1-Benzyl-6,8-dimethyl-4-phenyl-2-tosyl-1,2,3,3a,4,6,7,8,9,9b-deca­hydro­pyrrolo[3,4-c]pyrano[6,5-d]pyrimidine-7,9-dione

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

doi:10.1107/S1600536809044341

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2907-o2908

https://doi.org/10.1107/S1600536809044341

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1-Benzyl-6,8-dimethyl-4-phenyl-2-tosyl-1,2,3,3a,4,6,7,8,9,9b-decahydropyrrolo[3,4-c]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 25 October 2009; accepted 25 October 2009; online 28 October 2009)

The molecule of the title compound, C₃₁H₃₁N₃O₅S, adopts a folded conformation, with the sulfonyl-bound phenyl ring lying over the pyrimidine ring [dihedral angle = 12.04 (6)° and centroid–centroid separation = 3.6986 (8) Å]. The pyrrolidine ring adopts a twist conformation, the dihydropyran ring is in a half-chair conformation and the two rings are cis-fused. The tosyl group is attached to the pyrrolidine ring in an equatorial position while the benzyl group is axially attached. The molecular structure is stabilized by weak C—H⋯O hydrogen bonds and C—H⋯π interactions. In the crystal, pairs of molecules related by inversion symmetry are linked by C—H⋯O hydrogen bonds, forming chains propagating along the c axis which are cross-linked into a three-dimensional framework by further C—H⋯O links.

Related literature

For the biological activity of pyranopyrimidine derivatives, see: Abdel Fattah et al. (2004 ); Bedair et al. (2000 , 2001 ); Bruno et al. (2000 ); Eid et al. (2004 ); Shamroukh et al. (2007 ). For a related structure, see: Chinnakali et al. (2007 ). For ring puckering parameters, see: Cremer & Pople (1975 ) and for asymmetry parameters, see: Duax et al. (1976 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₃₁H₃₁N₃O₅S
M_r = 557.65
Monoclinic, P 2₁ /c
a = 13.2778 (2) Å
b = 15.8888 (2) Å
c = 13.0886 (2) Å
β = 99.019 (1)°
V = 2727.14 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 100 K
0.29 × 0.24 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.875, T_max = 0.976
39155 measured reflections
7888 independent reflections
6269 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.127
S = 1.07
7888 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.45 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	2.45	3.0586 (16)	120
C2—H2⋯Cg1	0.98	2.67	3.5377 (15)	148
C22—H22⋯O4ⁱ	0.93	2.57	3.258 (2)	132
C24—H24B⋯O5ⁱⁱ	0.96	2.48	3.4236 (17)	169
C30—H30⋯O1ⁱⁱⁱ	0.93	2.40	3.180 (2)	142
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+1, -z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C26–C31 ring.

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: https://doi.org/10.1107/S1600536809044341/hb5182sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044341/hb5182Isup2.hkl

checkCIF report

Comment top

Pyranopyrimidine derivatives exhibit antipyretic, analgesic and antiplatelet (Bruno et al., 2000), antiviral (Shamroukh et al., 2007) and antimicrobial (Bedair et al., 2000, 2001; Eid et al., 2004; Abdel Fattah et al., 2004) activities. We report here the crystal structure of the title compound, a pyranopyrimidine derivative.

Bond lengths and angles are comparable with those observed in a related structure (Chinnakali et al., 2007). The pyrimidine ring is planar, with an r.m.s. deviation of fitted atoms of 0.032 Å, and atoms O4, O5, C23 and C24 deviating by 0.079 (1), -0.146 (1), 0.021 (2) and 0.142 (2) Å, respectively. The pyrrolidine ring adopts a twist conformation, with twist about the C2—C3 bond; the puckering parameters (Cremer & Pople, 1975) q2 = 0.345 (2) Å and φ = 87.2 (2)°, and asymmetry parameter (Duax et al., 1976) ΔC₂[C2—C3] = 3.13 (14)°. The tosyl group is attached to the pyrrolidine ring in an equatorial position while the benzyl group is axially attached. The dihydropyran ring adopts a half-chair conformation, with atoms C2 and C5 deviating from the O3/C3/C6/C7 plane by -0.302 (2) Å and 0.427 (2) Å, respectively. The asymmetry parameter ΔC₂[C2—C5] is 6.4 (2)°, and the puckering parameters Q, θ and φ are 0.478 (1) Å, 54.1 (2)° and 86.1 (2)°, respectively. The phenyl group is axially attached to the dihydropyran ring. The pyrrolidine ring is cis-fused to the dihydropyran ring.

The molecule is in a folded conformation, with the sulfonyl-bound phenyl ring lying over the pyrimidine ring [dihedral angle = 12.04 (6)°]. The folded conformation is stabilized by weak π-π interaction between phenyl and pyrimidine rings (centroid-to-centroid distance = 3.6986 (8) Å), C4—H4···O5 hydrogen bonds and C2—H2···π interaction involving the benzyl phenyl ring (C26—C31). The dihedral angle between the C17—C22 and C26—C31 phenyl rings is 57.50 (8)°.

Pairs of molecules related by inversion are linked into R₂²(10) (Bernstein et al., 1995) dimers by C24—H24B···O5 hydrogen bonds, and dimers related by inversion are linked into chains along the c axis by pairs of C22—H22···O4 hydrogen bonds which generate an R₂²(18) motif. The adjacent chains are cross-linked through C30—H30···O1 hydrogen bonds to form a three-dimensional framework.

Related literature top

For the biological activity of pyranopyrimidine derivatives, see: Abdel Fattah et al. (2004); Bedair et al. (2000, 2001); Bruno et al. (2000); Eid et al. (2004); Shamroukh et al. (2007). For a related structure, see: Chinnakali et al. (2007). For ring puckering parameters, see: Cremer & Pople (1975) and for asymmetry parameters, see: Duax et al. (1976). For hydrogen-bond motifs, see: Bernstein et al. (1995). Cg1 is the centroid of the C26–C31 ring.

Experimental top

To a solution of 1,3-dimethyl-pyrimidine-2,4,6-trione (1 mmol) in dry toluene (20 ml), the corresponding 2-(N-cinnamyl-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 to yield colourless blocks of (I).

Structure description top

For the biological activity of pyranopyrimidine derivatives, see: Abdel Fattah et al. (2004); Bedair et al. (2000, 2001); Bruno et al. (2000); Eid et al. (2004); Shamroukh et al. (2007). For a related structure, see: Chinnakali et al. (2007). For ring puckering parameters, see: Cremer & Pople (1975) and for asymmetry parameters, see: Duax et al. (1976). For hydrogen-bond motifs, see: Bernstein et al. (1995). Cg1 is the centroid of the C26–C31 ring.

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 (I) with displacement ellipsoids drawn at the 50% probability level. Dashed and dotted lines indicate C—H···O and C—H···π interactions, respectively. The π-π interaction is shown by a dashed solid line.
	Fig. 2. Part of the crystal packing of (I), showing hydrogen-bonded (dashed lines) chains. For the sake of clarity, H atoms not involved in intermolecular hydrogen bonds have been omitted.

1-Benzyl-6,8-dimethyl-4-phenyl-2-tosyl-1,2,3,3a,4,6,7,8,9,9b- decahydropyrrolo[3,4-c]pyrano[6,5-d]pyrimidine-7,9-dione top

Crystal data top

C₃₁H₃₁N₃O₅S	F(000) = 1176
M_r = 557.65	D_x = 1.358 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9929 reflections
a = 13.2778 (2) Å	θ = 2.6–32.3°
b = 15.8888 (2) Å	µ = 0.17 mm⁻¹
c = 13.0886 (2) Å	T = 100 K
β = 99.019 (1)°	Block, colourless
V = 2727.14 (7) Å³	0.29 × 0.24 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	7888 independent reflections
Radiation source: fine-focus sealed tube	6269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→18
T_min = 0.875, T_max = 0.976	k = −22→21
39155 measured reflections	l = −17→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0645P)² + 0.8585P] where P = (F_o² + 2F_c²)/3
7888 reflections	(Δ/σ)_max = 0.001
363 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₃₁H₃₁N₃O₅S	V = 2727.14 (7) Å³
M_r = 557.65	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2778 (2) Å	µ = 0.17 mm⁻¹
b = 15.8888 (2) Å	T = 100 K
c = 13.0886 (2) Å	0.29 × 0.24 × 0.15 mm
β = 99.019 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	7888 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6269 reflections with I > 2σ(I)
T_min = 0.875, T_max = 0.976	R_int = 0.042
39155 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.07	Δρ_max = 0.38 e Å⁻³
7888 reflections	Δρ_min = −0.45 e Å⁻³
363 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	Occ. (<1)
S1	0.24002 (3)	0.27919 (2)	0.08504 (3)	0.01786 (9)
O1	0.29691 (8)	0.20418 (7)	0.11604 (8)	0.0244 (2)
O2	0.22163 (8)	0.30362 (7)	−0.02164 (8)	0.0227 (2)
O3	0.22116 (7)	0.42241 (7)	0.41969 (7)	0.0192 (2)
O4	−0.12019 (8)	0.44236 (7)	0.32394 (8)	0.0230 (2)
O5	0.07992 (7)	0.55421 (6)	0.10506 (7)	0.0180 (2)
N1	0.30062 (9)	0.35642 (7)	0.14908 (9)	0.0172 (2)
N2	0.05214 (9)	0.43750 (7)	0.37124 (9)	0.0169 (2)
N3	−0.02062 (8)	0.49601 (7)	0.21216 (8)	0.0154 (2)
C1	0.33158 (11)	0.34751 (9)	0.26213 (10)	0.0193 (3)
H1A	0.3954	0.3171	0.2781	0.023*
H1B	0.2797	0.3184	0.2931	0.023*
C2	0.34345 (10)	0.43876 (9)	0.30011 (10)	0.0161 (3)
H2	0.4127	0.4579	0.2954	0.019*
C3	0.26717 (10)	0.48911 (8)	0.22261 (10)	0.0142 (2)
H3	0.2889	0.5479	0.2195	0.017*
C4	0.27054 (10)	0.44416 (8)	0.11846 (10)	0.0151 (2)
H4	0.2019	0.4438	0.0779	0.018*
C5	0.32387 (10)	0.45051 (9)	0.41091 (10)	0.0179 (3)
H5	0.3721	0.4147	0.4558	0.021*
C6	0.14751 (10)	0.44924 (8)	0.34517 (10)	0.0155 (2)
C7	0.16259 (10)	0.48378 (8)	0.25380 (10)	0.0145 (2)
C8	0.12079 (11)	0.26992 (9)	0.12787 (11)	0.0182 (3)
C9	0.03512 (11)	0.31028 (9)	0.07404 (11)	0.0203 (3)
H9	0.0408	0.3436	0.0168	0.024*
C10	−0.05862 (12)	0.30012 (9)	0.10679 (12)	0.0233 (3)
H10	−0.1159	0.3261	0.0701	0.028*
C11	−0.06866 (12)	0.25174 (9)	0.19372 (12)	0.0241 (3)
C12	0.01881 (12)	0.21432 (9)	0.24816 (12)	0.0247 (3)
H12	0.0139	0.1836	0.3077	0.030*
C13	0.11282 (12)	0.22190 (9)	0.21553 (11)	0.0220 (3)
H13	0.1699	0.1953	0.2517	0.026*
C14	−0.17063 (13)	0.23950 (12)	0.22861 (15)	0.0331 (4)
H14A	−0.2101	0.2902	0.2164	0.050*	0.50
H14B	−0.1605	0.2266	0.3011	0.050*	0.50
H14C	−0.2063	0.1940	0.1905	0.050*	0.50
H14D	−0.1745	0.1836	0.2557	0.050*	0.50
H14E	−0.2241	0.2472	0.1709	0.050*	0.50
H14F	−0.1782	0.2798	0.2815	0.050*	0.50
C15	−0.03560 (10)	0.45740 (9)	0.30321 (10)	0.0168 (3)
C16	0.07514 (10)	0.51458 (8)	0.18497 (10)	0.0141 (2)
C17	0.34013 (11)	0.54080 (9)	0.44869 (10)	0.0192 (3)
C18	0.42511 (12)	0.58588 (10)	0.42851 (12)	0.0237 (3)
H18	0.4716	0.5604	0.3921	0.028*
C19	0.44095 (13)	0.66829 (11)	0.46223 (14)	0.0316 (4)
H19	0.4976	0.6979	0.4480	0.038*
C20	0.37218 (15)	0.70650 (12)	0.51717 (15)	0.0389 (4)
H20	0.3824	0.7619	0.5395	0.047*
C21	0.28856 (15)	0.66214 (13)	0.53870 (14)	0.0388 (4)
H21	0.2426	0.6878	0.5757	0.047*
C22	0.27261 (13)	0.57937 (11)	0.50547 (12)	0.0282 (3)
H22	0.2167	0.5497	0.5212	0.034*
C23	0.03991 (12)	0.39397 (11)	0.46792 (11)	0.0257 (3)
H23A	0.0907	0.4137	0.5231	0.039*
H23B	0.0477	0.3344	0.4593	0.039*
H23C	−0.0267	0.4054	0.4844	0.039*
C24	−0.11133 (10)	0.51453 (10)	0.13584 (11)	0.0194 (3)
H24A	−0.1674	0.4807	0.1501	0.029*
H24B	−0.0974	0.5020	0.0677	0.029*
H24C	−0.1285	0.5730	0.1398	0.029*
C25	0.34547 (10)	0.48309 (9)	0.05318 (10)	0.0173 (3)
H25A	0.3490	0.4471	−0.0060	0.021*
H25B	0.3193	0.5373	0.0274	0.021*
C26	0.45176 (10)	0.49478 (10)	0.11237 (11)	0.0195 (3)
C27	0.51924 (12)	0.42716 (11)	0.13215 (13)	0.0274 (3)
H27	0.5021	0.3748	0.1027	0.033*
C28	0.61285 (13)	0.43864 (14)	0.19648 (14)	0.0385 (5)
H28	0.6568	0.3931	0.2109	0.046*
C29	0.64105 (13)	0.51625 (15)	0.23891 (13)	0.0411 (5)
H29	0.7032	0.5228	0.2821	0.049*
C30	0.57666 (13)	0.58375 (14)	0.21684 (13)	0.0364 (4)
H30	0.5959	0.6366	0.2435	0.044*
C31	0.48241 (12)	0.57272 (11)	0.15439 (12)	0.0254 (3)
H31	0.4390	0.6186	0.1405	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02082 (17)	0.01614 (16)	0.01588 (16)	0.00094 (12)	0.00059 (12)	−0.00164 (12)
O1	0.0276 (6)	0.0181 (5)	0.0265 (5)	0.0056 (4)	0.0010 (4)	−0.0017 (4)
O2	0.0285 (5)	0.0242 (5)	0.0148 (5)	−0.0001 (4)	0.0019 (4)	−0.0030 (4)
O3	0.0159 (5)	0.0257 (5)	0.0149 (4)	−0.0012 (4)	−0.0014 (3)	0.0062 (4)
O4	0.0166 (5)	0.0317 (6)	0.0213 (5)	−0.0017 (4)	0.0048 (4)	0.0035 (4)
O5	0.0201 (5)	0.0194 (5)	0.0143 (4)	0.0030 (4)	0.0025 (4)	0.0036 (4)
N1	0.0193 (6)	0.0157 (5)	0.0155 (5)	0.0001 (4)	−0.0008 (4)	0.0001 (4)
N2	0.0173 (5)	0.0196 (6)	0.0137 (5)	−0.0011 (4)	0.0018 (4)	0.0049 (4)
N3	0.0137 (5)	0.0182 (5)	0.0137 (5)	0.0014 (4)	0.0002 (4)	0.0012 (4)
C1	0.0216 (7)	0.0191 (7)	0.0156 (6)	0.0030 (5)	−0.0024 (5)	0.0004 (5)
C2	0.0149 (6)	0.0175 (6)	0.0147 (6)	0.0003 (5)	−0.0011 (5)	−0.0008 (5)
C3	0.0136 (6)	0.0158 (6)	0.0126 (5)	−0.0003 (5)	0.0001 (4)	0.0014 (4)
C4	0.0150 (6)	0.0163 (6)	0.0134 (6)	−0.0001 (5)	0.0001 (4)	0.0005 (5)
C5	0.0152 (6)	0.0237 (7)	0.0138 (6)	0.0000 (5)	−0.0008 (5)	0.0017 (5)
C6	0.0157 (6)	0.0149 (6)	0.0150 (6)	0.0002 (5)	−0.0006 (5)	0.0008 (5)
C7	0.0151 (6)	0.0146 (6)	0.0132 (6)	0.0000 (5)	0.0002 (4)	0.0005 (4)
C8	0.0210 (7)	0.0141 (6)	0.0183 (6)	−0.0017 (5)	−0.0003 (5)	−0.0019 (5)
C9	0.0252 (7)	0.0159 (6)	0.0185 (6)	0.0005 (5)	−0.0004 (5)	−0.0008 (5)
C10	0.0230 (7)	0.0178 (7)	0.0274 (7)	0.0027 (5)	−0.0013 (6)	−0.0029 (6)
C11	0.0260 (7)	0.0169 (7)	0.0297 (7)	−0.0018 (6)	0.0056 (6)	−0.0053 (6)
C12	0.0308 (8)	0.0196 (7)	0.0238 (7)	−0.0039 (6)	0.0041 (6)	0.0014 (5)
C13	0.0242 (7)	0.0176 (7)	0.0225 (7)	−0.0013 (5)	−0.0010 (5)	0.0031 (5)
C14	0.0290 (8)	0.0312 (9)	0.0410 (9)	−0.0012 (7)	0.0117 (7)	−0.0034 (7)
C15	0.0178 (6)	0.0176 (6)	0.0147 (6)	0.0010 (5)	0.0021 (5)	0.0004 (5)
C16	0.0160 (6)	0.0135 (6)	0.0126 (5)	0.0012 (5)	0.0010 (4)	−0.0011 (4)
C17	0.0200 (7)	0.0240 (7)	0.0120 (6)	0.0001 (5)	−0.0022 (5)	−0.0008 (5)
C18	0.0213 (7)	0.0272 (8)	0.0215 (7)	−0.0011 (6)	−0.0001 (5)	−0.0031 (6)
C19	0.0292 (8)	0.0299 (9)	0.0335 (9)	−0.0066 (7)	−0.0023 (7)	−0.0040 (7)
C20	0.0445 (10)	0.0314 (9)	0.0379 (10)	−0.0029 (8)	−0.0024 (8)	−0.0151 (8)
C21	0.0434 (10)	0.0434 (11)	0.0306 (9)	0.0022 (8)	0.0091 (8)	−0.0166 (8)
C22	0.0299 (8)	0.0360 (9)	0.0195 (7)	−0.0016 (7)	0.0061 (6)	−0.0063 (6)
C23	0.0256 (7)	0.0331 (8)	0.0189 (7)	−0.0027 (6)	0.0050 (5)	0.0124 (6)
C24	0.0149 (6)	0.0253 (7)	0.0166 (6)	0.0025 (5)	−0.0014 (5)	0.0002 (5)
C25	0.0166 (6)	0.0207 (7)	0.0145 (6)	0.0000 (5)	0.0020 (5)	0.0012 (5)
C26	0.0163 (6)	0.0268 (7)	0.0160 (6)	−0.0005 (5)	0.0043 (5)	0.0034 (5)
C27	0.0222 (7)	0.0347 (9)	0.0277 (8)	0.0071 (6)	0.0108 (6)	0.0083 (6)
C28	0.0204 (8)	0.0622 (13)	0.0346 (9)	0.0161 (8)	0.0095 (7)	0.0195 (9)
C29	0.0188 (8)	0.0798 (15)	0.0239 (8)	−0.0074 (9)	0.0011 (6)	0.0083 (9)
C30	0.0258 (8)	0.0571 (12)	0.0256 (8)	−0.0166 (8)	0.0023 (6)	−0.0016 (8)
C31	0.0227 (7)	0.0303 (8)	0.0228 (7)	−0.0057 (6)	0.0020 (6)	0.0032 (6)

Geometric parameters (Å, º) top

S1—O2	1.4328 (10)	C12—H12	0.93
S1—O1	1.4351 (11)	C13—H13	0.93
S1—N1	1.6261 (12)	C14—H14A	0.96
S1—C8	1.7664 (15)	C14—H14B	0.96
O3—C6	1.3380 (15)	C14—H14C	0.96
O3—C5	1.4566 (16)	C14—H14D	0.96
O4—C15	1.2198 (17)	C14—H14E	0.96
O5—C16	1.2309 (15)	C14—H14F	0.96
N1—C1	1.4791 (17)	C17—C22	1.393 (2)
N1—C4	1.4878 (17)	C17—C18	1.396 (2)
N2—C6	1.3748 (18)	C18—C19	1.387 (2)
N2—C15	1.3873 (17)	C18—H18	0.93
N2—C23	1.4733 (17)	C19—C20	1.388 (3)
N3—C15	1.3822 (17)	C19—H19	0.93
N3—C16	1.4043 (17)	C20—C21	1.381 (3)
N3—C24	1.4690 (16)	C20—H20	0.93
C1—C2	1.5327 (19)	C21—C22	1.391 (3)
C1—H1A	0.97	C21—H21	0.93
C1—H1B	0.97	C22—H22	0.93
C2—C5	1.5245 (18)	C23—H23A	0.96
C2—C3	1.5403 (17)	C23—H23B	0.96
C2—H2	0.98	C23—H23C	0.96
C3—C7	1.5100 (18)	C24—H24A	0.96
C3—C4	1.5457 (18)	C24—H24B	0.96
C3—H3	0.98	C24—H24C	0.96
C4—C25	1.5391 (19)	C25—C26	1.5111 (19)
C4—H4	0.98	C25—H25A	0.97
C5—C17	1.522 (2)	C25—H25B	0.97
C5—H5	0.98	C26—C31	1.390 (2)
C6—C7	1.3589 (18)	C26—C27	1.397 (2)
C7—C16	1.4392 (17)	C27—C28	1.400 (2)
C8—C13	1.396 (2)	C27—H27	0.93
C8—C9	1.3965 (19)	C28—C29	1.380 (3)
C9—C10	1.388 (2)	C28—H28	0.93
C9—H9	0.93	C29—C30	1.374 (3)
C10—C11	1.397 (2)	C29—H29	0.93
C10—H10	0.93	C30—C31	1.394 (2)
C11—C12	1.397 (2)	C30—H30	0.93
C11—C14	1.508 (2)	C31—H31	0.93
C12—C13	1.386 (2)

O2—S1—O1	120.15 (7)	C11—C14—H14D	109.5
O2—S1—N1	107.03 (6)	H14A—C14—H14D	141.1
O1—S1—N1	106.55 (6)	H14B—C14—H14D	56.3
O2—S1—C8	107.91 (6)	H14C—C14—H14D	56.3
O1—S1—C8	107.41 (7)	C11—C14—H14E	109.5
N1—S1—C8	107.15 (6)	H14A—C14—H14E	56.3
C6—O3—C5	115.54 (10)	H14B—C14—H14E	141.1
C1—N1—C4	112.33 (10)	H14C—C14—H14E	56.3
C1—N1—S1	118.75 (9)	H14D—C14—H14E	109.5
C4—N1—S1	118.55 (8)	C11—C14—H14F	109.5
C6—N2—C15	121.56 (11)	H14A—C14—H14F	56.3
C6—N2—C23	120.44 (11)	H14B—C14—H14F	56.3
C15—N2—C23	117.62 (12)	H14C—C14—H14F	141.1
C15—N3—C16	124.76 (11)	H14D—C14—H14F	109.5
C15—N3—C24	117.50 (11)	H14E—C14—H14F	109.5
C16—N3—C24	117.64 (11)	O4—C15—N3	122.73 (12)
N1—C1—C2	103.43 (11)	O4—C15—N2	121.50 (12)
N1—C1—H1A	111.1	N3—C15—N2	115.76 (12)
C2—C1—H1A	111.1	O5—C16—N3	119.48 (11)
N1—C1—H1B	111.1	O5—C16—C7	124.18 (12)
C2—C1—H1B	111.1	N3—C16—C7	116.33 (11)
H1A—C1—H1B	109.0	C22—C17—C18	118.82 (14)
C5—C2—C1	113.59 (12)	C22—C17—C5	121.18 (14)
C5—C2—C3	111.73 (11)	C18—C17—C5	119.99 (13)
C1—C2—C3	104.73 (10)	C19—C18—C17	120.71 (15)
C5—C2—H2	108.9	C19—C18—H18	119.6
C1—C2—H2	108.9	C17—C18—H18	119.6
C3—C2—H2	108.9	C18—C19—C20	119.91 (17)
C7—C3—C2	109.29 (11)	C18—C19—H19	120.0
C7—C3—C4	111.56 (10)	C20—C19—H19	120.0
C2—C3—C4	103.52 (10)	C21—C20—C19	119.86 (17)
C7—C3—H3	110.7	C21—C20—H20	120.1
C2—C3—H3	110.7	C19—C20—H20	120.1
C4—C3—H3	110.7	C20—C21—C22	120.44 (17)
N1—C4—C25	110.89 (11)	C20—C21—H21	119.8
N1—C4—C3	103.83 (10)	C22—C21—H21	119.8
C25—C4—C3	114.49 (11)	C21—C22—C17	120.24 (16)
N1—C4—H4	109.1	C21—C22—H22	119.9
C25—C4—H4	109.1	C17—C22—H22	119.9
C3—C4—H4	109.1	N2—C23—H23A	109.5
O3—C5—C17	110.50 (11)	N2—C23—H23B	109.5
O3—C5—C2	109.81 (10)	H23A—C23—H23B	109.5
C17—C5—C2	112.83 (11)	N2—C23—H23C	109.5
O3—C5—H5	107.8	H23A—C23—H23C	109.5
C17—C5—H5	107.8	H23B—C23—H23C	109.5
C2—C5—H5	107.8	N3—C24—H24A	109.5
O3—C6—C7	125.35 (12)	N3—C24—H24B	109.5
O3—C6—N2	111.86 (11)	H24A—C24—H24B	109.5
C7—C6—N2	122.79 (12)	N3—C24—H24C	109.5
C6—C7—C16	118.20 (12)	H24A—C24—H24C	109.5
C6—C7—C3	121.95 (11)	H24B—C24—H24C	109.5
C16—C7—C3	119.84 (11)	C26—C25—C4	113.45 (11)
C13—C8—C9	120.33 (14)	C26—C25—H25A	108.9
C13—C8—S1	119.58 (11)	C4—C25—H25A	108.9
C9—C8—S1	120.08 (11)	C26—C25—H25B	108.9
C10—C9—C8	119.33 (14)	C4—C25—H25B	108.9
C10—C9—H9	120.3	H25A—C25—H25B	107.7
C8—C9—H9	120.3	C31—C26—C27	118.19 (14)
C9—C10—C11	121.35 (14)	C31—C26—C25	120.30 (13)
C9—C10—H10	119.3	C27—C26—C25	121.39 (14)
C11—C10—H10	119.3	C26—C27—C28	119.64 (17)
C10—C11—C12	118.17 (15)	C26—C27—H27	120.2
C10—C11—C14	121.51 (15)	C28—C27—H27	120.2
C12—C11—C14	120.33 (15)	C29—C28—C27	121.20 (17)
C13—C12—C11	121.51 (14)	C29—C28—H28	119.4
C13—C12—H12	119.2	C27—C28—H28	119.4
C11—C12—H12	119.2	C30—C29—C28	119.50 (16)
C12—C13—C8	119.26 (14)	C30—C29—H29	120.3
C12—C13—H13	120.4	C28—C29—H29	120.3
C8—C13—H13	120.4	C29—C30—C31	119.80 (18)
C11—C14—H14A	109.5	C29—C30—H30	120.1
C11—C14—H14B	109.5	C31—C30—H30	120.1
H14A—C14—H14B	109.5	C26—C31—C30	121.62 (17)
C11—C14—H14C	109.5	C26—C31—H31	119.2
H14A—C14—H14C	109.5	C30—C31—H31	119.2
H14B—C14—H14C	109.5

O2—S1—N1—C1	−178.78 (10)	S1—C8—C9—C10	177.94 (11)
O1—S1—N1—C1	−49.05 (12)	C8—C9—C10—C11	1.3 (2)
C8—S1—N1—C1	65.68 (11)	C9—C10—C11—C12	0.8 (2)
O2—S1—N1—C4	38.87 (12)	C9—C10—C11—C14	−179.07 (14)
O1—S1—N1—C4	168.59 (10)	C10—C11—C12—C13	−2.3 (2)
C8—S1—N1—C4	−76.68 (11)	C14—C11—C12—C13	177.51 (14)
C4—N1—C1—C2	−12.74 (15)	C11—C12—C13—C8	1.8 (2)
S1—N1—C1—C2	−157.29 (9)	C9—C8—C13—C12	0.4 (2)
N1—C1—C2—C5	151.72 (11)	S1—C8—C13—C12	−179.44 (11)
N1—C1—C2—C3	29.54 (14)	C16—N3—C15—O4	179.99 (13)
C5—C2—C3—C7	−39.77 (15)	C24—N3—C15—O4	−3.7 (2)
C1—C2—C3—C7	83.61 (13)	C16—N3—C15—N2	0.86 (19)
C5—C2—C3—C4	−158.76 (11)	C24—N3—C15—N2	177.18 (12)
C1—C2—C3—C4	−35.38 (13)	C6—N2—C15—O4	175.59 (13)
C1—N1—C4—C25	114.32 (12)	C23—N2—C15—O4	2.7 (2)
S1—N1—C4—C25	−101.05 (11)	C6—N2—C15—N3	−5.27 (19)
C1—N1—C4—C3	−9.10 (14)	C23—N2—C15—N3	−178.21 (12)
S1—N1—C4—C3	135.53 (10)	C15—N3—C16—O5	−175.14 (12)
C7—C3—C4—N1	−90.39 (12)	C24—N3—C16—O5	8.55 (18)
C2—C3—C4—N1	27.02 (13)	C15—N3—C16—C7	5.83 (19)
C7—C3—C4—C25	148.58 (11)	C24—N3—C16—C7	−170.48 (12)
C2—C3—C4—C25	−94.01 (12)	C6—C7—C16—O5	172.74 (13)
C6—O3—C5—C17	78.79 (14)	C3—C7—C16—O5	−8.3 (2)
C6—O3—C5—C2	−46.30 (15)	C6—C7—C16—N3	−8.28 (18)
C1—C2—C5—O3	−58.54 (14)	C3—C7—C16—N3	170.68 (11)
C3—C2—C5—O3	59.67 (14)	O3—C5—C17—C22	14.05 (17)
C1—C2—C5—C17	177.71 (11)	C2—C5—C17—C22	137.41 (13)
C3—C2—C5—C17	−64.08 (14)	O3—C5—C17—C18	−167.34 (12)
C5—O3—C6—C7	14.77 (19)	C2—C5—C17—C18	−43.98 (17)
C5—O3—C6—N2	−165.52 (11)	C22—C17—C18—C19	−1.5 (2)
C15—N2—C6—O3	−177.06 (12)	C5—C17—C18—C19	179.87 (14)
C23—N2—C6—O3	−4.32 (18)	C17—C18—C19—C20	0.4 (2)
C15—N2—C6—C7	2.6 (2)	C18—C19—C20—C21	0.4 (3)
C23—N2—C6—C7	175.40 (13)	C19—C20—C21—C22	−0.1 (3)
O3—C6—C7—C16	−175.88 (12)	C20—C21—C22—C17	−1.0 (3)
N2—C6—C7—C16	4.4 (2)	C18—C17—C22—C21	1.8 (2)
O3—C6—C7—C3	5.2 (2)	C5—C17—C22—C21	−179.60 (15)
N2—C6—C7—C3	−174.49 (12)	N1—C4—C25—C26	−65.58 (15)
C2—C3—C7—C6	8.60 (17)	C3—C4—C25—C26	51.48 (16)
C4—C3—C7—C6	122.47 (13)	C4—C25—C26—C31	−98.15 (16)
C2—C3—C7—C16	−170.33 (11)	C4—C25—C26—C27	77.65 (17)
C4—C3—C7—C16	−56.46 (16)	C31—C26—C27—C28	2.7 (2)
O2—S1—C8—C13	159.31 (11)	C25—C26—C27—C28	−173.20 (14)
O1—S1—C8—C13	28.42 (13)	C26—C27—C28—C29	−1.6 (2)
N1—S1—C8—C13	−85.74 (12)	C27—C28—C29—C30	−0.7 (3)
O2—S1—C8—C9	−20.53 (13)	C28—C29—C30—C31	1.8 (3)
O1—S1—C8—C9	−151.41 (11)	C27—C26—C31—C30	−1.6 (2)
N1—S1—C8—C9	94.43 (12)	C25—C26—C31—C30	174.38 (14)
C13—C8—C9—C10	−1.9 (2)	C29—C30—C31—C26	−0.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5	0.98	2.45	3.0586 (16)	120
C2—H2···Cg1	0.98	2.67	3.5377 (15)	148
C22—H22···O4ⁱ	0.93	2.57	3.258 (2)	132
C24—H24B···O5ⁱⁱ	0.96	2.48	3.4236 (17)	169
C30—H30···O1ⁱⁱⁱ	0.93	2.40	3.180 (2)	142
C25—H25A···Cg1^iv	0.97	2.88	3.5110 (15)	123

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

Experimental details

Crystal data
Chemical formula	C₃₁H₃₁N₃O₅S
M_r	557.65
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.2778 (2), 15.8888 (2), 13.0886 (2)
β (°)	99.019 (1)
V (Å³)	2727.14 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.29 × 0.24 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.875, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	39155, 7888, 6269
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.127, 1.07
No. of reflections	7888
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.45

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	2.45	3.0586 (16)	120
C2—H2···Cg1	0.98	2.67	3.5377 (15)	148
C22—H22···O4ⁱ	0.93	2.57	3.258 (2)	132
C24—H24B···O5ⁱⁱ	0.96	2.48	3.4236 (17)	169
C30—H30···O1ⁱⁱⁱ	0.93	2.40	3.180 (2)	142

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

Footnotes

‡Working at: Department of Physics, R.M.K Engineering Collge, R.S.M 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.

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