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In the title compound, C12H9BrClN3O3, the nitro group lies in the plane of the imidazole ring, whereas the benzene and acetyl groups are markedly twisted relative to the heterocyclic ring. A weak C—H...O inter­action helps to establish the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010124/hb2306sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010124/hb2306Isup2.hkl
Contains datablock I

CCDC reference: 643002

Key indicators

  • Single-crystal X-ray study
  • T = 220 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.022
  • wR factor = 0.054
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Br .. Cl .. 3.55 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.55 From the CIF: _reflns_number_total 2565 Count of symmetry unique reflns 1372 Completeness (_total/calc) 186.95% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1193 Fraction of Friedel pairs measured 0.870 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989) and Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

2-(5-Bromo-2-methyl-4-nitroimidazol-1-yl)-1-(2-chlorophenyl)ethanone top
Crystal data top
C12H9BrClN3O3F(000) = 712
Mr = 358.58Dx = 1.813 Mg m3
Monoclinic, CcMelting point: 438 K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71073 Å
a = 8.4929 (8) ÅCell parameters from 6662 reflections
b = 23.8609 (13) Åθ = 4–25°
c = 7.5005 (5) ŵ = 3.34 mm1
β = 120.190 (7)°T = 220 K
V = 1313.80 (19) Å3Prism, colourless
Z = 40.6 × 0.5 × 0.3 mm
Data collection top
Kuma KM-4 CCD κ-geometry
diffractometer
2476 reflections with I > 2σ(I)
ω scansRint = 0.023
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2004)
θmax = 26.6°, θmin = 3.4°
Tmin = 0.135, Tmax = 0.367h = 1010
6500 measured reflectionsk = 2329
2565 independent reflectionsl = 99
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.022 w = 1/[σ2(Fo2) + (0.0258P)2 + 0.8352P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.054(Δ/σ)max < 0.001
S = 1.10Δρmax = 0.27 e Å3
2565 reflectionsΔρmin = 0.42 e Å3
182 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0017 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 1193 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.008 (6)
Special details top

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 (Å2) top
xyzUiso*/Ueq
Br0.01570 (5)0.132160 (12)0.82709 (5)0.04182 (10)
Cl0.35807 (11)0.03924 (3)0.67951 (14)0.0482 (2)
N10.1425 (3)0.17544 (9)0.5724 (3)0.0273 (5)
C20.0814 (3)0.20138 (11)0.3871 (4)0.0266 (6)
C140.2010 (4)0.21991 (14)0.3097 (5)0.0388 (7)
H14A0.12870.23590.17490.058*
H14B0.26770.18840.30220.058*
H14C0.28480.24750.40160.058*
N30.0967 (3)0.20899 (10)0.2916 (4)0.0270 (5)
C40.1495 (3)0.18681 (11)0.4199 (4)0.0253 (5)
N20.3360 (3)0.18653 (9)0.3665 (3)0.0293 (5)
O20.3738 (3)0.16650 (9)0.4908 (3)0.0431 (5)
O30.4490 (2)0.20623 (9)0.1997 (3)0.0435 (5)
C50.0044 (3)0.16559 (11)0.5954 (4)0.0264 (5)
C60.3272 (3)0.15541 (11)0.7106 (4)0.0309 (6)
H6A0.35900.16160.85270.037*
H6B0.41250.17620.68570.037*
C70.3403 (4)0.09294 (13)0.6747 (5)0.0309 (7)
O10.2140 (3)0.07010 (11)0.5333 (4)0.0632 (9)
C80.5137 (4)0.06424 (9)0.8200 (6)0.0250 (4)
C90.5346 (4)0.00590 (10)0.8329 (6)0.0283 (5)
C100.6982 (4)0.01860 (14)0.9729 (5)0.0404 (7)
H100.70920.05740.97960.048*
C110.8455 (4)0.01427 (13)1.1027 (4)0.0383 (7)
H110.95550.00241.19660.046*
C120.8298 (4)0.07133 (14)1.0936 (5)0.0346 (7)
H120.92920.09351.18030.042*
C130.6654 (4)0.09599 (13)0.9548 (5)0.0291 (6)
H130.65580.13490.95140.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.04432 (14)0.04347 (16)0.02877 (12)0.00158 (16)0.01177 (10)0.00742 (16)
Cl0.0430 (4)0.0342 (4)0.0565 (5)0.0104 (4)0.0168 (4)0.0112 (4)
N10.0182 (9)0.0250 (11)0.0261 (10)0.0031 (8)0.0019 (8)0.0010 (9)
C20.0231 (12)0.0226 (14)0.0271 (14)0.0029 (10)0.0073 (10)0.0014 (10)
C140.0276 (13)0.051 (2)0.0362 (14)0.0007 (12)0.0147 (11)0.0036 (13)
N30.0214 (10)0.0268 (12)0.0266 (11)0.0035 (9)0.0073 (9)0.0020 (9)
C40.0217 (11)0.0220 (13)0.0272 (12)0.0039 (9)0.0087 (9)0.0003 (10)
N20.0246 (10)0.0241 (11)0.0346 (11)0.0027 (8)0.0115 (9)0.0009 (9)
O20.0352 (10)0.0486 (14)0.0504 (12)0.0041 (9)0.0251 (10)0.0103 (11)
O30.0235 (9)0.0518 (14)0.0432 (11)0.0096 (9)0.0078 (8)0.0140 (10)
C50.0235 (11)0.0220 (13)0.0261 (12)0.0006 (9)0.0069 (9)0.0019 (10)
C60.0177 (10)0.0267 (13)0.0314 (13)0.0035 (10)0.0003 (9)0.0024 (11)
C70.0225 (13)0.0315 (15)0.0282 (15)0.0052 (12)0.0050 (11)0.0013 (13)
O10.0360 (12)0.0452 (16)0.0548 (17)0.0117 (11)0.0169 (12)0.0233 (13)
C80.0224 (9)0.0264 (11)0.0237 (9)0.0030 (14)0.0096 (8)0.0000 (14)
C90.0272 (13)0.0287 (12)0.0295 (11)0.0048 (12)0.0145 (10)0.0062 (14)
C100.0425 (17)0.0305 (16)0.0456 (18)0.0121 (14)0.0202 (14)0.0059 (14)
C110.0281 (13)0.0413 (17)0.0360 (15)0.0112 (12)0.0089 (12)0.0121 (12)
C120.0239 (13)0.0345 (18)0.0340 (16)0.0056 (12)0.0060 (12)0.0022 (13)
C130.0222 (13)0.0251 (15)0.0305 (15)0.0056 (11)0.0062 (12)0.0036 (12)
Geometric parameters (Å, º) top
Br—C51.840 (3)C6—C71.529 (4)
Cl—C91.731 (3)C6—H6A0.9700
N1—C51.363 (3)C6—H6B0.9700
N1—C21.363 (3)C7—O11.195 (4)
N1—C61.459 (3)C7—C81.487 (4)
C2—N31.321 (3)C8—C131.395 (4)
C2—C141.469 (4)C8—C91.401 (3)
C14—H14A0.9600C9—C101.381 (4)
C14—H14B0.9600C10—C111.379 (5)
C14—H14C0.9600C10—H100.9300
N3—C41.357 (4)C11—C121.366 (5)
C4—C51.369 (3)C11—H110.9300
C4—N21.425 (3)C12—C131.385 (4)
N2—O31.225 (3)C12—H120.9300
N2—O21.225 (3)C13—H130.9300
C5—N1—C2107.68 (19)N1—C6—H6B109.7
C5—N1—C6125.4 (2)C7—C6—H6B109.7
C2—N1—C6126.5 (2)H6A—C6—H6B108.2
N3—C2—N1111.1 (2)O1—C7—C8123.8 (3)
N3—C2—C14125.1 (3)O1—C7—C6119.2 (3)
N1—C2—C14123.7 (2)C8—C7—C6116.9 (2)
C2—C14—H14A109.5C13—C8—C9116.8 (3)
C2—C14—H14B109.5C13—C8—C7119.6 (2)
H14A—C14—H14B109.5C9—C8—C7123.6 (3)
C2—C14—H14C109.5C10—C9—C8121.2 (3)
H14A—C14—H14C109.5C10—C9—Cl116.5 (2)
H14B—C14—H14C109.5C8—C9—Cl122.4 (2)
C2—N3—C4105.0 (2)C11—C10—C9120.3 (3)
N3—C4—C5111.6 (2)C11—C10—H10119.9
N3—C4—N2121.3 (2)C9—C10—H10119.9
C5—C4—N2127.1 (2)C12—C11—C10120.0 (3)
O3—N2—O2123.8 (2)C12—C11—H11120.0
O3—N2—C4118.3 (2)C10—C11—H11120.0
O2—N2—C4117.9 (2)C11—C12—C13119.8 (3)
N1—C5—C4104.7 (2)C11—C12—H12120.1
N1—C5—Br122.54 (17)C13—C12—H12120.1
C4—C5—Br132.8 (2)C12—C13—C8121.9 (3)
N1—C6—C7110.0 (2)C12—C13—H13119.0
N1—C6—H6A109.7C8—C13—H13119.0
C7—C6—H6A109.7
C5—N1—C2—N30.5 (3)C5—N1—C6—C775.5 (3)
C6—N1—C2—N3173.6 (2)C2—N1—C6—C796.4 (3)
C5—N1—C2—C14178.5 (3)N1—C6—C7—O17.6 (5)
C6—N1—C2—C148.4 (4)N1—C6—C7—C8172.9 (3)
N1—C2—N3—C40.5 (3)O1—C7—C8—C13167.6 (3)
C14—C2—N3—C4178.4 (3)C6—C7—C8—C1311.8 (6)
C2—N3—C4—C50.2 (3)O1—C7—C8—C913.4 (6)
C2—N3—C4—N2179.0 (2)C6—C7—C8—C9167.2 (3)
N3—C4—N2—O31.0 (4)C13—C8—C9—C100.0 (6)
C5—C4—N2—O3178.1 (3)C7—C8—C9—C10179.1 (3)
N3—C4—N2—O2179.0 (2)C13—C8—C9—Cl178.8 (3)
C5—C4—N2—O21.8 (4)C7—C8—C9—Cl0.2 (6)
C2—N1—C5—C40.4 (3)C8—C9—C10—C110.4 (6)
C6—N1—C5—C4173.5 (2)Cl—C9—C10—C11179.3 (3)
C2—N1—C5—Br178.88 (18)C9—C10—C11—C120.1 (5)
C6—N1—C5—Br8.0 (4)C10—C11—C12—C130.5 (5)
N3—C4—C5—N10.1 (3)C11—C12—C13—C80.9 (6)
N2—C4—C5—N1179.3 (2)C9—C8—C13—C120.7 (6)
N3—C4—C5—Br178.4 (2)C7—C8—C13—C12179.8 (3)
N2—C4—C5—Br2.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O3i0.972.513.395 (3)152
Symmetry code: (i) x+1, y, z+1.
 

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