cis-1-Ethyl-4,4,6,8-tetra­methyl-2-tosyl-2,3,3a,4,6,7,8,9-octa­hydro-1H-pyrrolo[3′,4′:3,4]pyrano[6,5-d]pyrimidine-7,9-dione

Chinnakali, K.; Sudha, D.; Jayagobi, M.; Raghunathan, R.; Fun, H.-K.

doi:10.1107/S1600536809026361

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o1862-o1863

doi:10.1107/S1600536809026361

Open

access

cis-1-Ethyl-4,4,6,8-tetramethyl-2-tosyl-2,3,3a,4,6,7,8,9-octahydro-1H-pyrrolo[3′,4′:3,4]pyrano[6,5-d]pyrimidine-7,9-dione

K. Chinnakali,^a ^* D. Sudha,^a ‡ M. Jayagobi,^b R. Raghunathan ^b and Hoong-Kun Fun ^c §

^aDepartment of Physics, Anna University Chennai, Chennai 600 025, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: kali@annauniv.edu

(Received 5 July 2009; accepted 7 July 2009; online 15 July 2009)

In the title compound, C₂₂H₂₉N₃O₅S, the pyrrolidine ring is cis-fused to the dihydropyran ring. The pyrrolidine and dihydropyran rings adopt twist and half-chair conformations, respectively. The molecule is in a folded conformation; the sulfonyl-bound benzene ring lies over the pyrimidinedione ring, with a weak π–π interaction [centroid–centroid distance = 3.6147 (4) Å]. A weak intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked into a three-dimensional network by C—H⋯O hydrogen bonds.

Related literature

For the trans isomer, see: Chinnakali et al. (2007 ). For the biological activity 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 ).

Experimental

Crystal data

C₂₂H₂₉N₃O₅S
M_r = 447.54
Monoclinic, P 2₁ /n
a = 13.2140 (2) Å
b = 9.5681 (2) Å
c = 16.8256 (3) Å
β = 98.946 (1)°
V = 2101.43 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.59 × 0.46 × 0.29 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.864, T_max = 0.945
92335 measured reflections
10993 independent reflections
9848 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.105
S = 1.08
10993 reflections
286 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O5	0.98	2.43	3.0422 (8)	120
C1—H1B⋯O4ⁱ	0.97	2.54	3.5072 (8)	177
C16—H16B⋯O5ⁱⁱ	0.96	2.57	3.3914 (8)	144
C19—H19C⋯O1ⁱⁱⁱ	0.96	2.52	3.4006 (9)	153
C20—H20C⋯O2^iv	0.96	2.51	3.2335 (8)	132
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026361/wn2336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026361/wn2336Isup2.hkl

checkCIF report

Comment top

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). Previously, we have reported the crystal structure of trans-1-ethyl-4,4,6,8-tetramethyl- 2-tosyl-2,3,3a,4,6,7,8,9-octahydro-1H-pyrrolo[3,4-c]pyrano[6,5-d]pyrimidine-7,9-dione (Chinnakali et al., 2007). Now we report the crystal structure of the title compound, a cis isomer.

In the title cis isomer, the pyrrolidine ring (N1/C1—C4) adopts a twist conformation compared to envelope conformations in the two independent molecules of the trans isomer. The relevant asymmetry parameter (Duax et al., 1976) ΔC₂[C2—C3] is 6.01 (6)°, and Cremer & Pople (1975) puckering parameters Q and ϕ are 0.3823 (7) Å and 264.96 (10)°, respectively. The dihydropyran ring adopts a half-chair conformation, with the local twofold axis passing through the midpoint of the C2—C5 and C6—C7 bonds. The asymmetry parameter ΔC₂[C2–C5] is 4.33 (7)° and the puckering parameters Q, θ and ϕ are 0.4800 (7) Å, 127.48 (7)° and 267.38 (9)°, respectively. In both independent molecules of the trans isomer, the dihydropyran ring adopts an envelope conformation. The tosyl group is equatorially attached to the pyrrolidine ring, whereas the ethyl group is axially attached. The sulfonyl group has a distorted tetrahedral geometry. The pyrrolidine ring is cis-fused to the dihydropyran ring. The dihedral angle between the pyrimidine and benzene rings is 10.84 (3)°. The corresponding bond lengths and angles in the two isomers agree with each other.

A superposition of non-H atoms in the dimethyl pyrimidine-7,9-dione unit of the cis isomer (title molecule) and molecule A of the trans isomer (Chinnakali et al., 2007) (Fig. 2) shows that the overall conformations of these isomers are different. The trans -fusion results in an extended ring system, with the tosyl group bending away from the fused ring system. In the cis-isomer, the molecule is in a folded conformation, with the sulfonyl-bound benzene ring lying over the pyrimidinedione ring. As a result of the folded conformation, the benzene and pyrimidinedione rings of the cis isomer are placed one over the other with weak π-π interactions (centroid-centroid distance = 3.6147 (4) Å).

A weak intramolecular C4—H4···O5 hydrogen bond generates an S(6) ring motif. The molecules exist as a C—H···O hydrogen-bonded dimer, generating a ring of graph-set motif R²₂(20). The dimers are linked into a three-dimensional network by C—H···O hydrogen bonds (Fig. 3).

Related literature top

For the trans isomer, see: Chinnakali et al. (2007). For the biological activity 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).

Experimental top

To a solution of barbituric acid (1 mmol) in toluene (20 ml) the corresponding 2-(N-prenyl-N-tosylamino]acetaldehyde (1 mmol) and a catalytic amount of the base ethylenediamine-N,N'-diacetate (EDDA) were added and the reaction mixture was refluxed for 12 h. After completion of the 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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius. The dashed open line indicates a π-π interaction and the dashed line indicates a hydrogen bond.
	Fig. 2. Fit of the title molecule (solid lines) on molecule A (dashed lines) of the trans isomer. H atoms have been omitted for clarity.
	Fig. 3. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in the interactions have been omitted.

cis-1-Ethyl-4,4,6,8-tetramethyl-2-tosyl-2,3,3a,4,6,7,8,9-octahydro-1H-pyrrolo[3',4':3,4]pyrano[6,5-d]pyrimidine-7,9-dione top

Crystal data top

C₂₂H₂₉N₃O₅S	F(000) = 952
M_r = 447.54	D_x = 1.415 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9302 reflections
a = 13.2140 (2) Å	θ = 2.5–40.9°
b = 9.5681 (2) Å	µ = 0.20 mm⁻¹
c = 16.8256 (3) Å	T = 100 K
β = 98.946 (1)°	Block, colourless
V = 2101.43 (7) Å³	0.59 × 0.46 × 0.29 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	10993 independent reflections
Radiation source: fine-focus sealed tube	9848 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 37.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −22→20
T_min = 0.864, T_max = 0.945	k = −16→16
92335 measured reflections	l = −28→28

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0595P)² + 0.4609P] where P = (F_o² + 2F_c²)/3
10993 reflections	(Δ/σ)_max = 0.002
286 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₂H₂₉N₃O₅S	V = 2101.43 (7) Å³
M_r = 447.54	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.2140 (2) Å	µ = 0.20 mm⁻¹
b = 9.5681 (2) Å	T = 100 K
c = 16.8256 (3) Å	0.59 × 0.46 × 0.29 mm
β = 98.946 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	10993 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	9848 reflections with I > 2σ(I)
T_min = 0.864, T_max = 0.945	R_int = 0.026
92335 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.08	Δρ_max = 0.60 e Å⁻³
10993 reflections	Δρ_min = −0.43 e Å⁻³
286 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.583987 (12)	0.842927 (15)	0.406869 (9)	0.01234 (4)
O1	0.65851 (4)	0.94222 (5)	0.38823 (4)	0.01920 (10)
O2	0.54783 (5)	0.84656 (6)	0.48296 (3)	0.01802 (10)
O3	0.48049 (4)	0.66605 (5)	0.12573 (3)	0.01221 (8)
O4	0.56281 (5)	0.22291 (5)	0.20707 (4)	0.01945 (10)
O5	0.34489 (4)	0.46219 (5)	0.34319 (3)	0.01542 (9)
N1	0.48436 (4)	0.86053 (6)	0.33745 (3)	0.01170 (8)
N2	0.52189 (4)	0.44704 (5)	0.16924 (3)	0.01178 (8)
N3	0.45765 (4)	0.34362 (5)	0.27803 (3)	0.01201 (9)
C1	0.50142 (5)	0.87879 (6)	0.25331 (4)	0.01246 (9)
H1A	0.5568	0.8197	0.2414	0.015*
H1B	0.5170	0.9753	0.2425	0.015*
C2	0.39850 (5)	0.83406 (6)	0.20456 (4)	0.01116 (9)
H2	0.3507	0.9129	0.2011	0.013*
C3	0.36105 (4)	0.71839 (6)	0.25639 (3)	0.01025 (9)
H3	0.2865	0.7081	0.2437	0.012*
C4	0.39216 (4)	0.77336 (6)	0.34312 (4)	0.01094 (9)
H4	0.4110	0.6948	0.3798	0.013*
C5	0.40701 (5)	0.78390 (6)	0.11965 (4)	0.01210 (9)
C6	0.46937 (4)	0.56814 (6)	0.18057 (3)	0.01023 (9)
C7	0.41350 (4)	0.58284 (6)	0.24165 (3)	0.01009 (9)
C8	0.63400 (5)	0.67386 (6)	0.39643 (4)	0.01179 (9)
C9	0.60216 (5)	0.56445 (7)	0.44136 (4)	0.01306 (10)
H9	0.5562	0.5809	0.4769	0.016*
C10	0.63973 (5)	0.43040 (7)	0.43263 (4)	0.01394 (10)
H10	0.6177	0.3572	0.4620	0.017*
C11	0.71018 (5)	0.40403 (7)	0.38037 (4)	0.01433 (10)
C12	0.74167 (5)	0.51562 (7)	0.33623 (4)	0.01645 (11)
H12	0.7884	0.4996	0.3012	0.020*
C13	0.70416 (5)	0.64999 (7)	0.34392 (4)	0.01486 (10)
H13	0.7257	0.7233	0.3143	0.018*
C14	0.75187 (6)	0.25884 (7)	0.37293 (5)	0.02037 (12)
H14A	0.7406	0.2040	0.4185	0.031*
H14B	0.8240	0.2640	0.3709	0.031*
H14C	0.7175	0.2160	0.3246	0.031*
C15	0.45325 (6)	0.89403 (7)	0.07111 (4)	0.01763 (11)
H15A	0.4595	0.8570	0.0191	0.026*
H15B	0.5198	0.9198	0.0987	0.026*
H15C	0.4097	0.9749	0.0649	0.026*
C16	0.30475 (5)	0.73203 (7)	0.07499 (4)	0.01565 (10)
H16A	0.3128	0.7040	0.0216	0.023*
H16B	0.2550	0.8057	0.0721	0.023*
H16C	0.2820	0.6537	0.1031	0.023*
C17	0.51744 (5)	0.33126 (6)	0.21815 (4)	0.01279 (9)
C18	0.40139 (5)	0.46334 (6)	0.29140 (4)	0.01094 (9)
C19	0.58284 (6)	0.43377 (7)	0.10385 (4)	0.01794 (12)
H19A	0.5632	0.5055	0.0646	0.027*
H19B	0.5709	0.3437	0.0790	0.027*
H19C	0.6542	0.4433	0.1252	0.027*
C20	0.45052 (6)	0.22000 (7)	0.32843 (4)	0.01626 (11)
H20A	0.5176	0.1809	0.3441	0.024*
H20B	0.4067	0.1518	0.2986	0.024*
H20C	0.4226	0.2464	0.3756	0.024*
C21	0.30950 (5)	0.86157 (7)	0.37333 (4)	0.01587 (11)
H21A	0.3397	0.9115	0.4214	0.019*
H21B	0.2841	0.9303	0.3327	0.019*
C22	0.21975 (5)	0.77395 (9)	0.39250 (4)	0.02000 (13)
H22A	0.1715	0.8334	0.4133	0.030*
H22B	0.2445	0.7044	0.4319	0.030*
H22C	0.1867	0.7290	0.3444	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01271 (7)	0.00984 (6)	0.01338 (7)	−0.00042 (4)	−0.00136 (5)	−0.00091 (4)
O1	0.0160 (2)	0.01258 (19)	0.0272 (3)	−0.00482 (16)	−0.00210 (18)	0.00116 (17)
O2	0.0232 (2)	0.0180 (2)	0.01203 (19)	0.00396 (17)	−0.00003 (17)	−0.00289 (15)
O3	0.01293 (18)	0.01207 (17)	0.01232 (18)	0.00183 (14)	0.00415 (14)	0.00262 (13)
O4	0.0223 (2)	0.01282 (19)	0.0246 (2)	0.00660 (17)	0.00808 (19)	0.00096 (17)
O5	0.0171 (2)	0.01400 (19)	0.0170 (2)	−0.00069 (15)	0.00842 (16)	0.00159 (15)
N1	0.0117 (2)	0.01097 (18)	0.01199 (19)	−0.00025 (15)	0.00035 (15)	0.00063 (15)
N2	0.0119 (2)	0.01108 (19)	0.0130 (2)	0.00168 (15)	0.00410 (15)	0.00013 (15)
N3	0.0144 (2)	0.00921 (18)	0.0128 (2)	0.00074 (15)	0.00319 (16)	0.00089 (14)
C1	0.0135 (2)	0.0111 (2)	0.0128 (2)	−0.00121 (17)	0.00190 (18)	0.00083 (17)
C2	0.0116 (2)	0.0103 (2)	0.0113 (2)	0.00114 (16)	0.00109 (17)	0.00142 (16)
C3	0.0096 (2)	0.0106 (2)	0.0106 (2)	0.00110 (16)	0.00170 (16)	0.00018 (16)
C4	0.0104 (2)	0.0110 (2)	0.0113 (2)	0.00091 (16)	0.00145 (16)	−0.00006 (16)
C5	0.0126 (2)	0.0122 (2)	0.0115 (2)	0.00189 (17)	0.00177 (17)	0.00231 (17)
C6	0.0096 (2)	0.00993 (19)	0.0111 (2)	0.00013 (16)	0.00149 (16)	0.00011 (16)
C7	0.0100 (2)	0.00933 (19)	0.0112 (2)	0.00002 (16)	0.00243 (16)	0.00026 (16)
C8	0.0106 (2)	0.0112 (2)	0.0131 (2)	0.00007 (16)	0.00020 (17)	0.00090 (17)
C9	0.0124 (2)	0.0130 (2)	0.0139 (2)	0.00026 (17)	0.00232 (18)	0.00160 (17)
C10	0.0134 (2)	0.0122 (2)	0.0162 (2)	0.00041 (18)	0.00204 (18)	0.00224 (18)
C11	0.0130 (2)	0.0128 (2)	0.0168 (2)	0.00140 (18)	0.00108 (19)	0.00025 (19)
C12	0.0151 (3)	0.0158 (2)	0.0196 (3)	0.0021 (2)	0.0060 (2)	0.0020 (2)
C13	0.0136 (2)	0.0139 (2)	0.0176 (3)	0.00009 (18)	0.0042 (2)	0.00289 (19)
C14	0.0212 (3)	0.0142 (2)	0.0264 (3)	0.0046 (2)	0.0058 (2)	0.0002 (2)
C15	0.0218 (3)	0.0159 (3)	0.0160 (2)	0.0006 (2)	0.0054 (2)	0.0053 (2)
C16	0.0140 (2)	0.0202 (3)	0.0120 (2)	0.0018 (2)	−0.00014 (18)	−0.00042 (19)
C17	0.0128 (2)	0.0109 (2)	0.0148 (2)	0.00118 (17)	0.00253 (18)	−0.00002 (17)
C18	0.0108 (2)	0.0098 (2)	0.0122 (2)	−0.00062 (16)	0.00179 (16)	−0.00023 (16)
C19	0.0202 (3)	0.0163 (3)	0.0197 (3)	0.0048 (2)	0.0108 (2)	0.0017 (2)
C20	0.0205 (3)	0.0109 (2)	0.0177 (3)	0.00067 (19)	0.0043 (2)	0.00368 (19)
C21	0.0147 (2)	0.0179 (3)	0.0153 (2)	0.0050 (2)	0.00301 (19)	−0.0024 (2)
C22	0.0132 (3)	0.0310 (4)	0.0163 (3)	0.0044 (2)	0.0041 (2)	0.0025 (2)

Geometric parameters (Å, º) top

S1—O2	1.4348 (6)	C8—C13	1.3954 (9)
S1—O1	1.4376 (6)	C9—C10	1.3914 (9)
S1—N1	1.6271 (6)	C9—H9	0.93
S1—C8	1.7665 (6)	C10—C11	1.3992 (9)
O3—C6	1.3391 (7)	C10—H10	0.93
O3—C5	1.4811 (8)	C11—C12	1.4003 (10)
O4—C17	1.2262 (8)	C11—C14	1.5068 (9)
O5—C18	1.2326 (7)	C12—C13	1.3912 (9)
N1—C1	1.4783 (8)	C12—H12	0.93
N1—C4	1.4917 (8)	C13—H13	0.93
N2—C6	1.3790 (8)	C14—H14A	0.96
N2—C17	1.3867 (8)	C14—H14B	0.96
N2—C19	1.4666 (8)	C14—H14C	0.96
N3—C17	1.3787 (8)	C15—H15A	0.96
N3—C18	1.4026 (8)	C15—H15B	0.96
N3—C20	1.4669 (8)	C15—H15C	0.96
C1—C2	1.5357 (9)	C16—H16A	0.96
C1—H1A	0.97	C16—H16B	0.96
C1—H1B	0.97	C16—H16C	0.96
C2—C5	1.5277 (9)	C19—H19A	0.96
C2—C3	1.5377 (8)	C19—H19B	0.96
C2—H2	0.98	C19—H19C	0.96
C3—C7	1.5091 (8)	C20—H20A	0.96
C3—C4	1.5455 (8)	C20—H20B	0.96
C3—H3	0.98	C20—H20C	0.96
C4—C21	1.5285 (9)	C21—C22	1.5273 (11)
C4—H4	0.98	C21—H21A	0.97
C5—C15	1.5185 (9)	C21—H21B	0.97
C5—C16	1.5236 (9)	C22—H22A	0.96
C6—C7	1.3627 (8)	C22—H22B	0.96
C7—C18	1.4405 (8)	C22—H22C	0.96
C8—C9	1.3940 (9)

O2—S1—O1	120.86 (3)	C9—C10—H10	119.5
O2—S1—N1	107.07 (3)	C11—C10—H10	119.5
O1—S1—N1	106.28 (3)	C10—C11—C12	118.52 (6)
O2—S1—C8	107.01 (3)	C10—C11—C14	120.40 (6)
O1—S1—C8	107.69 (3)	C12—C11—C14	121.08 (6)
N1—S1—C8	107.27 (3)	C13—C12—C11	121.05 (6)
C6—O3—C5	116.05 (5)	C13—C12—H12	119.5
C1—N1—C4	112.02 (5)	C11—C12—H12	119.5
C1—N1—S1	118.22 (4)	C12—C13—C8	119.44 (6)
C4—N1—S1	118.29 (4)	C12—C13—H13	120.3
C6—N2—C17	121.36 (5)	C8—C13—H13	120.3
C6—N2—C19	121.55 (5)	C11—C14—H14A	109.5
C17—N2—C19	117.06 (5)	C11—C14—H14B	109.5
C17—N3—C18	124.43 (5)	H14A—C14—H14B	109.5
C17—N3—C20	116.67 (5)	C11—C14—H14C	109.5
C18—N3—C20	118.85 (5)	H14A—C14—H14C	109.5
N1—C1—C2	102.97 (5)	H14B—C14—H14C	109.5
N1—C1—H1A	111.2	C5—C15—H15A	109.5
C2—C1—H1A	111.2	C5—C15—H15B	109.5
N1—C1—H1B	111.2	H15A—C15—H15B	109.5
C2—C1—H1B	111.2	C5—C15—H15C	109.5
H1A—C1—H1B	109.1	H15A—C15—H15C	109.5
C5—C2—C1	113.53 (5)	H15B—C15—H15C	109.5
C5—C2—C3	112.41 (5)	C5—C16—H16A	109.5
C1—C2—C3	103.53 (5)	C5—C16—H16B	109.5
C5—C2—H2	109.1	H16A—C16—H16B	109.5
C1—C2—H2	109.1	C5—C16—H16C	109.5
C3—C2—H2	109.1	H16A—C16—H16C	109.5
C7—C3—C2	109.20 (5)	H16B—C16—H16C	109.5
C7—C3—C4	112.71 (5)	O4—C17—N3	122.21 (6)
C2—C3—C4	103.22 (5)	O4—C17—N2	121.22 (6)
C7—C3—H3	110.5	N3—C17—N2	116.56 (5)
C2—C3—H3	110.5	O5—C18—N3	120.03 (5)
C4—C3—H3	110.5	O5—C18—C7	123.51 (5)
N1—C4—C21	110.21 (5)	N3—C18—C7	116.46 (5)
N1—C4—C3	103.29 (5)	N2—C19—H19A	109.5
C21—C4—C3	113.77 (5)	N2—C19—H19B	109.5
N1—C4—H4	109.8	H19A—C19—H19B	109.5
C21—C4—H4	109.8	N2—C19—H19C	109.5
C3—C4—H4	109.8	H19A—C19—H19C	109.5
O3—C5—C15	104.54 (5)	H19B—C19—H19C	109.5
O3—C5—C16	107.92 (5)	N3—C20—H20A	109.5
C15—C5—C16	111.16 (5)	N3—C20—H20B	109.5
O3—C5—C2	108.51 (5)	H20A—C20—H20B	109.5
C15—C5—C2	112.29 (5)	N3—C20—H20C	109.5
C16—C5—C2	112.02 (5)	H20A—C20—H20C	109.5
O3—C6—C7	125.30 (5)	H20B—C20—H20C	109.5
O3—C6—N2	112.40 (5)	C22—C21—C4	112.69 (6)
C7—C6—N2	122.30 (5)	C22—C21—H21A	109.1
C6—C7—C18	118.58 (5)	C4—C21—H21A	109.1
C6—C7—C3	121.95 (5)	C22—C21—H21B	109.1
C18—C7—C3	119.43 (5)	C4—C21—H21B	109.1
C9—C8—C13	120.45 (6)	H21A—C21—H21B	107.8
C9—C8—S1	118.99 (5)	C21—C22—H22A	109.5
C13—C8—S1	120.56 (5)	C21—C22—H22B	109.5
C10—C9—C8	119.49 (6)	H22A—C22—H22B	109.5
C10—C9—H9	120.3	C21—C22—H22C	109.5
C8—C9—H9	120.3	H22A—C22—H22C	109.5
C9—C10—C11	121.05 (6)	H22B—C22—H22C	109.5

O2—S1—N1—C1	172.18 (4)	N2—C6—C7—C3	176.56 (5)
O1—S1—N1—C1	41.74 (5)	C2—C3—C7—C6	−10.74 (8)
C8—S1—N1—C1	−73.25 (5)	C4—C3—C7—C6	−124.84 (6)
O2—S1—N1—C4	−47.28 (5)	C2—C3—C7—C18	171.67 (5)
O1—S1—N1—C4	−177.72 (5)	C4—C3—C7—C18	57.57 (7)
C8—S1—N1—C4	67.29 (5)	O2—S1—C8—C9	21.57 (6)
C4—N1—C1—C2	15.62 (6)	O1—S1—C8—C9	152.92 (5)
S1—N1—C1—C2	158.49 (4)	N1—S1—C8—C9	−93.05 (5)
N1—C1—C2—C5	−155.54 (5)	O2—S1—C8—C13	−158.55 (5)
N1—C1—C2—C3	−33.37 (6)	O1—S1—C8—C13	−27.20 (6)
C5—C2—C3—C7	41.74 (6)	N1—S1—C8—C13	86.83 (6)
C1—C2—C3—C7	−81.18 (5)	C13—C8—C9—C10	−0.94 (9)
C5—C2—C3—C4	161.86 (5)	S1—C8—C9—C10	178.93 (5)
C1—C2—C3—C4	38.94 (6)	C8—C9—C10—C11	0.98 (10)
C1—N1—C4—C21	−113.51 (6)	C9—C10—C11—C12	−0.55 (10)
S1—N1—C4—C21	103.65 (5)	C9—C10—C11—C14	178.68 (6)
C1—N1—C4—C3	8.38 (6)	C10—C11—C12—C13	0.07 (10)
S1—N1—C4—C3	−134.46 (4)	C14—C11—C12—C13	−179.16 (7)
C7—C3—C4—N1	88.77 (5)	C11—C12—C13—C8	−0.04 (11)
C2—C3—C4—N1	−28.91 (6)	C9—C8—C13—C12	0.48 (10)
C7—C3—C4—C21	−151.76 (5)	S1—C8—C13—C12	−179.40 (5)
C2—C3—C4—C21	90.56 (6)	C18—N3—C17—O4	−177.65 (6)
C6—O3—C5—C15	165.61 (5)	C20—N3—C17—O4	−0.07 (10)
C6—O3—C5—C16	−75.98 (6)	C18—N3—C17—N2	0.78 (9)
C6—O3—C5—C2	45.61 (7)	C20—N3—C17—N2	178.35 (6)
C1—C2—C5—O3	57.44 (6)	C6—N2—C17—O4	178.74 (6)
C3—C2—C5—O3	−59.67 (6)	C19—N2—C17—O4	0.17 (10)
C1—C2—C5—C15	−57.61 (7)	C6—N2—C17—N3	0.30 (9)
C3—C2—C5—C15	−174.72 (5)	C19—N2—C17—N3	−178.27 (6)
C1—C2—C5—C16	176.47 (5)	C17—N3—C18—O5	175.47 (6)
C3—C2—C5—C16	59.37 (7)	C20—N3—C18—O5	−2.06 (9)
C5—O3—C6—C7	−15.49 (8)	C17—N3—C18—C7	−4.13 (9)
C5—O3—C6—N2	164.75 (5)	C20—N3—C18—C7	178.34 (6)
C17—N2—C6—O3	−177.85 (5)	C6—C7—C18—O5	−173.12 (6)
C19—N2—C6—O3	0.65 (8)	C3—C7—C18—O5	4.56 (9)
C17—N2—C6—C7	2.38 (9)	C6—C7—C18—N3	6.47 (8)
C19—N2—C6—C7	−179.12 (6)	C3—C7—C18—N3	−175.86 (5)
O3—C6—C7—C18	174.43 (6)	N1—C4—C21—C22	−171.35 (5)
N2—C6—C7—C18	−5.82 (9)	C3—C4—C21—C22	73.20 (7)
O3—C6—C7—C3	−3.19 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5	0.98	2.43	3.0422 (8)	120
C1—H1B···O4ⁱ	0.97	2.54	3.5072 (8)	177
C16—H16B···O5ⁱⁱ	0.96	2.57	3.3914 (8)	144
C19—H19C···O1ⁱⁱⁱ	0.96	2.52	3.4006 (9)	153
C20—H20C···O2^iv	0.96	2.51	3.2335 (8)	132

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₉N₃O₅S
M_r	447.54
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	13.2140 (2), 9.5681 (2), 16.8256 (3)
β (°)	98.946 (1)
V (Å³)	2101.43 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.59 × 0.46 × 0.29

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.864, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	92335, 10993, 9848
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.857

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.105, 1.08
No. of reflections	10993
No. of parameters	286
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.43

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5	0.98	2.43	3.0422 (8)	120
C1—H1B···O4ⁱ	0.97	2.54	3.5072 (8)	177
C16—H16B···O5ⁱⁱ	0.96	2.57	3.3914 (8)	144
C19—H19C···O1ⁱⁱⁱ	0.96	2.52	3.4006 (9)	153
C20—H20C···O2^iv	0.96	2.51	3.2335 (8)	132

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1.

Footnotes

‡Working at: Department of Physics, RMK Engineering Collge, RSM Nagar, Kavaraipettai 601 206, Tamil Nadu, India.

§Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

HKF thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Abdel Fattah, M. E., Atta, A. H., Abdel Gawad, I. I. & Mina, S. M. (2004). Orient. J. Chem. 20, 257–262. CAS Google Scholar
Bedair, A. H., El-Hady, N. A., El-Latif, A., Fakery, A. H. & El-Agrody, A. M. (2000). Farmaco, 55, 708–714. Web of Science CrossRef PubMed CAS Google Scholar
Bedair, A. H., Emam, H. A., El-Hady, N. A., Ahmed, K. A. & El-Agrody, A. M. (2001). Farmaco, 56, 965–973. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chinnakali, K., Sudha, D., Jayagopi, M., Raghunathan, R. & Fun, H.-K. (2007). Acta Cryst. E63, o4434–o4435. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. L. Allinger, pp. 271–383. New York: John Wiley. Google Scholar
Eid, F. A., Abd El-Wahab, A. H., Ali, G. A. & Khafagy, M. M. (2004). Acta Pharm. 54, 13–26. PubMed CAS Google Scholar
Shamroukh, A. H., Zaki, M. E., Morsy, E. M., Abdel-Motti, F. M. & Abdel-Megeid, F. M. (2007). Arch. Pharm. (Weinheim), 340, 236–343. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o1862-o1863

doi:10.1107/S1600536809026361

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

cis-1-Ethyl-4,4,6,8-tetra­methyl-2-tosyl-2,3,3a,4,6,7,8,9-octa­hydro-1H-pyrrolo[3′,4′:3,4]pyrano[6,5-d]pyrimidine-7,9-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

cis-1-Ethyl-4,4,6,8-tetramethyl-2-tosyl-2,3,3a,4,6,7,8,9-octahydro-1H-pyrrolo[3′,4′:3,4]pyrano[6,5-d]pyrimidine-7,9-dione