5H -Thiochromeno[2,3-b ]pyridine-5,10,10-trione
Muhammad Naeem Khan,a,b M.Nawaz Tahir,c *
Misbahul Ain Khan,a Salma Rehman b and Abdul Qayyum Ather b
a
Department of Chemistry,Islamia University,Bahawalpur,Pakistan,b Applied Chemistry Rearch Center,PCSIR Laboratories Complex,Lahore 54600,Pakistan,and c Department of Physics,University of Sargodha,Sargodha,Pakistan Correspondence e-mail:**********************Received 19September 2010;accepted 24September 2010
Key indicators:single-crystal X-ray study;T =296K;mean (C–C)=0.005A
˚;R factor =0.041;wR factor =0.094;data-to-parameter ratio =12.1.
The asymmetric unit of the title compound,C 12H 7NO 3S,contains two independent molecules with different geometric-al configurations.The dihedral angles between the benzene and pyridine rings in the two molecules are 3.7(2)and 5.40(19) .The central heterocyclic fud rings have different
puckering parameters [Q =0.122(3)A
˚, =100.4(13),’=185.3(19) in one molecule,0.101(3)A
˚,101.4(3)and 2(2) in the other].The SO 2group is oriented at dihedral angles of 81.06(14)and 82.58(15) with the benzene and pyridine rings,respectively,in one molecule [87.21(14)and 87.66(14) in the cond].In the crystal,the molecules are linked into zigzag polymeric chains along the b axis by intermolecular C—H ÁÁÁO hydrogen bonding. – interactions with centroid–centroid
distances in the range 3.825(3)–4.153(3)A
˚stabilize the structure.S—O ÁÁÁ and C—O ÁÁÁ interactions are also obrved.
Related literature
For background to our work on pyridine-and thio-containing heterocyclic rings and for related structures,e:Khan et al.(2008a,b ).For the preparation,e:Khan et al.(2008a,b );Kruger &Mann (1954).For puckering parameters,e:Cremer &Pople
(1975).
Experimental
atapi
Crystal data
C 12H 7NO 3S M r =245.25
Orthorhombic,Pca 21visitors
a =12.157(5)A ˚
b =11.483(5)A ˚
c =14.964(7)A
pepsin
˚V =2089.0(16)A
˚3Z =8
Mo K radiation =0.30mm À1T =296K
0.35Â0.14Â0.12mm
Data collection
Bruker Kappa APEXII CCD diffractometer
Absorption correction:multi-scan (SADABS ;Bruker,2005)T min =0.968,T max =0.985
29502measured reflections 3718independent reflections 2838reflections with I >2 (I )R int =0.061
Refinement
R [F 2>2 (F 2)]=0.041wR (F 2)=0.094S =1.04
3718reflections 307parameters 1restraint
H-atom parameters constrained
Á max =0.20e A ˚À3Á min =À0.25e A
˚À3Absolute structure:Flack (1983),1749Friedel pairs
Flack parameter:0.13(9)
Table 1
Hydrogen-bond geometry (A
˚, ).Cg 1and Cg 2are the centroids of the S1/C1/C6/C7/C8/C12and S2/C13/C18/
C19/C20/C24rings,respectively.D —H ÁÁÁA D —H H ÁÁÁA D ÁÁÁA D —H ÁÁÁA C3—H3ÁÁÁO5i 0.93 2.59 3.372(5)142C4—H4ÁÁÁO3ii 0.93 2.57 3.472(5)164C15—H15ÁÁÁO2iii 0.93 2.58 3.367(5)143S1—O3ÁÁÁCg 2iii 1.43(1) 3.21(1) 4.421(3)141(1)C19—O4ÁÁÁCg 1ii
1.21(1)
翻译软件哪个好2.87(1)
3.585
(4)
117(1)
Symmetry codes:(i)Àx þ32;y ;z À12;(ii)x À12;Ày þ1;z ;(iii)Àx þ32;y þ1;z þ1
2.
Data collection:APEX2(Bruker,2009);cell refinement:SAINT (Bruker,2009);data reduction:SAINT ;program(s)ud to solve structure:SHELXS97(Sheldrick,2008);program(s)ud to refine structure:SHELXL97(Sheldrick,2008);molecular graphics:ORTEP-3for Windows (Farrugia,1997)and PLATON (Spek,2009);software ud to prepare material for publication:WinGX (Farrugia,1999)and PLATON .
The authors acknowledge the provision of funds for the purcha of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary,Vice Chancellor,University of Sargodha,Pakistan.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference:BQ2235).
References
Bruker (2005).SADABS .Bruker AXS Inc.,Madison,Wisconsin,USA.
srfcBruker (2009).APEX2and SAINT .Bruker AXS Inc.,Madison,Wisconsin,USA.
Cremer,D.&Pople,J.A.(1975).J.Am.Chem.Soc.97,1354–1358.Farrugia,L.J.(1997).J.Appl.Cryst.30,565.Farrugia,L.J.(1999).J.Appl.Cryst.32,837–838.Flack,H.D.(1983).Acta Cryst.A 39,876–881.
Khan,M.N.,Tahir,M.N.,Khan,M.A.,Khan,I.U.&Arshad,M.N.(2008a )anic compounds
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
reply的用法
Khan,M.N.,Tahir,M.N.,Khan,M.A.,Khan,I.U.&Arshad,M.N.(2008b). Acta Cryst.E64,o1704.
Kruger,S.&Mann,F.G.(1954).J.Chem.Soc.pp.3905–3910.Sheldrick,G.M.(2008).Acta Cryst.A64,112–122. Spek,A.L.(2009).Acta Cryst.D65,148–155.
organic compounds
supplementary materials
supplementary materials
Acta Cryst. (2010). E66, o2673-o2674 [ doi:10.1107/S1600536810038171 ]
5H-Thiochromeno[2,3-b]pyridine-5,10,10-trione
M. N. Khan, M. N. Tahir, M. A. Khan, S. Rehman and A. Q. Ather
Comment
The title compound (I, Fig. 1) is an extension to our work related to pyridine and thio containing heterocyclic rings (Khan et al., 2008a, b). We have reported previously the crystal structures of (II) i.
e. 7-nitro-5H-1-benzothiopyrano[2,3-b]-pyrid-in-5-one (Khan et al., 2008a) and 5H-1-benzothiopyrano[2,3-b]pyridin-5-one (Khan et al., 2008b), which are related to the title compound.
The title compound consist of two independent molecules having different configuration. In one molecule, the phenyl ring A (C1—C6) and pyridine ring B (C8—C11/N1/C12) are planar with r. m. s. deviation of 0.0077 and 0.0063 Å, respectively. The dihedral angle between A/B is 5.40 (19)°. The heterocyclic central fud ring C (S1/C1/C6—C8/C12) is slightly twisted with puckering parameters (Cremer & Pople, 1975) given by Q = 0.122 (3) Å, θ = 100.4 (14)°, φ = 185.3 (18)°. The SO2 group D (O2/S1/O3) of this molecule makes dihedral angle of 87.21 (14) and 87.66 (14) ° with the phenyl ring A and pyridine ring B, respectively. In the cond molecule, the phenyl ring E (C13—C18) and pyridine ring F (C20—C23/N2/C24) are planar with r. m. s. deviation of 0.0040 and 0.0018 Å, respectively. The dihedral angle between E/F is 3.72 (20)°. The puckering parameters of the central fud ring G (S2/C13/C18—C20/C24) are given by Q = 0.101 (3) Å, θ = 101.4 (3)°, φ= 2(2)°. In this molecule, the SO2 group H (O5/S2/O6) makes dihedral angle of 81.06 (14) and 82.58 (15)° with the parent phenyl ring E and pyridine ring F, respectively. There exist intermolecular H-bonding of C—H···O type (Table 1) due to which molecules establish zigzag polymeric chains. The π–π interactions in the range of 3.825 (3)–4.153 (3) Å exist which plays important role in stabilizing the molecules.
Experimental
5H-1-Benzothiopyrano[2,3-b]pyridin-5-one was prepared freshly (Khan et al., 2008b) and was oxidized using acetic acid and hydrogen peroxide according to the method described by Kruger & Mann, 1954.
Refinement
The H-atoms were positioned geometrically (C–H = 0.93 Å) and refined as riding with U iso(H) = x U eq(C), where x = 1.2 for all aryl H-atoms.
Figures
高级英语第一册
Fig. 1. View of the title compound with the atom numbering scheme. The thermal displace-
ments are drawn at the 50% probability level.
omniasupplementary materials
Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form poly-
meric chains extending along the b axis.
5H-Thiochromeno[2,3-b]pyridine-5,10,10-trione
Crystal data
C12H7NO3S F(000) = 1008公务员考试培训班
trirockM r = 245.25D x = 1.560 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac Cell parameters from 2838 reflections
a = 12.157 (5) Åθ = 2.2–25.2°
b = 11.483 (5) ŵ = 0.30 mm−1
c = 14.964 (7) ÅT = 296 K
V = 2089.0 (16) Å3Needle, white
Z = 80.35 × 0.14 × 0.12 mm
Data collection
Bruker Kappa APEXII CCD
diffractometer3718 independent reflections
Radiation source: fine-focus aled tube2838 reflections with I > 2σ(I)
graphite R int = 0.061
Detector resolution: 8.10 pixels mm-1θmax = 25.2°, θmin = 2.4°
ω scans h = −14→14
Absorption correction: multi-scan
(SADABS; Bruker, 2005)k = −13→13
T min = 0.968, T max = 0.985l = −17→17
29502 measured reflections
Refinement
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring
sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.094w = 1/[σ2(F o2) + (0.043P)2 + 0.3395P] where P = (F o2 + 2F c2)/3
S = 1.04(Δ/σ)max < 0.001
3718 reflectionsΔρmax = 0.20 e Å−3
307 parametersΔρmin = −0.25 e Å−3
1 restraint Absolute structure: Flack (1983), 1749 Friedal pairs
