 (4) Å	µ = 3.46 mm^−1
α = 89.073 (6)°	T = 298 K
β = 86.903 (6)°	Prism, pale yellow
γ = 73.097 (6)°	0.40 × 0.35 × 0.35 mm
V = 457.9 (3) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	1553 independent reflections
Radiation source: fine-focus sealed tube	1410 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.265, Tmax = 0.298	k = −7→9
2006 measured reflections	l = −10→11

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 1.1805P] where P = (Fo^2 + 2Fc^2)/3
1553 reflections	(Δ/σ)max = 0.004
110 parameters	Δρmax = 0.94 e Å^−3
0 restraints	Δρmin = −0.88 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	0.35079 (7)	0.78709 (6)	0.48668 (4)	0.0764 (2)
C1	−0.2485 (9)	0.7410 (7)	0.1442 (5)	0.0493 (12)
O1	0.0792 (9)	0.1550 (6)	0.1691 (6)	0.0806 (13)
N2	−0.3651 (7)	0.6482 (7)	0.0827 (5)	0.0559 (11)
N1	−0.0618 (8)	0.6305 (6)	0.1987 (5)	0.0531 (11)
O2	0.2355 (10)	0.3092 (7)	0.2881 (6)	0.103 (2)
C2	−0.2521 (9)	0.4735 (8)	0.1011 (5)	0.0525 (13)
H4	−0.2948	0.3769	0.0688	0.063*
N3	0.0929 (9)	0.2976 (6)	0.2133 (5)	0.0616 (12)
C3	−0.0688 (9)	0.4570 (7)	0.1727 (5)	0.0492 (12)
C4	−0.3122 (12)	0.9402 (8)	0.1500 (7)	0.0704 (17)
H1A	−0.2274	0.9841	0.0813	0.106*
H1B	−0.2799	0.9771	0.2361	0.106*
H1C	−0.4708	0.9888	0.1366	0.106*
C5	0.1260 (11)	0.6920 (9)	0.2550 (6)	0.0648 (15)
H11A	0.2720	0.6076	0.2306	0.078*
H11B	0.1235	0.8102	0.2202	0.078*
C6	0.0857 (13)	0.6992 (11)	0.4026 (7)	0.0770 (18)
H10A	0.0879	0.5809	0.4371	0.092*
H10B	−0.0608	0.7832	0.4266	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0749 (3)	0.0771 (4)	0.0824 (4)	−0.0232 (2)	−0.0375 (2)	−0.0180 (2)
C1	0.051 (3)	0.045 (3)	0.052 (3)	−0.010 (2)	−0.014 (2)	−0.006 (2)
O1	0.091 (3)	0.045 (2)	0.108 (4)	−0.020 (2)	−0.018 (3)	−0.007 (2)
N2	0.047 (2)	0.060 (3)	0.064 (3)	−0.019 (2)	−0.018 (2)	−0.013 (2)
N1	0.055 (2)	0.045 (2)	0.063 (3)	−0.015 (2)	−0.024 (2)	−0.007 (2)
O2	0.114 (4)	0.060 (3)	0.127 (5)	0.000 (3)	−0.078 (4)	−0.010 (3)
C2	0.050 (3)	0.059 (3)	0.056 (3)	−0.027 (3)	−0.008 (2)	−0.010 (2)
N3	0.068 (3)	0.044 (3)	0.072 (3)	−0.013 (2)	−0.017 (3)	−0.004 (2)
C3	0.053 (3)	0.045 (3)	0.052 (3)	−0.015 (2)	−0.010 (2)	−0.006 (2)
C4	0.078 (4)	0.048 (3)	0.082 (4)	−0.008 (3)	−0.030 (3)	−0.010 (3)
C5	0.066 (4)	0.064 (4)	0.065 (4)	−0.019 (3)	−0.004 (3)	−0.003 (3)
C6	0.083 (4)	0.084 (5)	0.069 (4)	−0.033 (4)	0.005 (3)	−0.014 (3)

Geometric parameters (Å, º)

I1—C6	2.163 (7)	C2—H4	0.9300
C1—N2	1.334 (7)	N3—C3	1.414 (7)
C1—N1	1.358 (7)	C4—H1A	0.9600
C1—C4	1.477 (8)	C4—H1B	0.9600
O1—N3	1.223 (6)	C4—H1C	0.9600
N2—C2	1.345 (7)	C5—C6	1.484 (9)
N1—C3	1.385 (7)	C5—H11A	0.9700
N1—C5	1.516 (8)	C5—H11B	0.9700
O2—N3	1.210 (7)	C6—H10A	0.9700
C2—C3	1.348 (8)	C6—H10B	0.9700
N2—C1—N1	111.8 (5)	C1—C4—H1B	109.5
N2—C1—C4	124.1 (5)	H1A—C4—H1B	109.5
N1—C1—C4	124.0 (5)	C1—C4—H1C	109.5
C1—N2—C2	105.3 (4)	H1A—C4—H1C	109.5
C1—N1—C3	105.1 (4)	H1B—C4—H1C	109.5
C1—N1—C5	125.0 (5)	C6—C5—N1	106.8 (5)
C3—N1—C5	129.3 (5)	C6—C5—H11A	110.4
N2—C2—C3	110.9 (5)	N1—C5—H11A	110.4
N2—C2—H4	124.5	C6—C5—H11B	110.4
C3—C2—H4	124.5	N1—C5—H11B	110.4
O2—N3—O1	124.0 (5)	H11A—C5—H11B	108.6
O2—N3—C3	119.1 (5)	C5—C6—I1	107.8 (5)
O1—N3—C3	116.9 (5)	C5—C6—H10A	110.1
C2—C3—N1	106.8 (5)	I1—C6—H10A	110.1
C2—C3—N3	128.6 (5)	C5—C6—H10B	110.1
N1—C3—N3	124.6 (5)	I1—C6—H10B	110.1
C1—C4—H1A	109.5	H10A—C6—H10B	108.5
N1—C1—N2—C2	1.4 (6)	C5—N1—C3—C2	−168.9 (5)
C4—C1—N2—C2	−179.8 (6)	C1—N1—C3—N3	−179.2 (5)
N2—C1—N1—C3	−2.2 (6)	C5—N1—C3—N3	9.8 (9)
C4—C1—N1—C3	179.0 (6)	O2—N3—C3—C2	−173.2 (7)
N2—C1—N1—C5	169.4 (5)	O1—N3—C3—C2	7.1 (9)
C4—C1—N1—C5	−9.5 (9)	O2—N3—C3—N1	8.3 (9)
C1—N2—C2—C3	0.1 (6)	O1—N3—C3—N1	−171.4 (6)
N2—C2—C3—N1	−1.4 (6)	C1—N1—C5—C6	100.2 (7)
N2—C2—C3—N3	179.9 (5)	C3—N1—C5—C6	−90.3 (7)
C1—N1—C3—C2	2.1 (6)	N1—C5—C6—I1	−179.9 (4)