organic compounds
7-Nitro-2-phenylimidazo[2,1-b][1,3]benzothiazole
aDepartment of Chemistry and Chemical Technology, Togliatti State University, 14 Belorusskaya St, Togliatti 445667, Russian Federation, bDepartment of Organic, Bioorganic and Medicinal Chemistry, Samara State University, 1 Akademician Pavlov St, Samara 443011, Russian Federation, and cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
*Correspondence e-mail: a.s.bunev@gmail.com
In the title molecule, C15H9N3O2S, the central imidazo[2,1-b][1,3]benzothiazole heterotricyclic unit is essentially planar (r.m.s. deviation = 0.021 Å). The terminal phenyl ring and nitro group are twisted by 9.06 (1) and 11.02 (4)°, respectively, from the mean plane of the heterotricycle. In the crystal, molecules are linked by π–π stacking interactions into columns along [100]; the interplanar distance between neighboring imidazo[2,1-b][1,3]benzothiazole planes within the columns is 3.370 (2) Å. Furthermore, the columns interact with each other by secondary S⋯O [2.9922 (10) and 3.1988 (11) Å] interactions, forming a three-dimensional framework.
CCDC reference: 980673
Related literature
For applications of imidazo[2,1–b][1,3]benzothiazoles, see: Ager et al. (1988); Sanfilippo et al. (1988); Barchéchath et al. (2005); Andreani et al. (2008); Chao et al. (2009); Kumbhare et al. (2011); Chandak et al. (2013). For the crystal structures of related compounds, see: Landreau et al. (2002); Adib et al. (2008); Fun, Asik et al. (2011); Fun, Hemamalini et al. (2011); Ghabbour et al. (2012); Bunev et al. (2013).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 980673
10.1107/S1600536814000476/rk2421sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000476/rk2421Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000476/rk2421Isup3.cml
The mixture of 6–nitrobenzothiazol–2–amine (1.95 g, 10 mmol) and 2–bromo–1–phenylethanone (1.99 g, 10 mmol) was dissolved in ethanole (40 ml). The reaction mixture was heated under reflux for 8 h. The resulting precipitate was collected after cooling to room temperature and dissolved in DMF (20 ml). The warm solution basified with 20% NH4OH (20 ml) yielded the expected imidazo[2,1–b][1,3]benzothiazole I after cooling at room temperature. The basified solution was extracted with CH2Cl2 (3×50 ml), the organic phase was dried (Na2SO4) and evaporated in vacuo. The residue crystallized from DMF. Yield is 82%. The single–crystal of the product I was obtained by slow crystallization from DMF. M.p. = 539–541 K. IR (KBr), ν/cm-1: 3131, 3073, 1580, 1523, 1501, 1337, 1144, 815, 714. 1H NMR (500 MHz, DMSO–d6, 304 K): 7.36–7.29 (m, 3H, CH), 7.95 (d, 1H, J = 8.9, CH), 8.18 (c, 1H, CH), 8.30 (d, 1H, J = 8.9, CH), 8.54 (dd, 2H, J = 2.2, CH). Anal. Calcd for C15H9N3O2S: C, 61.01; H, 3.07. Found: C, 61.10; H, 3.12.
All hydrogen atoms were placed in the calculated positions with C—H = 0.95Å and refined in the riding model with fixed isotropic displacement parameters: Uiso(H) = 1.2Ueq(C)].
Imidazo[2,1–b][1,3]benzothiazole are of great interest due to their biological properties. These compounds and their derivatives demonstrate the antitumor (Andreani et al., 2008), antiallergic (Ager et al., 1988), anesthetic (Sanfilippo et al., 1988) and anticancer (Kumbhare et al., 2011) activities as well as the inhibition activity of apoptosis in testiculargerm cells (Chandak et al., 2013), lymphocytes (Barchéchath et al., 2005), and FMS–like tyrosine kinase–3 (FLT3) (Chao et al., 2009).
In this work, a 7–nitro–2–phenylimidazo[2,1–b][1,3]benzothiazole, C15H9N3O2S, (I) was prepared by the reaction of 2–amino–6–nitro–1,3–benzothiazole with 2–bromo–1–phenylethanone (Fig. 1), and its structure was unambiguously established by the X–ray diffraction study (Fig. 2).
The bond lengths and angles within the molecule of I are in a good agreement with those found in the related compounds (Landreau et al., 2002; Adib et al., 2008; Fun, Asik et al., 2011; Fun, Hemamalini et al., 2011; Ghabbour et al., 2012; Bunev et al., 2013). The central imidazo[2,1–b][1,3]benzothiazole tricycle in I is essentially planar (r.m.s. deviation is 0.021Å). The terminal phenyl ring and nitro–group are twisted at 9.06 (1) and 11.02 (4)°, respectively, from the mean plane of the tricycle.
In the crystal, the molecules of I are linked by the intermolecular π···π–stacking interactions into columns along [100] (Fig. 3). The molecules within the columns are arranged alternatively by their planar rotation of 180° (Fig. 3). The interplane distance between neighboring imidazo[2,1–b][1,3]benzothiazole planes is 3.370 (2)Å). Further the columns are bound to each other by the intermolecular secondary S9···O1i (3.1988 (11)Å) and S9···O2ii (2.9922 (10)Å) interactions into three–dimensional framework (Fig. 3). Symmetry codes: (i) x, y, 1+z; (ii) x, 1.5-y, 0.5-z.
For applications of imidazo[2,1–b][1,3]benzothiazoles, see: Ager et al. (1988); Sanfilippo et al. (1988); Barchéchath et al. (2005); Andreani et al. (2008); Chao et al. (2009); Kumbhare et al. (2011); Chandak et al. (2013). For the crystal structures of related compounds, see: Landreau et al. (2002); Adib et al. (2008); Fun, Asik et al. (2011); Fun, Hemamalini et al. (2011); Ghabbour et al. (2012); Bunev et al. (2013).
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C15H9N3O2S | F(000) = 608 |
Mr = 295.32 | Dx = 1.565 Mg m−3 |
Monoclinic, P21/c | Melting point = 539–541 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8068 (3) Å | Cell parameters from 6622 reflections |
b = 21.0244 (9) Å | θ = 2.5–32.7° |
c = 9.0699 (4) Å | µ = 0.27 mm−1 |
β = 105.077 (1)° | T = 120 K |
V = 1253.30 (9) Å3 | Prism, yellow |
Z = 4 | 0.30 × 0.10 × 0.10 mm |
Bruker APEXII CCD diffractometer | 4586 independent reflections |
Radiation source: fine–focus sealed tube | 3740 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 32.7°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→10 |
Tmin = 0.924, Tmax = 0.974 | k = −31→30 |
19380 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.058P)2 + 0.471P] where P = (Fo2 + 2Fc2)/3 |
4586 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C15H9N3O2S | V = 1253.30 (9) Å3 |
Mr = 295.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.8068 (3) Å | µ = 0.27 mm−1 |
b = 21.0244 (9) Å | T = 120 K |
c = 9.0699 (4) Å | 0.30 × 0.10 × 0.10 mm |
β = 105.077 (1)° |
Bruker APEXII CCD diffractometer | 4586 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 3740 reflections with I > 2σ(I) |
Tmin = 0.924, Tmax = 0.974 | Rint = 0.041 |
19380 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.54 e Å−3 |
4586 reflections | Δρmin = −0.38 e Å−3 |
190 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.28591 (16) | 0.51605 (5) | 0.71585 (12) | 0.01553 (19) | |
C2 | 0.28524 (17) | 0.45307 (5) | 0.66432 (13) | 0.0135 (2) | |
C3 | 0.25724 (17) | 0.45089 (5) | 0.50820 (14) | 0.0142 (2) | |
H3 | 0.2503 | 0.4142 | 0.4460 | 0.017* | |
N4 | 0.24150 (15) | 0.51394 (5) | 0.46181 (11) | 0.01305 (18) | |
C4A | 0.21228 (17) | 0.54833 (5) | 0.32729 (13) | 0.0128 (2) | |
C5 | 0.19297 (18) | 0.52421 (6) | 0.18123 (13) | 0.0145 (2) | |
H5 | 0.2035 | 0.4799 | 0.1647 | 0.017* | |
C6 | 0.15793 (18) | 0.56688 (6) | 0.06069 (13) | 0.0151 (2) | |
H6 | 0.1450 | 0.5522 | −0.0405 | 0.018* | |
C7 | 0.14192 (17) | 0.63163 (6) | 0.08972 (13) | 0.0141 (2) | |
N7 | 0.09229 (16) | 0.67506 (5) | −0.04063 (12) | 0.0179 (2) | |
O1 | 0.03830 (18) | 0.65210 (5) | −0.16990 (11) | 0.0285 (2) | |
O2 | 0.10321 (17) | 0.73262 (5) | −0.01562 (12) | 0.0264 (2) | |
C8 | 0.16850 (18) | 0.65707 (5) | 0.23520 (13) | 0.0147 (2) | |
H8 | 0.1621 | 0.7016 | 0.2514 | 0.018* | |
C8A | 0.20485 (17) | 0.61398 (6) | 0.35558 (13) | 0.0137 (2) | |
S9 | 0.23601 (5) | 0.631304 (14) | 0.55005 (3) | 0.01708 (8) | |
C9A | 0.25920 (18) | 0.55010 (6) | 0.59108 (13) | 0.0146 (2) | |
C10 | 0.31635 (17) | 0.39985 (5) | 0.77247 (13) | 0.0136 (2) | |
C11 | 0.37199 (18) | 0.41148 (6) | 0.92960 (14) | 0.0156 (2) | |
H11 | 0.3843 | 0.4540 | 0.9661 | 0.019* | |
C12 | 0.4096 (2) | 0.36113 (6) | 1.03320 (14) | 0.0191 (2) | |
H12 | 0.4474 | 0.3695 | 1.1398 | 0.023* | |
C13 | 0.3919 (2) | 0.29863 (6) | 0.98110 (15) | 0.0203 (2) | |
H13 | 0.4205 | 0.2644 | 1.0517 | 0.024* | |
C14 | 0.3318 (2) | 0.28656 (6) | 0.82445 (15) | 0.0202 (2) | |
H14 | 0.3163 | 0.2440 | 0.7884 | 0.024* | |
C15 | 0.29452 (19) | 0.33662 (6) | 0.72114 (14) | 0.0169 (2) | |
H15 | 0.2539 | 0.3280 | 0.6147 | 0.020* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0196 (5) | 0.0129 (4) | 0.0138 (4) | 0.0008 (3) | 0.0038 (4) | 0.0005 (3) |
C2 | 0.0125 (5) | 0.0133 (5) | 0.0148 (5) | 0.0005 (4) | 0.0037 (4) | 0.0006 (4) |
C3 | 0.0156 (5) | 0.0124 (5) | 0.0151 (5) | 0.0005 (4) | 0.0047 (4) | 0.0003 (4) |
N4 | 0.0148 (4) | 0.0122 (4) | 0.0120 (4) | 0.0009 (3) | 0.0033 (3) | 0.0004 (3) |
C4A | 0.0120 (5) | 0.0129 (5) | 0.0137 (5) | −0.0003 (4) | 0.0037 (4) | 0.0012 (4) |
C5 | 0.0160 (5) | 0.0137 (5) | 0.0142 (5) | 0.0004 (4) | 0.0049 (4) | −0.0005 (4) |
C6 | 0.0159 (5) | 0.0162 (5) | 0.0134 (5) | −0.0002 (4) | 0.0045 (4) | 0.0001 (4) |
C7 | 0.0140 (5) | 0.0150 (5) | 0.0136 (5) | 0.0004 (4) | 0.0043 (4) | 0.0026 (4) |
N7 | 0.0195 (5) | 0.0187 (5) | 0.0164 (5) | 0.0027 (4) | 0.0063 (4) | 0.0035 (4) |
O1 | 0.0448 (6) | 0.0278 (5) | 0.0129 (4) | 0.0087 (5) | 0.0076 (4) | 0.0022 (4) |
O2 | 0.0387 (6) | 0.0155 (4) | 0.0248 (5) | −0.0007 (4) | 0.0076 (4) | 0.0058 (4) |
C8 | 0.0159 (5) | 0.0131 (5) | 0.0157 (5) | −0.0003 (4) | 0.0053 (4) | 0.0008 (4) |
C8A | 0.0146 (5) | 0.0132 (5) | 0.0131 (5) | −0.0002 (4) | 0.0033 (4) | −0.0002 (4) |
S9 | 0.02653 (16) | 0.01152 (13) | 0.01288 (13) | 0.00037 (10) | 0.00455 (11) | −0.00043 (9) |
C9A | 0.0173 (5) | 0.0131 (5) | 0.0132 (5) | 0.0002 (4) | 0.0036 (4) | −0.0010 (4) |
C10 | 0.0127 (5) | 0.0134 (5) | 0.0152 (5) | 0.0008 (4) | 0.0044 (4) | 0.0020 (4) |
C11 | 0.0165 (5) | 0.0160 (5) | 0.0146 (5) | −0.0011 (4) | 0.0044 (4) | 0.0010 (4) |
C12 | 0.0205 (6) | 0.0218 (6) | 0.0153 (5) | −0.0011 (4) | 0.0050 (4) | 0.0032 (4) |
C13 | 0.0234 (6) | 0.0180 (5) | 0.0209 (6) | 0.0008 (4) | 0.0083 (5) | 0.0068 (4) |
C14 | 0.0264 (6) | 0.0142 (5) | 0.0217 (6) | 0.0009 (4) | 0.0090 (5) | 0.0022 (4) |
C15 | 0.0203 (5) | 0.0144 (5) | 0.0164 (5) | 0.0016 (4) | 0.0056 (4) | 0.0009 (4) |
N1—C9A | 1.3112 (15) | N7—O1 | 1.2323 (15) |
N1—C2 | 1.4038 (15) | C8—C8A | 1.3905 (16) |
C2—C3 | 1.3795 (16) | C8—H8 | 0.9500 |
C2—C10 | 1.4666 (16) | C8A—S9 | 1.7590 (12) |
C3—N4 | 1.3865 (15) | S9—C9A | 1.7457 (12) |
C3—H3 | 0.9500 | C10—C11 | 1.3977 (16) |
N4—C9A | 1.3761 (15) | C10—C15 | 1.4034 (16) |
N4—C4A | 1.3873 (14) | C11—C12 | 1.3942 (17) |
C4A—C5 | 1.3924 (16) | C11—H11 | 0.9500 |
C4A—C8A | 1.4073 (16) | C12—C13 | 1.3909 (19) |
C5—C6 | 1.3861 (16) | C12—H12 | 0.9500 |
C5—H5 | 0.9500 | C13—C14 | 1.3957 (19) |
C6—C7 | 1.3962 (17) | C13—H13 | 0.9500 |
C6—H6 | 0.9500 | C14—C15 | 1.3880 (17) |
C7—C8 | 1.3913 (16) | C14—H14 | 0.9500 |
C7—N7 | 1.4621 (15) | C15—H15 | 0.9500 |
N7—O2 | 1.2298 (15) | ||
C9A—N1—C2 | 103.89 (10) | C7—C8—H8 | 121.7 |
C3—C2—N1 | 111.14 (10) | C8—C8A—C4A | 120.22 (11) |
C3—C2—C10 | 128.20 (11) | C8—C8A—S9 | 127.08 (9) |
N1—C2—C10 | 120.64 (10) | C4A—C8A—S9 | 112.66 (9) |
C2—C3—N4 | 105.00 (10) | C9A—S9—C8A | 89.54 (5) |
C2—C3—H3 | 127.5 | N1—C9A—N4 | 113.29 (10) |
N4—C3—H3 | 127.5 | N1—C9A—S9 | 134.63 (9) |
C9A—N4—C3 | 106.68 (10) | N4—C9A—S9 | 112.07 (8) |
C9A—N4—C4A | 114.97 (10) | C11—C10—C15 | 118.77 (11) |
C3—N4—C4A | 138.35 (10) | C11—C10—C2 | 120.14 (10) |
N4—C4A—C5 | 127.12 (10) | C15—C10—C2 | 121.09 (11) |
N4—C4A—C8A | 110.77 (10) | C12—C11—C10 | 120.52 (11) |
C5—C4A—C8A | 122.12 (10) | C12—C11—H11 | 119.7 |
C6—C5—C4A | 117.98 (11) | C10—C11—H11 | 119.7 |
C6—C5—H5 | 121.0 | C13—C12—C11 | 120.25 (12) |
C4A—C5—H5 | 121.0 | C13—C12—H12 | 119.9 |
C5—C6—C7 | 119.22 (11) | C11—C12—H12 | 119.9 |
C5—C6—H6 | 120.4 | C12—C13—C14 | 119.61 (12) |
C7—C6—H6 | 120.4 | C12—C13—H13 | 120.2 |
C8—C7—C6 | 123.81 (11) | C14—C13—H13 | 120.2 |
C8—C7—N7 | 118.19 (10) | C15—C14—C13 | 120.21 (12) |
C6—C7—N7 | 118.00 (10) | C15—C14—H14 | 119.9 |
O2—N7—O1 | 123.34 (11) | C13—C14—H14 | 119.9 |
O2—N7—C7 | 118.37 (11) | C14—C15—C10 | 120.61 (11) |
O1—N7—C7 | 118.28 (11) | C14—C15—H15 | 119.7 |
C8A—C8—C7 | 116.54 (11) | C10—C15—H15 | 119.7 |
C8A—C8—H8 | 121.7 | ||
C9A—N1—C2—C3 | −0.18 (13) | N4—C4A—C8A—S9 | 0.33 (12) |
C9A—N1—C2—C10 | 178.54 (10) | C5—C4A—C8A—S9 | −179.35 (9) |
N1—C2—C3—N4 | 0.39 (13) | C8—C8A—S9—C9A | 177.73 (11) |
C10—C2—C3—N4 | −178.21 (11) | C4A—C8A—S9—C9A | 0.12 (9) |
C2—C3—N4—C9A | −0.43 (12) | C2—N1—C9A—N4 | −0.11 (14) |
C2—C3—N4—C4A | −179.63 (13) | C2—N1—C9A—S9 | 178.45 (11) |
C9A—N4—C4A—C5 | 178.88 (11) | C3—N4—C9A—N1 | 0.36 (14) |
C3—N4—C4A—C5 | −2.0 (2) | C4A—N4—C9A—N1 | 179.77 (10) |
C9A—N4—C4A—C8A | −0.78 (14) | C3—N4—C9A—S9 | −178.54 (8) |
C3—N4—C4A—C8A | 178.38 (13) | C4A—N4—C9A—S9 | 0.88 (13) |
N4—C4A—C5—C6 | 177.96 (11) | C8A—S9—C9A—N1 | −179.12 (13) |
C8A—C4A—C5—C6 | −2.41 (17) | C8A—S9—C9A—N4 | −0.55 (9) |
C4A—C5—C6—C7 | −0.48 (17) | C3—C2—C10—C11 | 170.54 (12) |
C5—C6—C7—C8 | 3.11 (18) | N1—C2—C10—C11 | −7.93 (17) |
C5—C6—C7—N7 | −176.24 (10) | C3—C2—C10—C15 | −8.38 (18) |
C8—C7—N7—O2 | 9.70 (17) | N1—C2—C10—C15 | 173.14 (11) |
C6—C7—N7—O2 | −170.91 (11) | C15—C10—C11—C12 | 1.45 (17) |
C8—C7—N7—O1 | −169.09 (11) | C2—C10—C11—C12 | −177.50 (11) |
C6—C7—N7—O1 | 10.30 (16) | C10—C11—C12—C13 | −0.06 (19) |
C6—C7—C8—C8A | −2.66 (17) | C11—C12—C13—C14 | −1.4 (2) |
N7—C7—C8—C8A | 176.69 (10) | C12—C13—C14—C15 | 1.5 (2) |
C7—C8—C8A—C4A | −0.31 (17) | C13—C14—C15—C10 | −0.10 (19) |
C7—C8—C8A—S9 | −177.77 (9) | C11—C10—C15—C14 | −1.37 (18) |
N4—C4A—C8A—C8 | −177.46 (10) | C2—C10—C15—C14 | 177.57 (11) |
C5—C4A—C8A—C8 | 2.86 (17) |
Experimental details
Crystal data | |
Chemical formula | C15H9N3O2S |
Mr | 295.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 6.8068 (3), 21.0244 (9), 9.0699 (4) |
β (°) | 105.077 (1) |
V (Å3) | 1253.30 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.30 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.924, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19380, 4586, 3740 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.759 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.110, 1.03 |
No. of reflections | 4586 |
No. of parameters | 190 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.38 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).
Acknowledgements
The authors are grateful to the Ministry of Education and Science of the Russian Federation (State program No. 3.1168.2011).
References
Adib, M., Sheibani, E., Zhu, L.-G. & Bijanzadeh, H. R. (2008). Synlett, pp. 2941–2944. Web of Science CSD CrossRef Google Scholar
Ager, I. R., Barnes, A. C., Danswan, G. W., Hairsine, P. W., Kay, D. P., Kennewell, P. D., Matharu, S. S., Miller, P. & Robson, P. (1988). J. Med. Chem. 31, 1098–1115. CrossRef CAS PubMed Web of Science Google Scholar
Andreani, A., Burnelli, S., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Varoli, L., Calonghi, N., Cappadone, C., Farruggia, G., Zini, M., Stefanelli, C., Masotti, L., Radin, N. S. & Shoemaker, R. H. (2008). J. Med. Chem. 51, 809–816. Web of Science CrossRef PubMed CAS Google Scholar
Barchéchath, S. D., Tawatao, R. I., Corr, V., Carson, D. I. & Cottam, H. B. (2005). J. Med. Chem. 48, 6409–6422. Web of Science PubMed Google Scholar
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bunev, A. S., Sukhonosova, E. V., Syrazhetdinova, D. R., Statsyuk, V. E., Ostapenko, G. I. & Khrustalev, V. N. (2013). Acta Cryst. E69, o531. CSD CrossRef IUCr Journals Google Scholar
Chandak, N., Bhardwaj, J. K., Sharma, R. K. & Sharma, P. K. (2013). Eur. J. Med. Chem. 59, 203–208. Web of Science CrossRef CAS PubMed Google Scholar
Chao, Q., Sprankle, K. G., Grotzfeld, R. M., Lai, A. G., Carter, T. A., Velasco, A. M., Gunawardane, R. N., Cramer, M. D., Gardner, M. F., James, J., Zarrinkar, P. P., Patel, H. K. & Bhagwat, S. S. (2009). J. Med. Chem. 52, 7808–7816. Web of Science CrossRef PubMed CAS Google Scholar
Fun, H.-K., Asik, S. I. J., Himaja, M., Munirajasekhar, D. & Sarojini, B. K. (2011). Acta Cryst. E67, o2810. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Umesha, K., Sarojini, B. K. & Narayana, B. (2011). Acta Cryst. E67, o3265–o3266. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ghabbour, H. A., Chia, T. S. & Fun, H.-K. (2012). Acta Cryst. E68, o1631–o1632. CSD CrossRef CAS IUCr Journals Google Scholar
Kumbhare, R. M., Kumar, K. V., Ramaiah, M. J., Dadmal, T., Pushpavalli, S. N., Mukhopadhyay, D., Divya, B., Devi, T. A., Kosurkar, U. & Pal-Bhadra, M. (2011). Eur. J. Med. Chem. 46, 4258–4266. Web of Science CrossRef CAS PubMed Google Scholar
Landreau, C., Deniaud, D., Evain, M., Reliquet, A. & Meslin, J.-C. (2002). J. Chem. Soc. Perkin Trans. 1, pp. 741–745. Web of Science CSD CrossRef Google Scholar
Sanfilippo, P. J., Urbanski, M., Press, J. B., Dubinsky, B. & Moore, J. B. Jr (1988). J. Med. Chem. 31, 2221–2227. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Imidazo[2,1–b][1,3]benzothiazole are of great interest due to their biological properties. These compounds and their derivatives demonstrate the antitumor (Andreani et al., 2008), antiallergic (Ager et al., 1988), anesthetic (Sanfilippo et al., 1988) and anticancer (Kumbhare et al., 2011) activities as well as the inhibition activity of apoptosis in testiculargerm cells (Chandak et al., 2013), lymphocytes (Barchéchath et al., 2005), and FMS–like tyrosine kinase–3 (FLT3) (Chao et al., 2009).
In this work, a 7–nitro–2–phenylimidazo[2,1–b][1,3]benzothiazole, C15H9N3O2S, (I) was prepared by the reaction of 2–amino–6–nitro–1,3–benzothiazole with 2–bromo–1–phenylethanone (Fig. 1), and its structure was unambiguously established by the X–ray diffraction study (Fig. 2).
The bond lengths and angles within the molecule of I are in a good agreement with those found in the related compounds (Landreau et al., 2002; Adib et al., 2008; Fun, Asik et al., 2011; Fun, Hemamalini et al., 2011; Ghabbour et al., 2012; Bunev et al., 2013). The central imidazo[2,1–b][1,3]benzothiazole tricycle in I is essentially planar (r.m.s. deviation is 0.021Å). The terminal phenyl ring and nitro–group are twisted at 9.06 (1) and 11.02 (4)°, respectively, from the mean plane of the tricycle.
In the crystal, the molecules of I are linked by the intermolecular π···π–stacking interactions into columns along [100] (Fig. 3). The molecules within the columns are arranged alternatively by their planar rotation of 180° (Fig. 3). The interplane distance between neighboring imidazo[2,1–b][1,3]benzothiazole planes is 3.370 (2)Å). Further the columns are bound to each other by the intermolecular secondary S9···O1i (3.1988 (11)Å) and S9···O2ii (2.9922 (10)Å) interactions into three–dimensional framework (Fig. 3). Symmetry codes: (i) x, y, 1+z; (ii) x, 1.5-y, 0.5-z.