Chloro­metronidazole

In the title compound, 1-(2-chloro­ethyl)-2-methyl-5-nitro-1H-imidazole, C₆H₈ClN₃O₂, the dihedral angle between the imidazole ring and the attached nitro group is 6.5 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.045
• wR factor = 0.128
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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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-chloroethyl)-2-methyl-5-nitro-1H-imidazole

Crystal data

C6H8ClN3O2	F(000) = 392
Mr = 189.60	Dx = 1.517 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1562 reflections
a = 12.098 (14) Å	θ = 6.3–27.4°
b = 11.007 (13) Å	µ = 0.42 mm^−1
c = 6.295 (7) Å	T = 298 K
β = 97.886 (18)°	Prism, colorless
V = 830.3 (16) Å^3	0.38 × 0.35 × 0.30 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	1778 independent reflections
Radiation source: fine-focus sealed tube	1293 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
Tmin = 0.850, Tmax = 0.890	k = −14→14
4602 measured reflections	l = −6→7

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0716P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
1778 reflections	Δρmax = 0.26 e Å^−3
111 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (6)

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
Cl1	0.26941 (5)	1.08697 (6)	1.18846 (9)	0.0648 (3)
N1	0.25179 (12)	0.97894 (14)	0.7240 (2)	0.0383 (4)
N3	0.11217 (14)	0.81284 (17)	0.6867 (3)	0.0481 (5)
C3	0.22186 (15)	0.85786 (18)	0.7036 (3)	0.0400 (5)
C4	0.18295 (17)	1.08359 (17)	0.7650 (4)	0.0476 (5)
H4A	0.1161	1.0839	0.6605	0.057*
H4B	0.2240	1.1576	0.7457	0.057*
O1	0.03299 (12)	0.88355 (15)	0.6762 (3)	0.0626 (5)
O2	0.10093 (14)	0.70113 (14)	0.6819 (3)	0.0704 (5)
C5	0.14968 (17)	1.08328 (19)	0.9867 (4)	0.0505 (5)
H5A	0.1063	1.0109	1.0052	0.061*
H5B	0.1031	1.1534	1.0032	0.061*
C2	0.31708 (18)	0.7931 (2)	0.6932 (3)	0.0498 (5)
H2A	0.3205	0.7091	0.6798	0.060*
N2	0.40514 (14)	0.86834 (17)	0.7051 (3)	0.0534 (5)
C1	0.36460 (15)	0.9803 (2)	0.7245 (3)	0.0459 (5)
C6	0.43437 (19)	1.0915 (2)	0.7436 (5)	0.0654 (7)
H6A	0.4388	1.1231	0.8866	0.098*
H6B	0.4016	1.1513	0.6431	0.098*
H6C	0.5080	1.0720	0.7133	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0661 (4)	0.0724 (5)	0.0524 (4)	0.0085 (3)	−0.0044 (3)	−0.0111 (3)
N1	0.0345 (8)	0.0444 (9)	0.0355 (8)	−0.0023 (7)	0.0030 (6)	0.0010 (7)
N3	0.0461 (10)	0.0573 (12)	0.0394 (9)	−0.0076 (8)	0.0002 (7)	−0.0047 (8)
C3	0.0394 (10)	0.0461 (11)	0.0331 (10)	−0.0025 (8)	0.0000 (8)	−0.0023 (8)
C4	0.0429 (11)	0.0418 (11)	0.0553 (13)	0.0045 (8)	−0.0036 (9)	0.0062 (9)
O1	0.0389 (8)	0.0768 (11)	0.0699 (11)	−0.0010 (8)	0.0000 (7)	−0.0057 (8)
O2	0.0725 (11)	0.0558 (11)	0.0816 (13)	−0.0214 (8)	0.0062 (9)	−0.0122 (8)
C5	0.0389 (11)	0.0502 (12)	0.0611 (13)	0.0074 (9)	0.0026 (9)	−0.0066 (10)
C2	0.0528 (13)	0.0529 (12)	0.0429 (11)	0.0057 (10)	0.0045 (9)	−0.0056 (9)
N2	0.0417 (10)	0.0693 (12)	0.0501 (10)	0.0053 (9)	0.0089 (8)	−0.0077 (9)
C1	0.0366 (11)	0.0643 (13)	0.0369 (10)	−0.0050 (9)	0.0053 (8)	0.0000 (9)
C6	0.0468 (13)	0.0797 (16)	0.0711 (16)	−0.0174 (11)	0.0130 (12)	−0.0019 (12)

Geometric parameters (Å, º)

Cl1—C5	1.791 (3)	C4—H4B	0.9700
N1—C1	1.364 (3)	C5—H5A	0.9700
N1—C3	1.382 (3)	C5—H5B	0.9700
N1—C4	1.465 (3)	C2—N2	1.344 (3)
N3—O1	1.229 (2)	C2—H2A	0.9300
N3—O2	1.237 (3)	N2—C1	1.338 (3)
N3—C3	1.407 (3)	C1—C6	1.482 (3)
C3—C2	1.364 (3)	C6—H6A	0.9600
C4—C5	1.504 (4)	C6—H6B	0.9600
C4—H4A	0.9700	C6—H6C	0.9600
C1—N1—C3	105.06 (16)	Cl1—C5—H5A	109.4
C1—N1—C4	125.71 (17)	C4—C5—H5B	109.4
C3—N1—C4	128.78 (17)	Cl1—C5—H5B	109.4
O1—N3—O2	123.09 (19)	H5A—C5—H5B	108.0
O1—N3—C3	120.07 (19)	N2—C2—C3	110.1 (2)
O2—N3—C3	116.84 (19)	N2—C2—H2A	125.0
C2—C3—N1	107.24 (18)	C3—C2—H2A	125.0
C2—C3—N3	127.3 (2)	C1—N2—C2	105.97 (18)
N1—C3—N3	125.38 (17)	N2—C1—N1	111.66 (18)
N1—C4—C5	113.12 (16)	N2—C1—C6	123.78 (19)
N1—C4—H4A	109.0	N1—C1—C6	124.57 (19)
C5—C4—H4A	109.0	C1—C6—H6A	109.5
N1—C4—H4B	109.0	C1—C6—H6B	109.5
C5—C4—H4B	109.0	H6A—C6—H6B	109.5
H4A—C4—H4B	107.8	C1—C6—H6C	109.5
C4—C5—Cl1	111.37 (16)	H6A—C6—H6C	109.5
C4—C5—H5A	109.4	H6B—C6—H6C	109.5
C1—N1—C3—C2	0.05 (19)	N1—C4—C5—Cl1	60.3 (2)
C4—N1—C3—C2	−172.56 (18)	N1—C3—C2—N2	−0.3 (2)
C1—N1—C3—N3	−177.18 (17)	N3—C3—C2—N2	176.85 (17)
C4—N1—C3—N3	10.2 (3)	C3—C2—N2—C1	0.4 (2)
O1—N3—C3—C2	−172.23 (19)	C2—N2—C1—N1	−0.4 (2)
O2—N3—C3—C2	7.4 (3)	C2—N2—C1—C6	179.7 (2)
O1—N3—C3—N1	4.4 (3)	C3—N1—C1—N2	0.2 (2)
O2—N3—C3—N1	−175.94 (16)	C4—N1—C1—N2	173.13 (17)
C1—N1—C4—C5	−102.6 (2)	C3—N1—C1—C6	−179.93 (19)
C3—N1—C4—C5	68.6 (2)	C4—N1—C1—C6	−7.0 (3)