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The title compound, C19H18N2O3S, shows favourable activity against HIV-1. The phenyl ring is twisted with respect to the pyrimidine ring by 61.56 (9)°. Inter­molecular N—H...O and C—H...O hydrogen bonding links the mol­ecules into a supra­molecular chain structure and stabilizes the crystal structure of the compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028218/xu2272sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028218/xu2272Isup2.hkl
Contains datablock I

CCDC reference: 654925

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.116
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of our ongoing investigation on the S-DABOs analogues (He et al., 2004), the title compound was synthesized as novel inhibitors and shows favorable activity of anti-HIV-1. Its molecular structure contains a pyrimidine, a furan and a benzene rings (Figure 1). The dihedral angles between the pyrimidine ring and the benzene ring is 61.56 (9)°. The C14—C13—C8 bond angle between the two rings is 117.1 (2)°.

Intermolecular N—H···O and C—H···O hydrogen bonding links the molecules into a chain supra-molecular structure and stabilizes the crystal structure of the compound.

Related literature top

For related literature, see: He et al. (2004).

Experimental top

The title compound was prepared according to the procedure of (He et al., 2004). Single crystals were obtained from an ethyl acetate solution by slow evaporation at room temperature.

Refinement top

Methyl H atoms were placed in calculated positions wit C—H = 0.96 Å and torsion angle was refined to fit the electron density with Uiso(H) = 1.5Ueq(C). Other H were placed in calculated positions with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and refined in riding mode, Uiso(H) = 1.2Ueq(C,N).

Structure description top

As part of our ongoing investigation on the S-DABOs analogues (He et al., 2004), the title compound was synthesized as novel inhibitors and shows favorable activity of anti-HIV-1. Its molecular structure contains a pyrimidine, a furan and a benzene rings (Figure 1). The dihedral angles between the pyrimidine ring and the benzene ring is 61.56 (9)°. The C14—C13—C8 bond angle between the two rings is 117.1 (2)°.

Intermolecular N—H···O and C—H···O hydrogen bonding links the molecules into a chain supra-molecular structure and stabilizes the crystal structure of the compound.

For related literature, see: He et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of title compound showing the intermolecular hydrogen bonding (dotted lines) [symmetry codes: (i) -x,-1/2 + y,1/2 - z; (ii) 1 - x,-y,1 - z].
4-Benzyl-5-ethyl-2-(2-furylcarbonylmethylsulfanyl)pyrimidin-6(1H)-one top
Crystal data top
C19H18N2O3SF(000) = 744
Mr = 354.41Dx = 1.346 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4116 reflections
a = 12.062 (2) Åθ = 1.7–28.3°
b = 9.3943 (16) ŵ = 0.21 mm1
c = 15.988 (3) ÅT = 293 K
β = 105.065 (2)°Block, colourless
V = 1749.4 (5) Å30.37 × 0.25 × 0.11 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2032 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 28.3°, θmin = 1.8°
φ and ω scansh = 1616
11092 measured reflectionsk = 1212
4116 independent reflectionsl = 209
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.039P)2]
where P = (Fo2 + 2Fc2)
4116 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C19H18N2O3SV = 1749.4 (5) Å3
Mr = 354.41Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.062 (2) ŵ = 0.21 mm1
b = 9.3943 (16) ÅT = 293 K
c = 15.988 (3) Å0.37 × 0.25 × 0.11 mm
β = 105.065 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2032 reflections with I > 2σ(I)
11092 measured reflectionsRint = 0.054
4116 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 0.99Δρmax = 0.17 e Å3
4116 reflectionsΔρmin = 0.21 e Å3
226 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.21735 (5)0.03809 (8)0.32866 (4)0.0558 (2)
O10.03737 (15)0.3007 (2)0.10972 (12)0.0681 (5)
O20.03442 (17)0.1848 (2)0.26973 (12)0.0829 (7)
O30.61953 (13)0.05256 (17)0.45976 (10)0.0514 (4)
N10.36113 (16)0.0657 (2)0.23957 (12)0.0504 (5)
N20.43313 (16)0.02249 (18)0.38744 (12)0.0421 (5)
H2A0.41730.00220.43480.051*
C10.0516 (3)0.3368 (3)0.0258 (2)0.0769 (9)
H1B0.09910.41000.00180.092*
C20.0103 (3)0.2551 (3)0.01204 (19)0.0767 (9)
H2B0.01590.26170.06880.092*
C30.0663 (2)0.1558 (3)0.05134 (17)0.0615 (8)
H3A0.11510.08290.04390.074*
C40.0360 (2)0.1864 (3)0.12422 (16)0.0491 (6)
C50.0637 (2)0.1276 (3)0.21057 (16)0.0508 (7)
C60.1246 (2)0.0145 (3)0.22227 (15)0.0506 (7)
H6A0.16950.02270.18020.061*
H6B0.06780.09000.21080.061*
C70.34761 (19)0.0250 (2)0.31377 (15)0.0418 (6)
C80.4720 (2)0.1010 (3)0.23741 (16)0.0492 (6)
C90.56412 (19)0.0970 (2)0.30779 (15)0.0426 (6)
C100.5446 (2)0.0578 (2)0.38995 (15)0.0406 (6)
C110.68681 (19)0.1267 (3)0.30770 (16)0.0582 (7)
H11A0.72180.18630.35700.070*
H11B0.68780.17910.25560.070*
C120.7578 (2)0.0081 (3)0.31167 (19)0.0806 (9)
H12A0.83500.01680.31160.121*
H12B0.72480.06660.26230.121*
H12C0.75860.05950.36370.121*
C130.4817 (2)0.1521 (3)0.14954 (16)0.0767 (9)
H13A0.47310.25480.14770.092*
H13B0.55870.13110.14510.092*
C140.3976 (2)0.0910 (3)0.07077 (16)0.0498 (6)
C150.3393 (2)0.1813 (3)0.00613 (17)0.0589 (7)
H15A0.34920.27920.01280.071*
C160.2657 (2)0.1267 (4)0.06902 (18)0.0673 (8)
H16A0.22720.18790.11270.081*
C170.2502 (3)0.0166 (4)0.07834 (18)0.0680 (8)
H17A0.20050.05330.12820.082*
C180.3077 (3)0.1066 (3)0.0144 (2)0.0749 (9)
H18A0.29750.20440.02100.090*
C190.3802 (2)0.0527 (3)0.05903 (19)0.0654 (8)
H19A0.41860.11490.10210.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0474 (4)0.0801 (5)0.0425 (4)0.0032 (4)0.0163 (3)0.0115 (4)
O10.0748 (12)0.0766 (13)0.0550 (13)0.0235 (11)0.0208 (10)0.0094 (11)
O20.1038 (15)0.1021 (16)0.0484 (12)0.0378 (13)0.0300 (12)0.0006 (11)
O30.0504 (10)0.0706 (12)0.0321 (10)0.0045 (9)0.0088 (8)0.0034 (9)
N10.0491 (12)0.0685 (15)0.0342 (12)0.0081 (10)0.0117 (10)0.0093 (10)
N20.0493 (12)0.0508 (12)0.0291 (11)0.0005 (10)0.0153 (10)0.0043 (9)
C10.086 (2)0.081 (2)0.061 (2)0.0149 (18)0.0143 (19)0.0207 (18)
C20.100 (2)0.085 (2)0.0506 (19)0.0040 (19)0.0280 (19)0.0078 (17)
C30.0742 (18)0.0634 (19)0.0526 (18)0.0057 (15)0.0268 (16)0.0009 (15)
C40.0450 (14)0.0560 (17)0.0463 (17)0.0050 (12)0.0120 (13)0.0006 (13)
C50.0437 (14)0.0673 (18)0.0424 (16)0.0027 (13)0.0131 (13)0.0042 (14)
C60.0459 (14)0.0622 (17)0.0412 (15)0.0021 (12)0.0069 (12)0.0007 (13)
C70.0454 (14)0.0487 (15)0.0337 (14)0.0024 (11)0.0144 (12)0.0018 (12)
C80.0568 (16)0.0560 (16)0.0370 (15)0.0091 (13)0.0163 (13)0.0067 (12)
C90.0487 (14)0.0475 (15)0.0336 (14)0.0038 (12)0.0146 (12)0.0017 (11)
C100.0482 (14)0.0407 (14)0.0345 (14)0.0003 (11)0.0137 (12)0.0007 (11)
C110.0505 (15)0.085 (2)0.0406 (16)0.0124 (15)0.0144 (13)0.0047 (14)
C120.0637 (19)0.120 (3)0.063 (2)0.0104 (18)0.0264 (17)0.0004 (19)
C130.0767 (19)0.113 (3)0.0392 (17)0.0310 (18)0.0126 (15)0.0206 (17)
C140.0544 (15)0.0644 (19)0.0363 (15)0.0039 (13)0.0220 (13)0.0119 (14)
C150.0814 (19)0.0544 (17)0.0454 (17)0.0039 (15)0.0245 (15)0.0066 (14)
C160.075 (2)0.085 (2)0.0412 (18)0.0098 (17)0.0143 (16)0.0203 (17)
C170.078 (2)0.089 (2)0.0405 (18)0.0181 (18)0.0218 (16)0.0121 (17)
C180.112 (3)0.061 (2)0.060 (2)0.0046 (19)0.039 (2)0.0063 (18)
C190.084 (2)0.063 (2)0.056 (2)0.0123 (16)0.0294 (17)0.0170 (16)
Geometric parameters (Å, º) top
S1—C71.752 (2)C9—C101.442 (3)
S1—C61.790 (2)C9—C111.506 (3)
O1—C11.350 (3)C11—C121.521 (4)
O1—C41.372 (3)C11—H11A0.9700
O2—C51.217 (3)C11—H11B0.9700
O3—C101.241 (2)C12—H12A0.9600
N1—C71.297 (3)C12—H12B0.9600
N1—C81.387 (3)C12—H12C0.9600
N2—C71.349 (3)C13—C141.510 (3)
N2—C101.375 (3)C13—H13A0.9700
N2—H2A0.8600C13—H13B0.9700
C1—C21.323 (4)C14—C191.372 (3)
C1—H1B0.9300C14—C151.380 (3)
C2—C31.413 (3)C15—C161.393 (3)
C2—H2B0.9300C15—H15A0.9300
C3—C41.340 (3)C16—C171.362 (4)
C3—H3A0.9300C16—H16A0.9300
C4—C51.443 (3)C17—C181.368 (4)
C5—C61.511 (3)C17—H17A0.9300
C6—H6A0.9700C18—C191.366 (4)
C6—H6B0.9700C18—H18A0.9300
C8—C91.361 (3)C19—H19A0.9300
C8—C131.518 (3)
C7—S1—C6100.94 (12)N2—C10—C9115.2 (2)
C1—O1—C4105.9 (2)C9—C11—C12112.9 (2)
C7—N1—C8116.4 (2)C9—C11—H11A109.0
C7—N2—C10122.76 (19)C12—C11—H11A109.0
C7—N2—H2A118.6C9—C11—H11B109.0
C10—N2—H2A118.6C12—C11—H11B109.0
C2—C1—O1111.6 (3)H11A—C11—H11B107.8
C2—C1—H1B124.2C11—C12—H12A109.5
O1—C1—H1B124.2C11—C12—H12B109.5
C1—C2—C3106.0 (3)H12A—C12—H12B109.5
C1—C2—H2B127.0C11—C12—H12C109.5
C3—C2—H2B127.0H12A—C12—H12C109.5
C4—C3—C2107.1 (2)H12B—C12—H12C109.5
C4—C3—H3A126.5C14—C13—C8117.1 (2)
C2—C3—H3A126.5C14—C13—H13A108.0
C3—C4—O1109.3 (2)C8—C13—H13A108.0
C3—C4—C5134.5 (2)C14—C13—H13B108.0
O1—C4—C5116.1 (2)C8—C13—H13B108.0
O2—C5—C4122.1 (2)H13A—C13—H13B107.3
O2—C5—C6121.6 (2)C19—C14—C15118.2 (2)
C4—C5—C6116.2 (2)C19—C14—C13122.3 (3)
C5—C6—S1112.99 (17)C15—C14—C13119.5 (3)
C5—C6—H6A109.0C14—C15—C16120.4 (3)
S1—C6—H6A109.0C14—C15—H15A119.8
C5—C6—H6B109.0C16—C15—H15A119.8
S1—C6—H6B109.0C17—C16—C15119.8 (3)
H6A—C6—H6B107.8C17—C16—H16A120.1
N1—C7—N2123.7 (2)C15—C16—H16A120.1
N1—C7—S1123.68 (18)C16—C17—C18120.0 (3)
N2—C7—S1112.62 (16)C16—C17—H17A120.0
C9—C8—N1123.9 (2)C18—C17—H17A120.0
C9—C8—C13122.1 (2)C19—C18—C17120.0 (3)
N1—C8—C13113.9 (2)C19—C18—H18A120.0
C8—C9—C10117.9 (2)C17—C18—H18A120.0
C8—C9—C11125.8 (2)C18—C19—C14121.5 (3)
C10—C9—C11116.2 (2)C18—C19—H19A119.2
O3—C10—N2119.7 (2)C14—C19—H19A119.2
O3—C10—C9125.2 (2)
C4—O1—C1—C21.7 (3)C13—C8—C9—C10175.1 (2)
O1—C1—C2—C31.9 (4)N1—C8—C9—C11176.6 (2)
C1—C2—C3—C41.3 (3)C13—C8—C9—C116.5 (4)
C2—C3—C4—O10.3 (3)C7—N2—C10—O3179.6 (2)
C2—C3—C4—C5179.3 (3)C7—N2—C10—C90.4 (3)
C1—O1—C4—C30.8 (3)C8—C9—C10—O3178.4 (2)
C1—O1—C4—C5179.5 (2)C11—C9—C10—O33.0 (4)
C3—C4—C5—O2171.6 (3)C8—C9—C10—N22.5 (3)
O1—C4—C5—O27.9 (4)C11—C9—C10—N2176.1 (2)
C3—C4—C5—C612.2 (4)C8—C9—C11—C12102.4 (3)
O1—C4—C5—C6168.3 (2)C10—C9—C11—C1276.1 (3)
O2—C5—C6—S133.7 (3)C9—C8—C13—C14151.7 (3)
C4—C5—C6—S1150.10 (19)N1—C8—C13—C1431.1 (4)
C7—S1—C6—C592.19 (19)C8—C13—C14—C1951.0 (4)
C8—N1—C7—N23.4 (4)C8—C13—C14—C15131.8 (3)
C8—N1—C7—S1174.52 (17)C19—C14—C15—C160.5 (4)
C10—N2—C7—N12.7 (3)C13—C14—C15—C16176.8 (2)
C10—N2—C7—S1175.38 (16)C14—C15—C16—C170.7 (4)
C6—S1—C7—N13.9 (2)C15—C16—C17—C180.6 (4)
C6—S1—C7—N2178.05 (16)C16—C17—C18—C190.4 (4)
C7—N1—C8—C91.0 (4)C17—C18—C19—C140.2 (4)
C7—N1—C8—C13178.2 (2)C15—C14—C19—C180.3 (4)
N1—C8—C9—C101.9 (4)C13—C14—C19—C18176.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.861.912.770 (2)179
C6—H6B···O2ii0.972.513.436 (3)160
Symmetry codes: (i) x+1, y, z+1; (ii) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H18N2O3S
Mr354.41
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.062 (2), 9.3943 (16), 15.988 (3)
β (°) 105.065 (2)
V3)1749.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.37 × 0.25 × 0.11
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11092, 4116, 2032
Rint0.054
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.116, 0.99
No. of reflections4116
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.861.912.770 (2)179
C6—H6B···O2ii0.972.513.436 (3)160
Symmetry codes: (i) x+1, y, z+1; (ii) x, y1/2, z+1/2.
 

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