3-Benzyl-7-meth­oxy-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-pyrrolo[3,4-b]quinoline

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

doi:10.1107/S1600536809044973

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2956-o2957

https://doi.org/10.1107/S1600536809044973

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3-Benzyl-7-methoxy-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexahydro-1H-pyrrolo[3,4-b]quinoline

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 26 October 2009; accepted 28 October 2009; online 31 October 2009)

In the title compound, C₃₂H₃₂N₂O₃S, the pyrrolidine ring adopts an envelope conformation with the methine C atom nearest to the phenyl ring as the flap atom. The tetrahydropyridine ring has a half-chair conformation. The two rings are trans-fused. The phenyl ring bound to the tetrahydropyridine is oriented almost perpendicular [dihedral angle = 86.35 (10)°] to the fused benzene ring. The dihedral angle between the benzylphenyl ring and the sulfonyl-bound phenyl ring is 69.43 (10)°. A very weak N—H⋯π interaction is observed in the molecular structure. In the crystal, molecules translated one unit along the b axis are linked into C(10) chains by C—H⋯O hydrogen bonds; adjacent chains are linked via C—H⋯π interactions, forming a two-dimensional network parallel to the bc plane.

Related literature

For biological activity of pyrroloquinoline derivatives, see: Ryu et al. (2009 ); Tsuji et al. (1995 ); Ferlin et al. (2001 ). For related structures, see: Sudha et al. (2007 , 2008a ,b ). For ring puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Duax et al. (1976 ).

Experimental

Crystal data

C₃₂H₃₂N₂O₃S
M_r = 524.66
Monoclinic, P 2₁ /c
a = 21.5063 (9) Å
b = 11.6188 (5) Å
c = 10.7616 (4) Å
β = 98.219 (2)°
V = 2661.46 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 100 K
0.32 × 0.30 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.636, T_max = 0.987
28181 measured reflections
6088 independent reflections
4661 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.155
S = 1.02
6088 reflections
349 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C30—H30⋯O3ⁱ	0.93	2.53	3.196 (3)	128
C24—H24⋯Cg1ⁱⁱ	0.93	2.56	3.476 (2)	169
N2—H1N2⋯Cg2	0.88 (2)	3.06	3.837 (2)	147
Symmetry codes: (i) x, y+1, z; (ii) $[x, -y-{\script{3\over 2}}, z-{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C4–C9 and C26–C31 rings, respectively.

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/S1600536809044973/lh2940sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044973/lh2940Isup2.hkl

checkCIF report

Comment top

Pyrroloquinoline compounds exhibit antifungal (Ryu et al., 2009), antibacterial (Tsuji et al., 1995) and antiproliferative (Ferlin et al., 2001) activities. We report here the crystal structure of the title compound, a pyrrolo[3,4-b]quinoline derivative.

The pyrrolidine ring adopts an envelope conformation with C2 as the flap atom. Atom C2 deviates by 0.663 (3) Å from the plane passing through the other four atoms of the ring (r.m.s. deviation 0.020 Å). The asymmetry parameter (Duax et al., 1976) ΔC_s[C2] = 5.4 (2)° and the puckering parameters (Cremer & Pople, 1975) q₂ = 0.439 (2) Å and φ = 78.2 (3)°. The tosyl group is attached to the pyrrolidine ring in a biaxial position. The tetrahydropyridine ring adopts a half-chair conformation with an asymmetry parameter ΔC₂[C2—C10] of 7.6 (2)°. The phenyl group attached to the tetrahydropyridine ring is also in a biaxial position. The dihedral angle between the C4—C9 and C19—C24 rings is 86.35 (10)° and that between the C12—C17 and C26—C31 rings is 69.43 (10)°. A very weak N—H···π interaction (Table 1) is observed in the molecular structure. Bond lengths and angles are comparable with those observed in related structures (Sudha et al., 2007,2008a,b).

In the crystal structure, molecules translated one unit along the b axis are linked into C(10) chains by C—H···O hydrogen bonds. Glide-related molecules in adjacent chains are linked via C—H···π interactions involving the C4—C9 ring, forming a two-dimensional network parallel to the bc plane (Fig. 2).

Related literature top

For biological activity of pyrroloquinoline derivatives, see: Ryu et al. (2009); Tsuji et al. (1995); Ferlin et al. (2001). For related structures, see: Sudha et al. (2007, 2008a,b). For ring puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Duax et al. (1976). Cg1 and Cg2 are the centroids of the C4–C9 and C26–C31 rings, respectively.

Experimental top

InCl₃ (20 mol%) was added to a mixture of 2-(N-cinnamyl-N-tosylamino)-3-phenyl propanal (1 mmol) and p-methoxy aniline (1 mmol) in acetonitrile (20 ml). The reaction mixture was stirred at room temperature for 1 min. On completion of the reaction, as indicated by TLC, the mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over Na₂SO₄. The solvent was evaporated in vacuo and the crude product was chromatographed on silica gel using a hexane-ethyl acetate (8.5:1.5 v/v) mixture to obtain the title compound. The compound was recrystallized from ethyl acetate solution by slow evaporation.

Structure description top

For biological activity of pyrroloquinoline derivatives, see: Ryu et al. (2009); Tsuji et al. (1995); Ferlin et al. (2001). For related structures, see: Sudha et al. (2007, 2008a,b). For ring puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Duax et al. (1976). Cg1 and Cg2 are the centroids of the C4–C9 and C26–C31 rings, respectively.

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. The dotted line indicates an N—H···π interaction.
	Fig. 2. Crystal packing of the title compound. C—H···O hydrogen bonds and C—H···π interactions are shown as dashed lines. For the sake of clarity, H atoms not involved in the interactions have been omitted.

3-Benzyl-7-methoxy-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexahydro-1H- pyrrolo[3,4-b]quinoline top

Crystal data top

C₃₂H₃₂N₂O₃S	F(000) = 1112
M_r = 524.66	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6305 reflections
a = 21.5063 (9) Å	θ = 2.6–28.5°
b = 11.6188 (5) Å	µ = 0.16 mm⁻¹
c = 10.7616 (4) Å	T = 100 K
β = 98.219 (2)°	Plate, colourless
V = 2661.46 (19) Å³	0.32 × 0.30 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6088 independent reflections
Radiation source: fine-focus sealed tube	4661 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
φ and ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −23→27
T_min = 0.636, T_max = 0.987	k = −15→14
28181 measured reflections	l = −13→13

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0891P)² + 0.9992P] where P = (F_o² + 2F_c²)/3
6088 reflections	(Δ/σ)_max = 0.001
349 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₃₂H₃₂N₂O₃S	V = 2661.46 (19) Å³
M_r = 524.66	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.5063 (9) Å	µ = 0.16 mm⁻¹
b = 11.6188 (5) Å	T = 100 K
c = 10.7616 (4) Å	0.32 × 0.30 × 0.08 mm
β = 98.219 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6088 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4661 reflections with I > 2σ(I)
T_min = 0.636, T_max = 0.987	R_int = 0.057
28181 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.46 e Å⁻³
6088 reflections	Δρ_min = −0.54 e Å⁻³
349 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	0.36811 (2)	0.64135 (4)	−0.09053 (5)	0.02080 (15)
O1	0.39510 (7)	0.60291 (13)	−0.19725 (13)	0.0264 (3)
O2	0.36734 (7)	0.76149 (12)	−0.06064 (14)	0.0266 (3)
O3	0.07988 (7)	0.14332 (12)	0.25445 (14)	0.0235 (3)
N1	0.29441 (8)	0.59952 (14)	−0.11262 (15)	0.0197 (4)
N2	0.18416 (8)	0.55576 (14)	0.11176 (16)	0.0202 (4)
H1N2	0.1626 (11)	0.619 (2)	0.122 (2)	0.024 (6)*
C1	0.28306 (10)	0.47333 (16)	−0.12239 (18)	0.0195 (4)
H1A	0.3222	0.4312	−0.1194	0.023*
H1B	0.2557	0.4539	−0.1991	0.023*
C2	0.25163 (9)	0.44865 (15)	−0.00752 (17)	0.0172 (4)
H2	0.2834	0.4530	0.0673	0.021*
C3	0.21612 (9)	0.33569 (15)	−0.00428 (17)	0.0169 (4)
H3	0.1899	0.3268	−0.0860	0.020*
C4	0.17183 (9)	0.34490 (16)	0.09480 (17)	0.0176 (4)
C5	0.14457 (9)	0.24516 (16)	0.13452 (18)	0.0182 (4)
H5	0.1546	0.1747	0.1016	0.022*
C6	0.10267 (9)	0.24795 (16)	0.22227 (18)	0.0194 (4)
C7	0.08772 (10)	0.35345 (17)	0.27171 (19)	0.0213 (4)
H7	0.0602	0.3569	0.3308	0.026*
C8	0.11424 (10)	0.45329 (17)	0.23202 (19)	0.0213 (4)
H8	0.1037	0.5236	0.2648	0.026*
C9	0.15627 (9)	0.45154 (16)	0.14423 (18)	0.0181 (4)
C10	0.20811 (9)	0.55138 (16)	−0.00791 (18)	0.0179 (4)
H10	0.1731	0.5435	−0.0764	0.022*
C11	0.24967 (10)	0.65334 (16)	−0.03459 (18)	0.0192 (4)
H11	0.2727	0.6828	0.0441	0.023*
C12	0.40517 (9)	0.56541 (17)	0.04217 (18)	0.0206 (4)
C13	0.40440 (10)	0.60984 (18)	0.16170 (19)	0.0231 (4)
H13	0.3878	0.6825	0.1723	0.028*
C14	0.42880 (10)	0.54439 (18)	0.2653 (2)	0.0249 (5)
H14	0.4288	0.5744	0.3454	0.030*
C15	0.45327 (10)	0.43488 (19)	0.2518 (2)	0.0251 (5)
C16	0.45382 (10)	0.39268 (18)	0.1305 (2)	0.0238 (4)
H16	0.4702	0.3199	0.1197	0.029*
C17	0.43044 (10)	0.45702 (17)	0.0261 (2)	0.0233 (4)
H17	0.4316	0.4281	−0.0541	0.028*
C18	0.47876 (12)	0.3636 (2)	0.3642 (2)	0.0334 (5)
H18A	0.4656	0.3963	0.4382	0.050*
H18B	0.5238	0.3627	0.3732	0.050*
H18C	0.4631	0.2864	0.3531	0.050*
C19	0.26098 (9)	0.23397 (16)	0.01226 (18)	0.0177 (4)
C20	0.30745 (10)	0.22449 (17)	0.11657 (19)	0.0220 (4)
H20	0.3105	0.2803	0.1791	0.026*
C21	0.34910 (10)	0.13259 (18)	0.1278 (2)	0.0254 (5)
H21	0.3800	0.1277	0.1974	0.030*
C22	0.34495 (11)	0.04784 (17)	0.0358 (2)	0.0268 (5)
H22	0.3725	−0.0143	0.0441	0.032*
C23	0.29953 (11)	0.05698 (17)	−0.0680 (2)	0.0269 (5)
H23	0.2968	0.0013	−0.1306	0.032*
C24	0.25761 (10)	0.14916 (17)	−0.0797 (2)	0.0223 (4)
H24	0.2270	0.1540	−0.1499	0.027*
C25	0.21481 (10)	0.75164 (17)	−0.10939 (19)	0.0227 (4)
H25A	0.2447	0.8112	−0.1230	0.027*
H25B	0.1962	0.7229	−0.1909	0.027*
C26	0.16400 (10)	0.80340 (16)	−0.04408 (18)	0.0202 (4)
C27	0.10099 (10)	0.77711 (17)	−0.0814 (2)	0.0249 (5)
H27	0.0900	0.7246	−0.1461	0.030*
C28	0.05413 (11)	0.82820 (19)	−0.0235 (2)	0.0276 (5)
H28	0.0122	0.8108	−0.0503	0.033*
C29	0.07005 (11)	0.90497 (18)	0.0741 (2)	0.0275 (5)
H29	0.0388	0.9400	0.1124	0.033*
C30	0.13279 (10)	0.92955 (17)	0.1147 (2)	0.0237 (4)
H30	0.1437	0.9797	0.1817	0.028*
C31	0.17939 (10)	0.87961 (16)	0.05583 (19)	0.0213 (4)
H31	0.2213	0.8971	0.0832	0.026*
C32	0.03712 (10)	0.14275 (18)	0.3447 (2)	0.0255 (5)
H32A	0.0236	0.0653	0.3568	0.038*
H32B	0.0014	0.1897	0.3150	0.038*
H32C	0.0577	0.1728	0.4230	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0206 (3)	0.0180 (3)	0.0242 (3)	−0.00236 (19)	0.0046 (2)	0.00132 (18)
O1	0.0265 (9)	0.0282 (8)	0.0259 (8)	−0.0026 (6)	0.0091 (6)	0.0015 (6)
O2	0.0252 (9)	0.0192 (7)	0.0353 (8)	−0.0044 (6)	0.0042 (7)	0.0022 (6)
O3	0.0211 (8)	0.0197 (7)	0.0313 (8)	−0.0037 (6)	0.0089 (6)	−0.0016 (6)
N1	0.0190 (9)	0.0161 (8)	0.0245 (9)	0.0001 (7)	0.0044 (7)	0.0006 (6)
N2	0.0250 (10)	0.0124 (8)	0.0243 (9)	0.0029 (7)	0.0075 (7)	−0.0008 (6)
C1	0.0199 (11)	0.0162 (9)	0.0222 (10)	0.0009 (7)	0.0029 (8)	−0.0006 (7)
C2	0.0164 (10)	0.0145 (9)	0.0204 (9)	0.0006 (7)	0.0014 (8)	−0.0007 (7)
C3	0.0156 (10)	0.0159 (9)	0.0189 (9)	0.0004 (7)	0.0015 (7)	−0.0002 (7)
C4	0.0150 (10)	0.0182 (9)	0.0188 (9)	0.0020 (7)	−0.0007 (7)	−0.0015 (7)
C5	0.0161 (10)	0.0155 (9)	0.0223 (10)	0.0012 (7)	0.0008 (8)	−0.0015 (7)
C6	0.0154 (10)	0.0179 (9)	0.0242 (10)	−0.0018 (7)	0.0007 (8)	0.0005 (7)
C7	0.0158 (10)	0.0246 (10)	0.0245 (10)	0.0012 (8)	0.0056 (8)	−0.0012 (8)
C8	0.0189 (11)	0.0180 (10)	0.0270 (10)	0.0039 (8)	0.0030 (8)	−0.0035 (8)
C9	0.0144 (10)	0.0169 (9)	0.0222 (10)	0.0002 (7)	−0.0009 (8)	−0.0010 (7)
C10	0.0182 (10)	0.0163 (9)	0.0190 (9)	0.0006 (7)	0.0017 (8)	−0.0003 (7)
C11	0.0196 (11)	0.0159 (9)	0.0224 (10)	0.0010 (7)	0.0038 (8)	−0.0009 (7)
C12	0.0152 (10)	0.0221 (10)	0.0248 (10)	−0.0020 (8)	0.0038 (8)	0.0008 (8)
C13	0.0208 (11)	0.0205 (10)	0.0282 (11)	−0.0011 (8)	0.0045 (8)	−0.0022 (8)
C14	0.0212 (11)	0.0296 (11)	0.0239 (10)	−0.0007 (9)	0.0035 (8)	−0.0036 (8)
C15	0.0151 (11)	0.0296 (11)	0.0301 (11)	−0.0011 (8)	0.0022 (8)	0.0031 (9)
C16	0.0151 (10)	0.0226 (10)	0.0336 (11)	0.0003 (8)	0.0035 (8)	−0.0014 (8)
C17	0.0205 (11)	0.0236 (10)	0.0266 (11)	−0.0016 (8)	0.0058 (8)	−0.0043 (8)
C18	0.0320 (14)	0.0355 (13)	0.0325 (12)	0.0057 (10)	0.0036 (10)	0.0063 (10)
C19	0.0160 (10)	0.0147 (9)	0.0235 (10)	−0.0002 (7)	0.0068 (8)	0.0028 (7)
C20	0.0225 (11)	0.0212 (10)	0.0228 (10)	0.0027 (8)	0.0046 (8)	0.0006 (8)
C21	0.0212 (11)	0.0280 (11)	0.0277 (11)	0.0056 (9)	0.0058 (9)	0.0086 (8)
C22	0.0267 (12)	0.0169 (10)	0.0399 (12)	0.0061 (8)	0.0152 (10)	0.0061 (8)
C23	0.0274 (12)	0.0169 (10)	0.0386 (12)	−0.0010 (8)	0.0127 (10)	−0.0058 (9)
C24	0.0199 (11)	0.0197 (10)	0.0277 (11)	−0.0021 (8)	0.0047 (8)	−0.0026 (8)
C25	0.0269 (12)	0.0178 (10)	0.0237 (10)	0.0034 (8)	0.0044 (9)	0.0038 (8)
C26	0.0241 (11)	0.0126 (9)	0.0238 (10)	0.0023 (7)	0.0032 (8)	0.0059 (7)
C27	0.0287 (12)	0.0176 (9)	0.0271 (11)	−0.0024 (8)	−0.0006 (9)	0.0027 (8)
C28	0.0189 (11)	0.0301 (11)	0.0331 (12)	−0.0022 (9)	0.0011 (9)	0.0079 (9)
C29	0.0248 (12)	0.0253 (11)	0.0342 (12)	0.0049 (9)	0.0099 (9)	0.0075 (9)
C30	0.0280 (12)	0.0173 (9)	0.0264 (10)	0.0005 (8)	0.0057 (9)	0.0021 (8)
C31	0.0193 (11)	0.0158 (9)	0.0282 (11)	0.0005 (8)	0.0015 (8)	0.0038 (8)
C32	0.0210 (11)	0.0261 (11)	0.0307 (11)	−0.0041 (8)	0.0080 (9)	0.0006 (9)

Geometric parameters (Å, º) top

S1—O1	1.4303 (15)	C14—H14	0.93
S1—O2	1.4332 (15)	C15—C16	1.396 (3)
S1—N1	1.6424 (18)	C15—C18	1.504 (3)
S1—C12	1.768 (2)	C16—C17	1.383 (3)
O3—C6	1.374 (2)	C16—H16	0.93
O3—C32	1.430 (2)	C17—H17	0.93
N1—C1	1.488 (2)	C18—H18A	0.96
N1—C11	1.501 (2)	C18—H18B	0.96
N2—C9	1.417 (2)	C18—H18C	0.96
N2—C10	1.455 (2)	C19—C24	1.391 (3)
N2—H1N2	0.88 (2)	C19—C20	1.396 (3)
C1—C2	1.519 (3)	C20—C21	1.388 (3)
C1—H1A	0.97	C20—H20	0.93
C1—H1B	0.97	C21—C22	1.390 (3)
C2—C10	1.516 (3)	C21—H21	0.93
C2—C3	1.521 (3)	C22—C23	1.379 (3)
C2—H2	0.98	C22—H22	0.93
C3—C19	1.520 (3)	C23—C24	1.394 (3)
C3—C4	1.532 (3)	C23—H23	0.93
C3—H3	0.98	C24—H24	0.93
C4—C5	1.393 (3)	C25—C26	1.506 (3)
C4—C9	1.407 (3)	C25—H25A	0.97
C5—C6	1.396 (3)	C25—H25B	0.97
C5—H5	0.93	C26—C27	1.391 (3)
C6—C7	1.392 (3)	C26—C31	1.396 (3)
C7—C8	1.387 (3)	C27—C28	1.392 (3)
C7—H7	0.93	C27—H27	0.93
C8—C9	1.398 (3)	C28—C29	1.383 (3)
C8—H8	0.93	C28—H28	0.93
C10—C11	1.536 (3)	C29—C30	1.387 (3)
C10—H10	0.98	C29—H29	0.93
C11—C25	1.530 (3)	C30—C31	1.387 (3)
C11—H11	0.98	C30—H30	0.93
C12—C13	1.388 (3)	C31—H31	0.93
C12—C17	1.392 (3)	C32—H32A	0.96
C13—C14	1.389 (3)	C32—H32B	0.96
C13—H13	0.93	C32—H32C	0.96
C14—C15	1.392 (3)

O1—S1—O2	120.22 (9)	C13—C14—C15	121.46 (19)
O1—S1—N1	106.58 (9)	C13—C14—H14	119.3
O2—S1—N1	106.18 (9)	C15—C14—H14	119.3
O1—S1—C12	107.76 (9)	C14—C15—C16	118.19 (19)
O2—S1—C12	108.85 (9)	C14—C15—C18	121.25 (19)
N1—S1—C12	106.47 (9)	C16—C15—C18	120.6 (2)
C6—O3—C32	117.56 (15)	C17—C16—C15	121.27 (19)
C1—N1—C11	109.76 (15)	C17—C16—H16	119.4
C1—N1—S1	116.56 (13)	C15—C16—H16	119.4
C11—N1—S1	118.58 (13)	C16—C17—C12	119.42 (19)
C9—N2—C10	113.85 (15)	C16—C17—H17	120.3
C9—N2—H1N2	115.6 (15)	C12—C17—H17	120.3
C10—N2—H1N2	113.5 (15)	C15—C18—H18A	109.5
N1—C1—C2	102.50 (15)	C15—C18—H18B	109.5
N1—C1—H1A	111.3	H18A—C18—H18B	109.5
C2—C1—H1A	111.3	C15—C18—H18C	109.5
N1—C1—H1B	111.3	H18A—C18—H18C	109.5
C2—C1—H1B	111.3	H18B—C18—H18C	109.5
H1A—C1—H1B	109.2	C24—C19—C20	118.32 (18)
C10—C2—C1	101.27 (15)	C24—C19—C3	120.00 (18)
C10—C2—C3	111.56 (16)	C20—C19—C3	121.65 (17)
C1—C2—C3	117.70 (15)	C21—C20—C19	120.63 (19)
C10—C2—H2	108.6	C21—C20—H20	119.7
C1—C2—H2	108.6	C19—C20—H20	119.7
C3—C2—H2	108.6	C20—C21—C22	120.5 (2)
C19—C3—C2	111.18 (16)	C20—C21—H21	119.7
C19—C3—C4	114.85 (15)	C22—C21—H21	119.7
C2—C3—C4	108.65 (15)	C23—C22—C21	119.24 (19)
C19—C3—H3	107.3	C23—C22—H22	120.4
C2—C3—H3	107.3	C21—C22—H22	120.4
C4—C3—H3	107.3	C22—C23—C24	120.41 (19)
C5—C4—C9	118.88 (18)	C22—C23—H23	119.8
C5—C4—C3	119.10 (16)	C24—C23—H23	119.8
C9—C4—C3	121.99 (17)	C19—C24—C23	120.9 (2)
C4—C5—C6	121.94 (17)	C19—C24—H24	119.6
C4—C5—H5	119.0	C23—C24—H24	119.6
C6—C5—H5	119.0	C26—C25—C11	112.71 (16)
O3—C6—C7	124.94 (18)	C26—C25—H25A	109.1
O3—C6—C5	115.99 (17)	C11—C25—H25A	109.1
C7—C6—C5	119.07 (18)	C26—C25—H25B	109.1
C8—C7—C6	119.42 (18)	C11—C25—H25B	109.1
C8—C7—H7	120.3	H25A—C25—H25B	107.8
C6—C7—H7	120.3	C27—C26—C31	118.40 (19)
C7—C8—C9	122.02 (18)	C27—C26—C25	121.28 (19)
C7—C8—H8	119.0	C31—C26—C25	120.32 (19)
C9—C8—H8	119.0	C26—C27—C28	121.0 (2)
C8—C9—C4	118.68 (17)	C26—C27—H27	119.5
C8—C9—N2	119.44 (17)	C28—C27—H27	119.5
C4—C9—N2	121.81 (17)	C29—C28—C27	119.9 (2)
N2—C10—C2	108.76 (15)	C29—C28—H28	120.0
N2—C10—C11	115.32 (16)	C27—C28—H28	120.0
C2—C10—C11	103.43 (16)	C28—C29—C30	119.7 (2)
N2—C10—H10	109.7	C28—C29—H29	120.1
C2—C10—H10	109.7	C30—C29—H29	120.1
C11—C10—H10	109.7	C31—C30—C29	120.2 (2)
N1—C11—C25	108.76 (15)	C31—C30—H30	119.9
N1—C11—C10	102.71 (14)	C29—C30—H30	119.9
C25—C11—C10	114.82 (17)	C30—C31—C26	120.7 (2)
N1—C11—H11	110.1	C30—C31—H31	119.7
C25—C11—H11	110.1	C26—C31—H31	119.7
C10—C11—H11	110.1	O3—C32—H32A	109.5
C13—C12—C17	120.53 (19)	O3—C32—H32B	109.5
C13—C12—S1	119.93 (16)	H32A—C32—H32B	109.5
C17—C12—S1	119.33 (15)	O3—C32—H32C	109.5
C12—C13—C14	119.12 (19)	H32A—C32—H32C	109.5
C12—C13—H13	120.4	H32B—C32—H32C	109.5
C14—C13—H13	120.4

O1—S1—N1—C1	61.38 (15)	N2—C10—C11—N1	148.55 (16)
O2—S1—N1—C1	−169.33 (13)	C2—C10—C11—N1	29.94 (19)
C12—S1—N1—C1	−53.44 (16)	N2—C10—C11—C25	−93.6 (2)
O1—S1—N1—C11	−163.96 (13)	C2—C10—C11—C25	147.81 (16)
O2—S1—N1—C11	−34.67 (16)	O1—S1—C12—C13	158.49 (16)
C12—S1—N1—C11	81.22 (15)	O2—S1—C12—C13	26.59 (19)
C11—N1—C1—C2	−23.1 (2)	N1—S1—C12—C13	−87.49 (18)
S1—N1—C1—C2	115.35 (15)	O1—S1—C12—C17	−26.68 (19)
N1—C1—C2—C10	40.98 (18)	O2—S1—C12—C17	−158.58 (16)
N1—C1—C2—C3	162.85 (16)	N1—S1—C12—C17	87.34 (18)
C10—C2—C3—C19	−173.02 (15)	C17—C12—C13—C14	−0.4 (3)
C1—C2—C3—C19	70.6 (2)	S1—C12—C13—C14	174.34 (16)
C10—C2—C3—C4	−45.7 (2)	C12—C13—C14—C15	−0.8 (3)
C1—C2—C3—C4	−162.10 (16)	C13—C14—C15—C16	1.2 (3)
C19—C3—C4—C5	−40.9 (2)	C13—C14—C15—C18	−179.1 (2)
C2—C3—C4—C5	−166.12 (17)	C14—C15—C16—C17	−0.4 (3)
C19—C3—C4—C9	141.09 (18)	C18—C15—C16—C17	179.9 (2)
C2—C3—C4—C9	15.9 (2)	C15—C16—C17—C12	−0.8 (3)
C9—C4—C5—C6	−0.4 (3)	C13—C12—C17—C16	1.2 (3)
C3—C4—C5—C6	−178.46 (18)	S1—C12—C17—C16	−173.61 (16)
C32—O3—C6—C7	0.6 (3)	C2—C3—C19—C24	−118.83 (19)
C32—O3—C6—C5	179.61 (18)	C4—C3—C19—C24	117.29 (19)
C4—C5—C6—O3	−179.17 (17)	C2—C3—C19—C20	59.2 (2)
C4—C5—C6—C7	−0.1 (3)	C4—C3—C19—C20	−64.7 (2)
O3—C6—C7—C8	179.58 (19)	C24—C19—C20—C21	0.0 (3)
C5—C6—C7—C8	0.6 (3)	C3—C19—C20—C21	−178.04 (18)
C6—C7—C8—C9	−0.6 (3)	C19—C20—C21—C22	−0.5 (3)
C7—C8—C9—C4	0.1 (3)	C20—C21—C22—C23	1.0 (3)
C7—C8—C9—N2	−177.01 (19)	C21—C22—C23—C24	−1.0 (3)
C5—C4—C9—C8	0.4 (3)	C20—C19—C24—C23	0.0 (3)
C3—C4—C9—C8	178.37 (17)	C3—C19—C24—C23	178.09 (18)
C5—C4—C9—N2	177.43 (18)	C22—C23—C24—C19	0.5 (3)
C3—C4—C9—N2	−4.6 (3)	N1—C11—C25—C26	174.16 (16)
C10—N2—C9—C8	−159.30 (18)	C10—C11—C25—C26	59.8 (2)
C10—N2—C9—C4	23.6 (3)	C11—C25—C26—C27	−102.6 (2)
C9—N2—C10—C2	−53.1 (2)	C11—C25—C26—C31	77.6 (2)
C9—N2—C10—C11	−168.66 (16)	C31—C26—C27—C28	2.0 (3)
C1—C2—C10—N2	−167.42 (15)	C25—C26—C27—C28	−177.81 (18)
C3—C2—C10—N2	66.5 (2)	C26—C27—C28—C29	−1.1 (3)
C1—C2—C10—C11	−44.36 (18)	C27—C28—C29—C30	−0.8 (3)
C3—C2—C10—C11	−170.41 (15)	C28—C29—C30—C31	1.6 (3)
C1—N1—C11—C25	−126.22 (17)	C29—C30—C31—C26	−0.5 (3)
S1—N1—C11—C25	96.32 (18)	C27—C26—C31—C30	−1.2 (3)
C1—N1—C11—C10	−4.1 (2)	C25—C26—C31—C30	178.62 (18)
S1—N1—C11—C10	−141.61 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30···O3ⁱ	0.93	2.53	3.196 (3)	128
C24—H24···Cg1ⁱⁱ	0.93	2.56	3.476 (2)	169
N2—H1N2···Cg2	0.88 (2)	3.06	3.837 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₃₂H₃₂N₂O₃S
M_r	524.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	21.5063 (9), 11.6188 (5), 10.7616 (4)
β (°)	98.219 (2)
V (Å³)	2661.46 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.32 × 0.30 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.636, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	28181, 6088, 4661
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.155, 1.02
No. of reflections	6088
No. of parameters	349
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.54

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
C30—H30···O3ⁱ	0.93	2.53	3.196 (3)	128
C24—H24···Cg1ⁱⁱ	0.93	2.56	3.476 (2)	169
N2—H1N2···Cg2	0.88 (2)	3.06	3.837 (2)	147

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