3-Benzyl-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/S1600536809044547

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2923

https://doi.org/10.1107/S1600536809044547

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3-Benzyl-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 24 October 2009; accepted 26 October 2009; online 31 October 2009)

In the title compound, C₃₁H₃₀N₂O₂S, the pyrrolidine ring adopts a twist conformation while the tetrahydropyridine ring is in a half-chair conformation. The two rings are trans-fused. The pyridine-bound phenyl ring forms dihedral angles of 17.7 (1) and 48.1 (1)°, respectively, with the tosyl and benzyl phenyl rings. The molecular structure is stabilized by an N—H⋯π interaction involving the benzyl phenyl ring. In the crystal structure, molecules translated by one unit along the a axis are linked into chains by C—H⋯π interactions involving the benzene ring of the tosyl group.

Related literature

For the biological activity of pyrroloquinoline derivatives, see: Ferlin et al. (2005 ); Dalla Via et al. (2008 ); Xiao et al. (2006 ); Fujita et al. (1996 ); Crenshaw et al. (1976 ). For the crystal structure of the 3-ethyl analogue, see: Sudha et al. (2008 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Duax et al. (1976 ).

Experimental

Crystal data

C₃₁H₃₀N₂O₂S
M_r = 494.63
Triclinic, $[P \overline 1]$
a = 10.9521 (3) Å
b = 11.2563 (3) Å
c = 12.5132 (3) Å
α = 100.930 (2)°
β = 108.577 (1)°
γ = 114.539 (1)°
V = 1234.00 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 100 K
0.48 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.761, T_max = 0.963
27773 measured reflections
6486 independent reflections
5001 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.112
S = 1.01
6486 reflections
330 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯Cg2	0.83 (2)	2.61 (2)	3.374 (2)	152 (2)
C29—H29⋯Cg1ⁱ	0.93	2.90	3.605 (2)	134
Symmetry code: (i) x+1, y, z. Cg1 and Cg2 are the centroids of the C19–C24 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/S1600536809044547/wn2361sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044547/wn2361Isup2.hkl

checkCIF report

Comment top

Pyrroloquinoline derivatives exhibit antitumor (Ferlin et al., 2005; Dalla Via et al., 2008), cytotoxic (Xiao et al., 2006), antibacterial (Fujita et al., 1996) and interferon-inducing activities (Crenshaw et al., 1976). As part of our studies on pyrroloquinoline derivatives, we report here the crystal structure of the title compound.

In the title molecule, the pyrrolidine ring adopts a twist conformation; the asymmetry parameter ΔC₂[C2—C10] (Duax et al., 1976) and the puckering parameters q₂ and φ (Cremer & Pople, 1975) are 7.5 (2)°, 0.394 (2) Å and 96.5 (3)°, respectively. The tosyl group is attached to the pyrrolidine ring in an equatorial position. The tetrahydropyridine ring adopts a half-chair conformation, with Q, θ, φ and ΔC₂[C4—C9] values of 0.543 (2) Å, 131.1 (2)°, 93.1 (3)° and 6.6 (2)°, respectively. The phenyl group is attached to the tetrahydropyridine ring in a biaxial position. The C19—C24 phenyl ring forms dihedral angles of 74.0 (1) and 17.7 (1)°, respectively, with the C4—C9 and C12—C17 benzene rings. The C12—C17 and C26—C31 rings are oriented at a dihedral angle of 48.1 (1)°. The molecular structure is stabilized by an N—H···π interaction (Table 1, Fig. 1). Bond lengths and angles are comparable to those observed in the 3-ethyl analogue (Sudha et al., 2008).

In the crystal structure, molecules translated by one unit along the a axis are linked into chains by C—H···π interactions (Fig.2, Table 1) involving the benzene ring of the tosyl group.

Related literature top

For biological activitiy of pyrroloquinoline derivatives, see: Ferlin et al. (2005); Dalla Via et al. (2008); Xiao et al. (2006); Fujita et al. (1996); Crenshaw et al. (1976). For the crystal structure of the 3-ethyl analogue, see: Sudha et al. (2008). For ring puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Duax et al. (1976). Cg1 and Cg2 are the centroids of the C19–C24 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 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

In the crystal structure, molecules translated by one unit along the a axis are linked into chains by C—H···π interactions (Fig.2, Table 1) involving the benzene ring of the tosyl group.

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

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

Crystal data top

C₃₁H₃₀N₂O₂S	Z = 2
M_r = 494.63	F(000) = 524
Triclinic, P1	D_x = 1.331 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.9521 (3) Å	Cell parameters from 9232 reflections
b = 11.2563 (3) Å	θ = 2.3–30.0°
c = 12.5132 (3) Å	µ = 0.16 mm⁻¹
α = 100.930 (2)°	T = 100 K
β = 108.577 (1)°	Block, colourless
γ = 114.539 (1)°	0.48 × 0.24 × 0.23 mm
V = 1234.00 (6) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6486 independent reflections
Radiation source: fine-focus sealed tube	5001 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 29.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
T_min = 0.761, T_max = 0.963	k = −15→15
27773 measured reflections	l = −17→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.046P)² + 0.7475P] where P = (F_o² + 2F_c²)/3
6486 reflections	(Δ/σ)_max = 0.001
330 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₃₁H₃₀N₂O₂S	γ = 114.539 (1)°
M_r = 494.63	V = 1234.00 (6) Å³
Triclinic, P1	Z = 2
a = 10.9521 (3) Å	Mo Kα radiation
b = 11.2563 (3) Å	µ = 0.16 mm⁻¹
c = 12.5132 (3) Å	T = 100 K
α = 100.930 (2)°	0.48 × 0.24 × 0.23 mm
β = 108.577 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6486 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5001 reflections with I > 2σ(I)
T_min = 0.761, T_max = 0.963	R_int = 0.040
27773 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.51 e Å⁻³
6486 reflections	Δρ_min = −0.42 e Å⁻³
330 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	0.36310 (4)	0.70596 (4)	−0.01644 (4)	0.01857 (10)
O1	0.25363 (13)	0.74003 (13)	−0.07610 (11)	0.0250 (3)
O2	0.40078 (13)	0.62325 (12)	−0.08784 (10)	0.0240 (3)
N1	0.51710 (14)	0.85539 (13)	0.07238 (12)	0.0173 (3)
N2	0.87750 (15)	1.02866 (14)	0.33742 (12)	0.0179 (3)
H1N2	0.939 (2)	1.009 (2)	0.3253 (18)	0.026 (5)*
C1	0.50851 (17)	0.96845 (16)	0.14938 (14)	0.0181 (3)
H1A	0.4181	0.9292	0.1604	0.022*
H1B	0.5109	1.0381	0.1136	0.022*
C2	0.64811 (17)	1.03222 (15)	0.26952 (14)	0.0150 (3)
H2	0.6244	0.9770	0.3194	0.018*
C3	0.72246 (17)	1.18825 (15)	0.34620 (14)	0.0151 (3)
H3	0.7343	1.2408	0.2925	0.018*
C4	0.87963 (17)	1.23749 (16)	0.44241 (14)	0.0158 (3)
C5	0.95793 (18)	1.36418 (16)	0.54193 (15)	0.0185 (3)
H5	0.9122	1.4167	0.5496	0.022*
C6	1.10111 (18)	1.41433 (17)	0.62954 (15)	0.0210 (3)
H6	1.1509	1.4995	0.6945	0.025*
C7	1.16958 (18)	1.33567 (17)	0.61916 (15)	0.0215 (3)
H7	1.2659	1.3683	0.6774	0.026*
C8	1.09513 (18)	1.20931 (17)	0.52270 (15)	0.0194 (3)
H8	1.1414	1.1570	0.5169	0.023*
C9	0.95044 (17)	1.15885 (16)	0.43336 (14)	0.0165 (3)
C10	0.75726 (17)	1.00918 (16)	0.23056 (14)	0.0156 (3)
H10	0.7982	1.0779	0.1954	0.019*
C11	0.66205 (17)	0.86091 (16)	0.13260 (14)	0.0171 (3)
H11	0.6487	0.7906	0.1703	0.021*
C12	0.30055 (17)	0.61554 (16)	0.07342 (14)	0.0183 (3)
C13	0.35945 (18)	0.53371 (16)	0.11236 (15)	0.0207 (3)
H13	0.4332	0.5291	0.0933	0.025*
C14	0.30604 (19)	0.45969 (17)	0.17978 (15)	0.0218 (3)
H14	0.3452	0.4057	0.2060	0.026*
C15	0.19503 (18)	0.46425 (16)	0.20920 (15)	0.0202 (3)
C16	0.13799 (18)	0.54575 (17)	0.16856 (15)	0.0217 (3)
H16	0.0632	0.5492	0.1866	0.026*
C17	0.19011 (18)	0.62183 (16)	0.10184 (15)	0.0208 (3)
H17	0.1515	0.6765	0.0764	0.025*
C18	0.1399 (2)	0.38679 (18)	0.28517 (17)	0.0254 (4)
H18A	0.0355	0.3553	0.2593	0.038*
H18B	0.1958	0.4487	0.3691	0.038*
H18C	0.1533	0.3070	0.2755	0.038*
C19	0.63082 (17)	1.21998 (16)	0.40329 (14)	0.0164 (3)
C20	0.61254 (18)	1.17490 (17)	0.49677 (15)	0.0205 (3)
H20	0.6525	1.1206	0.5211	0.025*
C21	0.53582 (19)	1.20987 (18)	0.55365 (16)	0.0254 (4)
H21	0.5250	1.1796	0.6160	0.031*
C22	0.47489 (19)	1.29029 (18)	0.51758 (17)	0.0270 (4)
H22	0.4227	1.3134	0.5553	0.032*
C23	0.49216 (19)	1.33563 (18)	0.42575 (16)	0.0248 (4)
H23	0.4523	1.3902	0.4021	0.030*
C24	0.56895 (18)	1.30027 (16)	0.36793 (15)	0.0200 (3)
H24	0.5789	1.3305	0.3054	0.024*
C25	0.72722 (18)	0.83906 (18)	0.04379 (15)	0.0213 (3)
H25A	0.6672	0.7416	−0.0120	0.026*
H25B	0.7235	0.8977	−0.0034	0.026*
C26	0.88731 (18)	0.87601 (17)	0.11140 (14)	0.0193 (3)
C27	1.00564 (19)	1.00373 (17)	0.12935 (15)	0.0219 (3)
H27	0.9855	1.0633	0.0942	0.026*
C28	1.1526 (2)	1.04302 (18)	0.19876 (16)	0.0251 (4)
H28	1.2304	1.1272	0.2077	0.030*
C29	1.18447 (19)	0.95779 (19)	0.25491 (16)	0.0262 (4)
H29	1.2833	0.9853	0.3030	0.031*
C30	1.0679 (2)	0.83100 (19)	0.23886 (17)	0.0259 (4)
H30	1.0886	0.7739	0.2773	0.031*
C31	0.92062 (19)	0.78886 (17)	0.16586 (16)	0.0226 (4)
H31	0.8434	0.7019	0.1531	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01624 (19)	0.01639 (19)	0.01461 (19)	0.00506 (15)	0.00412 (15)	0.00178 (14)
O1	0.0177 (6)	0.0274 (6)	0.0207 (6)	0.0083 (5)	0.0026 (5)	0.0090 (5)
O2	0.0232 (6)	0.0204 (6)	0.0171 (6)	0.0060 (5)	0.0082 (5)	−0.0016 (5)
N1	0.0150 (6)	0.0137 (6)	0.0176 (7)	0.0066 (5)	0.0048 (5)	0.0009 (5)
N2	0.0174 (7)	0.0189 (7)	0.0163 (7)	0.0124 (6)	0.0047 (5)	0.0017 (5)
C1	0.0167 (7)	0.0165 (7)	0.0197 (8)	0.0095 (6)	0.0072 (6)	0.0033 (6)
C2	0.0156 (7)	0.0141 (7)	0.0158 (7)	0.0083 (6)	0.0074 (6)	0.0043 (6)
C3	0.0156 (7)	0.0134 (7)	0.0160 (7)	0.0076 (6)	0.0070 (6)	0.0042 (6)
C4	0.0149 (7)	0.0154 (7)	0.0166 (7)	0.0069 (6)	0.0077 (6)	0.0053 (6)
C5	0.0200 (8)	0.0152 (7)	0.0207 (8)	0.0091 (6)	0.0106 (6)	0.0046 (6)
C6	0.0179 (8)	0.0163 (7)	0.0188 (8)	0.0042 (6)	0.0062 (6)	0.0012 (6)
C7	0.0146 (7)	0.0235 (8)	0.0186 (8)	0.0064 (6)	0.0052 (6)	0.0042 (7)
C8	0.0178 (8)	0.0227 (8)	0.0206 (8)	0.0129 (7)	0.0088 (6)	0.0074 (7)
C9	0.0172 (7)	0.0164 (7)	0.0158 (7)	0.0081 (6)	0.0085 (6)	0.0048 (6)
C10	0.0157 (7)	0.0144 (7)	0.0154 (7)	0.0078 (6)	0.0064 (6)	0.0035 (6)
C11	0.0153 (7)	0.0154 (7)	0.0164 (7)	0.0074 (6)	0.0049 (6)	0.0022 (6)
C12	0.0179 (8)	0.0135 (7)	0.0148 (7)	0.0045 (6)	0.0047 (6)	0.0011 (6)
C13	0.0203 (8)	0.0175 (7)	0.0209 (8)	0.0094 (7)	0.0091 (7)	0.0016 (6)
C14	0.0270 (9)	0.0176 (7)	0.0226 (8)	0.0135 (7)	0.0112 (7)	0.0055 (6)
C15	0.0212 (8)	0.0136 (7)	0.0184 (8)	0.0059 (6)	0.0071 (6)	0.0013 (6)
C16	0.0182 (8)	0.0198 (8)	0.0246 (9)	0.0089 (7)	0.0097 (7)	0.0052 (7)
C17	0.0182 (8)	0.0163 (7)	0.0229 (8)	0.0082 (6)	0.0063 (7)	0.0042 (6)
C18	0.0301 (9)	0.0217 (8)	0.0292 (9)	0.0142 (7)	0.0165 (8)	0.0109 (7)
C19	0.0138 (7)	0.0133 (7)	0.0163 (7)	0.0050 (6)	0.0056 (6)	0.0012 (6)
C20	0.0201 (8)	0.0176 (7)	0.0220 (8)	0.0088 (6)	0.0096 (7)	0.0058 (6)
C21	0.0212 (8)	0.0238 (8)	0.0224 (9)	0.0050 (7)	0.0119 (7)	0.0029 (7)
C22	0.0177 (8)	0.0249 (9)	0.0282 (9)	0.0077 (7)	0.0109 (7)	−0.0037 (7)
C23	0.0201 (8)	0.0224 (8)	0.0289 (9)	0.0138 (7)	0.0081 (7)	0.0016 (7)
C24	0.0185 (8)	0.0165 (7)	0.0203 (8)	0.0086 (6)	0.0062 (6)	0.0030 (6)
C25	0.0215 (8)	0.0218 (8)	0.0173 (8)	0.0116 (7)	0.0073 (7)	0.0018 (6)
C26	0.0212 (8)	0.0201 (8)	0.0157 (7)	0.0120 (7)	0.0090 (6)	0.0002 (6)
C27	0.0253 (8)	0.0210 (8)	0.0200 (8)	0.0126 (7)	0.0113 (7)	0.0053 (7)
C28	0.0229 (8)	0.0221 (8)	0.0231 (9)	0.0070 (7)	0.0118 (7)	0.0024 (7)
C29	0.0191 (8)	0.0304 (9)	0.0229 (9)	0.0123 (7)	0.0075 (7)	0.0019 (7)
C30	0.0296 (9)	0.0260 (9)	0.0277 (9)	0.0198 (8)	0.0124 (8)	0.0082 (7)
C31	0.0243 (8)	0.0183 (8)	0.0245 (9)	0.0114 (7)	0.0124 (7)	0.0030 (7)

Geometric parameters (Å, º) top

S1—O1	1.4360 (12)	C14—C15	1.395 (2)
S1—O2	1.4401 (12)	C14—H14	0.93
S1—N1	1.6277 (13)	C15—C16	1.393 (2)
S1—C12	1.7649 (17)	C15—C18	1.507 (2)
N1—C11	1.4934 (19)	C16—C17	1.387 (2)
N1—C1	1.4996 (19)	C16—H16	0.93
N2—C9	1.406 (2)	C17—H17	0.93
N2—C10	1.448 (2)	C18—H18A	0.96
N2—H1N2	0.83 (2)	C18—H18B	0.96
C1—C2	1.526 (2)	C18—H18C	0.96
C1—H1A	0.97	C19—C24	1.393 (2)
C1—H1B	0.97	C19—C20	1.399 (2)
C2—C10	1.521 (2)	C20—C21	1.385 (2)
C2—C3	1.531 (2)	C20—H20	0.93
C2—H2	0.98	C21—C22	1.390 (3)
C3—C19	1.518 (2)	C21—H21	0.93
C3—C4	1.534 (2)	C22—C23	1.377 (3)
C3—H3	0.98	C22—H22	0.93
C4—C5	1.397 (2)	C23—C24	1.395 (2)
C4—C9	1.409 (2)	C23—H23	0.93
C5—C6	1.384 (2)	C24—H24	0.93
C5—H5	0.93	C25—C26	1.510 (2)
C6—C7	1.390 (2)	C25—H25A	0.97
C6—H6	0.93	C25—H25B	0.97
C7—C8	1.380 (2)	C26—C27	1.393 (2)
C7—H7	0.93	C26—C31	1.397 (2)
C8—C9	1.402 (2)	C27—C28	1.383 (2)
C8—H8	0.93	C27—H27	0.93
C10—C11	1.530 (2)	C28—C29	1.383 (3)
C10—H10	0.98	C28—H28	0.93
C11—C25	1.534 (2)	C29—C30	1.386 (3)
C11—H11	0.98	C29—H29	0.93
C12—C17	1.389 (2)	C30—C31	1.387 (2)
C12—C13	1.402 (2)	C30—H30	0.93
C13—C14	1.387 (2)	C31—H31	0.93
C13—H13	0.93

O1—S1—O2	119.68 (7)	C14—C13—C12	118.98 (15)
O1—S1—N1	106.27 (7)	C14—C13—H13	120.5
O2—S1—N1	106.96 (7)	C12—C13—H13	120.5
O1—S1—C12	107.58 (8)	C13—C14—C15	121.68 (15)
O2—S1—C12	107.09 (7)	C13—C14—H14	119.2
N1—S1—C12	108.93 (7)	C15—C14—H14	119.2
C11—N1—C1	111.99 (12)	C16—C15—C14	118.02 (16)
C11—N1—S1	120.85 (10)	C16—C15—C18	120.34 (15)
C1—N1—S1	118.57 (10)	C14—C15—C18	121.62 (15)
C9—N2—C10	114.33 (12)	C17—C16—C15	121.59 (16)
C9—N2—H1N2	111.4 (14)	C17—C16—H16	119.2
C10—N2—H1N2	116.0 (14)	C15—C16—H16	119.2
N1—C1—C2	103.14 (12)	C16—C17—C12	119.40 (15)
N1—C1—H1A	111.1	C16—C17—H17	120.3
C2—C1—H1A	111.1	C12—C17—H17	120.3
N1—C1—H1B	111.1	C15—C18—H18A	109.5
C2—C1—H1B	111.1	C15—C18—H18B	109.5
H1A—C1—H1B	109.1	H18A—C18—H18B	109.5
C10—C2—C1	103.00 (12)	C15—C18—H18C	109.5
C10—C2—C3	109.13 (12)	H18A—C18—H18C	109.5
C1—C2—C3	118.14 (13)	H18B—C18—H18C	109.5
C10—C2—H2	108.7	C24—C19—C20	118.41 (15)
C1—C2—H2	108.7	C24—C19—C3	120.85 (14)
C3—C2—H2	108.7	C20—C19—C3	120.67 (14)
C19—C3—C2	113.47 (12)	C21—C20—C19	120.97 (16)
C19—C3—C4	111.61 (12)	C21—C20—H20	119.5
C2—C3—C4	108.54 (12)	C19—C20—H20	119.5
C19—C3—H3	107.7	C20—C21—C22	120.01 (17)
C2—C3—H3	107.7	C20—C21—H21	120.0
C4—C3—H3	107.7	C22—C21—H21	120.0
C5—C4—C9	117.86 (14)	C23—C22—C21	119.69 (16)
C5—C4—C3	120.29 (13)	C23—C22—H22	120.2
C9—C4—C3	121.85 (13)	C21—C22—H22	120.2
C6—C5—C4	122.35 (15)	C22—C23—C24	120.49 (16)
C6—C5—H5	118.8	C22—C23—H23	119.8
C4—C5—H5	118.8	C24—C23—H23	119.8
C5—C6—C7	119.10 (15)	C19—C24—C23	120.42 (16)
C5—C6—H6	120.4	C19—C24—H24	119.8
C7—C6—H6	120.4	C23—C24—H24	119.8
C8—C7—C6	120.19 (15)	C26—C25—C11	110.75 (13)
C8—C7—H7	119.9	C26—C25—H25A	109.5
C6—C7—H7	119.9	C11—C25—H25A	109.5
C7—C8—C9	120.77 (15)	C26—C25—H25B	109.5
C7—C8—H8	119.6	C11—C25—H25B	109.5
C9—C8—H8	119.6	H25A—C25—H25B	108.1
C8—C9—N2	119.04 (14)	C27—C26—C31	118.39 (15)
C8—C9—C4	119.73 (14)	C27—C26—C25	120.46 (15)
N2—C9—C4	121.22 (14)	C31—C26—C25	120.94 (15)
N2—C10—C2	107.97 (13)	C28—C27—C26	120.86 (16)
N2—C10—C11	115.04 (12)	C28—C27—H27	119.6
C2—C10—C11	104.70 (12)	C26—C27—H27	119.6
N2—C10—H10	109.6	C27—C28—C29	120.38 (16)
C2—C10—H10	109.6	C27—C28—H28	119.8
C11—C10—H10	109.6	C29—C28—H28	119.8
N1—C11—C10	100.91 (11)	C28—C29—C30	119.44 (16)
N1—C11—C25	112.14 (13)	C28—C29—H29	120.3
C10—C11—C25	113.02 (13)	C30—C29—H29	120.3
N1—C11—H11	110.2	C29—C30—C31	120.37 (17)
C10—C11—H11	110.2	C29—C30—H30	119.8
C25—C11—H11	110.2	C31—C30—H30	119.8
C17—C12—C13	120.33 (15)	C30—C31—C26	120.50 (16)
C17—C12—S1	120.10 (13)	C30—C31—H31	119.8
C13—C12—S1	119.54 (13)	C26—C31—H31	119.8

O1—S1—N1—C11	−169.30 (12)	N2—C10—C11—C25	−86.66 (17)
O2—S1—N1—C11	−40.37 (14)	C2—C10—C11—C25	155.01 (13)
C12—S1—N1—C11	75.06 (13)	O1—S1—C12—C17	−16.92 (15)
O1—S1—N1—C1	45.43 (13)	O2—S1—C12—C17	−146.77 (13)
O2—S1—N1—C1	174.35 (12)	N1—S1—C12—C17	97.88 (14)
C12—S1—N1—C1	−70.22 (13)	O1—S1—C12—C13	160.95 (12)
C11—N1—C1—C2	−7.78 (16)	O2—S1—C12—C13	31.10 (14)
S1—N1—C1—C2	140.39 (11)	N1—S1—C12—C13	−84.25 (13)
N1—C1—C2—C10	29.34 (15)	C17—C12—C13—C14	−0.2 (2)
N1—C1—C2—C3	149.66 (13)	S1—C12—C13—C14	−178.03 (12)
C10—C2—C3—C19	−172.66 (13)	C12—C13—C14—C15	0.3 (2)
C1—C2—C3—C19	70.25 (18)	C13—C14—C15—C16	0.1 (2)
C10—C2—C3—C4	−47.97 (16)	C13—C14—C15—C18	−178.40 (15)
C1—C2—C3—C4	−165.07 (13)	C14—C15—C16—C17	−0.7 (2)
C19—C3—C4—C5	−38.87 (19)	C18—C15—C16—C17	177.88 (15)
C2—C3—C4—C5	−164.65 (14)	C15—C16—C17—C12	0.8 (2)
C19—C3—C4—C9	141.90 (15)	C13—C12—C17—C16	−0.4 (2)
C2—C3—C4—C9	16.12 (19)	S1—C12—C17—C16	177.50 (12)
C9—C4—C5—C6	0.7 (2)	C2—C3—C19—C24	−113.47 (16)
C3—C4—C5—C6	−178.57 (15)	C4—C3—C19—C24	123.52 (15)
C4—C5—C6—C7	−0.5 (3)	C2—C3—C19—C20	69.60 (18)
C5—C6—C7—C8	−0.1 (3)	C4—C3—C19—C20	−53.42 (18)
C6—C7—C8—C9	0.6 (3)	C24—C19—C20—C21	−0.5 (2)
C7—C8—C9—N2	−179.10 (15)	C3—C19—C20—C21	176.54 (14)
C7—C8—C9—C4	−0.4 (2)	C19—C20—C21—C22	0.4 (2)
C10—N2—C9—C8	−159.03 (14)	C20—C21—C22—C23	−0.4 (3)
C10—N2—C9—C4	22.3 (2)	C21—C22—C23—C24	0.6 (3)
C5—C4—C9—C8	−0.2 (2)	C20—C19—C24—C23	0.7 (2)
C3—C4—C9—C8	179.05 (14)	C3—C19—C24—C23	−176.33 (14)
C5—C4—C9—N2	178.46 (15)	C22—C23—C24—C19	−0.8 (2)
C3—C4—C9—N2	−2.3 (2)	N1—C11—C25—C26	167.76 (13)
C9—N2—C10—C2	−55.04 (17)	C10—C11—C25—C26	54.52 (18)
C9—N2—C10—C11	−171.53 (13)	C11—C25—C26—C27	−102.25 (18)
C1—C2—C10—N2	−164.09 (12)	C11—C25—C26—C31	72.43 (19)
C3—C2—C10—N2	69.58 (15)	C31—C26—C27—C28	0.4 (2)
C1—C2—C10—C11	−41.05 (15)	C25—C26—C27—C28	175.20 (15)
C3—C2—C10—C11	−167.38 (12)	C26—C27—C28—C29	−2.0 (3)
C1—N1—C11—C10	−16.78 (16)	C27—C28—C29—C30	1.4 (3)
S1—N1—C11—C10	−164.12 (11)	C28—C29—C30—C31	0.9 (3)
C1—N1—C11—C25	−137.32 (14)	C29—C30—C31—C26	−2.5 (3)
S1—N1—C11—C25	75.33 (16)	C27—C26—C31—C30	1.9 (2)
N2—C10—C11—N1	153.42 (13)	C25—C26—C31—C30	−172.91 (15)
C2—C10—C11—N1	35.09 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Cg2	0.83 (2)	2.61 (2)	3.374 (2)	152 (2)
C29—H29···Cg1ⁱ	0.93	2.90	3.605 (2)	134

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₃₁H₃₀N₂O₂S
M_r	494.63
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.9521 (3), 11.2563 (3), 12.5132 (3)
α, β, γ (°)	100.930 (2), 108.577 (1), 114.539 (1)
V (Å³)	1234.00 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.48 × 0.24 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.761, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	27773, 6486, 5001
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.112, 1.01
No. of reflections	6486
No. of parameters	330
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.42

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
N2—H1N2···Cg2	0.83 (2)	2.61 (2)	3.374 (2)	152 (2)
C29—H29···Cg1ⁱ	0.93	2.90	3.605 (2)	134

Symmetry code: (i) x+1, y, z.

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.

References

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