Tris­(cyclo­hexyl­methyl)­amine

organic papers

o1100

Structure Reports Online

ISSN 1600-5368

Tris(cyclohexylmethyl)amine

Kai-Sven MuÈller, Markus SchuÈrmann, Hans Preut* and Peter Eilbracht

Fachbereich Chemie, UniversitaÈt Dortmund, Otto-Hahn-Straûe 6, 44221 Dortmund, Germany

Correspondence e-mail:

[email protected]

Key indicators Single-crystal X-ray study T= 291 K

Mean(C±C) = 0.004 AÊ Rfactor = 0.034 wRfactor = 0.065

Data-to-parameter ratio = 10.5

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

#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved

The title compound, C21H39N, is a sterically hindered amine

with three cyclohexane rings, all having chair conformations. The bond angles at the N atom are 111.3 (2), 111.58 (19) and 110.3 (2)_.

Comment

In order to study the rhodium-catalysed hydroaminomethyl-ation (Rische & Eilbracht, 1997) of urea with cyclohexene, different conditions were used. Under acidic conditions crys-tals of the title compound (Katritzkyet al., 1989; Striegler & Weber, 1965), (I), were surprisingly obtained, but only in poor yields and small amounts.

The molecular structure of (I) is illustrated in Fig. 1. On performing the same reaction under optimized conditions, (I)

Received 10 May 2004 Accepted 12 May 2004 Online 29 May 2004

Figure 1

can be obtained as the only product in 74% yield. The formation of (I) occurs by hydrolysis of the urea to ammonia, which was alkylated by a series of condensation and reduction reactions to the tertiary amine. Due to the low concentration of ammonia, the tertiary amine is selectively formed. This is in contrast to the direct conversion of ammonia, which leads preferentially to the formation of the secondary amine (Rischeet al., 1998).

Experimental

A solution of 0.821 g (10 mmol) cyclohexene in 90 ml dioxane, 9 ml of methanol and 1 ml of glacial acetic acid in the presence of 0.606 g (10 mmol) urea was treated over a period of 3 d under hydro-aminomethylation conditions, under 80 bar syngas (40 bar hydrogen, 40 bar carbon monoxide) at 393 K with 0.3 mol% of the [Rh(cod)Cl]2

(cod is 1,5-cyclooctadiene) catalyst. The solvent was evaporated and the aquous mixture treated with 20 ml of a concentrated solution of sodium hydroxide and 20 ml of water. The mixture was extracted with ethyl acetate, and the organic layer was dried over sodium sulfate and evaporated to obtain the crude material, which was puri®ed by column chromatography on neutral aluminium oxide (act. III) with cyclohexane/methyltert-butyl ether in a 10:1 ratio as eluant to obtain 0.752 g (2.5 mmol) of (I) in a yield of 74%. Product (I) was recrys-tallized from a mixture of diethyl ether/methanol in a 1:1 ratio. The purity of (I) (m.p. 366±367 K) was con®rmed by elemental analysis (calculated: C 82.55, H 12.86, N 4.59%; found: C 82.4, H 12.6, N 4.5%).1_{H NMR (500 MHz, CDCl}

3):2.01 (d, 6H,3J= 7.0 Hz, H17,

H27, H37), 1.64±1.79 (15H, ring CH2), 1.13±1.38 (12H, ring CH2),

0.75±0.82 (6H, ring CH2);13C NMR (125 MHz, CDCl3):63.26, (C17,

C27, C37), 36.27 (C11, C21, C31), 31.90 (ring CH2), 27.03 (ring CH2),

26.28 (ring CH2); IR (Film, NaCl):~[cmÿ1] 2922 (vs), 2846 (vs), 2792

(s), 1448 (s), 1275 (m), 1261 (m), 1244 (m), 1171 (m), 1115 (m), 1074 (m), 1061 (m), 1051 (m), 966 (m), 868 (m), 841 (m), 582 (w); ESI MS (m/z): 306.25 ([M+ (H+_{)]); GC±MS (EI, 70 eV): m/z(%) = 305 (M}+_,

7), 222 (100), 140 (51), 58 (51), 55 (51).

Crystal data C21H39N

Mr= 305.53

Orthorhombic,P212121

a= 11.050 (3) AÊ

b= 11.2116 (4) AÊ

c= 16.3949 (6) AÊ

V= 2031.2 (6) AÊ3

Z= 4

Dx= 0.999 Mg mÿ3

MoKradiation

Cell parameters from 10 616 re¯ections

= 3.1±25.3

= 0.06 mmÿ1

T= 291 (1) K Block, colourless 0.120.120.08 mm

Data collection

Nonius KappaCCD diffractometer

!scans

Absorption correction: none 10616 measured re¯ections 2101 independent re¯ections 882 re¯ections withI> 2(I)

Rint= 0.037

max= 25.3

h=ÿ13!13

k=ÿ13!13

l=ÿ19!19

Re®nement Re®nement onF2

R[F2_{> 2(F}2_{)] = 0.034}

wR(F2_{) = 0.065}

S= 0.88 2101 re¯ections 200 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0162P)2]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001 max= 0.08 e AÊÿ3 min=ÿ0.08 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.0226 (10)

H atoms were placed in calculated positions, with CÐH = 0.97± 0.98 AÊ, and were re®ned as riding, withUiso= 1.2Ueq(C) of the carrier

atom. In the absence of signi®cant anomalous cattering, Friedel pairs were merged.

Data collection: COLLECT (Nonius, 1998); cell re®nement:

DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

SHELXTL-Plus(Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and

PLATON(Spek, 2001).

References

Katritzky, A. R., Yannakopoulou, K., Lue, P., Rasala, D. & Urogdi, L. (1989).

J. Chem. Soc. Perkin. Trans.1, pp. 225±233. Nardelli, M. (1995).J. Appl. Cryst.28, 659.

Nonius (1998).COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,

Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307±326. New York: Academic Press.

Rische, T. & Eilbracht, P. (1997).Synthesis, pp. 1331±1337.

Rische, T., Kitsos-Rzychon, B. & Eilbracht, P. (1998).Tetrahedron,54, 2723± 2742.

Sheldrick, G. M. (1990).Acta Cryst.A46, 467±473.

Sheldrick, G. M. (1991). XP in SHELXTL-Plus. Release 4.1. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

supporting information

sup-1 Acta Cryst. (2004). E60, o1100–o1101

supporting information

Acta Cryst. (2004). E60, o1100–o1101 [https://doi.org/10.1107/S1600536804011535]

Tris(cyclohexylmethyl)amine

Kai-Sven M

ü

ller, Markus Sch

ü

rmann, Hans Preut and Peter Eilbracht

(I)

Crystal data

C21H39N

Mr = 305.53

Orthorhombic, P212121

Hall symbol: P 2ac 2ab

a = 11.050 (3) Å

b = 11.2116 (4) Å

c = 16.3949 (6) Å

V = 2031.2 (6) Å3

Z = 4

F(000) = 688

Dx = 0.999 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 10616 reflections

θ = 3.1–25.3°

µ = 0.06 mm−1

T = 291 K Block, colourless 0.12 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

Detector resolution: 19 vertical, 18 horizontal pixels mm-1

197 frames via ω–rotation (Δω=1°) and two times 30 s per frame (two sets at different κ– angles) scans

2101 measured reflections 2101 independent reflections 882 reflections with I > 2σ(I)

Rint = 0.037

θmax = 25.3°, θmin = 3.1°

h = −13→13

k = −13→13

l = −19→19

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.034}

wR(F2_{) = 0.065}

S = 0.88 2101 reflections 200 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0162P)2]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.08 e Å−3

Δρmin = −0.08 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4

Extinction coefficient: 0.0226 (10) Absolute structure: Flack (1983)

Special details

Refinement. Refinement of F2 _{against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

N1 0.2752 (2) 0.55534 (19) 0.14983 (12) 0.0657 (6)

C11 0.4071 (3) 0.3807 (3) 0.11635 (16) 0.0732 (8)

H11A 0.4270 0.4229 0.0657 0.088*

C12 0.3065 (3) 0.2948 (3) 0.09758 (18) 0.0884 (9)

H12A 0.2381 0.3388 0.0759 0.106*

H12B 0.2807 0.2568 0.1478 0.106*

C13 0.3428 (3) 0.1995 (3) 0.03696 (18) 0.1056 (11)

H13A 0.2763 0.1440 0.0297 0.127*

H13B 0.3596 0.2362 −0.0154 0.127*

C14 0.4526 (4) 0.1328 (3) 0.0653 (2) 0.1154 (12)

H14A 0.4769 0.0760 0.0238 0.139*

H14B 0.4332 0.0887 0.1145 0.139*

C15 0.5558 (3) 0.2176 (3) 0.0823 (2) 0.1187 (13)

H15A 0.5810 0.2550 0.0317 0.142*

H15B 0.6241 0.1731 0.1037 0.142*

C16 0.5199 (3) 0.3146 (3) 0.14374 (18) 0.0974 (11)

H16A 0.5053 0.2783 0.1965 0.117*

H16B 0.5861 0.3708 0.1497 0.117*

C17 0.3695 (3) 0.4736 (3) 0.17903 (15) 0.0790 (9)

H17A 0.3403 0.4331 0.2274 0.095*

H17B 0.4401 0.5199 0.1945 0.095*

C21 0.2423 (2) 0.7032 (2) 0.03774 (15) 0.0612 (8)

H21A 0.1655 0.7229 0.0645 0.073*

C22 0.2165 (2) 0.6131 (2) −0.02790 (15) 0.0749 (9)

H22A 0.1801 0.5430 −0.0034 0.090*

H22B 0.2922 0.5889 −0.0529 0.090*

C23 0.1324 (3) 0.6613 (3) −0.09346 (15) 0.0853 (10)

H23A 0.1225 0.6018 −0.1359 0.102*

H23B 0.0536 0.6771 −0.0699 0.102*

C24 0.1821 (3) 0.7749 (3) −0.13043 (16) 0.0897 (10)

H24A 0.2562 0.7573 −0.1597 0.108*

H24B 0.1241 0.8070 −0.1690 0.108*

C25 0.2072 (3) 0.8660 (3) −0.06500 (16) 0.0888 (10)

H25A 0.1316 0.8899 −0.0398 0.107*

H25B 0.2435 0.9362 −0.0895 0.107*

C26 0.2922 (3) 0.8166 (2) 0.00022 (15) 0.0752 (8)

H26A 0.3705 0.8002 −0.0240 0.090*

H26B 0.3034 0.8760 0.0426 0.090*

C27 0.3273 (2) 0.6535 (2) 0.10205 (15) 0.0709 (8)

supporting information

sup-3 Acta Cryst. (2004). E60, o1100–o1101

H27B 0.3500 0.7173 0.1389 0.085*

C31 0.1026 (3) 0.5198 (2) 0.24604 (16) 0.0699 (8)

H31A 0.1392 0.4423 0.2586 0.084*

C32 0.0431 (3) 0.5667 (3) 0.32333 (16) 0.0922 (10)

H32A 0.1036 0.5731 0.3660 0.111*

H32B 0.0112 0.6459 0.3130 0.111*

C33 −0.0583 (4) 0.4866 (3) 0.35229 (19) 0.1144 (12)

H33A −0.0252 0.4099 0.3683 0.137*

H33B −0.0964 0.5219 0.3998 0.137*

C34 −0.1519 (3) 0.4683 (3) 0.2867 (2) 0.1131 (12)

H34A −0.2129 0.4128 0.3058 0.136*

H34B −0.1914 0.5436 0.2748 0.136*

C35 −0.0942 (3) 0.4203 (3) 0.2102 (2) 0.1004 (10)

H35A −0.1549 0.4140 0.1677 0.120*

H35B −0.0627 0.3410 0.2208 0.120*

C36 0.0085 (3) 0.5008 (3) 0.18090 (16) 0.0867 (10)

H36A 0.0463 0.4651 0.1334 0.104*

H36B −0.0246 0.5773 0.1647 0.104*

C37 0.2022 (3) 0.6028 (2) 0.21770 (15) 0.0780 (9)

H37A 0.1661 0.6776 0.2007 0.094*

H37B 0.2553 0.6195 0.2634 0.094*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

N1 0.0711 (18) 0.0585 (16) 0.0675 (14) −0.0008 (14) 0.0078 (13) 0.0070 (13)

C11 0.068 (2) 0.075 (2) 0.076 (2) 0.010 (2) 0.0033 (16) 0.0120 (18)

C12 0.080 (3) 0.076 (2) 0.110 (2) 0.017 (2) −0.002 (2) −0.005 (2)

C13 0.105 (3) 0.087 (3) 0.125 (3) 0.026 (2) −0.007 (2) −0.013 (2)

C14 0.110 (4) 0.099 (3) 0.138 (3) 0.035 (3) 0.011 (2) −0.002 (2)

C15 0.083 (3) 0.132 (4) 0.141 (3) 0.042 (3) 0.015 (2) 0.016 (3)

C16 0.069 (3) 0.104 (3) 0.119 (3) 0.017 (2) −0.0029 (19) 0.020 (2)

C17 0.084 (2) 0.079 (2) 0.0742 (19) 0.0019 (19) −0.0086 (17) 0.015 (2)

C21 0.062 (2) 0.057 (2) 0.0643 (17) 0.0004 (16) 0.0043 (15) 0.0047 (16)

C22 0.082 (2) 0.068 (2) 0.0740 (18) −0.0075 (19) 0.0061 (18) −0.0043 (17)

C23 0.095 (3) 0.098 (3) 0.0627 (18) −0.015 (2) −0.0027 (19) −0.0078 (19)

C24 0.091 (3) 0.108 (3) 0.070 (2) 0.001 (2) 0.0000 (19) 0.009 (2)

C25 0.101 (3) 0.083 (2) 0.083 (2) 0.001 (2) 0.0049 (19) 0.0181 (19)

C26 0.081 (2) 0.064 (2) 0.0804 (18) −0.0085 (19) −0.0002 (18) 0.0058 (16)

C27 0.068 (2) 0.064 (2) 0.0805 (18) −0.0067 (17) 0.0011 (17) 0.0050 (17)

C31 0.082 (2) 0.058 (2) 0.0692 (19) 0.0072 (18) 0.0093 (17) 0.0092 (16)

C32 0.117 (3) 0.084 (2) 0.076 (2) −0.004 (2) 0.0204 (19) 0.0047 (19)

C33 0.127 (4) 0.110 (3) 0.106 (3) 0.008 (3) 0.038 (3) 0.023 (2)

C34 0.095 (3) 0.096 (3) 0.148 (3) 0.007 (2) 0.041 (3) 0.027 (3)

C35 0.083 (3) 0.091 (3) 0.127 (3) −0.006 (2) 0.006 (2) 0.009 (2)

C36 0.085 (3) 0.088 (3) 0.087 (2) −0.003 (2) 0.012 (2) 0.0021 (19)

Geometric parameters (Å, º)

N1—C17 1.468 (3) C23—H23B 0.9700

N1—C27 1.468 (3) C24—C25 1.508 (3)

N1—C37 1.474 (3) C24—H24A 0.9700

C11—C12 1.503 (3) C24—H24B 0.9700

C11—C16 1.518 (3) C25—C26 1.527 (3)

C11—C17 1.521 (3) C25—H25A 0.9700

C11—H11A 0.9800 C25—H25B 0.9700

C12—C13 1.513 (3) C26—H26A 0.9700

C12—H12A 0.9700 C26—H26B 0.9700

C12—H12B 0.9700 C27—H27A 0.9700

C13—C14 1.498 (4) C27—H27B 0.9700

C13—H13A 0.9700 C31—C36 1.506 (3)

C13—H13B 0.9700 C31—C37 1.514 (3)

C14—C15 1.511 (4) C31—C32 1.521 (3)

C14—H14A 0.9700 C31—H31A 0.9800

C14—H14B 0.9700 C32—C33 1.513 (4)

C15—C16 1.534 (4) C32—H32A 0.9700

C15—H15A 0.9700 C32—H32B 0.9700

C15—H15B 0.9700 C33—C34 1.506 (4)

C16—H16A 0.9700 C33—H33A 0.9700

C16—H16B 0.9700 C33—H33B 0.9700

C17—H17A 0.9700 C34—C35 1.505 (4)

C17—H17B 0.9700 C34—H34A 0.9700

C21—C22 1.503 (3) C34—H34B 0.9700

C21—C26 1.516 (3) C35—C36 1.527 (3)

C21—C27 1.518 (3) C35—H35A 0.9700

C21—H21A 0.9800 C35—H35B 0.9700

C22—C23 1.520 (3) C36—H36A 0.9700

C22—H22A 0.9700 C36—H36B 0.9700

C22—H22B 0.9700 C37—H37A 0.9700

C23—C24 1.513 (3) C37—H37B 0.9700

C23—H23A 0.9700

C17—N1—C27 111.3 (2) C23—C24—H24A 109.5

C17—N1—C37 111.58 (19) C25—C24—H24B 109.5

C27—N1—C37 110.3 (2) C23—C24—H24B 109.5

C12—C11—C16 110.8 (2) H24A—C24—H24B 108.1

C12—C11—C17 112.1 (2) C24—C25—C26 111.5 (2)

C16—C11—C17 111.0 (2) C24—C25—H25A 109.3

C12—C11—H11A 107.6 C26—C25—H25A 109.3

C16—C11—H11A 107.6 C24—C25—H25B 109.3

C17—C11—H11A 107.6 C26—C25—H25B 109.3

C11—C12—C13 113.0 (3) H25A—C25—H25B 108.0

C11—C12—H12A 109.0 C21—C26—C25 111.4 (2)

C13—C12—H12A 109.0 C21—C26—H26A 109.4

supporting information

sup-5 Acta Cryst. (2004). E60, o1100–o1101

C13—C12—H12B 109.0 C21—C26—H26B 109.4

H12A—C12—H12B 107.8 C25—C26—H26B 109.4

C14—C13—C12 111.3 (3) H26A—C26—H26B 108.0

C14—C13—H13A 109.4 N1—C27—C21 113.8 (2)

C12—C13—H13A 109.4 N1—C27—H27A 108.8

C14—C13—H13B 109.4 C21—C27—H27A 108.8

C12—C13—H13B 109.4 N1—C27—H27B 108.8

H13A—C13—H13B 108.0 C21—C27—H27B 108.8

C13—C14—C15 110.8 (3) H27A—C27—H27B 107.7

C13—C14—H14A 109.5 C36—C31—C37 111.8 (2)

C15—C14—H14A 109.5 C36—C31—C32 109.9 (3)

C13—C14—H14B 109.5 C37—C31—C32 110.9 (2)

C15—C14—H14B 109.5 C36—C31—H31A 108.0

H14A—C14—H14B 108.1 C37—C31—H31A 108.0

C14—C15—C16 111.9 (3) C32—C31—H31A 108.0

C14—C15—H15A 109.2 C33—C32—C31 112.1 (3)

C16—C15—H15A 109.2 C33—C32—H32A 109.2

C14—C15—H15B 109.2 C31—C32—H32A 109.2

C16—C15—H15B 109.2 C33—C32—H32B 109.2

H15A—C15—H15B 107.9 C31—C32—H32B 109.2

C11—C16—C15 111.3 (3) H32A—C32—H32B 107.9

C11—C16—H16A 109.4 C34—C33—C32 111.4 (3)

C15—C16—H16A 109.4 C34—C33—H33A 109.3

C11—C16—H16B 109.4 C32—C33—H33A 109.3

C15—C16—H16B 109.4 C34—C33—H33B 109.3

H16A—C16—H16B 108.0 C32—C33—H33B 109.3

N1—C17—C11 113.6 (2) H33A—C33—H33B 108.0

N1—C17—H17A 108.8 C35—C34—C33 110.7 (3)

C11—C17—H17A 108.8 C35—C34—H34A 109.5

N1—C17—H17B 108.8 C33—C34—H34A 109.5

C11—C17—H17B 108.8 C35—C34—H34B 109.5

H17A—C17—H17B 107.7 C33—C34—H34B 109.5

C22—C21—C26 110.0 (2) H34A—C34—H34B 108.1

C22—C21—C27 111.5 (2) C34—C35—C36 111.4 (3)

C26—C21—C27 111.4 (2) C34—C35—H35A 109.3

C22—C21—H21A 107.9 C36—C35—H35A 109.3

C26—C21—H21A 107.9 C34—C35—H35B 109.3

C27—C21—H21A 107.9 C36—C35—H35B 109.3

C21—C22—C23 112.5 (2) H35A—C35—H35B 108.0

C21—C22—H22A 109.1 C31—C36—C35 111.9 (2)

C23—C22—H22A 109.1 C31—C36—H36A 109.2

C21—C22—H22B 109.1 C35—C36—H36A 109.2

C23—C22—H22B 109.1 C31—C36—H36B 109.2

H22A—C22—H22B 107.8 C35—C36—H36B 109.2

C24—C23—C22 111.2 (2) H36A—C36—H36B 107.9

C24—C23—H23A 109.4 N1—C37—C31 114.1 (2)

C22—C23—H23A 109.4 N1—C37—H37A 108.7

C22—C23—H23B 109.4 N1—C37—H37B 108.7

H23A—C23—H23B 108.0 C31—C37—H37B 108.7

C25—C24—C23 110.6 (2) H37A—C37—H37B 107.6

C25—C24—H24A 109.5

C16—C11—C12—C13 −53.9 (3) C27—C21—C26—C25 179.5 (2)

C17—C11—C12—C13 −178.5 (2) C24—C25—C26—C21 −56.3 (3)

C11—C12—C13—C14 55.6 (3) C17—N1—C27—C21 151.4 (2)

C12—C13—C14—C15 −55.4 (4) C37—N1—C27—C21 −84.2 (3)

C13—C14—C15—C16 55.5 (4) C22—C21—C27—N1 −66.1 (3)

C12—C11—C16—C15 52.8 (3) C26—C21—C27—N1 170.5 (2)

C17—C11—C16—C15 177.9 (2) C36—C31—C32—C33 54.8 (3)

C14—C15—C16—C11 −54.4 (4) C37—C31—C32—C33 179.0 (3)

C27—N1—C17—C11 −83.3 (3) C31—C32—C33—C34 −55.9 (4)

C37—N1—C17—C11 153.0 (2) C32—C33—C34—C35 55.6 (4)

C12—C11—C17—N1 −66.2 (3) C33—C34—C35—C36 −55.4 (4)

C16—C11—C17—N1 169.3 (2) C37—C31—C36—C35 −178.2 (2)

C26—C21—C22—C23 −55.3 (3) C32—C31—C36—C35 −54.5 (3)

C27—C21—C22—C23 −179.5 (2) C34—C35—C36—C31 55.9 (4)

C21—C22—C23—C24 55.7 (3) C17—N1—C37—C31 −82.0 (3)

C22—C23—C24—C25 −54.9 (3) C27—N1—C37—C31 153.7 (2)

C23—C24—C25—C26 55.6 (3) C36—C31—C37—N1 −64.9 (3)