Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050799/is2221sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050799/is2221Isup2.hkl |
CCDC reference: 667390
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.128
- Data-to-parameter ratio = 26.6
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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
To a solution of 1,3-dimethyl pyrimidine-2,4,6-trione (1 mmol) in dry toluene (20 ml), the corresponding 2-[N-(3-methylbut-2-enyl)-N-tosylamino] acetaldehyde (1 mmol), and catalytic amount of the base ethylenediamine-N,N'-diacetate (EDDA) were added and the reaction mixture was refluxed for 12 h. After completion of reaction, the solvent was evaporated under reduced pressure and the crude product was chromatographed using a hexane-ethyl acetate (8:2 v/v) mixture to obtain the title compound. The compound was recrystallized from ethyl acetate solution by slow evaporation.
H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). A rotating group model was used for the methyl groups attached to aromatic rings.
Pyranopyrimidine derivatives exhibit antiviral (Shamroukh et al., 2007) and antimicrobial activities (Bedair et al., 2000, 2001; Eid et al., 2004; Abdel Fattah et al., 2004). We report here the crystal structure of the title compound, a pyranopyrimidine derivative.
In the molecule of the title compound (Fig. 1), bond lengths are within normal ranges (Allen et al., 1987). The sum of the angles at the atom N1 of the pyrrolidine ring (347.9°) is in accordance with sp3 hybridization. Atom S1 has a distorted tetrahedral configuration, with the angle O2—S1—O1 [120.33 (6)°] deviating significantly from the ideal tetrahedral value.
The pyrimidine ring is planar, with an r.m.s. deviation of fitted atoms of 0.009 Å, and atoms O4, O5, C19 and C20 deviating by 0.040 (2), 0.012 (2), 0.051 (2) and -0.011 (2) Å, respectively. The pyrrolidine ring adopts a twist conformation, confirmed by its ring-puckering parameters (Cremer & Pople, 1975) q2 = 0.443 (1) Å and φ2 = 92.3 (2)°, and asymmetry parameter (Duax et al., 1976) ΔC2[C2—C3] = 2.9 (1)°. The pyran ring adopts an envelope conformation, with atom C2 deviating from the C5/O3/C6/C7/C3 plane by 0.684 (2) Å. The asymmetry parameter ΔCs[C2] is 3.8 (1)°, and the puckering parameters Q, θ and φ are 0.502 (1) Å, 129.5 (1)° and 295.3 (2)°, respectively. The tosyl group is attached to the pyrrolidine in a biaxial position and its benzene ring forms a dihedral angle of 85.61 (4)° with the pyrimidine ring. The dihedral angle between the C5/O3/C6/C7/C3 plane and the pyrimidine ring is 2.70 (8)°. The pyrrolidine ring is trans-fused to the dihydropyran ring.
In the crystal structure, inversion-related molecules are alternately linked by a pair each of C15—H15A···O4i and C20—H20C···O5ii hydrogen bonds to form a chain along the b axis (Fig. 2). Glide-related molecules in the adjacent chains are linked via C19—H19B···O2iii hydrogen bonds, forming a two-dimensional network parallel to the bc plane. Screw-related molecules in the adjacent networks are cross-linked by C14—H14B···O1iv hydrogen bonds (symmetry codes are given in Table 1) into a three-dimensional framework (Fig. 3).
For biological activities of pyranopyrimidine derivatives, see: Abdel Fattah et al. (2004); Bedair et al. (2000, 2001); Eid et al. (2004); Shamroukh et al. (2007). For ring puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Duax et al. (1976). For bond-length data, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).
C20H25N3O5S | F(000) = 888 |
Mr = 419.49 | Dx = 1.398 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7931 reflections |
a = 14.5605 (2) Å | θ = 2.6–34.9° |
b = 8.9142 (1) Å | µ = 0.20 mm−1 |
c = 15.3963 (3) Å | T = 100 K |
β = 94.316 (1)° | Block, light-yellow |
V = 1992.70 (5) Å3 | 0.50 × 0.30 × 0.22 mm |
Z = 4 |
Bruker SMART APEX2 CCD area-detector diffractometer | 7053 independent reflections |
Radiation source: fine-focus sealed tube | 5564 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 8.33 pixels mm-1 | θmax = 32.5°, θmin = 1.4° |
ω scans | h = −21→21 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −13→13 |
Tmin = 0.906, Tmax = 0.958 | l = −21→23 |
26688 measured reflections |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0646P)2 + 0.4491P] where P = (Fo2 + 2Fc2)/3 |
7053 reflections | (Δ/σ)max = 0.001 |
265 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C20H25N3O5S | V = 1992.70 (5) Å3 |
Mr = 419.49 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.5605 (2) Å | µ = 0.20 mm−1 |
b = 8.9142 (1) Å | T = 100 K |
c = 15.3963 (3) Å | 0.50 × 0.30 × 0.22 mm |
β = 94.316 (1)° |
Bruker SMART APEX2 CCD area-detector diffractometer | 7053 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 5564 reflections with I > 2σ(I) |
Tmin = 0.906, Tmax = 0.958 | Rint = 0.036 |
26688 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.48 e Å−3 |
7053 reflections | Δρmin = −0.38 e Å−3 |
265 parameters |
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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 | 0.31057 (2) | 0.11286 (3) | 0.21463 (2) | 0.01524 (8) | |
O1 | 0.33383 (6) | 0.19239 (11) | 0.13827 (6) | 0.02021 (19) | |
O2 | 0.27045 (6) | −0.03417 (10) | 0.20717 (7) | 0.01941 (19) | |
O3 | 0.17594 (6) | 0.57429 (10) | 0.47387 (7) | 0.01950 (19) | |
O4 | 0.00954 (7) | 0.39530 (12) | 0.68758 (7) | 0.0247 (2) | |
O5 | 0.12949 (6) | 0.05091 (10) | 0.50809 (7) | 0.01987 (19) | |
N1 | 0.23857 (7) | 0.21847 (11) | 0.26204 (8) | 0.0164 (2) | |
N2 | 0.09159 (7) | 0.48102 (12) | 0.57743 (8) | 0.0184 (2) | |
N3 | 0.06741 (7) | 0.22240 (12) | 0.59639 (8) | 0.0185 (2) | |
C1 | 0.26274 (9) | 0.38059 (13) | 0.27282 (9) | 0.0182 (2) | |
H1A | 0.2419 | 0.4382 | 0.2217 | 0.022* | |
H1B | 0.3286 | 0.3944 | 0.2847 | 0.022* | |
C2 | 0.21053 (8) | 0.42342 (13) | 0.35102 (9) | 0.0154 (2) | |
H2 | 0.1457 | 0.4359 | 0.3302 | 0.018* | |
C3 | 0.21703 (8) | 0.28259 (13) | 0.40731 (9) | 0.0148 (2) | |
H3 | 0.2810 | 0.2693 | 0.4305 | 0.018* | |
C4 | 0.19337 (8) | 0.16103 (13) | 0.33970 (9) | 0.0168 (2) | |
H4A | 0.2185 | 0.0647 | 0.3586 | 0.020* | |
H4B | 0.1273 | 0.1517 | 0.3275 | 0.020* | |
C5 | 0.23892 (8) | 0.56320 (13) | 0.40294 (9) | 0.0169 (2) | |
C6 | 0.14398 (8) | 0.44905 (14) | 0.50888 (9) | 0.0160 (2) | |
C7 | 0.15809 (8) | 0.30612 (13) | 0.48152 (8) | 0.0151 (2) | |
C8 | 0.41258 (8) | 0.09762 (14) | 0.28349 (9) | 0.0157 (2) | |
C9 | 0.42372 (8) | −0.01963 (13) | 0.34305 (9) | 0.0164 (2) | |
H9 | 0.3764 | −0.0882 | 0.3486 | 0.020* | |
C10 | 0.50606 (9) | −0.03344 (14) | 0.39420 (9) | 0.0179 (2) | |
H10 | 0.5135 | −0.1118 | 0.4340 | 0.021* | |
C11 | 0.57798 (8) | 0.06859 (14) | 0.38686 (9) | 0.0175 (2) | |
C12 | 0.56465 (9) | 0.18709 (15) | 0.32874 (10) | 0.0225 (3) | |
H12 | 0.6112 | 0.2575 | 0.3244 | 0.027* | |
C13 | 0.48266 (9) | 0.20210 (15) | 0.27689 (10) | 0.0216 (3) | |
H13 | 0.4748 | 0.2817 | 0.2380 | 0.026* | |
C14 | 0.66833 (9) | 0.04688 (16) | 0.43953 (10) | 0.0226 (3) | |
H14A | 0.7119 | 0.1198 | 0.4223 | 0.034* | |
H14B | 0.6913 | −0.0521 | 0.4296 | 0.034* | |
H14C | 0.6594 | 0.0591 | 0.5003 | 0.034* | |
C15 | 0.21943 (9) | 0.70446 (14) | 0.35015 (10) | 0.0215 (3) | |
H15A | 0.1574 | 0.7016 | 0.3243 | 0.032* | |
H15B | 0.2614 | 0.7109 | 0.3051 | 0.032* | |
H15C | 0.2271 | 0.7904 | 0.3875 | 0.032* | |
C16 | 0.33649 (9) | 0.55984 (15) | 0.44606 (10) | 0.0237 (3) | |
H16A | 0.3487 | 0.6518 | 0.4773 | 0.035* | |
H16B | 0.3796 | 0.5488 | 0.4023 | 0.035* | |
H16C | 0.3427 | 0.4768 | 0.4858 | 0.035* | |
C17 | 0.05352 (8) | 0.36716 (15) | 0.62489 (9) | 0.0191 (2) | |
C18 | 0.11981 (8) | 0.18359 (14) | 0.52689 (9) | 0.0162 (2) | |
C19 | 0.08075 (9) | 0.63604 (15) | 0.60710 (10) | 0.0229 (3) | |
H19A | 0.0715 | 0.7011 | 0.5575 | 0.034* | |
H19B | 0.1352 | 0.6662 | 0.6418 | 0.034* | |
H19C | 0.0285 | 0.6422 | 0.6414 | 0.034* | |
C20 | 0.02666 (10) | 0.09960 (16) | 0.64391 (10) | 0.0238 (3) | |
H20A | 0.0043 | 0.1378 | 0.6967 | 0.036* | |
H20B | 0.0725 | 0.0242 | 0.6579 | 0.036* | |
H20C | −0.0235 | 0.0564 | 0.6083 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01498 (13) | 0.01655 (13) | 0.01413 (16) | 0.00030 (9) | 0.00080 (10) | −0.00044 (10) |
O1 | 0.0227 (4) | 0.0243 (4) | 0.0139 (5) | 0.0021 (3) | 0.0032 (4) | 0.0016 (4) |
O2 | 0.0184 (4) | 0.0180 (4) | 0.0215 (5) | −0.0012 (3) | −0.0005 (4) | −0.0032 (3) |
O3 | 0.0231 (4) | 0.0155 (4) | 0.0204 (5) | −0.0011 (3) | 0.0048 (4) | −0.0012 (3) |
O4 | 0.0218 (5) | 0.0345 (5) | 0.0185 (5) | −0.0006 (4) | 0.0051 (4) | −0.0030 (4) |
O5 | 0.0197 (4) | 0.0182 (4) | 0.0218 (5) | −0.0005 (3) | 0.0019 (4) | 0.0029 (4) |
N1 | 0.0164 (4) | 0.0150 (4) | 0.0180 (5) | −0.0001 (3) | 0.0035 (4) | 0.0013 (4) |
N2 | 0.0182 (5) | 0.0209 (5) | 0.0161 (5) | 0.0006 (4) | 0.0008 (4) | −0.0033 (4) |
N3 | 0.0172 (5) | 0.0230 (5) | 0.0153 (5) | −0.0020 (4) | 0.0020 (4) | 0.0017 (4) |
C1 | 0.0215 (6) | 0.0143 (5) | 0.0193 (7) | −0.0007 (4) | 0.0057 (5) | 0.0020 (4) |
C2 | 0.0155 (5) | 0.0147 (5) | 0.0161 (6) | −0.0004 (4) | 0.0015 (4) | 0.0021 (4) |
C3 | 0.0141 (5) | 0.0144 (5) | 0.0160 (6) | −0.0003 (4) | 0.0013 (4) | 0.0015 (4) |
C4 | 0.0169 (5) | 0.0151 (5) | 0.0187 (6) | −0.0009 (4) | 0.0042 (4) | 0.0007 (4) |
C5 | 0.0170 (5) | 0.0164 (5) | 0.0177 (6) | −0.0009 (4) | 0.0032 (4) | 0.0006 (4) |
C6 | 0.0153 (5) | 0.0185 (5) | 0.0138 (6) | −0.0006 (4) | −0.0009 (4) | 0.0001 (4) |
C7 | 0.0139 (5) | 0.0169 (5) | 0.0142 (6) | −0.0005 (4) | 0.0002 (4) | 0.0009 (4) |
C8 | 0.0137 (5) | 0.0191 (5) | 0.0146 (6) | −0.0002 (4) | 0.0017 (4) | −0.0003 (4) |
C9 | 0.0169 (5) | 0.0169 (5) | 0.0156 (6) | −0.0015 (4) | 0.0013 (4) | −0.0008 (4) |
C10 | 0.0196 (5) | 0.0184 (5) | 0.0155 (6) | 0.0003 (4) | 0.0000 (4) | 0.0003 (4) |
C11 | 0.0142 (5) | 0.0216 (5) | 0.0168 (6) | 0.0010 (4) | 0.0011 (4) | −0.0029 (5) |
C12 | 0.0168 (5) | 0.0232 (6) | 0.0275 (8) | −0.0048 (4) | 0.0013 (5) | 0.0029 (5) |
C13 | 0.0178 (5) | 0.0227 (6) | 0.0243 (7) | −0.0026 (4) | 0.0013 (5) | 0.0077 (5) |
C14 | 0.0176 (5) | 0.0290 (7) | 0.0207 (7) | 0.0015 (5) | −0.0021 (5) | −0.0041 (5) |
C15 | 0.0240 (6) | 0.0150 (5) | 0.0257 (7) | −0.0015 (4) | 0.0025 (5) | 0.0028 (5) |
C16 | 0.0197 (6) | 0.0221 (6) | 0.0285 (8) | −0.0032 (4) | −0.0028 (5) | −0.0019 (5) |
C17 | 0.0149 (5) | 0.0274 (6) | 0.0148 (6) | −0.0011 (4) | −0.0006 (4) | −0.0018 (5) |
C18 | 0.0130 (5) | 0.0212 (5) | 0.0139 (6) | −0.0008 (4) | −0.0014 (4) | 0.0025 (4) |
C19 | 0.0215 (6) | 0.0229 (6) | 0.0240 (7) | 0.0035 (4) | −0.0004 (5) | −0.0064 (5) |
C20 | 0.0244 (6) | 0.0289 (7) | 0.0187 (7) | −0.0053 (5) | 0.0051 (5) | 0.0049 (5) |
S1—O1 | 1.4350 (10) | C6—C7 | 1.3624 (17) |
S1—O2 | 1.4360 (9) | C7—C18 | 1.4318 (17) |
S1—N1 | 1.6228 (11) | C8—C13 | 1.3910 (17) |
S1—C8 | 1.7639 (13) | C8—C9 | 1.3919 (18) |
O3—C6 | 1.3384 (15) | C9—C10 | 1.3894 (18) |
O3—C5 | 1.4812 (16) | C9—H9 | 0.93 |
O4—C17 | 1.2238 (16) | C10—C11 | 1.3980 (17) |
O5—C18 | 1.2283 (15) | C10—H10 | 0.93 |
N1—C1 | 1.4938 (16) | C11—C12 | 1.3886 (19) |
N1—C4 | 1.4977 (16) | C11—C14 | 1.5051 (18) |
N2—C6 | 1.3778 (17) | C12—C13 | 1.3917 (19) |
N2—C17 | 1.3901 (17) | C12—H12 | 0.93 |
N2—C19 | 1.4677 (17) | C13—H13 | 0.93 |
N3—C17 | 1.3827 (17) | C14—H14A | 0.96 |
N3—C18 | 1.4035 (17) | C14—H14B | 0.96 |
N3—C20 | 1.4666 (17) | C14—H14C | 0.96 |
C1—C2 | 1.5202 (18) | C15—H15A | 0.96 |
C1—H1A | 0.97 | C15—H15B | 0.96 |
C1—H1B | 0.97 | C15—H15C | 0.96 |
C2—C5 | 1.5207 (17) | C16—H16A | 0.96 |
C2—C3 | 1.5244 (17) | C16—H16B | 0.96 |
C2—H2 | 0.98 | C16—H16C | 0.96 |
C3—C7 | 1.4945 (17) | C19—H19A | 0.96 |
C3—C4 | 1.5240 (18) | C19—H19B | 0.96 |
C3—H3 | 0.98 | C19—H19C | 0.96 |
C4—H4A | 0.97 | C20—H20A | 0.96 |
C4—H4B | 0.97 | C20—H20B | 0.96 |
C5—C15 | 1.5140 (18) | C20—H20C | 0.96 |
C5—C16 | 1.5225 (18) | ||
O1—S1—O2 | 120.33 (6) | C13—C8—S1 | 119.58 (10) |
O1—S1—N1 | 106.40 (6) | C9—C8—S1 | 120.33 (9) |
O2—S1—N1 | 107.02 (5) | C10—C9—C8 | 119.52 (11) |
O1—S1—C8 | 106.89 (6) | C10—C9—H9 | 120.2 |
O2—S1—C8 | 107.27 (6) | C8—C9—H9 | 120.2 |
N1—S1—C8 | 108.52 (6) | C9—C10—C11 | 121.07 (12) |
C6—O3—C5 | 119.64 (10) | C9—C10—H10 | 119.5 |
C1—N1—C4 | 110.86 (10) | C11—C10—H10 | 119.5 |
C1—N1—S1 | 117.16 (8) | C12—C11—C10 | 118.55 (12) |
C4—N1—S1 | 119.89 (8) | C12—C11—C14 | 121.27 (12) |
C6—N2—C17 | 121.15 (11) | C10—C11—C14 | 120.16 (12) |
C6—N2—C19 | 120.79 (11) | C11—C12—C13 | 121.00 (12) |
C17—N2—C19 | 117.87 (11) | C11—C12—H12 | 119.5 |
C17—N3—C18 | 124.95 (11) | C13—C12—H12 | 119.5 |
C17—N3—C20 | 117.64 (11) | C8—C13—C12 | 119.74 (12) |
C18—N3—C20 | 117.38 (11) | C8—C13—H13 | 120.1 |
N1—C1—C2 | 101.73 (9) | C12—C13—H13 | 120.1 |
N1—C1—H1A | 111.4 | C11—C14—H14A | 109.5 |
C2—C1—H1A | 111.4 | C11—C14—H14B | 109.5 |
N1—C1—H1B | 111.4 | H14A—C14—H14B | 109.5 |
C2—C1—H1B | 111.4 | C11—C14—H14C | 109.5 |
H1A—C1—H1B | 109.3 | H14A—C14—H14C | 109.5 |
C1—C2—C5 | 119.32 (10) | H14B—C14—H14C | 109.5 |
C1—C2—C3 | 103.30 (9) | C5—C15—H15A | 109.5 |
C5—C2—C3 | 111.91 (11) | C5—C15—H15B | 109.5 |
C1—C2—H2 | 107.2 | H15A—C15—H15B | 109.5 |
C5—C2—H2 | 107.2 | C5—C15—H15C | 109.5 |
C3—C2—H2 | 107.2 | H15A—C15—H15C | 109.5 |
C7—C3—C4 | 120.58 (10) | H15B—C15—H15C | 109.5 |
C7—C3—C2 | 107.72 (10) | C5—C16—H16A | 109.5 |
C4—C3—C2 | 101.31 (10) | C5—C16—H16B | 109.5 |
C7—C3—H3 | 108.9 | H16A—C16—H16B | 109.5 |
C4—C3—H3 | 108.9 | C5—C16—H16C | 109.5 |
C2—C3—H3 | 108.9 | H16A—C16—H16C | 109.5 |
N1—C4—C3 | 102.24 (9) | H16B—C16—H16C | 109.5 |
N1—C4—H4A | 111.3 | O4—C17—N3 | 122.63 (12) |
C3—C4—H4A | 111.3 | O4—C17—N2 | 121.19 (12) |
N1—C4—H4B | 111.3 | N3—C17—N2 | 116.17 (12) |
C3—C4—H4B | 111.3 | O5—C18—N3 | 119.71 (11) |
H4A—C4—H4B | 109.2 | O5—C18—C7 | 124.32 (12) |
O3—C5—C15 | 103.82 (10) | N3—C18—C7 | 115.96 (11) |
O3—C5—C2 | 106.47 (9) | N2—C19—H19A | 109.5 |
C15—C5—C2 | 111.51 (11) | N2—C19—H19B | 109.5 |
O3—C5—C16 | 106.80 (11) | H19A—C19—H19B | 109.5 |
C15—C5—C16 | 112.43 (10) | N2—C19—H19C | 109.5 |
C2—C5—C16 | 114.89 (10) | H19A—C19—H19C | 109.5 |
O3—C6—C7 | 126.20 (12) | H19B—C19—H19C | 109.5 |
O3—C6—N2 | 111.42 (11) | N3—C20—H20A | 109.5 |
C7—C6—N2 | 122.36 (11) | N3—C20—H20B | 109.5 |
C6—C7—C18 | 119.30 (12) | H20A—C20—H20B | 109.5 |
C6—C7—C3 | 118.44 (11) | N3—C20—H20C | 109.5 |
C18—C7—C3 | 122.20 (11) | H20A—C20—H20C | 109.5 |
C13—C8—C9 | 120.07 (12) | H20B—C20—H20C | 109.5 |
O1—S1—N1—C1 | −46.84 (11) | C4—C3—C7—C6 | −142.71 (12) |
O2—S1—N1—C1 | −176.68 (9) | C2—C3—C7—C6 | −27.39 (15) |
C8—S1—N1—C1 | 67.86 (11) | C4—C3—C7—C18 | 40.19 (17) |
O1—S1—N1—C4 | 174.01 (9) | C2—C3—C7—C18 | 155.52 (11) |
O2—S1—N1—C4 | 44.17 (11) | O1—S1—C8—C13 | 25.07 (12) |
C8—S1—N1—C4 | −71.29 (10) | O2—S1—C8—C13 | 155.40 (11) |
C4—N1—C1—C2 | −12.07 (13) | N1—S1—C8—C13 | −89.30 (12) |
S1—N1—C1—C2 | −154.71 (9) | O1—S1—C8—C9 | −153.79 (10) |
N1—C1—C2—C5 | 160.36 (11) | O2—S1—C8—C9 | −23.47 (12) |
N1—C1—C2—C3 | 35.44 (12) | N1—S1—C8—C9 | 91.83 (11) |
C1—C2—C3—C7 | −173.40 (10) | C13—C8—C9—C10 | −1.55 (19) |
C5—C2—C3—C7 | 57.00 (12) | S1—C8—C9—C10 | 177.31 (10) |
C1—C2—C3—C4 | −45.92 (11) | C8—C9—C10—C11 | 0.01 (19) |
C5—C2—C3—C4 | −175.53 (9) | C9—C10—C11—C12 | 1.7 (2) |
C1—N1—C4—C3 | −15.84 (12) | C9—C10—C11—C14 | −176.80 (12) |
S1—N1—C4—C3 | 125.64 (9) | C10—C11—C12—C13 | −1.9 (2) |
C7—C3—C4—N1 | 155.66 (10) | C14—C11—C12—C13 | 176.59 (13) |
C2—C3—C4—N1 | 37.06 (11) | C9—C8—C13—C12 | 1.4 (2) |
C6—O3—C5—C15 | 150.57 (11) | S1—C8—C13—C12 | −177.51 (11) |
C6—O3—C5—C2 | 32.76 (14) | C11—C12—C13—C8 | 0.4 (2) |
C6—O3—C5—C16 | −90.44 (13) | C18—N3—C17—O4 | −177.69 (12) |
C1—C2—C5—O3 | −179.96 (10) | C20—N3—C17—O4 | 0.39 (19) |
C3—C2—C5—O3 | −59.28 (12) | C18—N3—C17—N2 | 3.09 (18) |
C1—C2—C5—C15 | 67.44 (14) | C20—N3—C17—N2 | −178.83 (11) |
C3—C2—C5—C15 | −171.88 (10) | C6—N2—C17—O4 | 177.54 (12) |
C1—C2—C5—C16 | −61.97 (16) | C19—N2—C17—O4 | 2.55 (19) |
C3—C2—C5—C16 | 58.71 (14) | C6—N2—C17—N3 | −3.23 (18) |
C5—O3—C6—C7 | −5.18 (19) | C19—N2—C17—N3 | −178.23 (11) |
C5—O3—C6—N2 | 176.01 (10) | C17—N3—C18—O5 | 178.37 (12) |
C17—N2—C6—O3 | −178.26 (11) | C20—N3—C18—O5 | 0.29 (17) |
C19—N2—C6—O3 | −3.41 (17) | C17—N3—C18—C7 | −2.33 (18) |
C17—N2—C6—C7 | 2.88 (19) | C20—N3—C18—C7 | 179.59 (11) |
C19—N2—C6—C7 | 177.73 (12) | C6—C7—C18—O5 | −179.08 (12) |
O3—C6—C7—C18 | 179.29 (12) | C3—C7—C18—O5 | −2.02 (19) |
N2—C6—C7—C18 | −2.02 (19) | C6—C7—C18—N3 | 1.65 (17) |
O3—C6—C7—C3 | 2.11 (19) | C3—C7—C18—N3 | 178.72 (11) |
N2—C6—C7—C3 | −179.20 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O4i | 0.96 | 2.57 | 3.4571 (17) | 153 |
C20—H20C···O5ii | 0.96 | 2.47 | 3.4125 (18) | 168 |
C19—H19B···O2iii | 0.96 | 2.44 | 3.1917 (17) | 134 |
C14—H14B···O1iv | 0.96 | 2.52 | 3.3787 (17) | 149 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H25N3O5S |
Mr | 419.49 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 14.5605 (2), 8.9142 (1), 15.3963 (3) |
β (°) | 94.316 (1) |
V (Å3) | 1992.70 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.50 × 0.30 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.906, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26688, 7053, 5564 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.128, 1.10 |
No. of reflections | 7053 |
No. of parameters | 265 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.38 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O4i | 0.96 | 2.57 | 3.4571 (17) | 153 |
C20—H20C···O5ii | 0.96 | 2.47 | 3.4125 (18) | 168 |
C19—H19B···O2iii | 0.96 | 2.44 | 3.1917 (17) | 134 |
C14—H14B···O1iv | 0.96 | 2.52 | 3.3787 (17) | 149 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y−1/2, −z+1/2. |
Pyranopyrimidine derivatives exhibit antiviral (Shamroukh et al., 2007) and antimicrobial activities (Bedair et al., 2000, 2001; Eid et al., 2004; Abdel Fattah et al., 2004). We report here the crystal structure of the title compound, a pyranopyrimidine derivative.
In the molecule of the title compound (Fig. 1), bond lengths are within normal ranges (Allen et al., 1987). The sum of the angles at the atom N1 of the pyrrolidine ring (347.9°) is in accordance with sp3 hybridization. Atom S1 has a distorted tetrahedral configuration, with the angle O2—S1—O1 [120.33 (6)°] deviating significantly from the ideal tetrahedral value.
The pyrimidine ring is planar, with an r.m.s. deviation of fitted atoms of 0.009 Å, and atoms O4, O5, C19 and C20 deviating by 0.040 (2), 0.012 (2), 0.051 (2) and -0.011 (2) Å, respectively. The pyrrolidine ring adopts a twist conformation, confirmed by its ring-puckering parameters (Cremer & Pople, 1975) q2 = 0.443 (1) Å and φ2 = 92.3 (2)°, and asymmetry parameter (Duax et al., 1976) ΔC2[C2—C3] = 2.9 (1)°. The pyran ring adopts an envelope conformation, with atom C2 deviating from the C5/O3/C6/C7/C3 plane by 0.684 (2) Å. The asymmetry parameter ΔCs[C2] is 3.8 (1)°, and the puckering parameters Q, θ and φ are 0.502 (1) Å, 129.5 (1)° and 295.3 (2)°, respectively. The tosyl group is attached to the pyrrolidine in a biaxial position and its benzene ring forms a dihedral angle of 85.61 (4)° with the pyrimidine ring. The dihedral angle between the C5/O3/C6/C7/C3 plane and the pyrimidine ring is 2.70 (8)°. The pyrrolidine ring is trans-fused to the dihydropyran ring.
In the crystal structure, inversion-related molecules are alternately linked by a pair each of C15—H15A···O4i and C20—H20C···O5ii hydrogen bonds to form a chain along the b axis (Fig. 2). Glide-related molecules in the adjacent chains are linked via C19—H19B···O2iii hydrogen bonds, forming a two-dimensional network parallel to the bc plane. Screw-related molecules in the adjacent networks are cross-linked by C14—H14B···O1iv hydrogen bonds (symmetry codes are given in Table 1) into a three-dimensional framework (Fig. 3).