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

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

doi:10.1107/S1600536808000482

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o425

doi:10.1107/S1600536808000482

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

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

^aDepartment of Physics, Anna University, 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, hkfun@usm.my

(Received 21 November 2007; accepted 7 January 2008; online 11 January 2008)

In the molecule of the title compound, C₂₆H₂₈N₂O₂S, the pyrrolidine ring adopts an envelope conformation and the tetrahydropyridine ring is in a half-chair conformation; these two rings are trans-fused. The dihedral angle between the pyridine- and sulfonyl-bound benzene rings is 36.15 (5)°. In the crystalline state, the molecules are linked into a two-dimensional network parallel to the ab plane by C—H⋯O and C—H⋯π interactions.

Related literature

For the orientations of phenyl and ethyl substituents with respect to the fused ring system in the related 7-chloro- and 7-bromo-derivatives, see: Sudha et al. (2007 , 2008 ). For biological activities of pyrrolo[3,4-b]quinoline derivatives, see: Anzini et al. (1990 , 1992 ); Crenshaw et al. (1976 ); Fujita et al. (1996 ); Xiao et al. (2006 ). For related literature, see: Duax et al. (1976 ); Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₆H₂₈N₂O₂S
M_r = 432.56
Triclinic, $[P \overline 1]$
a = 9.3990 (1) Å
b = 10.9077 (2) Å
c = 12.5654 (3) Å
α = 64.3190 (8)°
β = 72.5291 (8)°
γ = 76.3803 (8)°
V = 1099.07 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 100.0 (1) K
0.48 × 0.37 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.878, T_max = 0.971
49024 measured reflections
11697 independent reflections
9445 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.122
S = 1.03
11697 reflections
285 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C4–C9, C12–C17 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.93	2.40	3.3215 (13)	171
C23—H23⋯O2ⁱⁱ	0.93	2.53	3.2821 (13)	138
C2—H2⋯Cg1	0.98	2.94	3.8269 (9)	151
C7—H7⋯Cg3ⁱ	0.93	2.95	3.7883 (12)	151
C10—H10⋯Cg2ⁱⁱⁱ	0.98	2.83	3.8072 (9)	178
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z; (iii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Version 5.1; Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000482/rz2188sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000482/rz2188Isup2.hkl

checkCIF report

Comment top

Pyrrolo[3,4-b]quinoline derivatives exhibit cytotoxic (Xiao et al., 2006) and antibacterial (Fujita et al., 1996) activities. The derivatives are also found to have interferon inducing activities (Crenshaw et al., 1976) and ability to bind benzodiazepine receptors (Anzini et al., 1990, 1992). We report here the crystal structure of the title compound, a pyrrolo[3,4-b]quinoline derivative (Fig. 1).

Bond lengths and angles are comparable with those in the 7-chloro- and 7-bromo- derivatives (Sudha et al., 2007a,b). The pyrrolidine ring adopts an envelope conformation, with the local mirror plane passing through C2 and the midpoint of the bond N1—C11. The relevant asymmetry parameters (Duax et al., 1976) are ΔC_s[C2] = 1.90 (7)° and the puckering parameters q₂ and ϕ₂ (Cremer & Pople, 1975) are 0.444 (1) Å and 74.6 (1)°. The tetrahydropyridine ring adopts a half-chair conformation, with the local twofold rotation axis passing through the midpoints of bonds C4—C9 and C2—C10. The asymmetry parameter ΔC₂[C4—c9] is 5.0 (1)°, and the puckering parameters Q, θ and ϕ are 0.505 (1) Å, 133.2 (1)° and 81.6 (1)°.

The tosyl group is attached to the pyrrolidine ring in a biaxial position. The sum of the bond angles around atoms N1 (342.6°) and N2 (347.2°) indicates sp³ hybridization. The pyrrolidine and tetrahydropyridine rings show trans-fusion. The C19–C24 phenyl ring is equatorially attached to the tetrahydropyridine ring, and it forms dihedral angles of 74.80 (5) and 36.15 (5)°, respectively, with the C4–C9 and C12–C17 benzene rings.

An intramolecular C—H···π interaction involving the sulfonyl-bound phenyl ring (C12–C17, centroid Cg1) is observed. In the solid state, the molecules exist as centrosymmetrically C—H···π hydrogen-bonded dimers involving the C10—H10 group of the molecule at (x, y, z) and the C4–C9 benzene ring (centroid Cg2) of the molecule at (2 - x, -y, 1 - z). The dimers are linked into a chain along the a axis through C8—H8···O1ⁱ hydrogen bonds, and C7—H7···π interaction involving the C19–C24 phenyl ring (centroid Cg3) of the molecule at (1 + x, y, z). The chains are cross-linked via C23—H23···O2ⁱⁱ hydrogen bonds (Table 1), forming a two-dimensional network parallel to the ab plane (Fig. 2).

Related literature top

For the orientations of phenyl and ethyl substituents with respect to the fused ring system in the related 7-chloro- and 7-bromo-derivatives, see: Sudha et al. (2007a,b). For biological activities of pyrrolo[3,4-b]quinoline derivatives, see: Anzini et al. (1990, 1992); Crenshaw et al. (1976); Fujita et al. (1996); Xiao et al. (2006). For related literature, see: Duax et al. (1976); Cremer & Pople (1975).

Experimental top

InCl₃ (20 mol%) was added to a mixture of 2-(N-cinnamyl-N-tosylamino)butanal (1 mmol) and arylamine (1 mmol) in acetonitrile (20 ml). The reaction mixture was stirred at room temperature for 30 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 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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Version 5.1; Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Version 5.1; Sheldrick, 2008); molecular graphics: SHELXTL (Version 5.1; Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Version 5.1; Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering. Displacement ellipsoids are drawn at the 80% probability level.
	Fig. 2. Part of the two-dimensional network in the title compound. Dashed and dotted lines indicate C—H···O and C—H···π interactions, respectively. For the sake of clarity, H atoms not involved in the interactions have been omitted.

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

Crystal data top

C₂₆H₂₈N₂O₂S	Z = 2
M_r = 432.56	F(000) = 460
Triclinic, P1	D_x = 1.307 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3990 (1) Å	Cell parameters from 7071 reflections
b = 10.9077 (2) Å	θ = 2.2–37.7°
c = 12.5654 (3) Å	µ = 0.17 mm⁻¹
α = 64.3190 (8)°	T = 100 K
β = 72.5291 (8)°	Block, colourless
γ = 76.3803 (8)°	0.48 × 0.37 × 0.17 mm
V = 1099.07 (4) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	11697 independent reflections
Radiation source: fine-focus sealed tube	9445 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 8.33 pixels mm^-1	θ_max = 37.8°, θ_min = 1.9°
ω scans	h = −15→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→18
T_min = 0.878, T_max = 0.971	l = −21→21
49024 measured reflections

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) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0632P)² + 0.2032P] where P = (F_o² + 2F_c²)/3
11697 reflections	(Δ/σ)_max = 0.001
285 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₆H₂₈N₂O₂S	γ = 76.3803 (8)°
M_r = 432.56	V = 1099.07 (4) Å³
Triclinic, P1	Z = 2
a = 9.3990 (1) Å	Mo Kα radiation
b = 10.9077 (2) Å	µ = 0.17 mm⁻¹
c = 12.5654 (3) Å	T = 100 K
α = 64.3190 (8)°	0.48 × 0.37 × 0.17 mm
β = 72.5291 (8)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	11697 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	9445 reflections with I > 2σ(I)
T_min = 0.878, T_max = 0.971	R_int = 0.038
49024 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.54 e Å⁻³
11697 reflections	Δρ_min = −0.47 e Å⁻³
285 parameters

Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	0.49683 (2)	0.424122 (19)	0.278537 (17)	0.01327 (5)
O1	0.35740 (7)	0.37308 (7)	0.30453 (6)	0.01740 (11)
O2	0.49608 (8)	0.55466 (6)	0.28077 (6)	0.01737 (11)
N1	0.59007 (8)	0.30981 (7)	0.37860 (6)	0.01346 (11)
N2	0.99769 (8)	0.23374 (7)	0.33005 (7)	0.01746 (13)
H1N2	1.0420 (18)	0.2777 (15)	0.3524 (14)	0.034 (4)*
C1	0.61499 (9)	0.16668 (8)	0.38536 (7)	0.01513 (13)
H1A	0.5572	0.1571	0.3377	0.018*
H1B	0.5887	0.1016	0.4685	0.018*
C2	0.78261 (9)	0.14729 (7)	0.33219 (7)	0.01321 (12)
H2	0.8007	0.2038	0.2451	0.016*
C3	0.86315 (9)	0.00361 (8)	0.34922 (7)	0.01390 (12)
H3	0.8397	−0.0548	0.4359	0.017*
C4	1.03201 (9)	0.01342 (8)	0.30922 (7)	0.01426 (12)
C5	1.13274 (10)	−0.08705 (8)	0.27522 (8)	0.01671 (13)
H5	1.0951	−0.1589	0.2757	0.020*
C6	1.28696 (10)	−0.08326 (9)	0.24074 (8)	0.01913 (15)
H6	1.3514	−0.1511	0.2179	0.023*
C7	1.34377 (11)	0.02374 (9)	0.24084 (9)	0.02159 (16)
H7	1.4469	0.0269	0.2193	0.026*
C8	1.24635 (10)	0.12555 (9)	0.27314 (9)	0.02058 (15)
H8	1.2851	0.1966	0.2730	0.025*
C9	1.09059 (9)	0.12303 (8)	0.30597 (7)	0.01567 (13)
C10	0.84289 (9)	0.21313 (8)	0.39204 (7)	0.01400 (12)
H10	0.8370	0.1535	0.4778	0.017*
C11	0.73416 (9)	0.34598 (8)	0.38053 (7)	0.01333 (12)
H11	0.7704	0.4197	0.3031	0.016*
C12	0.60265 (9)	0.42650 (8)	0.13594 (7)	0.01398 (12)
C13	0.71831 (10)	0.50922 (8)	0.07365 (7)	0.01698 (14)
H13	0.7306	0.5714	0.1016	0.020*
C14	0.81489 (11)	0.49778 (9)	−0.03058 (8)	0.01997 (15)
H14	0.8916	0.5533	−0.0727	0.024*
C15	0.79834 (11)	0.40407 (9)	−0.07292 (7)	0.01950 (15)
C16	0.67845 (11)	0.32643 (9)	−0.01229 (7)	0.01902 (15)
H16	0.6639	0.2667	−0.0420	0.023*
C17	0.58026 (10)	0.33691 (8)	0.09193 (7)	0.01663 (13)
H17	0.5006	0.2847	0.1318	0.020*
C18	0.90773 (13)	0.38731 (12)	−0.18222 (9)	0.0290 (2)
H18A	0.9524	0.2936	−0.1608	0.044*
H18B	0.9849	0.4455	−0.2104	0.044*
H18C	0.8558	0.4122	−0.2452	0.044*
C19	0.81012 (9)	−0.05736 (8)	0.28198 (7)	0.01477 (13)
C20	0.83943 (11)	−0.00052 (9)	0.15531 (8)	0.01856 (14)
H20	0.8949	0.0734	0.1120	0.022*
C21	0.78685 (12)	−0.05303 (10)	0.09319 (9)	0.02300 (17)
H21	0.8071	−0.0142	0.0089	0.028*
C22	0.70390 (12)	−0.16372 (10)	0.15726 (11)	0.02572 (19)
H22	0.6683	−0.1987	0.1159	0.031*
C23	0.67453 (11)	−0.22161 (9)	0.28268 (11)	0.02484 (18)
H23	0.6191	−0.2956	0.3256	0.030*
C24	0.72808 (10)	−0.16905 (8)	0.34479 (9)	0.01953 (15)
H24	0.7088	−0.2090	0.4290	0.023*
C25	0.70648 (10)	0.39338 (8)	0.48343 (7)	0.01598 (13)
H25A	0.6292	0.4716	0.4719	0.019*
H25B	0.6690	0.3204	0.5594	0.019*
C26	0.84606 (11)	0.43310 (10)	0.49243 (8)	0.01998 (15)
H26A	0.8211	0.4619	0.5587	0.030*
H26B	0.8826	0.5069	0.4183	0.030*
H26C	0.9224	0.3556	0.5059	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01224 (8)	0.01495 (8)	0.01383 (8)	−0.00040 (6)	−0.00266 (6)	−0.00755 (6)
O1	0.0120 (3)	0.0218 (3)	0.0199 (3)	−0.0020 (2)	−0.0028 (2)	−0.0102 (2)
O2	0.0197 (3)	0.0158 (2)	0.0195 (3)	0.0003 (2)	−0.0050 (2)	−0.0105 (2)
N1	0.0123 (3)	0.0147 (2)	0.0142 (2)	−0.0013 (2)	−0.0032 (2)	−0.0064 (2)
N2	0.0121 (3)	0.0180 (3)	0.0266 (3)	−0.0015 (2)	−0.0028 (3)	−0.0138 (3)
C1	0.0138 (3)	0.0146 (3)	0.0168 (3)	−0.0023 (2)	−0.0026 (3)	−0.0063 (2)
C2	0.0128 (3)	0.0135 (3)	0.0138 (3)	−0.0018 (2)	−0.0026 (2)	−0.0060 (2)
C3	0.0142 (3)	0.0133 (3)	0.0140 (3)	−0.0022 (2)	−0.0030 (2)	−0.0050 (2)
C4	0.0141 (3)	0.0138 (3)	0.0154 (3)	−0.0009 (2)	−0.0041 (2)	−0.0061 (2)
C5	0.0172 (3)	0.0152 (3)	0.0190 (3)	0.0005 (3)	−0.0054 (3)	−0.0083 (2)
C6	0.0166 (4)	0.0190 (3)	0.0225 (4)	0.0021 (3)	−0.0046 (3)	−0.0108 (3)
C7	0.0139 (4)	0.0220 (3)	0.0297 (4)	0.0003 (3)	−0.0032 (3)	−0.0133 (3)
C8	0.0131 (3)	0.0207 (3)	0.0304 (4)	−0.0021 (3)	−0.0032 (3)	−0.0133 (3)
C9	0.0136 (3)	0.0157 (3)	0.0193 (3)	−0.0006 (2)	−0.0036 (3)	−0.0089 (2)
C10	0.0132 (3)	0.0153 (3)	0.0147 (3)	−0.0010 (2)	−0.0032 (2)	−0.0073 (2)
C11	0.0124 (3)	0.0155 (3)	0.0132 (3)	−0.0018 (2)	−0.0021 (2)	−0.0071 (2)
C12	0.0147 (3)	0.0147 (3)	0.0128 (3)	0.0001 (2)	−0.0035 (2)	−0.0064 (2)
C13	0.0179 (4)	0.0175 (3)	0.0155 (3)	−0.0033 (3)	−0.0027 (3)	−0.0066 (2)
C14	0.0184 (4)	0.0224 (3)	0.0160 (3)	−0.0037 (3)	−0.0012 (3)	−0.0058 (3)
C15	0.0201 (4)	0.0206 (3)	0.0146 (3)	0.0033 (3)	−0.0035 (3)	−0.0073 (3)
C16	0.0248 (4)	0.0182 (3)	0.0152 (3)	0.0000 (3)	−0.0048 (3)	−0.0087 (3)
C17	0.0190 (4)	0.0172 (3)	0.0154 (3)	−0.0020 (3)	−0.0046 (3)	−0.0077 (2)
C18	0.0290 (5)	0.0336 (5)	0.0188 (4)	0.0037 (4)	0.0008 (4)	−0.0130 (3)
C19	0.0138 (3)	0.0130 (3)	0.0187 (3)	−0.0014 (2)	−0.0038 (3)	−0.0073 (2)
C20	0.0202 (4)	0.0185 (3)	0.0195 (3)	−0.0021 (3)	−0.0059 (3)	−0.0090 (3)
C21	0.0232 (4)	0.0267 (4)	0.0266 (4)	0.0031 (3)	−0.0108 (3)	−0.0169 (3)
C22	0.0211 (4)	0.0255 (4)	0.0431 (5)	0.0049 (3)	−0.0149 (4)	−0.0237 (4)
C23	0.0187 (4)	0.0187 (3)	0.0428 (5)	−0.0015 (3)	−0.0103 (4)	−0.0153 (4)
C24	0.0167 (4)	0.0151 (3)	0.0266 (4)	−0.0026 (3)	−0.0046 (3)	−0.0078 (3)
C25	0.0151 (3)	0.0199 (3)	0.0153 (3)	−0.0019 (3)	−0.0019 (3)	−0.0101 (3)
C26	0.0190 (4)	0.0267 (4)	0.0198 (3)	−0.0047 (3)	−0.0036 (3)	−0.0136 (3)

Geometric parameters (Å, º) top

S1—O2	1.4346 (6)	C12—C17	1.3930 (11)
S1—O1	1.4363 (7)	C12—C13	1.3955 (12)
S1—N1	1.6406 (7)	C13—C14	1.3890 (12)
S1—C12	1.7613 (8)	C13—H13	0.93
N1—C1	1.4913 (10)	C14—C15	1.3957 (13)
N1—C11	1.5068 (10)	C14—H14	0.93
N2—C9	1.4049 (10)	C15—C16	1.3936 (14)
N2—C10	1.4478 (11)	C15—C18	1.5026 (13)
N2—H1N2	0.874 (15)	C16—C17	1.3907 (12)
C1—C2	1.5188 (11)	C16—H16	0.93
C1—H1A	0.97	C17—H17	0.93
C1—H1B	0.97	C18—H18A	0.96
C2—C10	1.5225 (11)	C18—H18B	0.96
C2—C3	1.5241 (10)	C18—H18C	0.96
C2—H2	0.98	C19—C24	1.3947 (11)
C3—C19	1.5167 (11)	C19—C20	1.3984 (12)
C3—C4	1.5289 (12)	C20—C21	1.3906 (12)
C3—H3	0.98	C20—H20	0.93
C4—C5	1.3979 (11)	C21—C22	1.3921 (15)
C4—C9	1.4100 (11)	C21—H21	0.93
C5—C6	1.3879 (13)	C22—C23	1.3846 (16)
C5—H5	0.93	C22—H22	0.93
C6—C7	1.3937 (13)	C23—C24	1.3967 (13)
C6—H6	0.93	C23—H23	0.93
C7—C8	1.3874 (12)	C24—H24	0.93
C7—H7	0.93	C25—C26	1.5234 (12)
C8—C9	1.4003 (12)	C25—H25A	0.97
C8—H8	0.93	C25—H25B	0.97
C10—C11	1.5410 (11)	C26—H26A	0.96
C10—H10	0.98	C26—H26B	0.96
C11—C25	1.5235 (10)	C26—H26C	0.96
C11—H11	0.98

O2—S1—O1	119.99 (4)	N1—C11—H11	109.5
O2—S1—N1	106.92 (4)	C25—C11—H11	109.5
O1—S1—N1	106.32 (4)	C10—C11—H11	109.5
O2—S1—C12	107.98 (4)	C17—C12—C13	120.56 (7)
O1—S1—C12	108.51 (4)	C17—C12—S1	120.00 (6)
N1—S1—C12	106.36 (4)	C13—C12—S1	119.15 (6)
C1—N1—C11	109.19 (6)	C14—C13—C12	119.34 (8)
C1—N1—S1	116.25 (5)	C14—C13—H13	120.3
C11—N1—S1	117.17 (5)	C12—C13—H13	120.3
C9—N2—C10	116.54 (7)	C13—C14—C15	120.86 (8)
C9—N2—H1N2	113.8 (10)	C13—C14—H14	119.6
C10—N2—H1N2	116.9 (10)	C15—C14—H14	119.6
N1—C1—C2	102.47 (6)	C16—C15—C14	118.90 (8)
N1—C1—H1A	111.3	C16—C15—C18	120.51 (9)
C2—C1—H1A	111.3	C14—C15—C18	120.59 (9)
N1—C1—H1B	111.3	C17—C16—C15	120.98 (8)
C2—C1—H1B	111.3	C17—C16—H16	119.5
H1A—C1—H1B	109.2	C15—C16—H16	119.5
C1—C2—C10	101.01 (6)	C16—C17—C12	119.25 (8)
C1—C2—C3	119.66 (6)	C16—C17—H17	120.4
C10—C2—C3	111.59 (6)	C12—C17—H17	120.4
C1—C2—H2	108.0	C15—C18—H18A	109.5
C10—C2—H2	108.0	C15—C18—H18B	109.5
C3—C2—H2	108.0	H18A—C18—H18B	109.5
C19—C3—C2	111.25 (6)	C15—C18—H18C	109.5
C19—C3—C4	113.39 (6)	H18A—C18—H18C	109.5
C2—C3—C4	107.44 (6)	H18B—C18—H18C	109.5
C19—C3—H3	108.2	C24—C19—C20	118.46 (8)
C2—C3—H3	108.2	C24—C19—C3	120.93 (7)
C4—C3—H3	108.2	C20—C19—C3	120.59 (7)
C5—C4—C9	118.20 (8)	C21—C20—C19	120.91 (8)
C5—C4—C3	120.56 (7)	C21—C20—H20	119.5
C9—C4—C3	121.24 (7)	C19—C20—H20	119.5
C6—C5—C4	122.28 (8)	C20—C21—C22	119.93 (9)
C6—C5—H5	118.9	C20—C21—H21	120.0
C4—C5—H5	118.9	C22—C21—H21	120.0
C5—C6—C7	118.98 (8)	C23—C22—C21	119.88 (8)
C5—C6—H6	120.5	C23—C22—H22	120.1
C7—C6—H6	120.5	C21—C22—H22	120.1
C8—C7—C6	119.98 (9)	C22—C23—C24	120.05 (9)
C8—C7—H7	120.0	C22—C23—H23	120.0
C6—C7—H7	120.0	C24—C23—H23	120.0
C7—C8—C9	121.06 (8)	C19—C24—C23	120.76 (9)
C7—C8—H8	119.5	C19—C24—H24	119.6
C9—C8—H8	119.5	C23—C24—H24	119.6
C8—C9—N2	118.22 (7)	C26—C25—C11	113.64 (7)
C8—C9—C4	119.46 (7)	C26—C25—H25A	108.8
N2—C9—C4	122.27 (8)	C11—C25—H25A	108.8
N2—C10—C2	108.59 (6)	C26—C25—H25B	108.8
N2—C10—C11	114.73 (6)	C11—C25—H25B	108.8
C2—C10—C11	103.44 (6)	H25A—C25—H25B	107.7
N2—C10—H10	109.9	C25—C26—H26A	109.5
C2—C10—H10	109.9	C25—C26—H26B	109.5
C11—C10—H10	109.9	H26A—C26—H26B	109.5
N1—C11—C25	109.71 (6)	C25—C26—H26C	109.5
N1—C11—C10	103.05 (6)	H26A—C26—H26C	109.5
C25—C11—C10	115.45 (6)	H26B—C26—H26C	109.5

O2—S1—N1—C1	−175.61 (6)	S1—N1—C11—C25	100.35 (7)
O1—S1—N1—C1	55.08 (6)	C1—N1—C11—C10	−1.35 (7)
C12—S1—N1—C1	−60.43 (6)	S1—N1—C11—C10	−136.16 (5)
O2—S1—N1—C11	−43.94 (6)	N2—C10—C11—N1	146.21 (6)
O1—S1—N1—C11	−173.24 (5)	C2—C10—C11—N1	28.11 (7)
C12—S1—N1—C11	71.25 (6)	N2—C10—C11—C25	−94.20 (8)
C11—N1—C1—C2	−25.88 (8)	C2—C10—C11—C25	147.70 (7)
S1—N1—C1—C2	109.40 (6)	O2—S1—C12—C17	−157.41 (7)
N1—C1—C2—C10	42.60 (7)	O1—S1—C12—C17	−25.90 (8)
N1—C1—C2—C3	165.43 (6)	N1—S1—C12—C17	88.13 (7)
C1—C2—C3—C19	66.47 (9)	O2—S1—C12—C13	28.75 (8)
C10—C2—C3—C19	−176.03 (6)	O1—S1—C12—C13	160.27 (7)
C1—C2—C3—C4	−168.88 (7)	N1—S1—C12—C13	−85.71 (7)
C10—C2—C3—C4	−51.38 (8)	C17—C12—C13—C14	−2.42 (13)
C19—C3—C4—C5	−34.90 (10)	S1—C12—C13—C14	171.38 (7)
C2—C3—C4—C5	−158.25 (7)	C12—C13—C14—C15	−0.53 (13)
C19—C3—C4—C9	145.35 (7)	C13—C14—C15—C16	3.15 (13)
C2—C3—C4—C9	22.00 (10)	C13—C14—C15—C18	−176.99 (9)
C9—C4—C5—C6	1.08 (12)	C14—C15—C16—C17	−2.88 (13)
C3—C4—C5—C6	−178.67 (7)	C18—C15—C16—C17	177.26 (8)
C4—C5—C6—C7	0.52 (13)	C15—C16—C17—C12	0.00 (13)
C5—C6—C7—C8	−1.07 (14)	C13—C12—C17—C16	2.68 (12)
C6—C7—C8—C9	0.01 (15)	S1—C12—C17—C16	−171.07 (6)
C7—C8—C9—N2	−175.93 (9)	C2—C3—C19—C24	−112.37 (8)
C7—C8—C9—C4	1.62 (14)	C4—C3—C19—C24	126.40 (8)
C10—N2—C9—C8	−165.08 (8)	C2—C3—C19—C20	66.09 (10)
C10—N2—C9—C4	17.45 (12)	C4—C3—C19—C20	−55.15 (10)
C5—C4—C9—C8	−2.12 (12)	C24—C19—C20—C21	0.65 (13)
C3—C4—C9—C8	177.63 (8)	C3—C19—C20—C21	−177.84 (8)
C5—C4—C9—N2	175.32 (8)	C19—C20—C21—C22	−0.05 (14)
C3—C4—C9—N2	−4.93 (12)	C20—C21—C22—C23	−0.27 (14)
C9—N2—C10—C2	−45.97 (9)	C21—C22—C23—C24	−0.02 (14)
C9—N2—C10—C11	−161.12 (7)	C20—C19—C24—C23	−0.94 (13)
C1—C2—C10—N2	−166.38 (6)	C3—C19—C24—C23	177.54 (8)
C3—C2—C10—N2	65.36 (8)	C22—C23—C24—C19	0.64 (14)
C1—C2—C10—C11	−44.09 (7)	N1—C11—C25—C26	−179.71 (7)
C3—C2—C10—C11	−172.34 (6)	C10—C11—C25—C26	64.43 (9)
C1—N1—C11—C25	−124.83 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.40	3.3215 (13)	171
C23—H23···O2ⁱⁱ	0.93	2.53	3.2821 (13)	138
C2—H2···Cg1	0.98	2.94	3.8269 (9)	151
C7—H7···Cg3ⁱ	0.93	2.95	3.7883 (12)	151
C10—H10···Cg2ⁱⁱⁱ	0.98	2.83	3.8072 (9)	178

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₈N₂O₂S
M_r	432.56
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.3990 (1), 10.9077 (2), 12.5654 (3)
α, β, γ (°)	64.3190 (8), 72.5291 (8), 76.3803 (8)
V (Å³)	1099.07 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.48 × 0.37 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.878, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	49024, 11697, 9445
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.863

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.122, 1.03
No. of reflections	11697
No. of parameters	285
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.47

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Version 5.1; Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.40	3.3215 (13)	171
C23—H23···O2ⁱⁱ	0.93	2.53	3.2821 (13)	138
C2—H2···Cg1	0.98	2.94	3.8269 (9)	151
C7—H7···Cg3ⁱ	0.93	2.95	3.7883 (12)	151
C10—H10···Cg2ⁱⁱⁱ	0.98	2.83	3.8072 (9)	178

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

Footnotes

‡Currently working at: Department of Physics, R. M. K. Engineering College, R. S. M. Nagar, Kavaraipettai 601 206, Tamil Nadu, India.

Acknowledgements

HKF thanks Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS), grant No. 203/PFIZIK/671064.

References

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