Literature DB >> 21522661

3-{[5-(4-Bromo-phen-yl)imidazo[2,1-b][1,3,4]thia-diazol-2-yl]meth-yl}-1,2-benzoxazole.

Afshan Banu, Mohamed Ziaulla, Noor Shahina Begum, Ravi S Lamani, I M Khazi.   

Abstract

In the title compound, C(18)H(11)BrN(4)OS, the imidazothia-diazole and benzisoxazole rings are individually planar with maximum deviations of 0.025 (3) 0.015 (4) Å, respectively, and are inclined at an angle of 23.51 (7)° with respect to each other. The planes of the imidazothia-diazole and bromo-phenyl rings are inclined at an angle of 27.34 (3)°. In the crystal, inter-molecular C-H⋯N inter-actions result in chains of mol-ecules along the b and c axes. Moreover, C-H⋯O inter-actions result in centrosymmetric head-to-head dimers with R(2) (2)(24) graph-set motifs. The mol-ecular packing is further stabilized by π-π stacking inter-actions between the imidazole rings with a shortest centroid-centroid distance of 3.492 (3) Å. In addition, C-H⋯π inter-actions are observed in the crystal structure.

Entities:  

Year:  2010        PMID： 21522661      PMCID： PMC3050133          DOI： 10.1107/S1600536810052232

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the biological activity of benzisoxazole derivatives, see: Priya et al. (2005 ▶). For the preparation of the title compound, see: Lamani et al. (2009 ▶). For a related structure, see: Sun & Zhang (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H11BrN4OS M = 411.28 Monoclinic, a = 38.985 (17) Å b = 5.764 (3) Å c = 14.925 (6) Å β = 109.191 (13)° V = 3167 (2) Å3 Z = 8 Mo Kα radiation μ = 2.74 mm−1 T = 423 K 0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.638, T max = 0.668 8879 measured reflections 3432 independent reflections 2534 reflections with I > 2σ(I) R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.142 S = 1.02 3432 reflections 226 parameters H-atom parameters constrained Δρmax = 1.10 e Å−3 Δρmin = −1.02 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1996) ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052232/pv2359sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052232/pv2359Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H11BrN4OSF(000) = 1648
Mr = 411.28Dx = 1.725 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3432 reflections
a = 38.985 (17) Åθ = 2.2–27.0°
b = 5.764 (3) ŵ = 2.74 mm−1
c = 14.925 (6) ÅT = 423 K
β = 109.191 (13)°Block, yellow
V = 3167 (2) Å30.18 × 0.16 × 0.16 mm
Z = 8
Bruker SMART APEX CCD detector diffractometer3432 independent reflections
Radiation source: Enhance (Mo) X-ray Source2534 reflections with I > 2σ(I)
graphiteRint = 0.081
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −44→49
Tmin = 0.638, Tmax = 0.668k = −7→7
8879 measured reflectionsl = −16→19
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0787P)2] where P = (Fo2 + 2Fc2)/3
3432 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 1.10 e Å−3
0 restraintsΔρmin = −1.02 e Å−3
Experimental. The compound was synthesized by following the procedure given in Lamani et al., (2009)
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.
xyzUiso*/Ueq
C10.14779 (11)0.5054 (7)0.4239 (3)0.0178 (8)
H10.16360.38130.44530.021*
C20.11246 (11)0.4910 (8)0.4268 (3)0.0213 (9)
H20.10480.35930.45070.026*
C30.08923 (11)0.6744 (7)0.3938 (3)0.0193 (9)
C40.10031 (12)0.8734 (7)0.3593 (3)0.0222 (9)
H40.08440.99720.33820.027*
C50.13517 (11)0.8857 (7)0.3567 (3)0.0200 (9)
H50.14261.01830.33270.024*
C60.15970 (11)0.7034 (7)0.3892 (3)0.0163 (8)
C70.19675 (11)0.7159 (7)0.3855 (3)0.0165 (8)
C80.21618 (11)0.9130 (7)0.3817 (3)0.0175 (8)
H80.20911.06670.38310.021*
C90.24700 (11)0.5928 (7)0.3759 (3)0.0166 (8)
C100.30080 (11)0.7731 (7)0.3592 (3)0.0178 (8)
C110.33397 (10)0.8402 (7)0.3361 (3)0.0168 (8)
H11A0.34210.98970.36510.020*
H11B0.32690.86160.26790.020*
C120.36595 (11)0.6779 (7)0.3653 (3)0.0178 (8)
C130.40073 (11)0.7153 (7)0.3545 (3)0.0162 (8)
C140.41996 (11)0.5140 (7)0.3897 (3)0.0187 (9)
C150.45543 (11)0.4746 (8)0.3946 (3)0.0212 (9)
H150.46770.33870.41970.025*
C160.47149 (12)0.6516 (8)0.3594 (3)0.0236 (9)
H160.49530.63410.36020.028*
C170.45273 (11)0.8557 (8)0.3228 (3)0.0216 (9)
H170.46430.97010.29940.026*
C180.41745 (12)0.8920 (8)0.3207 (3)0.0207 (9)
H180.40531.02950.29740.025*
Br10.040967 (11)0.65163 (8)0.39690 (3)0.02724 (18)
N10.21625 (9)0.5149 (6)0.3825 (2)0.0171 (7)
N20.24852 (9)0.8310 (6)0.3753 (2)0.0172 (7)
N30.27848 (9)0.9330 (6)0.3650 (2)0.0198 (7)
N40.36389 (9)0.4744 (6)0.4012 (2)0.0210 (8)
O10.39822 (8)0.3642 (5)0.4181 (2)0.0221 (7)
S10.28738 (3)0.48552 (18)0.36718 (7)0.0188 (2)
U11U22U33U12U13U23
C10.0170 (19)0.009 (2)0.027 (2)0.0004 (16)0.0056 (16)0.0014 (15)
C20.022 (2)0.019 (2)0.024 (2)−0.0042 (18)0.0089 (17)0.0014 (17)
C30.0144 (19)0.022 (2)0.0217 (19)−0.0019 (17)0.0057 (16)−0.0048 (16)
C40.022 (2)0.016 (2)0.027 (2)0.0043 (18)0.0051 (18)−0.0010 (16)
C50.020 (2)0.015 (2)0.027 (2)−0.0028 (17)0.0088 (17)−0.0008 (16)
C60.0138 (19)0.015 (2)0.0197 (19)0.0023 (16)0.0050 (15)−0.0014 (15)
C70.0150 (19)0.015 (2)0.0200 (19)−0.0008 (16)0.0056 (16)0.0012 (15)
C80.0155 (19)0.013 (2)0.025 (2)0.0029 (16)0.0085 (17)−0.0007 (15)
C90.017 (2)0.012 (2)0.0201 (19)−0.0007 (16)0.0043 (16)0.0005 (14)
C100.016 (2)0.013 (2)0.022 (2)−0.0030 (17)0.0033 (16)0.0018 (16)
C110.0127 (19)0.014 (2)0.024 (2)−0.0023 (16)0.0063 (16)0.0041 (16)
C120.017 (2)0.011 (2)0.0223 (19)−0.0011 (16)0.0028 (16)−0.0012 (15)
C130.016 (2)0.011 (2)0.0196 (19)0.0012 (16)0.0028 (16)0.0006 (14)
C140.018 (2)0.012 (2)0.026 (2)0.0009 (16)0.0072 (16)0.0017 (16)
C150.017 (2)0.014 (2)0.030 (2)0.0055 (17)0.0052 (17)−0.0019 (17)
C160.018 (2)0.025 (3)0.027 (2)−0.0016 (19)0.0060 (17)−0.0013 (18)
C170.019 (2)0.020 (2)0.027 (2)−0.0024 (18)0.0091 (17)0.0020 (17)
C180.021 (2)0.016 (2)0.024 (2)−0.0013 (17)0.0063 (17)0.0019 (16)
Br10.0161 (2)0.0308 (3)0.0357 (3)−0.00248 (19)0.00975 (18)−0.00722 (19)
N10.0158 (16)0.0112 (18)0.0244 (17)0.0023 (14)0.0066 (14)−0.0005 (13)
N20.0159 (17)0.0112 (18)0.0254 (17)−0.0007 (14)0.0082 (14)−0.0012 (13)
N30.0128 (16)0.0151 (19)0.0324 (19)−0.0055 (14)0.0089 (15)−0.0014 (15)
N40.0151 (17)0.018 (2)0.0303 (19)0.0007 (15)0.0085 (14)0.0026 (14)
O10.0177 (15)0.0107 (15)0.0403 (17)0.0047 (12)0.0127 (13)0.0085 (12)
S10.0156 (5)0.0106 (5)0.0308 (5)−0.0009 (4)0.0085 (4)−0.0002 (4)
C1—C61.393 (6)C10—C111.495 (5)
C1—C21.395 (6)C10—S11.754 (4)
C1—H10.9300C11—C121.504 (5)
C2—C31.374 (6)C11—H11A0.9700
C2—H20.9300C11—H11B0.9700
C3—C41.383 (6)C12—N41.303 (5)
C3—Br11.902 (4)C12—C131.433 (6)
C4—C51.374 (6)C13—C141.387 (5)
C4—H40.9300C13—C181.390 (6)
C5—C61.396 (6)C14—O11.371 (5)
C5—H50.9300C14—C151.379 (6)
C6—C71.465 (5)C15—C161.387 (6)
C7—C81.377 (6)C15—H150.9300
C7—N11.395 (5)C16—C171.398 (6)
C8—N21.379 (5)C16—H160.9300
C8—H80.9300C17—C181.381 (6)
C9—N11.314 (5)C17—H170.9300
C9—N21.374 (5)C18—H180.9300
C9—S11.736 (4)N2—N31.360 (5)
C10—N31.290 (5)N4—O11.427 (4)
C6—C1—C2120.9 (4)C10—C11—H11B107.8
C6—C1—H1119.6C12—C11—H11B107.8
C2—C1—H1119.6H11A—C11—H11B107.1
C3—C2—C1119.0 (4)N4—C12—C13111.7 (4)
C3—C2—H2120.5N4—C12—C11121.5 (4)
C1—C2—H2120.5C13—C12—C11126.7 (4)
C2—C3—C4121.5 (4)C14—C13—C18119.4 (4)
C2—C3—Br1118.6 (3)C14—C13—C12104.2 (3)
C4—C3—Br1119.9 (3)C18—C13—C12136.4 (4)
C5—C4—C3119.1 (4)O1—C14—C15126.2 (4)
C5—C4—H4120.5O1—C14—C13109.4 (3)
C3—C4—H4120.5C15—C14—C13124.4 (4)
C4—C5—C6121.5 (4)C14—C15—C16115.4 (4)
C4—C5—H5119.3C14—C15—H15122.3
C6—C5—H5119.3C16—C15—H15122.3
C1—C6—C5118.1 (4)C15—C16—C17121.6 (4)
C1—C6—C7120.5 (4)C15—C16—H16119.2
C5—C6—C7121.4 (4)C17—C16—H16119.2
C8—C7—N1111.8 (4)C18—C17—C16121.7 (4)
C8—C7—C6127.2 (4)C18—C17—H17119.2
N1—C7—C6121.0 (4)C16—C17—H17119.2
C7—C8—N2104.4 (4)C17—C18—C13117.6 (4)
C7—C8—H8127.8C17—C18—H18121.2
N2—C8—H8127.8C13—C18—H18121.2
N1—C9—N2112.6 (4)C9—N1—C7103.8 (3)
N1—C9—S1139.1 (3)N3—N2—C9118.2 (3)
N2—C9—S1108.3 (3)N3—N2—C8134.3 (4)
N3—C10—C11119.0 (4)C9—N2—C8107.4 (3)
N3—C10—S1116.6 (3)C10—N3—N2108.8 (3)
C11—C10—S1124.1 (3)C12—N4—O1107.0 (3)
C10—C11—C12118.0 (3)C14—O1—N4107.7 (3)
C10—C11—H11A107.8C9—S1—C1088.1 (2)
C12—C11—H11A107.8
C6—C1—C2—C30.8 (6)C13—C14—C15—C16−1.3 (6)
C1—C2—C3—C4−1.0 (6)C14—C15—C16—C170.7 (6)
C1—C2—C3—Br1179.3 (3)C15—C16—C17—C180.6 (6)
C2—C3—C4—C51.1 (6)C16—C17—C18—C13−1.3 (6)
Br1—C3—C4—C5−179.3 (3)C14—C13—C18—C170.8 (6)
C3—C4—C5—C6−0.9 (6)C12—C13—C18—C17−179.8 (4)
C2—C1—C6—C5−0.7 (6)N2—C9—N1—C70.5 (4)
C2—C1—C6—C7−179.4 (3)S1—C9—N1—C7−179.3 (4)
C4—C5—C6—C10.7 (6)C8—C7—N1—C9−0.6 (4)
C4—C5—C6—C7179.4 (4)C6—C7—N1—C9177.6 (3)
C1—C6—C7—C8−158.6 (4)N1—C9—N2—N3−177.5 (3)
C5—C6—C7—C822.8 (6)S1—C9—N2—N32.4 (4)
C1—C6—C7—N123.5 (5)N1—C9—N2—C8−0.2 (4)
C5—C6—C7—N1−155.2 (4)S1—C9—N2—C8179.7 (3)
N1—C7—C8—N20.5 (4)C7—C8—N2—N3176.5 (4)
C6—C7—C8—N2−177.6 (4)C7—C8—N2—C9−0.2 (4)
N3—C10—C11—C12156.9 (4)C11—C10—N3—N2172.8 (3)
S1—C10—C11—C12−30.0 (5)S1—C10—N3—N2−0.8 (4)
C10—C11—C12—N46.7 (6)C9—N2—N3—C10−1.1 (5)
C10—C11—C12—C13−176.4 (4)C8—N2—N3—C10−177.5 (4)
N4—C12—C13—C14−1.2 (4)C13—C12—N4—O10.9 (4)
C11—C12—C13—C14−178.4 (4)C11—C12—N4—O1178.3 (3)
N4—C12—C13—C18179.3 (4)C15—C14—O1—N4179.5 (4)
C11—C12—C13—C182.2 (7)C13—C14—O1—N4−0.5 (4)
C18—C13—C14—O1−179.4 (3)C12—N4—O1—C14−0.3 (4)
C12—C13—C14—O11.0 (4)N1—C9—S1—C10177.7 (5)
C18—C13—C14—C150.5 (6)N2—C9—S1—C10−2.1 (3)
C12—C13—C14—C15−179.0 (4)N3—C10—S1—C91.8 (3)
O1—C14—C15—C16178.7 (4)C11—C10—S1—C9−171.5 (3)
Cg4 and Cg5 are the centroids of the C1–C6 and C13–C18 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.383.219 (6)150
C8—H8···N1ii0.932.603.469 (6)156
C11—H11B···N1iii0.972.483.358 (6)150
C4—H4···Cg5iii0.932.963.554 (5)123
C18—H18···Cg4iii0.932.833.496 (5)130
Table 1

Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the C1–C6 and C13–C18 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2⋯O1i0.932.383.219 (6)150
C8—H8⋯N1ii0.932.603.469 (6)156
C11—H11B⋯N1iii0.972.483.358 (6)150
C4—H4⋯Cg5iii0.932.963.554 (5)123
C18—H18⋯Cg4iii0.932.833.496 (5)130

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

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Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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4.  Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazole derivatives.

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