2-[(1R,3S)-6,7-Dimeth­oxy-1-phenyl-1,2,3,4-tetra­hydro­isoquinolin-3-yl]-4-phenyl-1,3-thia­zole

Pawar, S.; Katharigatta, V.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536811037494

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2722

https://doi.org/10.1107/S1600536811037494

Open

access

2-[(1R,3S)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]-4-phenyl-1,3-thiazole

Sunayna Pawar,^a Venugopala Katharigatta,^b Thavendran Govender,^a Hendrik G. Kruger ^b and Glenn E. M. Maguire ^b ^*

^aSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa, and ^bSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 12 September 2011; accepted 14 September 2011; online 30 September 2011)

In the title compound, C₂₆H₂₄N₂O₂S, the dihedral angle between the thiazole ring and the adjacent phenyl ring is 3.02 (15)°. The N-containing six-membered ring of the tetrahydroisoquinoline unit adopts a half-chair conformation. The dihedral angle between the least-squares plane of the tetrahydroisoquinoline ring system and its nearest phenyl ring is 76.90 (13)°. No classical hydrogen bonds nor π–π interactions were found in the crystal structure.

Related literature

For reactions associated with TIQ ligands, see: Chakka et al. (2010 ); Naicker et al. (2010 ). For related structures, see: Naicker et al. (2011a ,b ).

Experimental

Crystal data

C₂₆H₂₄N₂O₂S
M_r = 428.53
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.9178 (2) Å
b = 16.6269 (9) Å
c = 22.8564 (11) Å
V = 2248.95 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 K
0.32 × 0.16 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.886, T_max = 0.978
92668 measured reflections
4948 independent reflections
3141 reflections with I > 2σ(I)
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.109
S = 1.21
4948 reflections
285 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ), 2094 Friedel pairs
Flack parameter: 0.01 (10)

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811037494/is2779sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037494/is2779Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037494/is2779Isup3.cml

checkCIF report

Comment top

As a part of our studies on the synthesis and application of new tetrahydroisoquinoline compounds for catalysis of asymmetric hydogenation reactions (Chakka et al., 2010) and the Diels-Alder reaction (Naicker et al., 2010), the title compound, a novel ligand containing a TIQ backbone with thiazole moiety, and its' analogues are currently being tested in our laboratory for the asymmetric Henry reaction.

The absolute stereochemistry was confirmed to be R and S at C1 and C9 positions, respectively, by two-dimensional NMR studies. From the crystal structure it is evident that the N-containing six-membered ring assumes a half chair conformation [Q = 0.446 (4) Å, θ = 54.0 (5)° and φ = 315.6 (6)°]. The torsion angle for C1—N1—C9—C10 is 57.9 (4)°. The maximum displacements from the C1/C2/C7–C9/N1 plane are 0.256 Å for N1 and 0.314 Å for C9 (Fig. 1). This is similar to our previously reported structures which also assume half chair conformations (Naicker et al., 2011a, b). There are no hydrogen bonding interactions nor π–π interactions in the crystal structure.

Related literature top

For reactions associated with TIQ ligands, see: Chakka et al. (2010); Naicker et al. (2010). For related structures, see: Naicker et al. (2011a,b).

Experimental top

A solution of Cbz protected thiazole compound (0.100 g, 0.177 mmol, 1 eq.) in dry DCM (4 ml) under argon atmosphere was treated with dipropylsulfide (0.788 ml, 5.338 mmol, 30 eq.), boron trifluoride diethyl etherate (0.230 ml, 10 eq.) and stirred at room temperature for 1.5 h, then dipropylsulfide (0.499 ml, 2.336 mmol, 20 eq.) was added, the reaction was allowed to proceed for another 2 h. The reaction was monitored by TLC using EtOAc/Hexane (20:80, R_f = 1/2). The mixture was then poured into water (5 ml) and 10% aqueous NH₄OH (10 ml) was added and extracted with ethylacetate (30 ml) followed by washing with water (2 × 10 ml). The organic layer was separated and dried over anhydrous MgSO₄ and the solvent evaporated under reduced pressure to afford crude thiazole, which was purified by column chromatography using silica gel (deactivated with 5% Et₃N) using 95:5 hexane/Et₃N - 10:90:5% EtOAc /hexane/Et₃N as the eluent to yield approximately 0.05 g (65%) of pure thiazole compound. M.p. = 388–390 K

Crystals suitable for X-ray analysis were grown at room temperature from a solution of EtOAc/hexane.

Structure description top

For reactions associated with TIQ ligands, see: Chakka et al. (2010); Naicker et al. (2010). For related structures, see: Naicker et al. (2011a,b).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Hydrogen atoms have been omitted for clarity.

2-[(1R,3S)-6,7-Dimethoxy-1-phenyl-1,2,3,4- tetrahydroisoquinolin-3-yl]-4-phenyl-1,3-thiazole top

Crystal data top

C₂₆H₂₄N₂O₂S	F(000) = 904
M_r = 428.53	D_x = 1.266 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 92668 reflections
a = 5.9178 (2) Å	θ = 3.0–27.1°
b = 16.6269 (9) Å	µ = 0.17 mm⁻¹
c = 22.8564 (11) Å	T = 293 K
V = 2248.95 (18) Å³	Block, colourless
Z = 4	0.32 × 0.16 × 0.13 mm

Data collection top

Nonius KappaCCD diffractometer	4948 independent reflections
Radiation source: fine-focus sealed tube	3141 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
1.2° φ scans and ω scans	θ_max = 27.1°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.886, T_max = 0.978	k = −21→21
92668 measured reflections	l = −29→29

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.075	w = 1/[σ²(F_o²) + (0.0259P)² + 0.4897P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.109	(Δ/σ)_max = 0.001
S = 1.21	Δρ_max = 0.18 e Å⁻³
4948 reflections	Δρ_min = −0.13 e Å⁻³
285 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0072 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2094 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (10)

Crystal data top

C₂₆H₂₄N₂O₂S	V = 2248.95 (18) Å³
M_r = 428.53	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.9178 (2) Å	µ = 0.17 mm⁻¹
b = 16.6269 (9) Å	T = 293 K
c = 22.8564 (11) Å	0.32 × 0.16 × 0.13 mm

Data collection top

Nonius KappaCCD diffractometer	4948 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3141 reflections with I > 2σ(I)
T_min = 0.886, T_max = 0.978	R_int = 0.093
92668 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	Δρ_max = 0.18 e Å⁻³
S = 1.21	Δρ_min = −0.13 e Å⁻³
4948 reflections	Absolute structure: Flack (1983), 2094 Friedel pairs
285 parameters	Absolute structure parameter: 0.01 (10)
1 restraint

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	0.31297 (13)	0.27081 (5)	0.16545 (4)	0.0756 (3)
O1	1.3723 (4)	0.11255 (15)	0.43058 (11)	0.0981 (8)
O2	1.4727 (4)	0.02633 (14)	0.34014 (11)	0.0864 (7)
N1	0.5823 (4)	0.23535 (15)	0.27440 (10)	0.0623 (6)
H1N	0.490 (4)	0.1910 (13)	0.2803 (11)	0.069 (9)*
N2	0.6162 (4)	0.18000 (14)	0.12153 (10)	0.0564 (6)
C1	0.7220 (5)	0.23931 (17)	0.32849 (12)	0.0620 (7)
H1	0.6242	0.2210	0.3604	0.074*
C2	0.9256 (5)	0.18372 (17)	0.32871 (13)	0.0595 (7)
C3	1.0545 (6)	0.17525 (19)	0.37999 (13)	0.0708 (9)
H3	1.0166	0.2054	0.4129	0.085*
C4	1.2354 (6)	0.1235 (2)	0.38266 (14)	0.0717 (9)
C5	1.2916 (5)	0.07670 (17)	0.33380 (15)	0.0663 (8)
C6	1.1660 (5)	0.08514 (16)	0.28383 (14)	0.0643 (8)
H6	1.2022	0.0542	0.2512	0.077*
C7	0.9852 (5)	0.13892 (16)	0.28054 (12)	0.0590 (7)
C8	0.8571 (5)	0.14618 (16)	0.22391 (13)	0.0651 (8)
H8A	0.7586	0.1000	0.2195	0.078*
H8B	0.9632	0.1461	0.1916	0.078*
C9	0.7172 (4)	0.22227 (16)	0.22165 (11)	0.0552 (7)
H9	0.8209	0.2679	0.2175	0.066*
C10	0.5672 (4)	0.22039 (16)	0.16855 (12)	0.0542 (7)
C11	0.2745 (5)	0.23434 (18)	0.09645 (12)	0.0668 (8)
H11	0.1493	0.2455	0.0732	0.080*
C12	0.4483 (5)	0.18743 (16)	0.07989 (12)	0.0543 (7)
C13	0.4750 (5)	0.14401 (16)	0.02377 (12)	0.0556 (7)
C14	0.6676 (6)	0.09961 (18)	0.01269 (14)	0.0673 (8)
H14	0.7819	0.0980	0.0406	0.081*
C15	0.6937 (7)	0.0574 (2)	−0.03919 (15)	0.0804 (10)
H15	0.8243	0.0277	−0.0460	0.096*
C16	0.5244 (8)	0.0598 (2)	−0.08076 (16)	0.0882 (11)
H16	0.5400	0.0315	−0.1156	0.106*
C17	0.3339 (7)	0.1041 (2)	−0.07042 (17)	0.0935 (11)
H17	0.2209	0.1064	−0.0987	0.112*
C18	0.3074 (6)	0.1455 (2)	−0.01871 (14)	0.0746 (9)
H18	0.1758	0.1748	−0.0122	0.089*
C19	0.7776 (5)	0.32691 (17)	0.34164 (12)	0.0592 (7)
C20	0.6135 (6)	0.3740 (2)	0.36789 (14)	0.0801 (10)
H20	0.4733	0.3518	0.3767	0.096*
C21	0.6556 (7)	0.4538 (2)	0.38112 (16)	0.0941 (12)
H21	0.5430	0.4849	0.3983	0.113*
C22	0.8609 (7)	0.4872 (2)	0.36917 (15)	0.0852 (11)
H22	0.8902	0.5405	0.3791	0.102*
C23	1.0220 (6)	0.44213 (19)	0.34258 (16)	0.0833 (10)
H23	1.1607	0.4652	0.3333	0.100*
C24	0.9825 (5)	0.36207 (18)	0.32905 (13)	0.0707 (8)
H24	1.0956	0.3318	0.3113	0.085*
C25	1.3075 (9)	0.1475 (3)	0.48294 (17)	0.153 (2)
H25A	1.4160	0.1346	0.5127	0.230*
H25B	1.1618	0.1274	0.4942	0.230*
H25C	1.2998	0.2048	0.4782	0.230*
C26	1.5162 (7)	−0.0274 (2)	0.29331 (17)	0.1042 (12)
H26A	1.6461	−0.0596	0.3024	0.156*
H26B	1.5445	0.0028	0.2582	0.156*
H26C	1.3876	−0.0616	0.2875	0.156*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0669 (5)	0.0765 (5)	0.0833 (6)	0.0138 (4)	−0.0023 (5)	−0.0113 (5)
O1	0.108 (2)	0.1159 (19)	0.0704 (16)	−0.0031 (16)	−0.0193 (15)	0.0182 (14)
O2	0.0864 (16)	0.0804 (15)	0.0922 (17)	0.0051 (14)	−0.0139 (14)	0.0272 (14)
N1	0.0589 (14)	0.0688 (16)	0.0591 (15)	−0.0141 (13)	0.0045 (13)	−0.0059 (13)
N2	0.0537 (14)	0.0571 (14)	0.0586 (15)	−0.0013 (12)	−0.0042 (12)	0.0025 (12)
C1	0.0660 (17)	0.0680 (18)	0.0521 (17)	−0.0134 (16)	0.0078 (15)	0.0001 (15)
C2	0.0680 (18)	0.0550 (16)	0.0553 (19)	−0.0132 (15)	−0.0013 (16)	0.0076 (15)
C3	0.088 (2)	0.067 (2)	0.0572 (19)	−0.015 (2)	−0.0008 (19)	0.0066 (16)
C4	0.083 (2)	0.075 (2)	0.058 (2)	−0.0156 (19)	−0.0130 (18)	0.0236 (18)
C5	0.072 (2)	0.0569 (18)	0.070 (2)	−0.0090 (17)	−0.004 (2)	0.0211 (17)
C6	0.073 (2)	0.0554 (17)	0.065 (2)	−0.0027 (17)	−0.0031 (18)	0.0074 (15)
C7	0.0682 (19)	0.0512 (16)	0.0577 (18)	−0.0083 (16)	−0.0037 (16)	0.0059 (15)
C8	0.073 (2)	0.0579 (17)	0.0642 (18)	0.0008 (16)	−0.0060 (16)	−0.0030 (15)
C9	0.0561 (16)	0.0525 (16)	0.0569 (17)	−0.0083 (14)	0.0004 (14)	0.0011 (14)
C10	0.0524 (15)	0.0470 (15)	0.0632 (18)	−0.0039 (13)	0.0024 (15)	0.0046 (16)
C11	0.0632 (19)	0.0667 (18)	0.071 (2)	0.0064 (17)	−0.0118 (16)	0.0021 (16)
C12	0.0542 (17)	0.0480 (16)	0.0608 (19)	−0.0026 (14)	−0.0030 (15)	0.0087 (14)
C13	0.0574 (18)	0.0494 (16)	0.0601 (18)	−0.0087 (15)	−0.0013 (15)	0.0080 (14)
C14	0.070 (2)	0.0705 (19)	0.062 (2)	−0.0012 (18)	0.0015 (17)	−0.0013 (16)
C15	0.085 (2)	0.071 (2)	0.085 (3)	−0.004 (2)	0.011 (2)	−0.0061 (19)
C16	0.100 (3)	0.089 (3)	0.076 (3)	−0.035 (2)	0.007 (2)	−0.019 (2)
C17	0.091 (3)	0.113 (3)	0.077 (3)	−0.029 (3)	−0.017 (2)	−0.011 (2)
C18	0.0670 (19)	0.084 (2)	0.073 (2)	−0.0108 (19)	−0.0110 (19)	0.0016 (18)
C19	0.0670 (19)	0.0643 (18)	0.0465 (16)	−0.0024 (16)	−0.0002 (15)	−0.0030 (14)
C20	0.070 (2)	0.091 (3)	0.079 (2)	−0.002 (2)	0.0061 (17)	−0.017 (2)
C21	0.102 (3)	0.085 (3)	0.095 (3)	0.016 (2)	0.004 (2)	−0.029 (2)
C22	0.108 (3)	0.063 (2)	0.084 (3)	−0.002 (2)	−0.015 (2)	−0.0087 (18)
C23	0.082 (2)	0.065 (2)	0.103 (3)	−0.0104 (19)	−0.002 (2)	0.008 (2)
C24	0.069 (2)	0.0606 (19)	0.082 (2)	−0.0033 (17)	0.0095 (18)	0.0037 (17)
C25	0.166 (4)	0.223 (6)	0.071 (3)	0.033 (5)	−0.032 (3)	−0.015 (3)
C26	0.108 (3)	0.080 (2)	0.125 (3)	0.022 (2)	−0.005 (3)	0.017 (2)

Geometric parameters (Å, º) top

S1—C11	1.705 (3)	C12—C13	1.480 (4)
S1—C10	1.724 (3)	C13—C14	1.381 (4)
O1—C4	1.374 (4)	C13—C18	1.388 (4)
O1—C25	1.385 (4)	C14—C15	1.386 (4)
O2—C5	1.368 (4)	C14—H14	0.9300
O2—C26	1.417 (4)	C15—C16	1.381 (5)
N1—C9	1.462 (3)	C15—H15	0.9300
N1—C1	1.489 (3)	C16—C17	1.368 (5)
N1—H1N	0.927 (17)	C16—H16	0.9300
N2—C10	1.300 (3)	C17—C18	1.376 (5)
N2—C12	1.381 (3)	C17—H17	0.9300
C1—C2	1.519 (4)	C18—H18	0.9300
C1—C19	1.523 (4)	C19—C24	1.377 (4)
C1—H1	0.9800	C19—C20	1.385 (4)
C2—C7	1.375 (4)	C20—C21	1.382 (5)
C2—C3	1.406 (4)	C20—H20	0.9300
C3—C4	1.376 (4)	C21—C22	1.364 (5)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.401 (4)	C22—C23	1.357 (5)
C5—C6	1.370 (4)	C22—H22	0.9300
C6—C7	1.397 (4)	C23—C24	1.386 (4)
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.505 (4)	C24—H24	0.9300
C8—C9	1.513 (4)	C25—H25A	0.9600
C8—H8A	0.9700	C25—H25B	0.9600
C8—H8B	0.9700	C25—H25C	0.9600
C9—C10	1.504 (4)	C26—H26A	0.9600
C9—H9	0.9800	C26—H26B	0.9600
C11—C12	1.345 (4)	C26—H26C	0.9600
C11—H11	0.9300

C11—S1—C10	88.95 (14)	C11—C12—C13	127.4 (3)
C4—O1—C25	118.1 (3)	N2—C12—C13	118.5 (2)
C5—O2—C26	116.6 (3)	C14—C13—C18	118.1 (3)
C9—N1—C1	112.8 (2)	C14—C13—C12	120.5 (3)
C9—N1—H1N	108.9 (17)	C18—C13—C12	121.4 (3)
C1—N1—H1N	103.9 (17)	C13—C14—C15	121.3 (3)
C10—N2—C12	111.3 (2)	C13—C14—H14	119.4
N1—C1—C2	114.6 (2)	C15—C14—H14	119.4
N1—C1—C19	109.0 (2)	C16—C15—C14	119.5 (4)
C2—C1—C19	114.2 (2)	C16—C15—H15	120.2
N1—C1—H1	106.1	C14—C15—H15	120.2
C2—C1—H1	106.1	C17—C16—C15	119.7 (3)
C19—C1—H1	106.1	C17—C16—H16	120.2
C7—C2—C3	118.3 (3)	C15—C16—H16	120.2
C7—C2—C1	122.0 (3)	C16—C17—C18	120.8 (4)
C3—C2—C1	119.6 (3)	C16—C17—H17	119.6
C4—C3—C2	121.5 (3)	C18—C17—H17	119.6
C4—C3—H3	119.3	C17—C18—C13	120.7 (3)
C2—C3—H3	119.3	C17—C18—H18	119.7
O1—C4—C3	125.2 (3)	C13—C18—H18	119.7
O1—C4—C5	115.0 (3)	C24—C19—C20	117.9 (3)
C3—C4—C5	119.8 (3)	C24—C19—C1	123.7 (3)
O2—C5—C6	125.2 (3)	C20—C19—C1	118.4 (3)
O2—C5—C4	116.2 (3)	C21—C20—C19	120.7 (3)
C6—C5—C4	118.6 (3)	C21—C20—H20	119.6
C5—C6—C7	121.7 (3)	C19—C20—H20	119.6
C5—C6—H6	119.1	C22—C21—C20	120.5 (4)
C7—C6—H6	119.1	C22—C21—H21	119.7
C2—C7—C6	120.0 (3)	C20—C21—H21	119.7
C2—C7—C8	121.1 (3)	C23—C22—C21	119.3 (3)
C6—C7—C8	118.9 (3)	C23—C22—H22	120.3
C7—C8—C9	111.8 (2)	C21—C22—H22	120.3
C7—C8—H8A	109.2	C22—C23—C24	120.8 (3)
C9—C8—H8A	109.2	C22—C23—H23	119.6
C7—C8—H8B	109.2	C24—C23—H23	119.6
C9—C8—H8B	109.2	C19—C24—C23	120.6 (3)
H8A—C8—H8B	107.9	C19—C24—H24	119.7
N1—C9—C10	110.3 (2)	C23—C24—H24	119.7
N1—C9—C8	113.3 (2)	O1—C25—H25A	109.5
C10—C9—C8	109.5 (2)	O1—C25—H25B	109.5
N1—C9—H9	107.9	H25A—C25—H25B	109.5
C10—C9—H9	107.9	O1—C25—H25C	109.5
C8—C9—H9	107.9	H25A—C25—H25C	109.5
N2—C10—C9	123.1 (2)	H25B—C25—H25C	109.5
N2—C10—S1	114.3 (2)	O2—C26—H26A	109.5
C9—C10—S1	122.6 (2)	O2—C26—H26B	109.5
C12—C11—S1	111.4 (2)	H26A—C26—H26B	109.5
C12—C11—H11	124.3	O2—C26—H26C	109.5
S1—C11—H11	124.3	H26A—C26—H26C	109.5
C11—C12—N2	114.1 (2)	H26B—C26—H26C	109.5

C9—N1—C1—C2	−35.5 (3)	C8—C9—C10—N2	−26.3 (3)
C9—N1—C1—C19	94.0 (3)	N1—C9—C10—S1	27.5 (3)
N1—C1—C2—C7	5.4 (3)	C8—C9—C10—S1	152.8 (2)
C19—C1—C2—C7	−121.4 (3)	C11—S1—C10—N2	0.0 (2)
N1—C1—C2—C3	−172.5 (2)	C11—S1—C10—C9	−179.2 (2)
C19—C1—C2—C3	60.6 (3)	C10—S1—C11—C12	0.3 (2)
C7—C2—C3—C4	−0.3 (4)	S1—C11—C12—N2	−0.4 (3)
C1—C2—C3—C4	177.7 (2)	S1—C11—C12—C13	178.9 (2)
C25—O1—C4—C3	9.3 (5)	C10—N2—C12—C11	0.4 (3)
C25—O1—C4—C5	−170.6 (4)	C10—N2—C12—C13	−179.0 (2)
C2—C3—C4—O1	178.9 (3)	C11—C12—C13—C14	178.3 (3)
C2—C3—C4—C5	−1.2 (4)	N2—C12—C13—C14	−2.4 (4)
C26—O2—C5—C6	−7.4 (4)	C11—C12—C13—C18	−2.7 (4)
C26—O2—C5—C4	173.5 (3)	N2—C12—C13—C18	176.6 (3)
O1—C4—C5—O2	0.4 (4)	C18—C13—C14—C15	−0.2 (4)
C3—C4—C5—O2	−179.6 (2)	C12—C13—C14—C15	178.9 (3)
O1—C4—C5—C6	−178.8 (2)	C13—C14—C15—C16	0.1 (5)
C3—C4—C5—C6	1.3 (4)	C14—C15—C16—C17	0.4 (5)
O2—C5—C6—C7	−179.0 (2)	C15—C16—C17—C18	−0.9 (6)
C4—C5—C6—C7	0.1 (4)	C16—C17—C18—C13	0.9 (5)
C3—C2—C7—C6	1.7 (4)	C14—C13—C18—C17	−0.3 (5)
C1—C2—C7—C6	−176.3 (2)	C12—C13—C18—C17	−179.3 (3)
C3—C2—C7—C8	−178.9 (2)	N1—C1—C19—C24	−101.3 (3)
C1—C2—C7—C8	3.2 (4)	C2—C1—C19—C24	28.4 (4)
C5—C6—C7—C2	−1.6 (4)	N1—C1—C19—C20	78.9 (3)
C5—C6—C7—C8	178.9 (3)	C2—C1—C19—C20	−151.4 (3)
C2—C7—C8—C9	17.6 (4)	C24—C19—C20—C21	−0.2 (5)
C6—C7—C8—C9	−162.9 (2)	C1—C19—C20—C21	179.6 (3)
C1—N1—C9—C10	−179.0 (2)	C19—C20—C21—C22	−0.8 (5)
C1—N1—C9—C8	58.0 (3)	C20—C21—C22—C23	1.9 (6)
C7—C8—C9—N1	−48.1 (3)	C21—C22—C23—C24	−1.9 (5)
C7—C8—C9—C10	−171.6 (2)	C20—C19—C24—C23	0.2 (4)
C12—N2—C10—C9	178.9 (2)	C1—C19—C24—C23	−179.6 (3)
C12—N2—C10—S1	−0.2 (3)	C22—C23—C24—C19	0.9 (5)
N1—C9—C10—N2	−151.6 (2)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄N₂O₂S
M_r	428.53
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	5.9178 (2), 16.6269 (9), 22.8564 (11)
V (Å³)	2248.95 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.32 × 0.16 × 0.13

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.886, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	92668, 4948, 3141
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.109, 1.21
No. of reflections	4948
No. of parameters	285
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.13
Absolute structure	Flack (1983), 2094 Friedel pairs
Absolute structure parameter	0.01 (10)

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

The authors thank Dr Hong Su of the University of Capetown for the data collection and structure refinement.

References

Chakka, S. K., Andersson, P. G., Maguire, G. E. M., Kruger, H. G. & Govender, T. (2010). Eur. J. Org. Chem. pp. 972–980. Web of Science CrossRef Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011a). Acta Cryst. E67, o67. Web of Science CrossRef IUCr Journals Google Scholar
Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011b). Acta Cryst. E67, o1403. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naicker, T., Petzold, K., Singh, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 2859–2867. Web of Science CrossRef CAS Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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