organic compounds
d]pyrimidine-7-carboxylate
of ethyl 2-phenyl-4-(prop-2-yn-1-yloxy)-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C21H19N3O3S, the 5,6,7,8-tetrahydropyridine ring adopts a half-chair conformation. The fused-thieno[2,3-d]pyrimidine ring system is essentially planar (r.m.s. deviation = 0.001 Å) and forms a dihedral angle of 2.66 (6)° with the attached phenyl ring. The three-dimensional crystal packing is stabilized by C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π interactions.
Keywords: crystal structure; thieno-pyrimidine; tetrahydropyridine ring; hydrogen bonding; C—H⋯π interactions.
CCDC reference: 1429186
1. Related literature
For general chemistry background to heterocyclic thieno[2,3-d]pyrimidines, see: Litvinov (2004). For the diversity of biological activities of thieno-pyrimidine derivatives, see: Nasr & Gineinah (2002); Bhuiyan et al. (2005); Chambhare et al. (2003); Alagarsamy et al. (2006). Kapustina et al. (1992). For related structures, see: Liu et al. (2005); Ren et al. (2006).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis PRO (Agilent, 2014); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 1429186
https://doi.org/10.1107/S2056989015018447/tk5390sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015018447/tk5390Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015018447/tk5390Isup3.cml
Propargyl bromide (1.1 g, 9 mmol) was added to a suspension of ethyl 4-hydroxy-2-phenyl-5,6-dihydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(8H)-carboxylate (1.07 g, 3 mmol) and K2CO3 (0.82 g, 6 mmol) in DMF (15 ml), and stirred at room temperature for 6 h. The excess solvent was evaporated to dryness in vacuo. The residue was diluted with water and then extracted with CH2Cl2 (3 x 30 ml). The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give colourless crystals in a sufficient quality for X-ray diffraction.
All H atoms were positioned geometrically and constrained to ride on their parent atoms (C—H = 0.93–0.97 Å) with Uiso(H) = 1.2 or 1.5 Ueq(C). The (-2 3 10), (6 1 24), (5 11 4), (-3 1 17), (-14 8 5), (6 5 11), (11 3 8) and (-3 4 24) reflections were omitted owing to very bad agreement.
Thieno[2,3-d]pyrimidines are a large group of
(Litvinov, 2004), and some of them showed antiviral (Nasr & Gineinah, 2002), antimicrobial (Bhuiyan et al., 2005; Chambhare et al., 2003), and antibacterial properties (Alagarsamy et al., 2006). Fused tri- and tetracyclic thieno[2,3-d]pyrimidin-4-ones are synthesized by many methods and among them some compounds have fungicidal, antibacterial, and anti-inflammatory activities (Kapustina et al., 1992). In this context, and following to our on-going study of bio-active molecules, we report here the synthesis and of the title compound.In the title compound (Fig. 1), the 5,6,7,8-tetrahydropyridine ring (N3/C11/-C15) adopts a half-chair conformation [the puckering parameters are QT = 0.4662 (14) Å, θ = 50.06 (17) ° and φ = 30.8 (2) °]. The fused-thieno[2,3-d]pyrimidine ring system (S1/N1/N2C7-C11/C15) is essentially planar (r.m.s. deviation = 0.001 Å) and forms a dihedral angle of 2.66 (6)° with the attached phenyl ring (C1–C6). The C8–O1–C19–C20, C13–N3–C16–O2 and N3–C16–O3–C17 torsion angles are -166.90 (12), -174.90 (13) and 179.78 (12)°, respectively. All bond lengths and angles in the title molecule are normal and comparable with those previously reported for related structures (Liu et al., 2005; Ren et al., 2006).
In the crystal, molecules are linked by C—H···O, C—H···N and C—H···π hydrogen bonds, forming a three dimensional network (Fig. 2 & Table 1).
For general chemistry background to heterocyclic thieno[2,3-d]pyrimidines, see: Litvinov (2004). For the diversity of biological activities of thieno-pyrimidine derivatives, see: Nasr & Gineinah (2002); Bhuiyan et al. (2005); Chambhare et al. (2003); Alagarsamy et al. (2006). Kapustina et al. (1992). For related structures, see: Liu et al. (2005); Ren et al. (2006).
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. | |
Fig. 2. The molecular packing viewed down a axis. H atoms not involved in H bonding are omitted for clarity. |
C21H19N3O3S | F(000) = 824 |
Mr = 393.45 | Dx = 1.396 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2782 reflections |
a = 13.143 (2) Å | θ = 3.7–32.7° |
b = 8.013 (2) Å | µ = 0.20 mm−1 |
c = 17.880 (2) Å | T = 296 K |
β = 96.129 (14)° | Prism, colourless |
V = 1872.3 (6) Å3 | 0.28 × 0.14 × 0.08 mm |
Z = 4 |
Agilent Xcalibur, Eos, Gemini diffractometer | 6319 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4721 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 33.1°, θmin = 3.1° |
ω scans | h = −16→19 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→5 |
Tmin = 0.834, Tmax = 1.000 | l = −25→26 |
14345 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0488P)2 + 0.4469P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6319 reflections | Δρmax = 0.35 e Å−3 |
254 parameters | Δρmin = −0.31 e Å−3 |
C21H19N3O3S | V = 1872.3 (6) Å3 |
Mr = 393.45 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.143 (2) Å | µ = 0.20 mm−1 |
b = 8.013 (2) Å | T = 296 K |
c = 17.880 (2) Å | 0.28 × 0.14 × 0.08 mm |
β = 96.129 (14)° |
Agilent Xcalibur, Eos, Gemini diffractometer | 6319 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 4721 reflections with I > 2σ(I) |
Tmin = 0.834, Tmax = 1.000 | Rint = 0.032 |
14345 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.35 e Å−3 |
6319 reflections | Δρmin = −0.31 e Å−3 |
254 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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 | ||
S1 | −0.00878 (3) | 0.26271 (5) | 1.21398 (2) | 0.0319 (1) | |
O1 | −0.08120 (7) | 0.17676 (13) | 0.94088 (4) | 0.0274 (3) | |
O2 | −0.38389 (8) | 0.19716 (14) | 1.25060 (6) | 0.0369 (3) | |
O3 | −0.45126 (7) | 0.06635 (13) | 1.14545 (5) | 0.0325 (3) | |
N1 | 0.06668 (8) | 0.31874 (14) | 0.98114 (5) | 0.0249 (3) | |
N2 | 0.11346 (8) | 0.37095 (15) | 1.11181 (6) | 0.0276 (3) | |
N3 | −0.28451 (9) | 0.03958 (16) | 1.18227 (6) | 0.0314 (3) | |
C1 | 0.24352 (11) | 0.48532 (17) | 0.94671 (7) | 0.0307 (4) | |
C2 | 0.33262 (12) | 0.5631 (2) | 0.93051 (8) | 0.0366 (4) | |
C3 | 0.40123 (11) | 0.6245 (2) | 0.98760 (9) | 0.0371 (4) | |
C4 | 0.38043 (11) | 0.6085 (2) | 1.06113 (8) | 0.0371 (4) | |
C5 | 0.29176 (10) | 0.5315 (2) | 1.07789 (8) | 0.0335 (4) | |
C6 | 0.22226 (10) | 0.46768 (16) | 1.02092 (7) | 0.0263 (3) | |
C7 | 0.12892 (9) | 0.38147 (16) | 1.03956 (7) | 0.0250 (3) | |
C8 | −0.01623 (9) | 0.23971 (16) | 0.99661 (6) | 0.0235 (3) | |
C9 | −0.04163 (9) | 0.21700 (16) | 1.07030 (6) | 0.0232 (3) | |
C10 | 0.02839 (10) | 0.28884 (17) | 1.12482 (7) | 0.0262 (3) | |
C11 | −0.12525 (9) | 0.13753 (16) | 1.10142 (6) | 0.0242 (3) | |
C12 | −0.21248 (10) | 0.04461 (17) | 1.06005 (7) | 0.0258 (3) | |
C13 | −0.26836 (11) | −0.05731 (18) | 1.11502 (7) | 0.0313 (4) | |
C14 | −0.19118 (10) | 0.0880 (2) | 1.22777 (7) | 0.0316 (4) | |
C15 | −0.11712 (10) | 0.15527 (17) | 1.17729 (7) | 0.0266 (3) | |
C16 | −0.37375 (10) | 0.10798 (17) | 1.19685 (7) | 0.0283 (3) | |
C17 | −0.54903 (11) | 0.1367 (2) | 1.15901 (9) | 0.0382 (4) | |
C18 | −0.62591 (13) | 0.0838 (2) | 1.09628 (10) | 0.0491 (6) | |
C19 | −0.05720 (10) | 0.20882 (18) | 0.86513 (6) | 0.0279 (3) | |
C20 | −0.14696 (11) | 0.1659 (2) | 0.81452 (7) | 0.0336 (4) | |
C21 | −0.21842 (12) | 0.1381 (3) | 0.77141 (9) | 0.0533 (6) | |
H1 | 0.19760 | 0.44460 | 0.90780 | 0.0370* | |
H2 | 0.34630 | 0.57400 | 0.88080 | 0.0440* | |
H3 | 0.46110 | 0.67630 | 0.97650 | 0.0450* | |
H4 | 0.42650 | 0.64990 | 1.09980 | 0.0440* | |
H5 | 0.27830 | 0.52210 | 1.12770 | 0.0400* | |
H12A | −0.18690 | −0.02910 | 1.02330 | 0.0310* | |
H12B | −0.25960 | 0.12300 | 1.03350 | 0.0310* | |
H13A | −0.33400 | −0.09310 | 1.09030 | 0.0380* | |
H13B | −0.22870 | −0.15630 | 1.12980 | 0.0380* | |
H14A | −0.16170 | −0.00790 | 1.25530 | 0.0380* | |
H14B | −0.20610 | 0.17250 | 1.26390 | 0.0380* | |
H17A | −0.54460 | 0.25750 | 1.16090 | 0.0460* | |
H17B | −0.56870 | 0.09700 | 1.20660 | 0.0460* | |
H18A | −0.69180 | 0.12800 | 1.10420 | 0.0740* | |
H18B | −0.62930 | −0.03590 | 1.09460 | 0.0740* | |
H18C | −0.60620 | 0.12500 | 1.04950 | 0.0740* | |
H19A | 0.00070 | 0.14160 | 0.85410 | 0.0330* | |
H19B | −0.04000 | 0.32550 | 0.85940 | 0.0330* | |
H21 | −0.27520 | 0.11590 | 0.73720 | 0.0640* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0328 (2) | 0.0447 (2) | 0.0173 (1) | −0.0006 (2) | −0.0014 (1) | −0.0032 (1) |
O1 | 0.0298 (4) | 0.0363 (5) | 0.0155 (4) | −0.0005 (4) | −0.0002 (3) | −0.0024 (3) |
O2 | 0.0381 (5) | 0.0412 (6) | 0.0326 (5) | −0.0020 (4) | 0.0090 (4) | −0.0131 (4) |
O3 | 0.0330 (5) | 0.0359 (5) | 0.0287 (4) | −0.0009 (4) | 0.0033 (4) | −0.0053 (4) |
N1 | 0.0258 (5) | 0.0280 (5) | 0.0201 (4) | 0.0051 (4) | −0.0008 (4) | −0.0011 (4) |
N2 | 0.0279 (5) | 0.0330 (6) | 0.0211 (5) | 0.0039 (4) | −0.0013 (4) | −0.0016 (4) |
N3 | 0.0328 (6) | 0.0374 (6) | 0.0243 (5) | 0.0000 (5) | 0.0051 (4) | −0.0073 (5) |
C1 | 0.0387 (7) | 0.0254 (6) | 0.0279 (6) | 0.0036 (5) | 0.0028 (5) | −0.0028 (5) |
C2 | 0.0459 (8) | 0.0332 (7) | 0.0326 (7) | 0.0015 (6) | 0.0125 (6) | −0.0016 (6) |
C3 | 0.0333 (7) | 0.0321 (7) | 0.0469 (8) | 0.0025 (6) | 0.0090 (6) | 0.0037 (6) |
C4 | 0.0317 (7) | 0.0403 (8) | 0.0375 (7) | −0.0004 (6) | −0.0039 (6) | 0.0015 (6) |
C5 | 0.0310 (6) | 0.0402 (8) | 0.0283 (6) | 0.0006 (6) | −0.0017 (5) | 0.0014 (6) |
C6 | 0.0280 (6) | 0.0240 (6) | 0.0264 (6) | 0.0073 (5) | 0.0002 (5) | −0.0005 (5) |
C7 | 0.0260 (6) | 0.0258 (6) | 0.0225 (5) | 0.0078 (5) | −0.0012 (4) | −0.0015 (4) |
C8 | 0.0267 (6) | 0.0248 (6) | 0.0179 (5) | 0.0075 (5) | −0.0023 (4) | −0.0019 (4) |
C9 | 0.0251 (6) | 0.0250 (6) | 0.0186 (5) | 0.0072 (4) | −0.0012 (4) | −0.0010 (4) |
C10 | 0.0277 (6) | 0.0317 (7) | 0.0184 (5) | 0.0063 (5) | −0.0018 (4) | −0.0008 (4) |
C11 | 0.0272 (6) | 0.0244 (6) | 0.0203 (5) | 0.0072 (5) | −0.0006 (4) | −0.0018 (4) |
C12 | 0.0284 (6) | 0.0275 (6) | 0.0211 (5) | 0.0052 (5) | 0.0006 (4) | −0.0049 (4) |
C13 | 0.0381 (7) | 0.0292 (7) | 0.0272 (6) | −0.0001 (6) | 0.0064 (5) | −0.0071 (5) |
C14 | 0.0351 (7) | 0.0395 (8) | 0.0204 (5) | 0.0013 (6) | 0.0035 (5) | −0.0010 (5) |
C15 | 0.0287 (6) | 0.0302 (6) | 0.0200 (5) | 0.0051 (5) | −0.0009 (4) | −0.0012 (5) |
C16 | 0.0351 (7) | 0.0268 (6) | 0.0237 (5) | −0.0031 (5) | 0.0066 (5) | −0.0002 (5) |
C17 | 0.0355 (7) | 0.0382 (8) | 0.0408 (7) | 0.0040 (6) | 0.0034 (6) | −0.0029 (6) |
C18 | 0.0413 (9) | 0.0483 (10) | 0.0556 (10) | −0.0036 (8) | −0.0050 (7) | −0.0020 (8) |
C19 | 0.0304 (6) | 0.0355 (7) | 0.0173 (5) | 0.0013 (5) | 0.0006 (4) | −0.0012 (5) |
C20 | 0.0339 (7) | 0.0465 (8) | 0.0203 (5) | 0.0003 (6) | 0.0028 (5) | −0.0047 (5) |
C21 | 0.0351 (8) | 0.0966 (16) | 0.0278 (7) | −0.0078 (9) | 0.0016 (6) | −0.0129 (8) |
S1—C10 | 1.7292 (14) | C11—C15 | 1.3568 (17) |
S1—C15 | 1.7319 (14) | C12—C13 | 1.5253 (19) |
O1—C8 | 1.3397 (15) | C14—C15 | 1.4968 (19) |
O1—C19 | 1.4461 (14) | C17—C18 | 1.489 (2) |
O2—C16 | 1.2163 (17) | C19—C20 | 1.4495 (19) |
O3—C16 | 1.3393 (16) | C20—C21 | 1.171 (2) |
O3—C17 | 1.4472 (18) | C1—H1 | 0.9300 |
N1—C7 | 1.3529 (16) | C2—H2 | 0.9300 |
N1—C8 | 1.3150 (16) | C3—H3 | 0.9300 |
N2—C7 | 1.3316 (17) | C4—H4 | 0.9300 |
N2—C10 | 1.3389 (18) | C5—H5 | 0.9300 |
N3—C13 | 1.4657 (18) | C12—H12A | 0.9700 |
N3—C14 | 1.4505 (18) | C12—H12B | 0.9700 |
N3—C16 | 1.3451 (18) | C13—H13A | 0.9700 |
C1—C2 | 1.384 (2) | C13—H13B | 0.9700 |
C1—C6 | 1.3921 (18) | C14—H14A | 0.9700 |
C2—C3 | 1.379 (2) | C14—H14B | 0.9700 |
C3—C4 | 1.377 (2) | C17—H17A | 0.9700 |
C4—C5 | 1.380 (2) | C17—H17B | 0.9700 |
C5—C6 | 1.3910 (19) | C18—H18A | 0.9600 |
C6—C7 | 1.4767 (18) | C18—H18B | 0.9600 |
C8—C9 | 1.4052 (16) | C18—H18C | 0.9600 |
C9—C10 | 1.3918 (18) | C19—H19A | 0.9700 |
C9—C11 | 1.4330 (17) | C19—H19B | 0.9700 |
C11—C12 | 1.4949 (18) | C21—H21 | 0.9300 |
C10—S1—C15 | 90.73 (6) | C2—C1—H1 | 120.00 |
C8—O1—C19 | 116.38 (10) | C6—C1—H1 | 120.00 |
C16—O3—C17 | 114.33 (11) | C1—C2—H2 | 120.00 |
C7—N1—C8 | 117.57 (10) | C3—C2—H2 | 120.00 |
C7—N2—C10 | 114.61 (11) | C2—C3—H3 | 120.00 |
C13—N3—C14 | 114.45 (11) | C4—C3—H3 | 120.00 |
C13—N3—C16 | 125.49 (11) | C3—C4—H4 | 120.00 |
C14—N3—C16 | 119.01 (11) | C5—C4—H4 | 120.00 |
C2—C1—C6 | 120.37 (13) | C4—C5—H5 | 120.00 |
C1—C2—C3 | 120.45 (13) | C6—C5—H5 | 120.00 |
C2—C3—C4 | 119.53 (14) | C11—C12—H12A | 110.00 |
C3—C4—C5 | 120.49 (14) | C11—C12—H12B | 110.00 |
C4—C5—C6 | 120.62 (13) | C13—C12—H12A | 110.00 |
C1—C6—C5 | 118.54 (12) | C13—C12—H12B | 110.00 |
C1—C6—C7 | 121.25 (12) | H12A—C12—H12B | 108.00 |
C5—C6—C7 | 120.21 (12) | N3—C13—H13A | 109.00 |
N1—C7—N2 | 125.67 (11) | N3—C13—H13B | 109.00 |
N1—C7—C6 | 116.61 (11) | C12—C13—H13A | 109.00 |
N2—C7—C6 | 117.71 (11) | C12—C13—H13B | 109.00 |
O1—C8—N1 | 120.10 (10) | H13A—C13—H13B | 108.00 |
O1—C8—C9 | 116.89 (11) | N3—C14—H14A | 110.00 |
N1—C8—C9 | 123.01 (11) | N3—C14—H14B | 110.00 |
C8—C9—C10 | 113.43 (11) | C15—C14—H14A | 110.00 |
C8—C9—C11 | 133.67 (11) | C15—C14—H14B | 110.00 |
C10—C9—C11 | 112.89 (10) | H14A—C14—H14B | 108.00 |
S1—C10—N2 | 122.89 (10) | O3—C17—H17A | 110.00 |
S1—C10—C9 | 111.40 (10) | O3—C17—H17B | 110.00 |
N2—C10—C9 | 125.70 (11) | C18—C17—H17A | 110.00 |
C9—C11—C12 | 127.49 (10) | C18—C17—H17B | 110.00 |
C9—C11—C15 | 111.09 (11) | H17A—C17—H17B | 109.00 |
C12—C11—C15 | 121.42 (11) | C17—C18—H18A | 110.00 |
C11—C12—C13 | 110.15 (10) | C17—C18—H18B | 109.00 |
N3—C13—C12 | 111.52 (12) | C17—C18—H18C | 110.00 |
N3—C14—C15 | 108.88 (10) | H18A—C18—H18B | 109.00 |
S1—C15—C11 | 113.87 (10) | H18A—C18—H18C | 109.00 |
S1—C15—C14 | 120.79 (9) | H18B—C18—H18C | 109.00 |
C11—C15—C14 | 125.33 (12) | O1—C19—H19A | 110.00 |
O2—C16—O3 | 123.30 (12) | O1—C19—H19B | 110.00 |
O2—C16—N3 | 124.33 (12) | C20—C19—H19A | 110.00 |
O3—C16—N3 | 112.37 (11) | C20—C19—H19B | 110.00 |
O3—C17—C18 | 107.83 (13) | H19A—C19—H19B | 108.00 |
O1—C19—C20 | 107.35 (11) | C20—C21—H21 | 180.00 |
C19—C20—C21 | 176.57 (18) | ||
C10—S1—C15—C11 | 0.63 (11) | C2—C3—C4—C5 | 0.1 (2) |
C15—S1—C10—N2 | 179.24 (12) | C3—C4—C5—C6 | 0.5 (2) |
C15—S1—C10—C9 | 0.26 (11) | C4—C5—C6—C7 | 178.35 (13) |
C10—S1—C15—C14 | 179.45 (12) | C4—C5—C6—C1 | −0.9 (2) |
C19—O1—C8—N1 | −3.14 (17) | C1—C6—C7—N2 | −179.40 (12) |
C8—O1—C19—C20 | −166.90 (12) | C5—C6—C7—N1 | −178.14 (13) |
C19—O1—C8—C9 | 176.72 (11) | C1—C6—C7—N1 | 1.06 (18) |
C17—O3—C16—N3 | 179.78 (12) | C5—C6—C7—N2 | 1.40 (19) |
C16—O3—C17—C18 | 178.23 (12) | O1—C8—C9—C11 | 0.2 (2) |
C17—O3—C16—O2 | 0.06 (19) | N1—C8—C9—C10 | 1.12 (19) |
C8—N1—C7—C6 | 179.19 (11) | O1—C8—C9—C10 | −178.73 (11) |
C7—N1—C8—C9 | −0.62 (19) | N1—C8—C9—C11 | −179.97 (14) |
C8—N1—C7—N2 | −0.3 (2) | C8—C9—C10—N2 | −0.8 (2) |
C7—N1—C8—O1 | 179.22 (11) | C8—C9—C10—S1 | 178.11 (9) |
C10—N2—C7—C6 | −178.91 (12) | C8—C9—C11—C15 | −177.42 (14) |
C10—N2—C7—N1 | 0.58 (19) | C10—C9—C11—C12 | −178.29 (13) |
C7—N2—C10—S1 | −178.78 (10) | C10—C9—C11—C15 | 1.50 (16) |
C7—N2—C10—C9 | 0.1 (2) | C8—C9—C11—C12 | 2.8 (2) |
C14—N3—C16—O2 | −7.3 (2) | C11—C9—C10—N2 | −180.00 (13) |
C13—N3—C16—O2 | −174.90 (13) | C11—C9—C10—S1 | −1.04 (15) |
C14—N3—C16—O3 | 172.98 (12) | C9—C11—C15—C14 | 179.93 (12) |
C13—N3—C14—C15 | 46.00 (16) | C12—C11—C15—S1 | 178.50 (10) |
C13—N3—C16—O3 | 5.37 (19) | C15—C11—C12—C13 | −14.47 (17) |
C14—N3—C13—C12 | −64.08 (15) | C9—C11—C15—S1 | −1.31 (15) |
C16—N3—C13—C12 | 104.02 (15) | C9—C11—C12—C13 | 165.30 (13) |
C16—N3—C14—C15 | −122.93 (13) | C12—C11—C15—C14 | −0.3 (2) |
C6—C1—C2—C3 | −0.2 (2) | C11—C12—C13—N3 | 44.25 (15) |
C2—C1—C6—C7 | −178.48 (13) | N3—C14—C15—S1 | 166.88 (10) |
C2—C1—C6—C5 | 0.7 (2) | N3—C14—C15—C11 | −14.4 (2) |
C1—C2—C3—C4 | −0.2 (2) |
Cg1 and Cg4 are the centroids of the S1,C9–C11/C15 and C1–C6 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N1 | 0.93 | 2.49 | 2.8050 (19) | 100 |
C5—H5···N2 | 0.93 | 2.47 | 2.7961 (19) | 101 |
C13—H13A···O3 | 0.97 | 2.30 | 2.7085 (19) | 104 |
C14—H14A···O2i | 0.97 | 2.44 | 3.294 (2) | 146 |
C14—H14B···O2 | 0.97 | 2.33 | 2.7509 (19) | 105 |
C21—H21···N2ii | 0.93 | 2.55 | 3.418 (2) | 156 |
C12—H12B···Cg4iii | 0.97 | 2.80 | 3.6643 (17) | 149 |
C19—H19A···Cg1iv | 0.97 | 2.92 | 3.6736 (18) | 136 |
Symmetry codes: (i) −x−1/2, y−1/2, −z+5/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z+2; (iv) −x, −y, −z+2. |
Cg1 and Cg4 are the centroids of the S1,C9–C11/C15 and C1–C6 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O2i | 0.97 | 2.44 | 3.294 (2) | 146 |
C21—H21···N2ii | 0.93 | 2.55 | 3.418 (2) | 156 |
C12—H12B···Cg4iii | 0.97 | 2.80 | 3.6643 (17) | 149 |
C19—H19A···Cg1iv | 0.97 | 2.92 | 3.6736 (18) | 136 |
Symmetry codes: (i) −x−1/2, y−1/2, −z+5/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z+2; (iv) −x, −y, −z+2. |
Acknowledgements
JPJ acknowledges the NSF–MRI program (grant No·CHE-1039027) for funds to purchase the X-ray diffractometer.
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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.
Thieno[2,3-d]pyrimidines are a large group of heterocyclic compounds (Litvinov, 2004), and some of them showed antiviral (Nasr & Gineinah, 2002), antimicrobial (Bhuiyan et al., 2005; Chambhare et al., 2003), and antibacterial properties (Alagarsamy et al., 2006). Fused tri- and tetracyclic thieno[2,3-d]pyrimidin-4-ones are synthesized by many methods and among them some compounds have fungicidal, antibacterial, and anti-inflammatory activities (Kapustina et al., 1992). In this context, and following to our on-going study of bio-active molecules, we report here the synthesis and crystal structure of the title compound.
In the title compound (Fig. 1), the 5,6,7,8-tetrahydropyridine ring (N3/C11/-C15) adopts a half-chair conformation [the puckering parameters are QT = 0.4662 (14) Å, θ = 50.06 (17) ° and φ = 30.8 (2) °]. The fused-thieno[2,3-d]pyrimidine ring system (S1/N1/N2C7-C11/C15) is essentially planar (r.m.s. deviation = 0.001 Å) and forms a dihedral angle of 2.66 (6)° with the attached phenyl ring (C1–C6). The C8–O1–C19–C20, C13–N3–C16–O2 and N3–C16–O3–C17 torsion angles are -166.90 (12), -174.90 (13) and 179.78 (12)°, respectively. All bond lengths and angles in the title molecule are normal and comparable with those previously reported for related structures (Liu et al., 2005; Ren et al., 2006).
In the crystal, molecules are linked by C—H···O, C—H···N and C—H···π hydrogen bonds, forming a three dimensional network (Fig. 2 & Table 1).