Literature DB >> 22606151

Ethyl 7-methyl-3-oxo-5-phenyl-2-(2,4,6-trimeth-oxy-benzyl-idene)-2,3-dihydro-5H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Noor Afshan Banu, V Bheema Raju.   

Abstract

In the title compound, C(26)H(26)N(2)O(6)S, the benzene ring is positioned axially to the thia-zolopyrimidine ring and bis-ects it with a dihedral angle of 80.94 (7)°. The pyrimidine ring adopts a flattened boat conformation. In the crystal, pairs of bifurcated C-H⋯O hydrogen bonds link the mol-ecules into chains along the c axis.

Entities:  

Year:  2012        PMID: 22606151      PMCID: PMC3344148          DOI: 10.1107/S1600536812012354

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


Related literature

For the pharmacological activity of pyrimidine derivatives, see: Alam et al. (2010 ▶). For a related crystal structure, see: Chen et al. (2012 ▶).

Experimental

Crystal data

C26H26N2O6S M = 494.55 Monoclinic, a = 7.5363 (19) Å b = 18.178 (5) Å c = 16.973 (4) Å β = 94.465 (5)° V = 2318.1 (10) Å3 Z = 4 Mo Kα radiation μ = 0.19 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 = 0.967, T max = 0.971 13918 measured reflections 5055 independent reflections 3500 reflections with I > 2σ(I) R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.168 S = 1.07 5055 reflections 321 parameters H-atom parameters constrained Δρmax = 0.59 e Å−3 Δρmin = −0.38 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/S1600536812012354/pv2518sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012354/pv2518Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812012354/pv2518Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H26N2O6SF(000) = 1040
Mr = 494.55Dx = 1.417 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5055 reflections
a = 7.5363 (19) Åθ = 2.2–27.0°
b = 18.178 (5) ŵ = 0.19 mm1
c = 16.973 (4) ÅT = 296 K
β = 94.465 (5)°Block, yellow
V = 2318.1 (10) Å30.18 × 0.16 × 0.16 mm
Z = 4
Bruker SMART APEX CCD detector diffractometer5055 independent reflections
Radiation source: fine-focus sealed tube3500 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −9→6
Tmin = 0.967, Tmax = 0.971k = −19→23
13918 measured reflectionsl = −21→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0854P)2] where P = (Fo2 + 2Fc2)/3
5055 reflections(Δ/σ)max = 0.001
321 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = −0.38 e Å3
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
S10.73105 (9)0.14251 (3)0.58179 (4)0.02186 (19)
O5−0.0478 (3)0.28751 (10)0.67802 (11)0.0280 (5)
O21.1137 (2)0.27911 (9)0.35791 (11)0.0259 (5)
O41.0502 (2)0.09339 (9)0.54509 (10)0.0250 (4)
N10.4401 (3)0.16361 (12)0.65853 (12)0.0224 (5)
O10.6191 (2)0.32009 (9)0.46396 (11)0.0252 (4)
O60.0574 (2)0.36348 (10)0.58753 (12)0.0285 (5)
N20.5119 (3)0.25231 (11)0.56348 (12)0.0209 (5)
O31.5463 (3)0.08397 (10)0.39073 (11)0.0276 (5)
C160.5164 (3)0.36754 (14)0.69908 (15)0.0218 (6)
H160.52700.32190.72370.026*
C110.4425 (3)0.37259 (14)0.62157 (15)0.0195 (6)
C60.2376 (4)0.26532 (14)0.62849 (15)0.0220 (6)
C100.0685 (4)0.30403 (14)0.63572 (16)0.0237 (6)
C201.3047 (4)0.08844 (14)0.46749 (15)0.0221 (6)
H201.34730.04590.49290.027*
C90.5401 (4)0.18888 (13)0.60625 (15)0.0207 (6)
C170.9132 (3)0.22160 (13)0.46628 (15)0.0201 (6)
H170.89680.26440.43650.024*
C70.2822 (4)0.20292 (14)0.66861 (15)0.0221 (6)
C20.7777 (3)0.21079 (13)0.51239 (15)0.0209 (6)
C50.3682 (3)0.30400 (13)0.57885 (16)0.0214 (6)
H50.30620.31860.52840.026*
C30.6336 (4)0.26750 (14)0.50774 (15)0.0218 (6)
C181.0776 (3)0.18488 (13)0.45027 (15)0.0204 (6)
C211.3967 (3)0.12094 (14)0.40848 (15)0.0220 (6)
C80.1730 (4)0.16755 (15)0.72924 (16)0.0288 (7)
H8A0.16860.19970.77390.043*
H8B0.22650.12170.74600.043*
H8C0.05440.15880.70630.043*
C191.1482 (4)0.12100 (14)0.48744 (14)0.0206 (6)
C150.5743 (4)0.43039 (14)0.73975 (16)0.0236 (6)
H150.62510.42680.79130.028*
C120.4283 (4)0.44127 (14)0.58605 (16)0.0242 (6)
H120.38050.44520.53400.029*
C221.3384 (3)0.18520 (14)0.37125 (15)0.0213 (6)
H221.40330.20700.33310.026*
C130.4841 (4)0.50407 (14)0.62696 (17)0.0261 (6)
H130.47280.54990.60270.031*
C231.1808 (4)0.21644 (13)0.39216 (15)0.0216 (6)
C251.6375 (4)0.11104 (16)0.32485 (17)0.0328 (7)
H25A1.55610.11270.27850.049*
H25B1.73480.07890.31570.049*
H25C1.68220.15960.33660.049*
C140.5563 (4)0.49832 (14)0.70364 (16)0.0247 (6)
H140.59340.54040.73130.030*
C261.1201 (4)0.03154 (14)0.58899 (15)0.0255 (6)
H26A1.1362−0.00870.55360.038*
H26B1.03860.01730.62700.038*
H26C1.23250.04440.61590.038*
C241.2289 (4)0.32127 (14)0.31204 (16)0.0267 (6)
H24A1.33560.33350.34400.040*
H24B1.16950.36570.29420.040*
H24C1.25870.29290.26720.040*
C1−0.0260 (4)0.48913 (16)0.6104 (2)0.0390 (8)
H1A0.02620.48980.66380.059*
H1B−0.12340.52330.60520.059*
H1C0.06200.50300.57520.059*
C4−0.0928 (4)0.41300 (15)0.59001 (19)0.0325 (7)
H4A−0.17030.39630.62940.039*
H4B−0.16060.41360.53900.039*
U11U22U33U12U13U23
S10.0216 (4)0.0219 (4)0.0231 (4)−0.0004 (3)0.0078 (3)0.0010 (3)
O50.0244 (11)0.0318 (11)0.0296 (11)−0.0015 (9)0.0135 (9)−0.0016 (8)
O20.0233 (11)0.0237 (10)0.0322 (11)0.0035 (8)0.0118 (8)0.0075 (8)
O40.0284 (11)0.0222 (10)0.0262 (10)0.0018 (8)0.0128 (8)0.0051 (7)
N10.0211 (13)0.0240 (11)0.0229 (12)−0.0026 (10)0.0072 (10)−0.0004 (9)
O10.0235 (11)0.0232 (10)0.0299 (11)0.0014 (8)0.0095 (8)0.0031 (8)
O60.0181 (10)0.0291 (10)0.0396 (12)0.0037 (8)0.0111 (9)0.0051 (8)
N20.0177 (12)0.0211 (11)0.0250 (12)−0.0024 (9)0.0081 (9)−0.0007 (9)
O30.0245 (11)0.0334 (11)0.0265 (10)0.0095 (9)0.0123 (8)0.0050 (8)
C160.0200 (14)0.0208 (13)0.0256 (14)0.0003 (11)0.0082 (11)0.0020 (10)
C110.0128 (13)0.0232 (13)0.0239 (14)−0.0011 (10)0.0098 (11)−0.0023 (10)
C60.0184 (14)0.0207 (13)0.0275 (14)−0.0013 (11)0.0064 (11)−0.0046 (11)
C100.0211 (15)0.0229 (14)0.0277 (15)−0.0056 (11)0.0059 (12)−0.0064 (11)
C200.0225 (15)0.0243 (13)0.0196 (13)0.0023 (11)0.0016 (11)0.0010 (10)
C90.0201 (14)0.0191 (13)0.0232 (14)−0.0026 (11)0.0038 (11)−0.0048 (10)
C170.0221 (15)0.0196 (13)0.0194 (13)−0.0020 (11)0.0062 (11)−0.0012 (10)
C70.0189 (14)0.0244 (14)0.0237 (14)−0.0079 (11)0.0065 (11)−0.0064 (11)
C20.0201 (14)0.0184 (13)0.0246 (14)−0.0011 (11)0.0050 (11)−0.0018 (10)
C50.0159 (14)0.0240 (13)0.0251 (14)0.0008 (11)0.0072 (11)−0.0012 (11)
C30.0207 (15)0.0243 (14)0.0211 (14)−0.0032 (11)0.0066 (11)−0.0026 (11)
C180.0190 (14)0.0204 (13)0.0227 (14)−0.0009 (11)0.0069 (11)−0.0019 (10)
C210.0173 (14)0.0273 (14)0.0215 (13)0.0023 (11)0.0029 (11)−0.0024 (11)
C80.0292 (17)0.0258 (14)0.0334 (16)−0.0049 (12)0.0143 (13)−0.0007 (12)
C190.0215 (14)0.0233 (13)0.0177 (13)−0.0036 (11)0.0064 (11)−0.0015 (10)
C150.0204 (14)0.0284 (14)0.0228 (14)0.0002 (12)0.0060 (11)−0.0034 (11)
C120.0212 (15)0.0286 (14)0.0234 (14)0.0015 (11)0.0057 (11)0.0042 (11)
C220.0173 (14)0.0282 (14)0.0191 (13)−0.0023 (11)0.0059 (11)−0.0022 (10)
C130.0258 (16)0.0161 (13)0.0376 (17)0.0012 (11)0.0095 (13)0.0043 (11)
C230.0215 (15)0.0187 (13)0.0252 (14)−0.0018 (11)0.0051 (11)−0.0014 (10)
C250.0297 (17)0.0396 (17)0.0311 (16)0.0119 (14)0.0146 (13)0.0078 (13)
C140.0207 (15)0.0222 (14)0.0323 (15)−0.0028 (11)0.0096 (12)−0.0053 (11)
C260.0276 (16)0.0230 (14)0.0265 (15)0.0008 (12)0.0063 (12)0.0031 (11)
C240.0296 (16)0.0240 (14)0.0276 (15)−0.0031 (12)0.0091 (13)0.0065 (11)
C10.0296 (18)0.0357 (17)0.053 (2)0.0054 (14)0.0103 (15)0.0013 (15)
C40.0186 (15)0.0355 (16)0.0447 (18)0.0046 (13)0.0103 (13)0.0040 (13)
S1—C91.745 (3)C2—C31.495 (4)
S1—C21.765 (3)C5—H50.9800
O5—C101.213 (3)C18—C191.406 (4)
O2—C231.359 (3)C18—C231.423 (3)
O2—C241.433 (3)C21—C221.383 (4)
O4—C191.367 (3)C8—H8A0.9600
O4—C261.427 (3)C8—H8B0.9600
N1—C91.292 (3)C8—H8C0.9600
N1—C71.410 (3)C15—C141.381 (4)
O1—C31.211 (3)C15—H150.9300
O6—C101.354 (3)C12—C131.385 (4)
O6—C41.449 (3)C12—H120.9300
N2—C91.370 (3)C22—C231.387 (3)
N2—C31.395 (3)C22—H220.9300
N2—C51.473 (3)C13—C141.375 (4)
O3—C211.367 (3)C13—H130.9300
O3—C251.443 (3)C25—H25A0.9600
C16—C151.387 (4)C25—H25B0.9600
C16—C111.391 (4)C25—H25C0.9600
C16—H160.9300C14—H140.9300
C11—C121.387 (3)C26—H26A0.9600
C11—C51.527 (3)C26—H26B0.9600
C6—C71.352 (4)C26—H26C0.9600
C6—C101.469 (4)C24—H24A0.9600
C6—C51.517 (3)C24—H24B0.9600
C20—C191.385 (3)C24—H24C0.9600
C20—C211.393 (3)C1—C41.504 (4)
C20—H200.9300C1—H1A0.9600
C17—C21.348 (3)C1—H1B0.9600
C17—C181.451 (3)C1—H1C0.9600
C17—H170.9300C4—H4A0.9700
C7—C81.511 (3)C4—H4B0.9700
C9—S1—C291.72 (12)C7—C8—H8C109.5
C23—O2—C24117.4 (2)H8A—C8—H8C109.5
C19—O4—C26117.7 (2)H8B—C8—H8C109.5
C9—N1—C7116.5 (2)O4—C19—C20122.4 (2)
C10—O6—C4119.3 (2)O4—C19—C18114.7 (2)
C9—N2—C3116.3 (2)C20—C19—C18122.9 (2)
C9—N2—C5121.9 (2)C14—C15—C16120.0 (3)
C3—N2—C5121.7 (2)C14—C15—H15120.0
C21—O3—C25117.0 (2)C16—C15—H15120.0
C15—C16—C11120.2 (2)C13—C12—C11120.9 (3)
C15—C16—H16119.9C13—C12—H12119.5
C11—C16—H16119.9C11—C12—H12119.5
C12—C11—C16118.8 (2)C21—C22—C23118.5 (2)
C12—C11—C5121.0 (2)C21—C22—H22120.8
C16—C11—C5120.0 (2)C23—C22—H22120.8
C7—C6—C10122.9 (2)C14—C13—C12119.6 (2)
C7—C6—C5121.5 (2)C14—C13—H13120.2
C10—C6—C5115.4 (2)C12—C13—H13120.2
O5—C10—O6122.8 (2)O2—C23—C22122.1 (2)
O5—C10—C6127.0 (3)O2—C23—C18115.4 (2)
O6—C10—C6110.2 (2)C22—C23—C18122.5 (2)
C19—C20—C21118.4 (2)O3—C25—H25A109.5
C19—C20—H20120.8O3—C25—H25B109.5
C21—C20—H20120.8H25A—C25—H25B109.5
N1—C9—N2126.0 (2)O3—C25—H25C109.5
N1—C9—S1121.8 (2)H25A—C25—H25C109.5
N2—C9—S1112.16 (18)H25B—C25—H25C109.5
C2—C17—C18137.5 (2)C13—C14—C15120.4 (2)
C2—C17—H17111.2C13—C14—H14119.8
C18—C17—H17111.2C15—C14—H14119.8
C6—C7—N1122.9 (2)O4—C26—H26A109.5
C6—C7—C8124.9 (2)O4—C26—H26B109.5
N1—C7—C8112.1 (2)H26A—C26—H26B109.5
C17—C2—C3116.7 (2)O4—C26—H26C109.5
C17—C2—S1133.6 (2)H26A—C26—H26C109.5
C3—C2—S1109.77 (18)H26B—C26—H26C109.5
N2—C5—C6108.7 (2)O2—C24—H24A109.5
N2—C5—C11110.9 (2)O2—C24—H24B109.5
C6—C5—C11110.2 (2)H24A—C24—H24B109.5
N2—C5—H5109.0O2—C24—H24C109.5
C6—C5—H5109.0H24A—C24—H24C109.5
C11—C5—H5109.0H24B—C24—H24C109.5
O1—C3—N2122.7 (2)C4—C1—H1A109.5
O1—C3—C2127.4 (2)C4—C1—H1B109.5
N2—C3—C2109.9 (2)H1A—C1—H1B109.5
C19—C18—C23115.8 (2)C4—C1—H1C109.5
C19—C18—C17126.5 (2)H1A—C1—H1C109.5
C23—C18—C17117.7 (2)H1B—C1—H1C109.5
O3—C21—C22123.6 (2)O6—C4—C1109.3 (2)
O3—C21—C20114.5 (2)O6—C4—H4A109.8
C22—C21—C20121.9 (2)C1—C4—H4A109.8
C7—C8—H8A109.5O6—C4—H4B109.8
C7—C8—H8B109.5C1—C4—H4B109.8
H8A—C8—H8B109.5H4A—C4—H4B108.3
C15—C16—C11—C120.1 (4)C5—N2—C3—O1−6.9 (4)
C15—C16—C11—C5−176.1 (2)C9—N2—C3—C2−3.8 (3)
C4—O6—C10—O54.6 (4)C5—N2—C3—C2172.4 (2)
C4—O6—C10—C6−175.1 (2)C17—C2—C3—O14.5 (4)
C7—C6—C10—O51.9 (4)S1—C2—C3—O1−176.6 (2)
C5—C6—C10—O5−172.4 (3)C17—C2—C3—N2−174.8 (2)
C7—C6—C10—O6−178.4 (2)S1—C2—C3—N24.1 (3)
C5—C6—C10—O67.3 (3)C2—C17—C18—C19−3.3 (5)
C7—N1—C9—N24.1 (4)C2—C17—C18—C23177.7 (3)
C7—N1—C9—S1−175.11 (18)C25—O3—C21—C22−5.5 (4)
C3—N2—C9—N1−177.5 (2)C25—O3—C21—C20174.1 (2)
C5—N2—C9—N16.3 (4)C19—C20—C21—O3−178.0 (2)
C3—N2—C9—S11.8 (3)C19—C20—C21—C221.7 (4)
C5—N2—C9—S1−174.44 (18)C26—O4—C19—C204.1 (4)
C2—S1—C9—N1180.0 (2)C26—O4—C19—C18−175.8 (2)
C2—S1—C9—N20.7 (2)C21—C20—C19—O4−179.4 (2)
C10—C6—C7—N1176.5 (2)C21—C20—C19—C180.6 (4)
C5—C6—C7—N1−9.6 (4)C23—C18—C19—O4177.6 (2)
C10—C6—C7—C8−4.2 (4)C17—C18—C19—O4−1.4 (4)
C5—C6—C7—C8169.8 (2)C23—C18—C19—C20−2.4 (4)
C9—N1—C7—C6−2.2 (4)C17—C18—C19—C20178.6 (2)
C9—N1—C7—C8178.3 (2)C11—C16—C15—C140.9 (4)
C18—C17—C2—C3179.5 (3)C16—C11—C12—C13−0.8 (4)
C18—C17—C2—S10.9 (5)C5—C11—C12—C13175.3 (2)
C9—S1—C2—C17175.9 (3)O3—C21—C22—C23177.6 (2)
C9—S1—C2—C3−2.7 (2)C20—C21—C22—C23−1.9 (4)
C9—N2—C5—C6−15.9 (3)C11—C12—C13—C140.6 (4)
C3—N2—C5—C6168.1 (2)C24—O2—C23—C22−13.5 (4)
C9—N2—C5—C11105.4 (3)C24—O2—C23—C18167.1 (2)
C3—N2—C5—C11−70.6 (3)C21—C22—C23—O2−179.4 (2)
C7—C6—C5—N217.4 (3)C21—C22—C23—C180.0 (4)
C10—C6—C5—N2−168.2 (2)C19—C18—C23—O2−178.5 (2)
C7—C6—C5—C11−104.3 (3)C17—C18—C23—O20.6 (3)
C10—C6—C5—C1170.0 (3)C19—C18—C23—C222.0 (4)
C12—C11—C5—N2115.6 (3)C17—C18—C23—C22−178.8 (2)
C16—C11—C5—N2−68.3 (3)C12—C13—C14—C150.3 (4)
C12—C11—C5—C6−123.9 (3)C16—C15—C14—C13−1.1 (4)
C16—C11—C5—C652.1 (3)C10—O6—C4—C1121.5 (3)
C9—N2—C3—O1176.8 (2)
D—H···AD—HH···AD···AD—H···A
C24—H24C···O5i0.962.633.537 (3)158
C25—H25A···O5i0.962.573.319 (3)135
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
C24—H24C⋯O5i0.962.633.537 (3)158
C25—H25A⋯O5i0.962.573.319 (3)135

Symmetry code: (i) .

  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.  (Z)-Ethyl 2-(2,4-dimethyl-benzyl-idene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Authors:  Xiao-Yan Chen; Han-Chu Wang; Qian Zhang; Zhi-Jian Song; Fei-Yun Zheng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-14
  2 in total

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