2-[(1R,3S)-6,7-Dimeth-oxy-1-phenyl-1,2,3,4-tetra-hydro-isoquinolin-3-yl]-4-phenyl-1,3-thia-zole.

In the title compound, C(26)H(24)N(2)O(2)S, the dihedral angle between the thia-zole ring and the adjacent phenyl ring is 3.02 (15)°. The N-containing six-membered ring of the tetra-hydro-isoquinoline unit adopts a half-chair conformation. The dihedral angle between the least-squares plane of the tetra-hydro-isoquinoline ring system and its nearest phenyl ring is 76.90 (13)°. No classical hydrogen bonds nor π-π inter-actions were found in the crystal structure.

Related literature

For reactions associated with TIQ ligands, see: Chakka et al. (2010 ▶); n class="Chemical">Naicker et al. (2010 ▶). For related structures, see: Naicker et al. (2011a ▶,b ▶).

Experimental

Crystal data

C26H24N2O2S

M = 428.53

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.109

S = 1.21

4948 reflections

285 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Absolute structure: Flack (1983 ▶), 2094 Friedel pairs

Flack parameter: 0.01 (10)

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DEn class="Chemical">NZO-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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811037494/is2779sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037494/is2779Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037494/is2779Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H24N2O2S	F(000) = 904
Mr = 428.53	Dx = 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

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

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(Fo2) + (0.0259P)2 + 0.4897P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109	(Δ/σ)max = 0.001
S = 1.21	Δρmax = 0.18 e Å−3
4948 reflections	Δρmin = −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	Flack parameter: 0.01 (10)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)