Literature DB >> 23125676

Ethyl 3-eth-oxy-carbonyl-methyl-7-methyl-5-phenyl-5H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

H Nagarajaiah1, Noor Shahina Begum.   

Abstract

In the title compound, C(20)H(22)N(2)O(4)S, the central pyrimidine ring incorporating a chiral C atom is significantly puckered and adopts a slight boat conformation with C atom bearing the phenyl ring and the N atom opposite displaced by 0.367 (2) and 0.107 (2) Å, respectively, from the plane formed by the remaining ring atoms. The benzene ring is positioned axially to the pyrimidine ring, making a dihedral angle of 88.99 (5)°. The thia-zole ring is essentially planar (r.m.s. deviation = 0.0033 Å). In the crystal, pairs of C-H⋯O inter-actions result in centrosymmetric dimers with graph-set motifs R(1) (2)(7) and R(2) (2)(8). A weak C-H⋯π contact is also observed.

Entities:  

Year:  2012        PMID： 23125676      PMCID： PMC3470232          DOI： 10.1107/S1600536812037828

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


Related literature

For the therapeutic potential of thia­zolopyrimidine derivatives, see: Zhi et al. (2008 ▶). For the synthesis of the title compound, see: Nagarajaiah et al. (2012 ▶). For a related structure, see: Nagarajaiah & Begum (2011) ▶. For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For carbonyl–π interactions, see: Gautrot et al. (2006 ▶).

Experimental

Crystal data

C20H22N2O4S M = 386.46 Monoclinic, a = 10.0861 (4) Å b = 7.7954 (3) Å c = 23.4088 (10) Å β = 95.000 (3)° V = 1833.52 (13) Å3 Z = 4 Mo Kα radiation μ = 0.21 mm−1 T = 296 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 = 0.964, T max = 0.968 11747 measured reflections 3982 independent reflections 3102 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.118 S = 1.00 3982 reflections 247 parameters H-atom parameters constrained Δρmax = 0.50 e Å−3 Δρmin = −0.29 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 datablock(s) global, I. DOI: 10.1107/S1600536812037828/pv2584sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037828/pv2584Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812037828/pv2584Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H22N2O4SF(000) = 816
Mr = 386.46Dx = 1.400 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3102 reflections
a = 10.0861 (4) Åθ = 1.8–27.0°
b = 7.7954 (3) ŵ = 0.21 mm−1
c = 23.4088 (10) ÅT = 296 K
β = 95.000 (3)°Block, yellow
V = 1833.52 (13) Å30.18 × 0.16 × 0.16 mm
Z = 4
Bruker SMART APEX CCD detector diffractometer3982 independent reflections
Radiation source: fine-focus sealed tube3102 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −12→12
Tmin = 0.964, Tmax = 0.968k = −6→9
11747 measured reflectionsl = −29→29
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0675P)2 + 0.5269P] where P = (Fo2 + 2Fc2)/3
3982 reflections(Δ/σ)max < 0.001
247 parametersΔρmax = 0.50 e Å−3
0 restraintsΔρmin = −0.29 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 > 2σ(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
S10.18621 (4)0.21888 (6)0.308470 (19)0.01968 (14)
O10.64536 (12)0.10949 (17)0.36984 (5)0.0216 (3)
O20.67845 (13)0.00457 (18)0.45941 (6)0.0260 (3)
O30.31568 (12)−0.40830 (18)0.48561 (5)0.0220 (3)
O40.12682 (12)−0.51826 (17)0.44357 (5)0.0199 (3)
N10.30250 (14)0.0076 (2)0.37900 (6)0.0150 (3)
N20.11268 (14)−0.1069 (2)0.32378 (6)0.0183 (3)
C1−0.00093 (18)−0.3634 (3)0.34719 (8)0.0228 (4)
H1A0.0277−0.48090.34770.034*
H1B−0.0437−0.33610.31000.034*
H1C−0.0625−0.34650.37570.034*
C20.32329 (18)0.2865 (3)0.35279 (7)0.0189 (4)
H20.35820.39690.35240.023*
C30.37267 (17)0.1622 (2)0.38743 (7)0.0157 (4)
C40.0304 (2)−0.7801 (3)0.47057 (10)0.0351 (5)
H4A−0.0546−0.72440.46520.053*
H4B0.0287−0.86460.50030.053*
H4C0.0495−0.83490.43550.053*
C50.34164 (16)−0.1592 (2)0.40446 (7)0.0149 (4)
H50.3749−0.14160.44460.018*
C60.21811 (16)−0.2722 (2)0.40233 (7)0.0150 (4)
C70.11731 (18)−0.2487 (2)0.35981 (7)0.0177 (4)
C80.1356 (2)−0.6503 (3)0.48718 (8)0.0256 (4)
H8A0.1217−0.60110.52420.031*
H8B0.2228−0.70350.48960.031*
C90.19752 (17)0.0147 (2)0.33814 (7)0.0165 (4)
C100.22567 (17)−0.4028 (2)0.44727 (7)0.0167 (4)
C110.44966 (17)−0.2466 (2)0.37322 (7)0.0147 (4)
C120.54419 (17)−0.3488 (2)0.40333 (7)0.0164 (4)
H120.5466−0.35480.44310.020*
C130.63526 (17)−0.4424 (2)0.37482 (8)0.0190 (4)
H130.6978−0.51100.39550.023*
C140.63328 (18)−0.4338 (2)0.31562 (8)0.0202 (4)
H140.6940−0.49680.29650.024*
C150.54006 (18)−0.3308 (3)0.28515 (8)0.0210 (4)
H150.5385−0.32420.24540.025*
C160.44914 (18)−0.2375 (2)0.31367 (7)0.0188 (4)
H160.3872−0.16820.29290.023*
C170.48437 (17)0.1764 (2)0.43372 (7)0.0181 (4)
H17A0.45360.13190.46890.022*
H17B0.50410.29710.43990.022*
C180.61252 (18)0.0854 (2)0.42323 (7)0.0190 (4)
C190.76628 (18)0.0231 (3)0.35511 (8)0.0237 (4)
H19A0.7534−0.10020.35510.028*
H19B0.83970.05080.38310.028*
C200.7966 (2)0.0815 (3)0.29736 (9)0.0362 (6)
H20A0.72130.06010.27030.054*
H20B0.87240.02010.28590.054*
H20C0.81560.20220.29840.054*
U11U22U33U12U13U23
S10.0253 (2)0.0184 (3)0.0147 (2)0.0029 (2)−0.00124 (17)0.00322 (18)
O10.0244 (6)0.0245 (8)0.0158 (6)0.0014 (6)0.0020 (5)0.0011 (5)
O20.0318 (7)0.0281 (8)0.0173 (7)0.0032 (6)−0.0033 (5)0.0032 (6)
O30.0260 (7)0.0255 (8)0.0138 (6)−0.0037 (6)−0.0028 (5)0.0060 (5)
O40.0233 (6)0.0185 (7)0.0180 (6)−0.0037 (6)0.0021 (5)0.0045 (5)
N10.0186 (7)0.0158 (8)0.0103 (7)0.0005 (6)−0.0001 (5)0.0002 (6)
N20.0208 (7)0.0194 (9)0.0141 (7)0.0005 (7)−0.0015 (6)0.0011 (6)
C10.0219 (9)0.0263 (11)0.0194 (9)−0.0026 (8)−0.0033 (7)0.0028 (8)
C20.0241 (9)0.0169 (10)0.0158 (9)−0.0006 (8)0.0018 (7)−0.0022 (7)
C30.0212 (8)0.0151 (10)0.0113 (8)−0.0003 (7)0.0038 (6)−0.0020 (7)
C40.0472 (13)0.0245 (12)0.0348 (12)−0.0122 (11)0.0094 (10)0.0019 (10)
C50.0208 (8)0.0151 (10)0.0084 (8)0.0001 (7)−0.0004 (6)0.0011 (6)
C60.0182 (8)0.0152 (10)0.0118 (8)−0.0012 (7)0.0021 (6)−0.0012 (7)
C70.0203 (9)0.0192 (10)0.0138 (8)0.0020 (8)0.0027 (6)−0.0010 (7)
C80.0347 (10)0.0195 (11)0.0230 (10)−0.0028 (9)0.0043 (8)0.0070 (8)
C90.0209 (8)0.0192 (10)0.0094 (8)0.0038 (8)0.0011 (6)0.0005 (7)
C100.0198 (8)0.0172 (10)0.0133 (8)0.0008 (8)0.0035 (7)−0.0012 (7)
C110.0179 (8)0.0130 (10)0.0129 (8)−0.0031 (7)0.0004 (6)−0.0002 (7)
C120.0209 (8)0.0159 (10)0.0122 (8)−0.0033 (7)−0.0006 (6)0.0017 (7)
C130.0205 (8)0.0158 (10)0.0201 (9)−0.0012 (8)−0.0017 (7)0.0004 (7)
C140.0216 (9)0.0187 (10)0.0209 (9)−0.0013 (8)0.0054 (7)−0.0043 (8)
C150.0254 (9)0.0265 (11)0.0112 (8)−0.0017 (8)0.0018 (7)−0.0012 (7)
C160.0211 (9)0.0224 (11)0.0125 (8)−0.0010 (8)−0.0008 (7)0.0028 (7)
C170.0246 (9)0.0170 (10)0.0125 (8)−0.0026 (8)0.0005 (7)−0.0010 (7)
C180.0259 (9)0.0160 (10)0.0146 (9)−0.0043 (8)−0.0013 (7)−0.0017 (7)
C190.0230 (9)0.0238 (11)0.0243 (10)0.0029 (8)0.0013 (7)−0.0007 (8)
C200.0342 (11)0.0451 (15)0.0307 (12)0.0145 (11)0.0109 (9)0.0093 (10)
S1—C91.7363 (19)C5—H50.9800
S1—C21.7367 (19)C6—C71.372 (2)
O1—C181.334 (2)C6—C101.461 (2)
O1—C191.460 (2)C8—H8A0.9700
O2—C181.208 (2)C8—H8B0.9700
O3—C101.220 (2)C11—C121.387 (2)
O4—C101.340 (2)C11—C161.395 (2)
O4—C81.447 (2)C12—C131.388 (3)
N1—C91.365 (2)C12—H120.9300
N1—C31.403 (2)C13—C141.386 (3)
N1—C51.470 (2)C13—H130.9300
N2—C91.302 (2)C14—C151.386 (3)
N2—C71.389 (2)C14—H140.9300
C1—C71.499 (3)C15—C161.386 (3)
C1—H1A0.9600C15—H150.9300
C1—H1B0.9600C16—H160.9300
C1—H1C0.9600C17—C181.513 (3)
C2—C31.332 (3)C17—H17A0.9700
C2—H20.9300C17—H17B0.9700
C3—C171.498 (2)C19—C201.483 (3)
C4—C81.493 (3)C19—H19A0.9700
C4—H4A0.9600C19—H19B0.9700
C4—H4B0.9600C20—H20A0.9600
C4—H4C0.9600C20—H20B0.9600
C5—C61.523 (2)C20—H20C0.9600
C5—C111.525 (2)
C9—S1—C291.05 (9)N2—C9—S1123.07 (13)
C18—O1—C19115.91 (14)N1—C9—S1109.73 (13)
C10—O4—C8115.64 (14)O3—C10—O4121.68 (16)
C9—N1—C3114.51 (15)O3—C10—C6122.88 (16)
C9—N1—C5118.99 (15)O4—C10—C6115.44 (15)
C3—N1—C5126.05 (14)C12—C11—C16118.65 (16)
C9—N2—C7115.87 (15)C12—C11—C5120.09 (15)
C7—C1—H1A109.5C16—C11—C5121.04 (15)
C7—C1—H1B109.5C11—C12—C13120.78 (16)
H1A—C1—H1B109.5C11—C12—H12119.6
C7—C1—H1C109.5C13—C12—H12119.6
H1A—C1—H1C109.5C14—C13—C12120.20 (17)
H1B—C1—H1C109.5C14—C13—H13119.9
C3—C2—S1112.24 (15)C12—C13—H13119.9
C3—C2—H2123.9C13—C14—C15119.50 (17)
S1—C2—H2123.9C13—C14—H14120.3
C2—C3—N1112.47 (16)C15—C14—H14120.3
C2—C3—C17127.16 (17)C14—C15—C16120.25 (17)
N1—C3—C17120.27 (16)C14—C15—H15119.9
C8—C4—H4A109.5C16—C15—H15119.9
C8—C4—H4B109.5C15—C16—C11120.62 (17)
H4A—C4—H4B109.5C15—C16—H16119.7
C8—C4—H4C109.5C11—C16—H16119.7
H4A—C4—H4C109.5C3—C17—C18116.57 (15)
H4B—C4—H4C109.5C3—C17—H17A108.2
N1—C5—C6107.96 (13)C18—C17—H17A108.2
N1—C5—C11112.26 (13)C3—C17—H17B108.2
C6—C5—C11110.02 (14)C18—C17—H17B108.2
N1—C5—H5108.8H17A—C17—H17B107.3
C6—C5—H5108.8O2—C18—O1124.34 (17)
C11—C5—H5108.8O2—C18—C17123.84 (16)
C7—C6—C10127.18 (16)O1—C18—C17111.80 (15)
C7—C6—C5119.94 (16)O1—C19—C20108.42 (16)
C10—C6—C5112.84 (14)O1—C19—H19A110.0
C6—C7—N2122.04 (17)C20—C19—H19A110.0
C6—C7—C1126.17 (17)O1—C19—H19B110.0
N2—C7—C1111.77 (15)C20—C19—H19B110.0
O4—C8—C4107.47 (16)H19A—C19—H19B108.4
O4—C8—H8A110.2C19—C20—H20A109.5
C4—C8—H8A110.2C19—C20—H20B109.5
O4—C8—H8B110.2H20A—C20—H20B109.5
C4—C8—H8B110.2C19—C20—H20C109.5
H8A—C8—H8B108.5H20A—C20—H20C109.5
N2—C9—N1127.15 (17)H20B—C20—H20C109.5
C9—S1—C2—C3−0.19 (14)C2—S1—C9—N2177.08 (15)
S1—C2—C3—N10.62 (19)C2—S1—C9—N1−0.30 (13)
S1—C2—C3—C17−175.77 (14)C8—O4—C10—O3−1.0 (2)
C9—N1—C3—C2−0.9 (2)C8—O4—C10—C6178.56 (15)
C5—N1—C3—C2171.25 (15)C7—C6—C10—O3−175.52 (17)
C9—N1—C3—C17175.79 (15)C5—C6—C10—O36.9 (2)
C5—N1—C3—C17−12.1 (2)C7—C6—C10—O44.9 (3)
C9—N1—C5—C6−28.50 (19)C5—C6—C10—O4−172.68 (14)
C3—N1—C5—C6159.69 (15)N1—C5—C11—C12147.17 (16)
C9—N1—C5—C1192.94 (17)C6—C5—C11—C12−92.58 (19)
C3—N1—C5—C11−78.87 (19)N1—C5—C11—C16−38.2 (2)
N1—C5—C6—C728.9 (2)C6—C5—C11—C1682.0 (2)
C11—C5—C6—C7−93.96 (19)C16—C11—C12—C13−1.0 (3)
N1—C5—C6—C10−153.39 (14)C5—C11—C12—C13173.77 (16)
C11—C5—C6—C1083.79 (17)C11—C12—C13—C140.4 (3)
C10—C6—C7—N2171.60 (16)C12—C13—C14—C150.2 (3)
C5—C6—C7—N2−11.0 (3)C13—C14—C15—C16−0.3 (3)
C10—C6—C7—C1−6.2 (3)C14—C15—C16—C11−0.3 (3)
C5—C6—C7—C1171.16 (16)C12—C11—C16—C150.9 (3)
C9—N2—C7—C6−10.1 (2)C5—C11—C16—C15−173.75 (17)
C9—N2—C7—C1167.97 (15)C2—C3—C17—C18−110.7 (2)
C10—O4—C8—C4−171.20 (16)N1—C3—C17—C1873.2 (2)
C7—N2—C9—N110.8 (3)C19—O1—C18—O23.2 (3)
C7—N2—C9—S1−166.12 (13)C19—O1—C18—C17−178.60 (15)
C3—N1—C9—N2−176.53 (16)C3—C17—C18—O2−138.12 (19)
C5—N1—C9—N210.7 (2)C3—C17—C18—O143.6 (2)
C3—N1—C9—S10.71 (17)C18—O1—C19—C20−172.85 (17)
C5—N1—C9—S1−172.02 (11)
D—H···AD—HH···AD···AD—H···A
C17—H17A···O2i0.972.473.415 (3)164
C5—H5···O2i0.982.593.429 (2)144
C20—H20B···N2ii0.962.703.516 (3)144
C4—H4C···Cg1iii0.963.033.897 (4)151
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the thia­zolopyrimidine ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C17—H17A⋯O2i 0.972.473.415 (3)164
C5—H5⋯O2i 0.982.593.429 (2)144
C4—H4C⋯Cg1ii 0.963.033.897 (4)151

Symmetry codes: (i) ; (ii) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Methyl 5-(4-hy-droxy-3-meth-oxy-phen-yl)-2-(4-meth-oxy-benzyl-idene)-7-methyl-3-oxo-2,3-dihydro-5H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Authors:  H Nagarajaiah; Noor Shahina Begum
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-25
  2 in total

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