Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028218/xu2272sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028218/xu2272Isup2.hkl |
CCDC reference: 654925
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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).
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).
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.
C19H18N2O3S | F(000) = 744 |
Mr = 354.41 | Dx = 1.346 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4116 reflections |
a = 12.062 (2) Å | θ = 1.7–28.3° |
b = 9.3943 (16) Å | µ = 0.21 mm−1 |
c = 15.988 (3) Å | T = 293 K |
β = 105.065 (2)° | Block, colourless |
V = 1749.4 (5) Å3 | 0.37 × 0.25 × 0.11 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2032 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.054 |
Graphite monochromator | θmax = 28.3°, θmin = 1.8° |
φ and ω scans | h = −16→16 |
11092 measured reflections | k = −12→12 |
4116 independent reflections | l = −20→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-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 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C19H18N2O3S | V = 1749.4 (5) Å3 |
Mr = 354.41 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.062 (2) Å | µ = 0.21 mm−1 |
b = 9.3943 (16) Å | T = 293 K |
c = 15.988 (3) Å | 0.37 × 0.25 × 0.11 mm |
β = 105.065 (2)° |
Bruker SMART CCD area-detector diffractometer | 2032 reflections with I > 2σ(I) |
11092 measured reflections | Rint = 0.054 |
4116 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.17 e Å−3 |
4116 reflections | Δρmin = −0.21 e Å−3 |
226 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.21735 (5) | −0.03809 (8) | 0.32866 (4) | 0.0558 (2) | |
O1 | −0.03737 (15) | 0.3007 (2) | 0.10972 (12) | 0.0681 (5) | |
O2 | 0.03442 (17) | 0.1848 (2) | 0.26973 (12) | 0.0829 (7) | |
O3 | 0.61953 (13) | 0.05256 (17) | 0.45976 (10) | 0.0514 (4) | |
N1 | 0.36113 (16) | 0.0657 (2) | 0.23957 (12) | 0.0504 (5) | |
N2 | 0.43313 (16) | 0.02249 (18) | 0.38744 (12) | 0.0421 (5) | |
H2A | 0.4173 | −0.0022 | 0.4348 | 0.051* | |
C1 | −0.0516 (3) | 0.3368 (3) | 0.0258 (2) | 0.0769 (9) | |
H1B | −0.0991 | 0.4100 | −0.0018 | 0.092* | |
C2 | 0.0103 (3) | 0.2551 (3) | −0.01204 (19) | 0.0767 (9) | |
H2B | 0.0159 | 0.2617 | −0.0688 | 0.092* | |
C3 | 0.0663 (2) | 0.1558 (3) | 0.05134 (17) | 0.0615 (8) | |
H3A | 0.1151 | 0.0829 | 0.0439 | 0.074* | |
C4 | 0.0360 (2) | 0.1864 (3) | 0.12422 (16) | 0.0491 (6) | |
C5 | 0.0637 (2) | 0.1276 (3) | 0.21057 (16) | 0.0508 (7) | |
C6 | 0.1246 (2) | −0.0145 (3) | 0.22227 (15) | 0.0506 (7) | |
H6A | 0.1695 | −0.0227 | 0.1802 | 0.061* | |
H6B | 0.0678 | −0.0900 | 0.2108 | 0.061* | |
C7 | 0.34761 (19) | 0.0250 (2) | 0.31377 (15) | 0.0418 (6) | |
C8 | 0.4720 (2) | 0.1010 (3) | 0.23741 (16) | 0.0492 (6) | |
C9 | 0.56412 (19) | 0.0970 (2) | 0.30779 (15) | 0.0426 (6) | |
C10 | 0.5446 (2) | 0.0578 (2) | 0.38995 (15) | 0.0406 (6) | |
C11 | 0.68681 (19) | 0.1267 (3) | 0.30770 (16) | 0.0582 (7) | |
H11A | 0.7218 | 0.1863 | 0.3570 | 0.070* | |
H11B | 0.6878 | 0.1791 | 0.2556 | 0.070* | |
C12 | 0.7578 (2) | −0.0081 (3) | 0.31167 (19) | 0.0806 (9) | |
H12A | 0.8350 | 0.0168 | 0.3116 | 0.121* | |
H12B | 0.7248 | −0.0666 | 0.2623 | 0.121* | |
H12C | 0.7586 | −0.0595 | 0.3637 | 0.121* | |
C13 | 0.4817 (2) | 0.1521 (3) | 0.14954 (16) | 0.0767 (9) | |
H13A | 0.4731 | 0.2548 | 0.1477 | 0.092* | |
H13B | 0.5587 | 0.1311 | 0.1451 | 0.092* | |
C14 | 0.3976 (2) | 0.0910 (3) | 0.07077 (16) | 0.0498 (6) | |
C15 | 0.3393 (2) | 0.1813 (3) | 0.00613 (17) | 0.0589 (7) | |
H15A | 0.3492 | 0.2792 | 0.0128 | 0.071* | |
C16 | 0.2657 (2) | 0.1267 (4) | −0.06902 (18) | 0.0673 (8) | |
H16A | 0.2272 | 0.1879 | −0.1127 | 0.081* | |
C17 | 0.2502 (3) | −0.0166 (4) | −0.07834 (18) | 0.0680 (8) | |
H17A | 0.2005 | −0.0533 | −0.1282 | 0.082* | |
C18 | 0.3077 (3) | −0.1066 (3) | −0.0144 (2) | 0.0749 (9) | |
H18A | 0.2975 | −0.2044 | −0.0210 | 0.090* | |
C19 | 0.3802 (2) | −0.0527 (3) | 0.05903 (19) | 0.0654 (8) | |
H19A | 0.4186 | −0.1149 | 0.1021 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0474 (4) | 0.0801 (5) | 0.0425 (4) | −0.0032 (4) | 0.0163 (3) | 0.0115 (4) |
O1 | 0.0748 (12) | 0.0766 (13) | 0.0550 (13) | 0.0235 (11) | 0.0208 (10) | 0.0094 (11) |
O2 | 0.1038 (15) | 0.1021 (16) | 0.0484 (12) | 0.0378 (13) | 0.0300 (12) | −0.0006 (11) |
O3 | 0.0504 (10) | 0.0706 (12) | 0.0321 (10) | −0.0045 (9) | 0.0088 (8) | 0.0034 (9) |
N1 | 0.0491 (12) | 0.0685 (15) | 0.0342 (12) | −0.0081 (10) | 0.0117 (10) | 0.0093 (10) |
N2 | 0.0493 (12) | 0.0508 (12) | 0.0291 (11) | −0.0005 (10) | 0.0153 (10) | 0.0043 (9) |
C1 | 0.086 (2) | 0.081 (2) | 0.061 (2) | 0.0149 (18) | 0.0143 (19) | 0.0207 (18) |
C2 | 0.100 (2) | 0.085 (2) | 0.0506 (19) | 0.0040 (19) | 0.0280 (19) | 0.0078 (17) |
C3 | 0.0742 (18) | 0.0634 (19) | 0.0526 (18) | 0.0057 (15) | 0.0268 (16) | 0.0009 (15) |
C4 | 0.0450 (14) | 0.0560 (17) | 0.0463 (17) | 0.0050 (12) | 0.0120 (13) | 0.0006 (13) |
C5 | 0.0437 (14) | 0.0673 (18) | 0.0424 (16) | 0.0027 (13) | 0.0131 (13) | −0.0042 (14) |
C6 | 0.0459 (14) | 0.0622 (17) | 0.0412 (15) | −0.0021 (12) | 0.0069 (12) | −0.0007 (13) |
C7 | 0.0454 (14) | 0.0487 (15) | 0.0337 (14) | 0.0024 (11) | 0.0144 (12) | 0.0018 (12) |
C8 | 0.0568 (16) | 0.0560 (16) | 0.0370 (15) | −0.0091 (13) | 0.0163 (13) | 0.0067 (12) |
C9 | 0.0487 (14) | 0.0475 (15) | 0.0336 (14) | −0.0038 (12) | 0.0146 (12) | 0.0017 (11) |
C10 | 0.0482 (14) | 0.0407 (14) | 0.0345 (14) | −0.0003 (11) | 0.0137 (12) | −0.0007 (11) |
C11 | 0.0505 (15) | 0.085 (2) | 0.0406 (16) | −0.0124 (15) | 0.0144 (13) | 0.0047 (14) |
C12 | 0.0637 (19) | 0.120 (3) | 0.063 (2) | 0.0104 (18) | 0.0264 (17) | −0.0004 (19) |
C13 | 0.0767 (19) | 0.113 (3) | 0.0392 (17) | −0.0310 (18) | 0.0126 (15) | 0.0206 (17) |
C14 | 0.0544 (15) | 0.0644 (19) | 0.0363 (15) | −0.0039 (13) | 0.0220 (13) | 0.0119 (14) |
C15 | 0.0814 (19) | 0.0544 (17) | 0.0454 (17) | −0.0039 (15) | 0.0245 (15) | 0.0066 (14) |
C16 | 0.075 (2) | 0.085 (2) | 0.0412 (18) | 0.0098 (17) | 0.0143 (16) | 0.0203 (17) |
C17 | 0.078 (2) | 0.089 (2) | 0.0405 (18) | −0.0181 (18) | 0.0218 (16) | −0.0121 (17) |
C18 | 0.112 (3) | 0.061 (2) | 0.060 (2) | −0.0046 (19) | 0.039 (2) | −0.0063 (18) |
C19 | 0.084 (2) | 0.063 (2) | 0.056 (2) | 0.0123 (16) | 0.0294 (17) | 0.0170 (16) |
S1—C7 | 1.752 (2) | C9—C10 | 1.442 (3) |
S1—C6 | 1.790 (2) | C9—C11 | 1.506 (3) |
O1—C1 | 1.350 (3) | C11—C12 | 1.521 (4) |
O1—C4 | 1.372 (3) | C11—H11A | 0.9700 |
O2—C5 | 1.217 (3) | C11—H11B | 0.9700 |
O3—C10 | 1.241 (2) | C12—H12A | 0.9600 |
N1—C7 | 1.297 (3) | C12—H12B | 0.9600 |
N1—C8 | 1.387 (3) | C12—H12C | 0.9600 |
N2—C7 | 1.349 (3) | C13—C14 | 1.510 (3) |
N2—C10 | 1.375 (3) | C13—H13A | 0.9700 |
N2—H2A | 0.8600 | C13—H13B | 0.9700 |
C1—C2 | 1.323 (4) | C14—C19 | 1.372 (3) |
C1—H1B | 0.9300 | C14—C15 | 1.380 (3) |
C2—C3 | 1.413 (3) | C15—C16 | 1.393 (3) |
C2—H2B | 0.9300 | C15—H15A | 0.9300 |
C3—C4 | 1.340 (3) | C16—C17 | 1.362 (4) |
C3—H3A | 0.9300 | C16—H16A | 0.9300 |
C4—C5 | 1.443 (3) | C17—C18 | 1.368 (4) |
C5—C6 | 1.511 (3) | C17—H17A | 0.9300 |
C6—H6A | 0.9700 | C18—C19 | 1.366 (4) |
C6—H6B | 0.9700 | C18—H18A | 0.9300 |
C8—C9 | 1.361 (3) | C19—H19A | 0.9300 |
C8—C13 | 1.518 (3) | ||
C7—S1—C6 | 100.94 (12) | N2—C10—C9 | 115.2 (2) |
C1—O1—C4 | 105.9 (2) | C9—C11—C12 | 112.9 (2) |
C7—N1—C8 | 116.4 (2) | C9—C11—H11A | 109.0 |
C7—N2—C10 | 122.76 (19) | C12—C11—H11A | 109.0 |
C7—N2—H2A | 118.6 | C9—C11—H11B | 109.0 |
C10—N2—H2A | 118.6 | C12—C11—H11B | 109.0 |
C2—C1—O1 | 111.6 (3) | H11A—C11—H11B | 107.8 |
C2—C1—H1B | 124.2 | C11—C12—H12A | 109.5 |
O1—C1—H1B | 124.2 | C11—C12—H12B | 109.5 |
C1—C2—C3 | 106.0 (3) | H12A—C12—H12B | 109.5 |
C1—C2—H2B | 127.0 | C11—C12—H12C | 109.5 |
C3—C2—H2B | 127.0 | H12A—C12—H12C | 109.5 |
C4—C3—C2 | 107.1 (2) | H12B—C12—H12C | 109.5 |
C4—C3—H3A | 126.5 | C14—C13—C8 | 117.1 (2) |
C2—C3—H3A | 126.5 | C14—C13—H13A | 108.0 |
C3—C4—O1 | 109.3 (2) | C8—C13—H13A | 108.0 |
C3—C4—C5 | 134.5 (2) | C14—C13—H13B | 108.0 |
O1—C4—C5 | 116.1 (2) | C8—C13—H13B | 108.0 |
O2—C5—C4 | 122.1 (2) | H13A—C13—H13B | 107.3 |
O2—C5—C6 | 121.6 (2) | C19—C14—C15 | 118.2 (2) |
C4—C5—C6 | 116.2 (2) | C19—C14—C13 | 122.3 (3) |
C5—C6—S1 | 112.99 (17) | C15—C14—C13 | 119.5 (3) |
C5—C6—H6A | 109.0 | C14—C15—C16 | 120.4 (3) |
S1—C6—H6A | 109.0 | C14—C15—H15A | 119.8 |
C5—C6—H6B | 109.0 | C16—C15—H15A | 119.8 |
S1—C6—H6B | 109.0 | C17—C16—C15 | 119.8 (3) |
H6A—C6—H6B | 107.8 | C17—C16—H16A | 120.1 |
N1—C7—N2 | 123.7 (2) | C15—C16—H16A | 120.1 |
N1—C7—S1 | 123.68 (18) | C16—C17—C18 | 120.0 (3) |
N2—C7—S1 | 112.62 (16) | C16—C17—H17A | 120.0 |
C9—C8—N1 | 123.9 (2) | C18—C17—H17A | 120.0 |
C9—C8—C13 | 122.1 (2) | C19—C18—C17 | 120.0 (3) |
N1—C8—C13 | 113.9 (2) | C19—C18—H18A | 120.0 |
C8—C9—C10 | 117.9 (2) | C17—C18—H18A | 120.0 |
C8—C9—C11 | 125.8 (2) | C18—C19—C14 | 121.5 (3) |
C10—C9—C11 | 116.2 (2) | C18—C19—H19A | 119.2 |
O3—C10—N2 | 119.7 (2) | C14—C19—H19A | 119.2 |
O3—C10—C9 | 125.2 (2) | ||
C4—O1—C1—C2 | −1.7 (3) | C13—C8—C9—C10 | 175.1 (2) |
O1—C1—C2—C3 | 1.9 (4) | N1—C8—C9—C11 | 176.6 (2) |
C1—C2—C3—C4 | −1.3 (3) | C13—C8—C9—C11 | −6.5 (4) |
C2—C3—C4—O1 | 0.3 (3) | C7—N2—C10—O3 | −179.6 (2) |
C2—C3—C4—C5 | −179.3 (3) | C7—N2—C10—C9 | −0.4 (3) |
C1—O1—C4—C3 | 0.8 (3) | C8—C9—C10—O3 | −178.4 (2) |
C1—O1—C4—C5 | −179.5 (2) | C11—C9—C10—O3 | 3.0 (4) |
C3—C4—C5—O2 | 171.6 (3) | C8—C9—C10—N2 | 2.5 (3) |
O1—C4—C5—O2 | −7.9 (4) | C11—C9—C10—N2 | −176.1 (2) |
C3—C4—C5—C6 | −12.2 (4) | C8—C9—C11—C12 | −102.4 (3) |
O1—C4—C5—C6 | 168.3 (2) | C10—C9—C11—C12 | 76.1 (3) |
O2—C5—C6—S1 | −33.7 (3) | C9—C8—C13—C14 | 151.7 (3) |
C4—C5—C6—S1 | 150.10 (19) | N1—C8—C13—C14 | −31.1 (4) |
C7—S1—C6—C5 | −92.19 (19) | C8—C13—C14—C19 | −51.0 (4) |
C8—N1—C7—N2 | 3.4 (4) | C8—C13—C14—C15 | 131.8 (3) |
C8—N1—C7—S1 | −174.52 (17) | C19—C14—C15—C16 | −0.5 (4) |
C10—N2—C7—N1 | −2.7 (3) | C13—C14—C15—C16 | 176.8 (2) |
C10—N2—C7—S1 | 175.38 (16) | C14—C15—C16—C17 | 0.7 (4) |
C6—S1—C7—N1 | −3.9 (2) | C15—C16—C17—C18 | −0.6 (4) |
C6—S1—C7—N2 | 178.05 (16) | C16—C17—C18—C19 | 0.4 (4) |
C7—N1—C8—C9 | −1.0 (4) | C17—C18—C19—C14 | −0.2 (4) |
C7—N1—C8—C13 | −178.2 (2) | C15—C14—C19—C18 | 0.3 (4) |
N1—C8—C9—C10 | −1.9 (4) | C13—C14—C19—C18 | −176.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 1.91 | 2.770 (2) | 179 |
C6—H6B···O2ii | 0.97 | 2.51 | 3.436 (3) | 160 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H18N2O3S |
Mr | 354.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.062 (2), 9.3943 (16), 15.988 (3) |
β (°) | 105.065 (2) |
V (Å3) | 1749.4 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.37 × 0.25 × 0.11 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11092, 4116, 2032 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.116, 0.99 |
No. of reflections | 4116 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.21 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 1.91 | 2.770 (2) | 179 |
C6—H6B···O2ii | 0.97 | 2.51 | 3.436 (3) | 160 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, y−1/2, −z+1/2. |
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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.