trans-rac-[1-Oxo-2-phenethyl-3-(2-thien­yl)-1,2,3,4-tetra­hydro­isoquinolin-4-yl]methyl 4-methyl­benzene­sulfonate

Akkurt, M.; Öztürk Yıldırım, S.; Bogdanov, M.G.; Kandinska, M.I.; Büyükgüngör, O.

doi:10.1107/S1600536808029309

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages o1955-o1956

doi:10.1107/S1600536808029309

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trans-rac-[1-Oxo-2-phenethyl-3-(2-thienyl)-1,2,3,4-tetrahydroisoquinolin-4-yl]methyl 4-methylbenzenesulfonate

Mehmet Akkurt,^a ^* Sema Öztürk Yıldırım,^a Milen G. Bogdanov,^b Meglena I. Kandinska ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bFaculty of Chemistry, University of Sofia, 1, James Bourchier blvd., 1164 Sofia, Bulgaria, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 9 September 2008; accepted 12 September 2008; online 17 September 2008)

The title compound, C₂₉H₂₇NO₄S₂, was synthesized by reaction of trans-rac-4-(hydroxymethyl)-2-phenethyl-3-(thiophen-2-yl)-3,4-dihydroisoquinolin-1(2H)-one and 4-methylbenzene-1-sulfonyl chloride in the presence of Et₃N in CH₂Cl₂. The relative orientations of the benzene ring (A) of the 3,4-dihydroisoquinolinone ring system, the thiophene ring (B), the benzene ring (C) of the methylbenzene group and the phenyl ring (D) result in the following dihedral angles: A/B = 80.91 (16), A/C = 22.79 (18), A/D = 9.9 (2), B/C = 80.73 (19), B/D = 88.9 (2) and C/D = 29.9 (2)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For chemical background, see: Kandinska et al. (2006 ); Rothweiler et al. (2008 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₉H₂₇NO₄S₂
M_r = 517.66
Triclinic, $[P \overline 1]$
a = 7.2529 (3) Å
b = 8.6727 (4) Å
c = 20.9899 (10) Å
α = 86.021 (4)°
β = 87.396 (4)°
γ = 78.330 (4)°
V = 1289.24 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.58 × 0.52 × 0.48 mm

Data collection

STOE IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.872, T_max = 0.892
24485 measured reflections
5417 independent reflections
4537 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.090
wR(F²) = 0.306
S = 1.36
5417 reflections
328 parameters
H-atom parameters constrained
Δρ_max = 2.04 e Å⁻³
Δρ_min = −1.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O4ⁱ	0.98	2.34	3.285 (3)	161
C12—H12⋯Cg1ⁱⁱ	0.93	2.65	3.567 (4)	168
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z. Cg1 is the centroid of the thiophene ring (S2/C18–C21).

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029309/hb2793sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029309/hb2793Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was synthesized as part of a research project (Kandinska et al., 2006) seeking precursors for the production of new tetrahydroquinolone derivatives with biological activity (Rothweiler et al., 2008).

In the molecule of (I) (Fig.1), the benzene ring A (C10—C15) of 3,4-dihydroisoquinolinone ring system is essentially planar, with an r.m.s. deviation of 0.005 (3) Å for C11 and its other six-membered part is not planar [its Puckering parameters (Cremer & Pople, 1975) are Q_T = 0.444 (3) Å, θ = 118.4 (4) ° and ϕ = 93.4 (4) °]. The thiophene ring B (S2—C18—C21) is almost planar, with an r.m.s. deviation for fitted atoms of 0.004 Å. The rings C (C1—C6) and D (C24—C29) are almost planar, with an r.m.s. deviation for fitted atoms of 0.012 Å and 0.021 Å, respectively. The dihedral angles between the planes of these rings are A/B = 80.91 (16), A/C = 22.79 (18), A/D = 9.9 (2), B/C = 80.73 (19), B/D = 88.9 (2) and C/D = 29.9 (2)°. An interesting feature of the crystal structure is the long C18—C19 bond of 1.594 (3) Å.

The crystal structure of (I) is stabilized by weak intra- and intermolecular C—H···O hydrogen bonds and C—H···π interactions (Table 1 and Fig. 2).

Related literature top

For chemical background, see: Kandinska et al. (2006); Rothweiler et al. (2008). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

Compound(I) was synthesized by reaction between trans-rac-4-(hydroxymethyl)-2-phenethyl-3-(thiophen-2-yl)-3,4-dihydroisoquinolin-1(2H)-one (5.91 g, 0.0163 mol) and 4-methylbenzene-1-sulfonyl chloride (6.22 g, 0.033 mol) in the presence of Et₃N (6.8 ml, 0.049 mol) in CH₂Cl₂. After working up the reaction mixture, compound (I) crystallized as colourless prisms from hexane–ethyl acetate (9:1 v/v) (yield 7.5 g, 89%; m.p. 385–386 K). Elemental analysis, calculated for C₂₉H₂₇NO₄S₂: C 67.29, H 5.26°; found: C 66.90, H 5.45°. IR (KBr) 3000 cm^-1 (C—H), 1647 cm-1 (C=O), 1603 cm-1 (ArH), 1467 cm^-1 (ArH), 1358 cm^-1 (S=O), 1172 cm^-1 (S=O). ¹H NMR (250 MHz, CDCl₃) δ (p.p.m.) = 2.32 (s, 3H, Ph—CH₃), 2.69 (t, 2H, J = 8.3 Hz, Ph—CH₂), 3.05–3.17 (m, 1H, N—CH₂^a), 3.45–3.54 (ddd, 1H, J = 1.3, 5.1 and 10 Hz, -OCH₂—CH), 3.69 (t, 1H, J = 10.3 Hz, -SO₃—CH₂^a), 4.04–4.23 (m, 2H, -SO₃—CH₂^b& N—CH₂^b), 5.10 (d, 1H, J = 0.8 Hz, Th—CH), 6.81 (dd, 1H, J = 3.5 and 4.9 Hz, Th-H), 6.76–6.81 (m, 1H, Ph-H), 7.06 (dd, 1H, J = 1.4 and 4.9 Hz, Th-H), 7.10–7.16 (m, 1H, Ph-H), 7.17–7.23 (m, 3H, H-Ph), 7.24–7.28 (m, 2H, Th-H, Ph-H), 7.28–7.33 (m, 2H, Ph-H), 7.40–7.48 (m, 2H, Ph-H), 7.78 (d, 2H, J = 8.3, Ph-H), 8.08–8.15 (m, 1H, Ph-H). ¹³C NMR (63 MHz, CDCl₃) δ = 162.8, 145.4, 142.7, 138.4,133.4, 132.6, 132.4, 130.1, 129.0, 128.8, 128.7, 128.5, 128.4, 127.8, 126.5,126.4, 125.6, 125.1, 70.0, 56.8, 48.5, 45.8, 34.1, 21.5.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), with 20% probability displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. View of the packing and C—H···O4(x + 1, y, z) hydrogen bonding interactions of (I).

trans-rac-[1-Oxo-2-phenethyl-3-(2-thienyl)-1,2,3,4-tetrahydroisoquinolin-4-yl]methyl 4-methylbenzenesulfonate top

Crystal data top

C₂₉H₂₇NO₄S₂	Z = 2
M_r = 517.66	F(000) = 544
Triclinic, P1	D_x = 1.334 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2529 (3) Å	Cell parameters from 39940 reflections
b = 8.6727 (4) Å	θ = 2.0–27.2°
c = 20.9899 (10) Å	µ = 0.24 mm⁻¹
α = 86.021 (4)°	T = 293 K
β = 87.396 (4)°	Prism, colourless
γ = 78.330 (4)°	0.58 × 0.52 × 0.48 mm
V = 1289.24 (10) Å³

Data collection top

STOE IPDS 2 diffractometer	5417 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	4537 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.026
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.8°, θ_min = 2.0°
ω scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
T_min = 0.872, T_max = 0.892	l = −26→26
24485 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)] = 0.091	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.307	H-atom parameters constrained
S = 1.36	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
5417 reflections	(Δ/σ)_max < 0.001
328 parameters	Δρ_max = 2.04 e Å⁻³
0 restraints	Δρ_min = −1.13 e Å⁻³

Crystal data top

C₂₉H₂₇NO₄S₂	γ = 78.330 (4)°
M_r = 517.66	V = 1289.24 (10) Å³
Triclinic, P1	Z = 2
a = 7.2529 (3) Å	Mo Kα radiation
b = 8.6727 (4) Å	µ = 0.24 mm⁻¹
c = 20.9899 (10) Å	T = 293 K
α = 86.021 (4)°	0.58 × 0.52 × 0.48 mm
β = 87.396 (4)°

Data collection top

STOE IPDS 2 diffractometer	5417 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	4537 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.892	R_int = 0.026
24485 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.091	0 restraints
wR(F²) = 0.307	H-atom parameters constrained
S = 1.36	Δρ_max = 2.04 e Å⁻³
5417 reflections	Δρ_min = −1.13 e Å⁻³
328 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.03368 (13)	0.63784 (11)	0.12882 (4)	0.0578 (3)
S2	−0.29088 (17)	0.44287 (14)	0.45285 (5)	0.0773 (4)
O1	−0.0694 (5)	0.7915 (3)	0.11138 (12)	0.0735 (10)
O2	0.2311 (4)	0.6020 (4)	0.11655 (14)	0.0790 (10)
O3	0.0077 (4)	0.6048 (3)	0.20349 (10)	0.0617 (8)
O4	−0.6871 (3)	0.6854 (3)	0.33989 (14)	0.0648 (9)
N1	−0.3988 (3)	0.5354 (3)	0.31787 (12)	0.0412 (7)
C1	−0.0691 (5)	0.4960 (4)	0.09658 (15)	0.0562 (10)
C2	0.0407 (6)	0.3512 (5)	0.0825 (2)	0.0755 (16)
C3	−0.0429 (8)	0.2421 (6)	0.0565 (3)	0.0875 (17)
C4	−0.2337 (7)	0.2725 (5)	0.04587 (19)	0.0735 (13)
C5	−0.3386 (6)	0.4142 (6)	0.0618 (2)	0.0726 (14)
C6	−0.2604 (5)	0.5268 (5)	0.08621 (18)	0.0635 (11)
C7	−0.3220 (11)	0.1501 (8)	0.0164 (3)	0.103 (2)
C8	−0.1329 (4)	0.7120 (3)	0.23876 (13)	0.0446 (8)
C9	−0.1186 (3)	0.6570 (3)	0.30901 (12)	0.0351 (7)
C10	−0.2305 (3)	0.7881 (3)	0.34681 (12)	0.0359 (7)
C11	−0.1458 (4)	0.9049 (3)	0.36804 (15)	0.0451 (8)
C12	−0.2536 (6)	1.0252 (4)	0.40202 (17)	0.0569 (10)
C13	−0.4427 (5)	1.0301 (4)	0.41386 (17)	0.0585 (10)
C14	−0.5271 (4)	0.9165 (4)	0.39273 (17)	0.0532 (9)
C15	−0.4213 (4)	0.7938 (3)	0.35887 (13)	0.0397 (7)
C16	−0.5138 (4)	0.6687 (4)	0.33822 (14)	0.0430 (8)
C17	−0.1943 (3)	0.5055 (3)	0.32432 (12)	0.0360 (7)
C18	−0.1405 (3)	0.4301 (3)	0.38941 (13)	0.0376 (7)
C19	0.0641 (3)	0.3302 (3)	0.40474 (9)	0.0283 (6)
C20	0.0312 (6)	0.2882 (5)	0.47633 (19)	0.0633 (11)
C21	−0.1398 (6)	0.3405 (4)	0.50120 (17)	0.0648 (13)
C22	−0.4795 (4)	0.3999 (4)	0.30376 (15)	0.0495 (9)
C23	−0.4857 (6)	0.3814 (5)	0.23322 (17)	0.0619 (11)
C24	−0.5652 (5)	0.2386 (4)	0.21943 (15)	0.0513 (9)
C25	−0.4571 (6)	0.1171 (5)	0.1868 (2)	0.0683 (12)
C26	−0.5350 (8)	−0.0092 (5)	0.1723 (3)	0.0870 (18)
C27	−0.7133 (8)	−0.0202 (5)	0.1926 (3)	0.090 (2)
C28	−0.8215 (7)	0.1004 (7)	0.2275 (3)	0.092 (2)
C29	−0.7476 (6)	0.2293 (5)	0.2385 (2)	0.0688 (14)
H2	0.16880	0.32830	0.09050	0.0910*
H3	0.03060	0.14590	0.04590	0.1050*
H5	−0.46770	0.43490	0.05570	0.0870*
H6	−0.33490	0.62340	0.09580	0.0760*
H7A	−0.35930	0.18720	−0.02620	0.1540*
H7B	−0.43050	0.13350	0.04180	0.1540*
H7C	−0.23190	0.05260	0.01500	0.1540*
H8A	−0.25770	0.71120	0.22420	0.0540*
H8B	−0.11040	0.81860	0.23240	0.0540*
H9	0.01370	0.63840	0.32080	0.0420*
H11	−0.01820	0.90240	0.35960	0.0540*
H12	−0.19770	1.10280	0.41680	0.0680*
H13	−0.51390	1.11130	0.43640	0.0700*
H14	−0.65510	0.92090	0.40090	0.0640*
H17	−0.13800	0.43030	0.29270	0.0430*
H19	0.17110	0.30490	0.37840	0.0340*
H20	0.12680	0.22890	0.50100	0.0760*
H21	−0.17070	0.31930	0.54400	0.0780*
H22A	−0.60630	0.41290	0.32220	0.0590*
H22B	−0.40510	0.30460	0.32370	0.0590*
H23A	−0.35940	0.37080	0.21450	0.0740*
H23B	−0.56290	0.47550	0.21340	0.0740*
H25	−0.33280	0.11990	0.17470	0.0820*
H26	−0.46430	−0.08790	0.14830	0.1040*
H27	−0.76280	−0.10670	0.18340	0.1070*
H28	−0.94180	0.09300	0.24300	0.1100*
H29	−0.82200	0.31230	0.25920	0.0830*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0696 (6)	0.0664 (6)	0.0362 (4)	−0.0129 (4)	0.0092 (3)	−0.0030 (3)
S2	0.0886 (8)	0.0798 (7)	0.0602 (6)	−0.0132 (5)	0.0112 (5)	−0.0016 (5)
O1	0.109 (2)	0.0652 (16)	0.0445 (13)	−0.0169 (14)	0.0046 (13)	0.0039 (11)
O2	0.0700 (16)	0.110 (2)	0.0585 (16)	−0.0238 (15)	0.0145 (13)	−0.0087 (15)
O3	0.0799 (16)	0.0613 (13)	0.0357 (11)	0.0033 (11)	0.0104 (10)	−0.0042 (9)
O4	0.0301 (10)	0.0819 (17)	0.0867 (18)	−0.0192 (10)	0.0030 (10)	−0.0149 (14)
N1	0.0336 (10)	0.0471 (12)	0.0478 (13)	−0.0179 (9)	−0.0014 (9)	−0.0082 (10)
C1	0.0664 (19)	0.0632 (18)	0.0348 (13)	−0.0045 (15)	0.0080 (13)	−0.0060 (12)
C2	0.070 (2)	0.077 (3)	0.074 (3)	0.0044 (19)	−0.0009 (19)	−0.023 (2)
C3	0.094 (3)	0.076 (3)	0.086 (3)	0.007 (2)	−0.009 (2)	−0.027 (2)
C4	0.100 (3)	0.078 (2)	0.0468 (18)	−0.028 (2)	0.0008 (18)	−0.0057 (17)
C5	0.061 (2)	0.098 (3)	0.057 (2)	−0.0111 (19)	−0.0052 (16)	−0.0051 (19)
C6	0.065 (2)	0.067 (2)	0.0523 (18)	0.0027 (16)	−0.0040 (15)	−0.0067 (15)
C7	0.141 (5)	0.107 (4)	0.074 (3)	−0.051 (4)	−0.013 (3)	−0.017 (3)
C8	0.0441 (13)	0.0495 (14)	0.0388 (14)	−0.0091 (11)	0.0072 (11)	0.0015 (11)
C9	0.0308 (10)	0.0401 (12)	0.0361 (12)	−0.0118 (9)	0.0023 (9)	−0.0035 (9)
C10	0.0378 (12)	0.0361 (12)	0.0359 (12)	−0.0130 (9)	−0.0006 (9)	−0.0004 (9)
C11	0.0488 (14)	0.0408 (13)	0.0491 (15)	−0.0170 (11)	−0.0061 (12)	−0.0009 (11)
C12	0.082 (2)	0.0363 (13)	0.0566 (18)	−0.0194 (14)	−0.0076 (16)	−0.0060 (12)
C13	0.077 (2)	0.0389 (14)	0.0564 (18)	−0.0045 (14)	0.0073 (16)	−0.0088 (13)
C14	0.0483 (15)	0.0509 (16)	0.0569 (18)	−0.0030 (12)	0.0096 (13)	−0.0064 (13)
C15	0.0369 (12)	0.0394 (13)	0.0427 (13)	−0.0078 (10)	0.0009 (10)	−0.0020 (10)
C16	0.0323 (12)	0.0529 (15)	0.0464 (14)	−0.0140 (10)	−0.0004 (10)	−0.0055 (12)
C17	0.0341 (11)	0.0405 (12)	0.0360 (12)	−0.0132 (9)	0.0024 (9)	−0.0066 (9)
C18	0.0398 (12)	0.0363 (12)	0.0384 (13)	−0.0117 (9)	0.0022 (10)	−0.0041 (9)
C19	0.0316 (10)	0.0348 (11)	0.0186 (9)	−0.0109 (8)	−0.0072 (7)	0.0149 (8)
C20	0.073 (2)	0.0623 (19)	0.0561 (19)	−0.0200 (16)	−0.0158 (16)	0.0135 (15)
C21	0.102 (3)	0.0588 (19)	0.0415 (16)	−0.0379 (19)	0.0130 (17)	−0.0047 (14)
C22	0.0547 (16)	0.0554 (16)	0.0473 (15)	−0.0309 (13)	−0.0040 (12)	−0.0044 (12)
C23	0.085 (2)	0.065 (2)	0.0466 (17)	−0.0408 (18)	−0.0047 (16)	−0.0017 (15)
C24	0.0588 (17)	0.0537 (16)	0.0467 (16)	−0.0195 (13)	−0.0095 (13)	−0.0098 (13)
C25	0.066 (2)	0.074 (2)	0.065 (2)	−0.0102 (17)	−0.0058 (17)	−0.0131 (18)
C26	0.115 (4)	0.054 (2)	0.091 (3)	−0.002 (2)	−0.018 (3)	−0.032 (2)
C27	0.112 (4)	0.058 (2)	0.110 (4)	−0.036 (2)	−0.027 (3)	−0.014 (2)
C28	0.084 (3)	0.102 (4)	0.106 (4)	−0.057 (3)	−0.009 (3)	−0.012 (3)
C29	0.064 (2)	0.068 (2)	0.081 (3)	−0.0231 (17)	0.0036 (18)	−0.026 (2)

Geometric parameters (Å, º) top

S1—O1	1.422 (3)	C24—C25	1.383 (5)
S1—O2	1.418 (3)	C24—C29	1.381 (6)
S1—O3	1.583 (2)	C25—C26	1.387 (7)
S1—C1	1.749 (4)	C26—C27	1.363 (8)
S2—C18	1.678 (3)	C27—C28	1.403 (8)
S2—C21	1.613 (4)	C28—C29	1.371 (7)
O3—C8	1.448 (4)	C2—H2	0.9300
O4—C16	1.235 (4)	C3—H3	0.9300
N1—C16	1.364 (4)	C5—H5	0.9300
N1—C17	1.464 (3)	C6—H6	0.9300
N1—C22	1.468 (4)	C7—H7A	0.9600
C1—C2	1.387 (5)	C7—H7B	0.9600
C1—C6	1.383 (5)	C7—H7C	0.9600
C2—C3	1.376 (7)	C8—H8A	0.9700
C3—C4	1.381 (8)	C8—H8B	0.9700
C4—C5	1.363 (7)	C9—H9	0.9800
C4—C7	1.524 (8)	C11—H11	0.9300
C5—C6	1.363 (6)	C12—H12	0.9300
C8—C9	1.520 (4)	C13—H13	0.9300
C9—C10	1.508 (4)	C14—H14	0.9300
C9—C17	1.532 (3)	C17—H17	0.9800
C10—C11	1.393 (4)	C19—H19	0.9300
C10—C15	1.387 (4)	C20—H20	0.9300
C11—C12	1.390 (5)	C21—H21	0.9300
C12—C13	1.375 (6)	C22—H22A	0.9700
C13—C14	1.368 (5)	C22—H22B	0.9700
C14—C15	1.397 (4)	C23—H23A	0.9700
C15—C16	1.484 (4)	C23—H23B	0.9700
C17—C18	1.506 (4)	C25—H25	0.9300
C18—C19	1.594 (3)	C26—H26	0.9300
C19—C20	1.541 (4)	C27—H27	0.9300
C20—C21	1.328 (6)	C28—H28	0.9300
C22—C23	1.504 (5)	C29—H29	0.9300
C23—C24	1.518 (6)

O1—S1—O2	119.4 (2)	C3—C2—H2	121.00
O1—S1—O3	108.65 (15)	C2—C3—H3	119.00
O1—S1—C1	109.86 (18)	C4—C3—H3	119.00
O2—S1—O3	104.97 (17)	C4—C5—H5	119.00
O2—S1—C1	109.28 (18)	C6—C5—H5	119.00
O3—S1—C1	103.47 (15)	C1—C6—H6	120.00
C18—S2—C21	94.67 (18)	C5—C6—H6	120.00
S1—O3—C8	119.2 (2)	C4—C7—H7A	109.00
C16—N1—C17	122.1 (2)	C4—C7—H7B	109.00
C16—N1—C22	119.8 (2)	C4—C7—H7C	109.00
C17—N1—C22	116.4 (2)	H7A—C7—H7B	109.00
S1—C1—C2	120.0 (3)	H7A—C7—H7C	110.00
S1—C1—C6	120.1 (3)	H7B—C7—H7C	109.00
C2—C1—C6	119.9 (4)	O3—C8—H8A	110.00
C1—C2—C3	118.9 (4)	O3—C8—H8B	110.00
C2—C3—C4	121.4 (5)	C9—C8—H8A	110.00
C3—C4—C5	118.3 (4)	C9—C8—H8B	110.00
C3—C4—C7	120.2 (5)	H8A—C8—H8B	109.00
C5—C4—C7	121.5 (5)	C8—C9—H9	109.00
C4—C5—C6	122.1 (4)	C10—C9—H9	109.00
C1—C6—C5	119.4 (4)	C17—C9—H9	109.00
O3—C8—C9	107.6 (2)	C10—C11—H11	120.00
C8—C9—C10	107.4 (2)	C12—C11—H11	120.00
C8—C9—C17	112.4 (2)	C11—C12—H12	120.00
C10—C9—C17	109.79 (19)	C13—C12—H12	120.00
C9—C10—C11	120.9 (2)	C12—C13—H13	120.00
C9—C10—C15	119.1 (2)	C14—C13—H13	120.00
C11—C10—C15	120.0 (2)	C13—C14—H14	120.00
C10—C11—C12	119.4 (3)	C15—C14—H14	120.00
C11—C12—C13	120.3 (3)	N1—C17—H17	108.00
C12—C13—C14	120.6 (3)	C9—C17—H17	108.00
C13—C14—C15	120.1 (3)	C18—C17—H17	108.00
C10—C15—C14	119.6 (3)	C18—C19—H19	131.00
C10—C15—C16	121.0 (2)	C20—C19—H19	131.00
C14—C15—C16	119.4 (3)	C19—C20—H20	122.00
O4—C16—N1	122.1 (3)	C21—C20—H20	122.00
O4—C16—C15	121.0 (3)	S2—C21—H21	122.00
N1—C16—C15	117.0 (3)	C20—C21—H21	122.00
N1—C17—C9	110.8 (2)	N1—C22—H22A	109.00
N1—C17—C18	110.7 (2)	N1—C22—H22B	109.00
C9—C17—C18	112.6 (2)	C23—C22—H22A	109.00
S2—C18—C17	123.12 (18)	C23—C22—H22B	109.00
S2—C18—C19	113.48 (18)	H22A—C22—H22B	108.00
C17—C18—C19	123.4 (2)	C22—C23—H23A	109.00
C18—C19—C20	98.8 (2)	C22—C23—H23B	109.00
C19—C20—C21	117.0 (3)	C24—C23—H23A	109.00
S2—C21—C20	116.0 (3)	C24—C23—H23B	109.00
N1—C22—C23	112.6 (3)	H23A—C23—H23B	108.00
C22—C23—C24	111.9 (3)	C24—C25—H25	120.00
C23—C24—C25	120.5 (3)	C26—C25—H25	120.00
C23—C24—C29	120.4 (3)	C25—C26—H26	119.00
C25—C24—C29	119.1 (4)	C27—C26—H26	119.00
C24—C25—C26	119.6 (4)	C26—C27—H27	120.00
C25—C26—C27	121.2 (5)	C28—C27—H27	120.00
C26—C27—C28	119.3 (5)	C27—C28—H28	120.00
C27—C28—C29	119.2 (5)	C29—C28—H28	120.00
C24—C29—C28	121.5 (4)	C24—C29—H29	119.00
C1—C2—H2	120.00	C28—C29—H29	119.00

O1—S1—O3—C8	11.0 (3)	C10—C9—C17—N1	50.8 (3)
O2—S1—O3—C8	139.7 (3)	C8—C9—C10—C11	−90.2 (3)
C1—S1—O3—C8	−105.8 (3)	C8—C9—C17—C18	166.7 (2)
O1—S1—C1—C2	152.1 (3)	C8—C9—C17—N1	−68.7 (3)
O2—S1—C1—C2	19.3 (4)	C9—C10—C11—C12	179.1 (3)
O3—S1—C1—C2	−92.1 (3)	C15—C10—C11—C12	0.9 (4)
O1—S1—C1—C6	−29.2 (3)	C11—C10—C15—C14	−0.5 (4)
O2—S1—C1—C6	−161.9 (3)	C9—C10—C15—C16	3.3 (4)
O3—S1—C1—C6	86.7 (3)	C11—C10—C15—C16	−178.4 (3)
C21—S2—C18—C19	0.4 (2)	C9—C10—C15—C14	−178.7 (3)
C18—S2—C21—C20	0.0 (3)	C10—C11—C12—C13	−0.9 (5)
C21—S2—C18—C17	−179.7 (2)	C11—C12—C13—C14	0.4 (5)
S1—O3—C8—C9	−176.8 (2)	C12—C13—C14—C15	0.1 (5)
C17—N1—C16—C15	8.5 (4)	C13—C14—C15—C10	−0.1 (5)
C17—N1—C16—O4	−171.1 (3)	C13—C14—C15—C16	178.0 (3)
C22—N1—C16—O4	−6.6 (4)	C10—C15—C16—O4	−168.7 (3)
C16—N1—C17—C18	85.2 (3)	C14—C15—C16—N1	−166.3 (3)
C17—N1—C22—C23	−89.1 (3)	C14—C15—C16—O4	13.4 (4)
C16—N1—C17—C9	−40.4 (3)	C10—C15—C16—N1	11.7 (4)
C22—N1—C16—C15	173.0 (3)	N1—C17—C18—C19	158.4 (2)
C16—N1—C22—C23	105.6 (3)	N1—C17—C18—S2	−21.5 (3)
C22—N1—C17—C18	−79.8 (3)	C9—C17—C18—C19	−77.0 (3)
C22—N1—C17—C9	154.6 (2)	C9—C17—C18—S2	103.1 (2)
C6—C1—C2—C3	1.9 (6)	S2—C18—C19—C20	−0.6 (3)
C2—C1—C6—C5	−0.4 (6)	C17—C18—C19—C20	179.5 (3)
S1—C1—C2—C3	−179.3 (4)	C18—C19—C20—C21	0.6 (4)
S1—C1—C6—C5	−179.2 (3)	C19—C20—C21—S2	−0.4 (5)
C1—C2—C3—C4	−1.8 (8)	N1—C22—C23—C24	178.7 (3)
C2—C3—C4—C5	0.0 (8)	C22—C23—C24—C25	−118.9 (4)
C2—C3—C4—C7	179.4 (5)	C22—C23—C24—C29	62.1 (5)
C7—C4—C5—C6	−177.8 (4)	C23—C24—C25—C26	−177.3 (4)
C3—C4—C5—C6	1.6 (7)	C29—C24—C25—C26	1.8 (6)
C4—C5—C6—C1	−1.4 (6)	C23—C24—C29—C28	−178.9 (4)
O3—C8—C9—C17	−72.4 (3)	C25—C24—C29—C28	2.0 (6)
O3—C8—C9—C10	166.8 (2)	C24—C25—C26—C27	−3.6 (8)
C8—C9—C10—C15	88.0 (3)	C25—C26—C27—C28	1.5 (9)
C10—C9—C17—C18	−73.8 (2)	C26—C27—C28—C29	2.2 (9)
C17—C9—C10—C11	147.2 (2)	C27—C28—C29—C24	−4.0 (8)
C17—C9—C10—C15	−34.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O4ⁱ	0.98	2.34	3.285 (3)	161
C12—H12···Cg1ⁱⁱ	0.93	2.65	3.567 (4)	168

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

Experimental details

Crystal data
Chemical formula	C₂₉H₂₇NO₄S₂
M_r	517.66
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.2529 (3), 8.6727 (4), 20.9899 (10)
α, β, γ (°)	86.021 (4), 87.396 (4), 78.330 (4)
V (Å³)	1289.24 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.58 × 0.52 × 0.48

Data collection
Diffractometer	STOE IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.872, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	24485, 5417, 4537
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.091, 0.307, 1.36
No. of reflections	5417
No. of parameters	328
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.04, −1.13

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O4ⁱ	0.98	2.34	3.285 (3)	161
C12—H12···Cg1ⁱⁱ	0.93	2.65	3.567 (4)	168

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kandinska, M. I., Kozekov, I. D. & Palamareva, M. D. (2006). Molecules, 11, 403–414. Web of Science CrossRef PubMed CAS Google Scholar
Rothweiler, U., Czarna, A., Krajewski, M., Ciombor, J., Kalinski, C., Khazak, V., Ross, G., Skobeleva, N., Weber, L. & Holak, T. A. (2008). Chem. Med. Chem. 3, 1118–1128. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar

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Volume 64| Part 10| October 2008| Pages o1955-o1956

doi:10.1107/S1600536808029309

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

trans-rac-[1-Oxo-2-phenethyl-3-(2-thien­yl)-1,2,3,4-tetra­hydro­isoquinolin-4-yl]methyl 4-methyl­benzene­sulfonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

trans-rac-[1-Oxo-2-phenethyl-3-(2-thienyl)-1,2,3,4-tetrahydroisoquinolin-4-yl]methyl 4-methylbenzenesulfonate