Literature DB >> 24764868

7-Nitro-2-phenyl-imidazo[2,1-b][1,3]benzo-thia-zole.

Alexander S Bunev¹, Elena V Sukhonosova², Vladimir E Statsyuk¹, Gennady I Ostapenko¹, Victor N Khrustalev³.

Abstract

In the title mol-ecule, C15H9N3O2S, the central imidazo[2,1-b][1,3]benzo-thia-zole 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, mol-ecules are linked by π-π stacking inter-actions into columns along [100]; the inter-planar distance between neighboring imidazo[2,1-b][1,3]benzo-thia-zole 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] inter-actions, forming a three-dimensional framework.

Entities: Chemical Disease Species

Year: 2014 PMID： 24764868 PMCID： PMC3998307 DOI： 10.1107/S1600536814000476

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

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

C15H9N3O2S M = 295.32 Monoclinic, a = 6.8068 (3) Å b = 21.0244 (9) Å c = 9.0699 (4) Å β = 105.077 (1)° V = 1253.30 (9) Å3 Z = 4 Mo Kα radiation μ = 0.27 mm−1 T = 120 K 0.30 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.924, T max = 0.974 19380 measured reflections 4586 independent reflections 3740 reflections with I > 2σ(I) R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.110 S = 1.03 4586 reflections 190 parameters H-atom parameters constrained Δρmax = 0.54 e Å−3 Δρmin = −0.38 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: 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. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814000476/rk2421sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000476/rk2421Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814000476/rk2421Isup3.cml CCDC reference: Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₅H₉N₃O₂S	F(000) = 608
M_r = 295.32	D_x = 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	R_int = 0.041
φ and ω scans	θ_max = 32.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→10
T_min = 0.924, T_max = 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(F_o²) + (0.058P)² + 0.471P] where P = (F_o² + 2F_c²)/3
4586 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

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	U_iso*/U_eq
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)

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Authors: Qi Chao; Kelly G Sprankle; Robert M Grotzfeld; Andiliy G Lai; Todd A Carter; Anne Marie Velasco; Ruwanthi N Gunawardane; Merryl D Cramer; Michael F Gardner; Joyce James; Patrick P Zarrinkar; Hitesh K Patel; Shripad S Bhagwat
Journal: J Med Chem Date: 2009-12-10 Impact factor: 7.446

7. New antitumor imidazo[2,1-b]thiazole guanylhydrazones and analogues.

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Journal: J Med Chem Date: 2008-02-06 Impact factor: 7.446