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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Sep 30;67(Pt 10):o2722. doi: 10.1107/S1600536811037494

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, Glenn E M Maguire b,*
PMCID: PMC3201443  PMID: 22065627

Abstract

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 ▶).graphic file with name e-67-o2722-scheme1.jpg

Experimental

Crystal data

  • C26H24N2O2S

  • M r = 428.53

  • Orthorhombic, Inline graphic

  • 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: 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.

Supplementary Material

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

e-67-o2722-sup1.cif (22.7KB, cif)

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

e-67-o2722-Isup2.hkl (242.4KB, hkl)

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

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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, Rf = 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.

Refinement

All H atoms, except atom H1N, were placed in idealized positions (C—H = 0.93–0.97 Å) and refined using a riding model, with Uiso(H) set at 1.2 or 1.5 times those of their parent atoms. The H1N was refined freely [N1—H1N = 0.927 (17) Å].

Figures

Fig. 1.

Fig. 1.

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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.

Crystal data

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
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Data collection

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
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Refinement

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)
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Special details

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

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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2779).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-67-o2722-sup1.cif (22.7KB, cif)

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

e-67-o2722-Isup2.hkl (242.4KB, hkl)

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

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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