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The title novel oxazole derivative, C8H9N2O3Br, is formed by displacement of one of the Br atoms in 5,6-di­bromo-2,3-di­hydro-2-methyl­imidazo­[2,1-b]­oxazole using metalation followed by reaction with methyl­cyano­formate. The cyclic moiety in the mol­ecule is slightly bent from a planar configuration. The shortened distance between the Br atom and oxy­gen of the carbonyl group of a neighboring mol­ecule is the only significant intermolecular interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023122/bt6366sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023122/bt63662sup2.hkl
Contains datablock 2

CCDC reference: 226988

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.040
  • wR factor = 0.107
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.97
Author Response: The orientation of the crystal made impossible 100% coverage as PLATFORM goniometer has option for CHI rotation

Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br1 .. O2 = 3.01 Ang.
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.10
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 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 3 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

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Methyl 6-bromo-2,3-dihydro-2-methylimidazo[2,1-b]oxazole-5-carboxylate top
Crystal data top
C8H9BrN2O3F(000) = 520
Mr = 261.08Dx = 1.837 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 684 reflections
a = 7.1338 (13) Åθ = 2.6–28.1°
b = 13.981 (3) ŵ = 4.34 mm1
c = 9.4670 (15) ÅT = 173 K
β = 90.614 (5)°Plate, colorless
V = 944.1 (3) Å30.24 × 0.22 × 0.09 mm
Z = 4
Data collection top
Bruker SMART1000 CCD
diffractometer
1958 independent reflections
Radiation source: fine-focus sealed tube1701 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ scansθmax = 28.2°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS in SAINT; Bruker, 2002)
h = 59
Tmin = 0.402, Tmax = 0.676k = 1810
3396 measured reflectionsl = 115
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0495P)2 + 1.5689P]
where P = (Fo2 + 2Fc2)/3
1958 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 1.10 e Å3
0 restraintsΔρmin = 0.64 e Å3
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
Br10.83195 (5)0.33411 (2)0.74002 (4)0.02667 (16)
C10.7659 (5)0.4528 (2)0.6625 (4)0.0214 (7)
C20.6614 (6)0.5914 (3)0.6605 (4)0.0275 (8)
C30.5779 (7)0.7259 (3)0.5410 (4)0.0367 (10)
H3A0.44130.72810.51630.044*
C40.6507 (10)0.8237 (3)0.5476 (5)0.0534 (16)
H4A0.57840.86080.61590.080*
H4B0.63970.85350.45420.080*
H4C0.78280.82230.57710.080*
C50.6776 (6)0.6578 (2)0.4375 (4)0.0245 (8)
H5A0.60020.64560.35200.029*
H5B0.80140.68300.40950.029*
C60.7700 (5)0.4798 (2)0.5226 (4)0.0206 (7)
C70.8251 (5)0.4291 (3)0.3945 (4)0.0229 (8)
C80.8236 (7)0.4353 (3)0.1447 (4)0.0376 (10)
H8A0.78580.47780.06710.056*
H8B0.75600.37460.13630.056*
H8C0.95880.42340.14010.056*
N10.6988 (5)0.5221 (2)0.7501 (3)0.0282 (7)
N20.6959 (5)0.5722 (2)0.5253 (3)0.0229 (7)
O10.6019 (5)0.6808 (2)0.6835 (3)0.0384 (8)
O20.8995 (4)0.35153 (19)0.3932 (3)0.0307 (7)
O30.7797 (4)0.48004 (18)0.2785 (3)0.0273 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0290 (3)0.0226 (2)0.0284 (2)0.00023 (14)0.00267 (16)0.00721 (14)
C10.0222 (18)0.0204 (16)0.0214 (17)0.0007 (14)0.0010 (15)0.0044 (14)
C20.038 (2)0.0256 (18)0.0192 (16)0.0060 (16)0.0030 (16)0.0010 (15)
C30.053 (3)0.033 (2)0.0239 (19)0.009 (2)0.0046 (19)0.0055 (17)
C40.107 (5)0.031 (2)0.022 (2)0.003 (3)0.008 (3)0.0001 (18)
C50.036 (2)0.0222 (17)0.0156 (16)0.0044 (15)0.0025 (16)0.0032 (13)
C60.0188 (18)0.0196 (16)0.0233 (17)0.0021 (13)0.0038 (14)0.0013 (14)
C70.0229 (19)0.0235 (18)0.0222 (17)0.0070 (14)0.0043 (15)0.0009 (14)
C80.056 (3)0.035 (2)0.0213 (19)0.001 (2)0.0027 (19)0.0043 (17)
N10.038 (2)0.0261 (16)0.0203 (15)0.0040 (14)0.0036 (14)0.0041 (12)
N20.0300 (17)0.0241 (15)0.0147 (13)0.0016 (13)0.0005 (13)0.0010 (12)
O10.071 (2)0.0275 (14)0.0169 (13)0.0175 (14)0.0091 (14)0.0047 (11)
O20.0434 (18)0.0222 (13)0.0263 (14)0.0049 (12)0.0043 (13)0.0046 (11)
O30.0374 (16)0.0249 (13)0.0193 (12)0.0017 (12)0.0033 (12)0.0030 (11)
Geometric parameters (Å, º) top
Br1—C11.873 (3)C4—H4C0.9800
C1—N11.365 (5)C5—N21.462 (4)
C1—C61.378 (5)C5—H5A0.9900
C2—N11.313 (5)C5—H5B0.9900
C2—N21.333 (5)C6—N21.396 (4)
C2—O11.340 (4)C6—C71.462 (5)
C3—C41.464 (6)C7—O21.207 (5)
C3—O11.497 (5)C7—O31.345 (4)
C3—C51.544 (5)C8—O31.450 (5)
C3—H3A1.0000C8—H8A0.9800
C4—H4A0.9800C8—H8B0.9800
C4—H4B0.9800C8—H8C0.9800
N1—C1—C6113.7 (3)N2—C5—H5B111.7
N1—C1—Br1118.6 (3)C3—C5—H5B111.7
C6—C1—Br1127.7 (3)H5A—C5—H5B109.4
N1—C2—N2115.7 (3)C1—C6—N2102.9 (3)
N1—C2—O1130.3 (3)C1—C6—C7132.3 (3)
N2—C2—O1113.9 (3)N2—C6—C7124.7 (3)
C4—C3—O1108.5 (4)O2—C7—O3124.7 (3)
C4—C3—C5115.9 (4)O2—C7—C6124.4 (4)
O1—C3—C5105.3 (3)O3—C7—C6110.9 (3)
C4—C3—H3A109.0O3—C8—H8A109.5
O1—C3—H3A109.0O3—C8—H8B109.5
C5—C3—H3A109.0H8A—C8—H8B109.5
C3—C4—H4A109.5O3—C8—H8C109.5
C3—C4—H4B109.5H8A—C8—H8C109.5
H4A—C4—H4B109.5H8B—C8—H8C109.5
C3—C4—H4C109.5C2—N1—C1101.6 (3)
H4A—C4—H4C109.5C2—N2—C6106.1 (3)
H4B—C4—H4C109.5C2—N2—C5111.4 (3)
N2—C5—C3100.5 (3)C6—N2—C5141.1 (3)
N2—C5—H5A111.7C2—O1—C3106.2 (3)
C3—C5—H5A111.7C7—O3—C8115.6 (3)
C4—C3—C5—N2135.5 (4)O1—C2—N2—C6175.3 (3)
O1—C3—C5—N215.6 (4)N1—C2—N2—C5171.2 (4)
N1—C1—C6—N21.3 (4)O1—C2—N2—C55.8 (5)
Br1—C1—C6—N2176.4 (3)C1—C6—N2—C21.7 (4)
N1—C1—C6—C7178.2 (4)C7—C6—N2—C2178.9 (4)
Br1—C1—C6—C70.6 (6)C1—C6—N2—C5166.0 (5)
C1—C6—C7—O28.2 (7)C7—C6—N2—C516.7 (7)
N2—C6—C7—O2175.4 (4)C3—C5—N2—C213.5 (5)
C1—C6—C7—O3171.0 (4)C3—C5—N2—C6177.3 (5)
N2—C6—C7—O35.4 (5)N1—C2—O1—C3178.2 (5)
N2—C2—N1—C10.9 (5)N2—C2—O1—C35.3 (5)
O1—C2—N1—C1175.6 (5)C4—C3—O1—C2138.1 (4)
C6—C1—N1—C20.3 (5)C5—C3—O1—C213.4 (5)
Br1—C1—N1—C2177.5 (3)O2—C7—O3—C80.8 (6)
N1—C2—N2—C61.7 (5)C6—C7—O3—C8178.5 (3)
 

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