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Acta Cryst.(2003). E59, o1293±o1295 DOI: 10.1107/S1600536803017446 Victor B. Rybakovet al. C18H17NOS

o1293

organic papers

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

2-(5-Methyl-4-phenyl-1,3-thiazol-2-yl)-1-phenylethanol

Victor B. Rybakov,a* Antonina Yu. Liakina,b Inna S. Popova,b

Andrey A. Formanovskyband Leonid A. Aslanova

aDepartment of Chemistry, Moscow State

University, 119992 Moscow, Russian Federation, andbM. M. Shemyakin and Yu. A.

Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 117781 Moscow, Russian Federation

Correspondence e-mail: rybakov@biocryst.phys.msu.su

Key indicators Single-crystal X-ray study

T= 293 K

Mean(C±C) = 0.003 AÊ

Rfactor = 0.040

wRfactor = 0.116

Data-to-parameter ratio = 15.4

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2003 International Union of Crystallography Printed in Great Britain ± all rights reserved

The title compound, C18H17NOS, (2), is the product of substitution at the methyl group, in the 2-position of 2,5-dimethyl-4-phenylthiazole, with benzaldehyde. Molecules of (2) form extended chains through OÐH N hydrogen bonds.

Comment

The metallation of 2,5-dimethyl-4-phenylthiazole by butyl-lithium can generate anionic methyl groups at positions 2 and 5. The title structure, (2), is the product of metallation and the subsequent reaction of the anion with benzaldehyde, and was prepared according to the Scheme below.

The 5-membered heterocycle (S1/C2/N3/C4/C5) (Fig. 1) is nearly planar and there is conjugation between it and the attached phenyl ring (C6±C11), the dihedral angle being 6.83 (11). An O13ÐH131 N3 intermolecular hydrogen

bond [H131 N3i= 1.96 (4) AÊ, O13 N3i= 2.831 (2) AÊ and O13ÐH131 N3i = 179 (3); symmetry code: (i) x, 1

2ÿy,

zÿ1

2] links the molecules in the crystal into extended chains.

Experimental

Solvents were dried and distilled under an inert atmosphere. The starting thiazole, (1), was prepared from thioacetamide and 2-bromo-1-phenylpropanone using the procedure of Hantch (1889). The reaction was carried out under an inert atmosphere (dry Argon). The 1H NMR spectrum of (2) was recorded on a Bruker AMX-400. The melting point was determined on a hot-stage BoeÈtius apparatus. BuLi in C6H14(6 ml, 1.6Msolution) was added to a solution of thiazole (1) (1 g, 5.3 mmol) in 20 ml Et2O/4 ml C4H8O for 10 min at 203 K (dry CO2/C7H8). Benzaldehyde (0.67 g, 6 mmol) in 2 ml of C4H8O was added dropwise to the reaction mixture after 30 min of stirring at 203 K. Then 10 ml of 1Maqueous citric acid were added after 30 min of stirring and the reaction mixture was left to warm to room temperature; it was then washed with water and brine, dried over Na2SO4and ®ltered. The solvent was evaporatedin vacuoand 20 ml of C6H14was added to the resulting yellow oil; after 15 min of heating the mixture was cooled, yielding 0.5 g (60%) of a white precipitate. The product was recrystallized from CH2Cl2/C6H14, m.p. 363±365 K. 1H NMR (CDCl

3, 400 MHz, p.p.m.): 7.64 (d, 2H, Ph), 7.43 (t, 4H, Ph), 7,35 (t, 3H, Ph), 7.28 (d, 1H, Ph), 5.19 (dd, 1H, CH), 3.30 (dd, 1H, CH2,J= 4.5 MHz), 3.25 (dd, 1H, CH2,J= 8.5 MHz), 2.53 (s, 3H, CH3).

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Victor B. Rybakovet al. C18H17NOS Acta Cryst.(2003). E59, o1293±o1295

Crystal data

C18H17NOS

Mr= 295.39

Monoclinic,P21=c a= 6.2820 (9) AÊ

b= 28.836 (4) AÊ

c= 8.4583 (13) AÊ

= 97.560 (10)

V= 1518.9 (4) AÊ3

Z= 4

Dx= 1.292 Mg mÿ3

CuKradiation Cell parameters from 25

re¯ections

= 33±35 = 1.86 mmÿ1

T= 293 (2) K Prism, colourless 0.300.300.30 mm

Data collection

Enraf±Nonius CAD-4 diffractometer Non-pro®led!/2scans Absorption correction: none 3201 measured re¯ections 2997 independent re¯ections 2613 re¯ections withI> 2(I)

Rint= 0.021

max= 74.9

h=ÿ7!7

k= 0!36

l= 0!9

1 standard re¯ection every 226 re¯ections frequency: 49 min intensity decay: 2%

Re®nement

Re®nement onF2

R[F2> 2(F2)] = 0.040

wR(F2) = 0.116

S= 1.05 2997 re¯ections 195 parameters

H atoms treated by a mixture of independent and constrained re®nement

w= 1/[2(F

o2) + (0.0712P)2

+ 0.2241P]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.001

max= 0.31 e AÊÿ3

min=ÿ0.28 e AÊÿ3

Table 1

Selected geometric parameters (AÊ,).

S1ÐC2 1.7126 (17) S1ÐC5 1.7270 (16) C2ÐN3 1.299 (2) C2ÐC12 1.505 (2) N3ÐC4 1.395 (2) C4ÐC5 1.375 (2) C4ÐC6 1.481 (2) C5ÐC51 1.497 (2) C6ÐC7 1.387 (3) C6ÐC11 1.395 (3) C7ÐC8 1.386 (3) C8ÐC9 1.373 (4)

C9ÐC10 1.375 (4) C10ÐC11 1.385 (3) C12ÐC13 1.535 (2) C13ÐO13 1.4203 (19) C13ÐC14 1.517 (2) O13ÐH131 0.87 (3) C14ÐC19 1.385 (2) C14ÐC15 1.388 (2) C15ÐC16 1.389 (3) C16ÐC17 1.373 (4) C17ÐC18 1.375 (3) C18ÐC19 1.387 (3) C2ÐS1ÐC5 90.68 (8)

N3ÐC2ÐC12 123.73 (15) N3ÐC2ÐS1 114.11 (12) C12ÐC2ÐS1 122.16 (12) C2ÐN3ÐC4 111.88 (14) C5ÐC4ÐN3 114.35 (14) C5ÐC4ÐC6 127.76 (15) N3ÐC4ÐC6 117.89 (15) C4ÐC5ÐC51 133.52 (16) C4ÐC5ÐS1 108.97 (12) C51ÐC5ÐS1 117.41 (13) C7ÐC6ÐC11 117.30 (17) C7ÐC6ÐC4 122.51 (17) C11ÐC6ÐC4 120.19 (16) C8ÐC7ÐC6 121.0 (2) C9ÐC8ÐC7 121.1 (2)

C8ÐC9ÐC10 118.8 (2) C9ÐC10ÐC11 120.6 (2) C10ÐC11ÐC6 121.2 (2) C2ÐC12ÐC13 112.99 (13) O13ÐC13ÐC14 111.21 (13) O13ÐC13ÐC12 108.40 (13) C14ÐC13ÐC12 110.66 (12) C13ÐO13ÐH131 107 (2) C19ÐC14ÐC15 118.74 (16) C19ÐC14ÐC13 121.07 (15) C15ÐC14ÐC13 120.19 (15) C14ÐC15ÐC16 120.40 (19) C17ÐC16ÐC15 120.3 (2) C16ÐC17ÐC18 119.68 (19) C17ÐC18ÐC19 120.4 (2) C14ÐC19ÐC18 120.43 (19)

Table 2

Hydrogen-bonding geometry (AÊ,).

DÐH A DÐH H A D A DÐH A

O13ÐH131 N3i 0.87 (4) 1.96 (4) 2.831 (2) 179 (3) Symmetry code: (i)x;1

2ÿy;zÿ12.

The hydroxyl H atom was re®ned isotropically to give an OÐH bond length of 0.87 (3) AÊ. H atoms bonded to C atoms were included in calculated positions and re®ned in the riding-motion approxim-ation (CÐH = 0.93±0.98 AÊ), withUiso= 1.2Ueq(1.5Ueqfor methyl) of the carrier atom.

Data collection: CAD-4 EXPRESS (Enraf±Nonius, 1994); cell re®nement:CAD-4EXPRESS(Enraf±Nonius, 1994); data reduction:

XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve struc-ture:SHELXS97 (Sheldrick, 1997); program(s) used to re®ne struc-ture: SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP-3

for Windows(Farrugia, 2003) andPLUTON97 (Spek, 1997); software used to prepare material for publication:WinGXpublication routines (Farrugia, 2003).

The authors are indebted to the Russian Foundation for Basic Research for covering the licence fee for use of the Cambridge Structural Database (project No. 02-07-90322).

References

Enraf±Nonius (1994).CAD-4Software. Version 5.0. Enraf±Nonius, Delft, The Netherlands.

Farrugia, L. J. (2003). WinGXandORTEP-3 for Windows. University of Glasgow, Scotland.

Figure 1

ORTEP-3 (Farrugia, 2003) plot of the molecule of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as spheres of arbitrary radius.

Figure 2

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Hantch, A. (1889).Liebigs Ann. Chem.250, 257±266..

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Ger-many.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.

Spek, A. L. (1997).PLUTON97. University of Utrecht, The Netherlands.

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Acta Cryst. (2003). E59, o1293–o1295

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Acta Cryst. (2003). E59, o1293–o1295 [doi:10.1107/S1600536803017446]

2-(5-Methyl-4-phenyl-1,3-thiazol-2-yl)-1-phenylethanol

Victor B. Rybakov, Antonina Yu. Liakina, Inna S. Popova, Andrey A. Formanovsky and Leonid A.

Aslanov

S1. Comment

The metallation of 2,5-dimethyl-4-phenylthiazole by butyllithium can generate anionic methyl groups at positions 2 and

5. The title structure, (2), is the product metallation and the subsequent reaction of the anion with benzaldehyde and was

prepared in according to the Scheme below.

The 5-membered heterocycle (S1/C2/N3/C4/C5) is nearly planar and there is conjugation between it and the phenyl ring

(C6–C11), the dihedral angle being 6.83 (11)°. The O13–H131···N3 intermolecular hydrogen bond [H131···N3i = 1.96 (4)

Å, O13···N3i = 2.831 (2) Å and O13–H131···N3i = 179 (3)°; symmetry code: (i) x, 1/2 − y, z − 1/2] links the molecules in

the crystal into extended chains.

S2. Experimental

Solvents were dried and distilled under an inert atmosphere. The starting thiazole, (1), was prepared from thioacetamide

and 2-bromo-1-phenylpropanone using th procedure of Hantch (1889). The reaction was carried out under an inert

atmosphere (dry Argon). The 1H NMR spectrum of (2) was recorded on a Bruker AMX-400. The melting point was

determined on a hot-stage Boëtius apparatus. BuLi in C6H14 (6 ml, 1.6 M solution) was added to a solution of thiazole (1)

(1 g, 5.3 mmol) in 20 ml Et2O/4 ml C4H8O for 10 min at 203 K (dry CO2/C6H6). Benzaldehyde (0.67 g, 6 mmol) in 2 ml

of C4H8O was added dropwise to the reaction mixture after 30 min of stirring at 203 K. Then 10 ml of 1 M aqueous citric

acid was added after 30 min of stirring and the reaction mixture was left to warm to room temperature, then it was

washed with water and brine, dried under Na2SO4 and filtered. Solvent was evaporated in vacuo and 20 ml of C6H14 was

added to the resulting yellow oil, after 15 min of heating the mixture was cooled, yielding 0.5 g (60%) of a white

precipitate. The product was recrystallized from CH2Cl2/C6H14, m.p. 363–365 K. 1H NMR (CDCl3, 400 MHz, p.p.m.):

7.64 (d, 2H, Ph), 7.43 (t, 4H, Ph), 7,35 (t, 3H, Ph), 7.28 (d, 1H, Ph), 5.19 (dd, 1H, CH), 3.30 (dd, 1H, CH2, J = 4.5 MHz),

3.25 (dd, 1H, CH2, J = 8.5 MHz), 2.53 (s, 3H, CH3).

S3. Refinement

The hydroxyl H atom was refined isotropically to give an O—H bond length of 0.87 (3) Å. H atoms bonded to C atoms

were included in calculated positions and included in the refinement in riding-motion approximation (C—H = 0.93–0.98

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[image:5.610.127.485.69.302.2]

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Acta Cryst. (2003). E59, o1293–o1295

Figure 1

ORTEP-3 (Farrugia, 2003) plot of the molecule of title compound. Displacement ellipsoids are shown at the 30%

probability level and H atoms asr shown as spheres of arbitrary radius.

Figure 2

PLUTON97 (Spek, 1997) packing diagram with the hydrogen-bond scheme shown with dashed lines.

2-(5-Methyl-4-phenyl-1,3-thiazol-2-yl)-1-phenylethanol

Crystal data

C18H17NOS Mr = 295.39 Monoclinic, P21/c Hall symbol: -P 2ybc a = 6.2820 (9) Å b = 28.836 (4) Å c = 8.4583 (13) Å β = 97.56 (1)°

V = 1518.9 (4) Å3 Z = 4

F(000) = 624 Dx = 1.292 Mg m−3

[image:5.610.127.483.357.544.2]
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Acta Cryst. (2003). E59, o1293–o1295

µ = 1.86 mm−1 T = 293 K

Prism, colourless 0.30 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

non–profiled ω/2θ scans 3201 measured reflections 2997 independent reflections 2613 reflections with I > 2σ(I)

Rint = 0.021

θmax = 74.9°, θmin = 3.1° h = −7→7

k = 0→36 l = 0→9

1 standard reflections every 226 reflections intensity decay: 2%

Refinement

Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.040 wR(F2) = 0.116 S = 1.05 2997 reflections 195 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: mixed

H atoms treated by a mixture of independent and constrained refinement

w = 1/[σ2(F

o2) + (0.0712P)2 + 0.2241P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001 Δρmax = 0.31 e Å−3 Δρmin = −0.28 e Å−3

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

x y z Uiso*/Ueq

S1 0.19563 (7) 0.255774 (14) 0.65532 (5) 0.04718 (15)

C2 −0.0259 (3) 0.24689 (5) 0.74978 (19) 0.0427 (3)

N3 −0.0604 (2) 0.20369 (4) 0.78171 (15) 0.0437 (3)

C4 0.0931 (3) 0.17445 (5) 0.72955 (18) 0.0416 (3)

C5 0.2457 (3) 0.19688 (6) 0.65539 (19) 0.0446 (4)

C51 0.4275 (3) 0.18051 (7) 0.5717 (3) 0.0624 (5)

H51A 0.5372 0.1672 0.6480 0.094*

H51B 0.4858 0.2063 0.5198 0.094*

H51C 0.3760 0.1576 0.4938 0.094*

C6 0.0732 (3) 0.12400 (6) 0.7571 (2) 0.0469 (4)

C7 0.2287 (4) 0.09247 (7) 0.7252 (3) 0.0769 (7)

H7 0.3513 0.1030 0.6858 0.092*

C8 0.2042 (5) 0.04542 (8) 0.7512 (4) 0.0927 (8)

H8 0.3108 0.0249 0.7292 0.111*

C9 0.0251 (5) 0.02857 (7) 0.8090 (3) 0.0785 (7)

H9 0.0081 −0.0031 0.8239 0.094*

C10 −0.1288 (4) 0.05941 (7) 0.8445 (3) 0.0697 (6)

H10 −0.2492 0.0486 0.8861 0.084*

C11 −0.1059 (3) 0.10649 (6) 0.8187 (2) 0.0548 (4)

H11 −0.2120 0.1268 0.8429 0.066*

C12 −0.1643 (3) 0.28628 (6) 0.7933 (2) 0.0487 (4)

H12A −0.0935 0.3014 0.8883 0.058*

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C13 −0.2100 (3) 0.32240 (5) 0.65984 (18) 0.0430 (3)

H13 −0.0731 0.3334 0.6301 0.052*

O13 −0.3284 (2) 0.30059 (4) 0.52548 (15) 0.0536 (3)

H131 −0.245 (5) 0.2997 (11) 0.451 (4) 0.120 (11)*

C14 −0.3319 (3) 0.36340 (5) 0.71575 (19) 0.0435 (4)

C15 −0.2379 (3) 0.39113 (6) 0.8397 (2) 0.0563 (4)

H15 −0.0985 0.3850 0.8869 0.068*

C16 −0.3506 (4) 0.42802 (6) 0.8939 (3) 0.0681 (6)

H16 −0.2873 0.4461 0.9782 0.082*

C17 −0.5552 (4) 0.43789 (7) 0.8236 (3) 0.0726 (6)

H17 −0.6302 0.4627 0.8599 0.087*

C18 −0.6485 (4) 0.41098 (7) 0.6993 (3) 0.0700 (6)

H18 −0.7867 0.4177 0.6511 0.084*

C19 −0.5378 (3) 0.37382 (6) 0.6453 (2) 0.0542 (4)

H19 −0.6024 0.3558 0.5612 0.065*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

S1 0.0458 (2) 0.0460 (2) 0.0502 (3) −0.00075 (15) 0.00793 (17) 0.00383 (15)

C2 0.0485 (9) 0.0444 (8) 0.0350 (8) 0.0036 (6) 0.0053 (6) 0.0006 (6)

N3 0.0491 (8) 0.0443 (7) 0.0382 (7) 0.0037 (5) 0.0073 (5) 0.0024 (5)

C4 0.0434 (8) 0.0445 (8) 0.0353 (8) 0.0032 (6) −0.0014 (6) −0.0013 (6)

C5 0.0389 (8) 0.0483 (8) 0.0459 (9) 0.0036 (6) 0.0028 (6) 0.0004 (6)

C51 0.0518 (11) 0.0669 (11) 0.0716 (13) 0.0124 (8) 0.0198 (9) 0.0054 (9)

C6 0.0538 (9) 0.0433 (8) 0.0415 (9) 0.0008 (7) −0.0021 (7) −0.0014 (6)

C7 0.0830 (16) 0.0504 (11) 0.1026 (18) 0.0092 (10) 0.0316 (13) 0.0003 (11)

C8 0.112 (2) 0.0480 (11) 0.121 (2) 0.0168 (12) 0.0294 (18) −0.0004 (12)

C9 0.1070 (19) 0.0427 (10) 0.0818 (16) −0.0022 (11) −0.0028 (13) 0.0043 (9) C10 0.0777 (14) 0.0571 (11) 0.0712 (14) −0.0136 (10) −0.0019 (11) 0.0117 (9)

C11 0.0567 (11) 0.0521 (9) 0.0538 (11) −0.0023 (8) 0.0009 (8) 0.0040 (7)

C12 0.0601 (10) 0.0460 (8) 0.0415 (9) 0.0098 (7) 0.0118 (7) 0.0033 (6)

C13 0.0443 (8) 0.0465 (8) 0.0380 (8) −0.0002 (6) 0.0053 (6) 0.0010 (6)

O13 0.0552 (7) 0.0640 (7) 0.0415 (7) 0.0000 (6) 0.0058 (5) −0.0089 (5)

C14 0.0515 (9) 0.0414 (7) 0.0379 (9) 0.0009 (6) 0.0072 (6) 0.0057 (6)

C15 0.0660 (12) 0.0471 (9) 0.0536 (11) 0.0001 (8) −0.0005 (8) −0.0018 (7)

C16 0.0993 (17) 0.0458 (9) 0.0575 (12) 0.0015 (10) 0.0041 (11) −0.0067 (8)

C17 0.0948 (17) 0.0489 (10) 0.0765 (15) 0.0208 (10) 0.0198 (12) 0.0010 (9) C18 0.0676 (13) 0.0589 (11) 0.0825 (15) 0.0205 (10) 0.0057 (11) 0.0048 (10)

C19 0.0551 (10) 0.0500 (9) 0.0554 (11) 0.0067 (7) −0.0007 (8) 0.0025 (7)

Geometric parameters (Å, º)

S1—C2 1.7126 (17) C10—H10 0.9300

S1—C5 1.7270 (16) C11—H11 0.9300

C2—N3 1.299 (2) C12—C13 1.535 (2)

C2—C12 1.505 (2) C12—H12A 0.9700

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C4—C5 1.375 (2) C13—O13 1.4203 (19)

C4—C6 1.481 (2) C13—C14 1.517 (2)

C5—C51 1.497 (2) C13—H13 0.9800

C51—H51A 0.9600 O13—H131 0.87 (3)

C51—H51B 0.9600 C14—C19 1.385 (2)

C51—H51C 0.9600 C14—C15 1.388 (2)

C6—C7 1.387 (3) C15—C16 1.389 (3)

C6—C11 1.395 (3) C15—H15 0.9300

C7—C8 1.386 (3) C16—C17 1.373 (4)

C7—H7 0.9300 C16—H16 0.9300

C8—C9 1.373 (4) C17—C18 1.375 (3)

C8—H8 0.9300 C17—H17 0.9300

C9—C10 1.375 (4) C18—C19 1.387 (3)

C9—H9 0.9300 C18—H18 0.9300

C10—C11 1.385 (3) C19—H19 0.9300

C2—S1—C5 90.68 (8) C10—C11—H11 119.4

N3—C2—C12 123.73 (15) C6—C11—H11 119.4

N3—C2—S1 114.11 (12) C2—C12—C13 112.99 (13)

C12—C2—S1 122.16 (12) C2—C12—H12A 109.0

C2—N3—C4 111.88 (14) C13—C12—H12A 109.0

C5—C4—N3 114.35 (14) C2—C12—H12B 109.0

C5—C4—C6 127.76 (15) C13—C12—H12B 109.0

N3—C4—C6 117.89 (15) H12A—C12—H12B 107.8

C4—C5—C51 133.52 (16) O13—C13—C14 111.21 (13)

C4—C5—S1 108.97 (12) O13—C13—C12 108.40 (13)

C51—C5—S1 117.41 (13) C14—C13—C12 110.66 (12)

C5—C51—H51A 109.5 O13—C13—H13 108.8

C5—C51—H51B 109.5 C14—C13—H13 108.8

H51A—C51—H51B 109.5 C12—C13—H13 108.8

C5—C51—H51C 109.5 C13—O13—H131 107 (2)

H51A—C51—H51C 109.5 C19—C14—C15 118.74 (16)

H51B—C51—H51C 109.5 C19—C14—C13 121.07 (15)

C7—C6—C11 117.30 (17) C15—C14—C13 120.19 (15)

C7—C6—C4 122.51 (17) C14—C15—C16 120.40 (19)

C11—C6—C4 120.19 (16) C14—C15—H15 119.8

C8—C7—C6 121.0 (2) C16—C15—H15 119.8

C8—C7—H7 119.5 C17—C16—C15 120.3 (2)

C6—C7—H7 119.5 C17—C16—H16 119.8

C9—C8—C7 121.1 (2) C15—C16—H16 119.8

C9—C8—H8 119.5 C16—C17—C18 119.68 (19)

C7—C8—H8 119.5 C16—C17—H17 120.2

C8—C9—C10 118.8 (2) C18—C17—H17 120.2

C8—C9—H9 120.6 C17—C18—C19 120.4 (2)

C10—C9—H9 120.6 C17—C18—H18 119.8

C9—C10—C11 120.6 (2) C19—C18—H18 119.8

C9—C10—H10 119.7 C14—C19—C18 120.43 (19)

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C10—C11—C6 121.2 (2) C18—C19—H19 119.8

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

O13—H131···N3i 0.87 (4) 1.96 (4) 2.831 (2) 179 (3)

Figure

Figure 2

References

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