organic papers
Acta Cryst.(2004). E60, o1523±o1524 DOI: 10.1107/S1600536804019002 Muharrem DincËeret al. C20H29NO
o1523
Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
1-(3-Mesityl-3-methylcyclobutyl)-2-(pyrrolidin-1-yl)-ethan-1-one
Muharrem DincËer,a* Namõk
OÈ zdemir,aAlaaddin CËukurovalõ,b
Ibrahim Yõlmazband Orhan
BuÈyuÈkguÈngoÈra
aOndokuz Mayõs University, Arts and Sciences Faculty, Department of Physics, 55139-Samsun, Turkey, andbFõrat University, Arts and Sciences Faculty, Department of Chemistry, 23119-ElazõgÆ, Turkey
Correspondence e-mail: mdincer@omu.edu.tr
Key indicators
Single-crystal X-ray study
T= 293 K
Mean(C±C) = 0.005 AÊ
Rfactor = 0.068
wRfactor = 0.194
Data-to-parameter ratio = 16.8
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
In the title molecule, C20H29NO, the cyclobutane ring is
puckered, with a dihedral angle of 19.8 (3)between the two
planes. The pyrrolidine ring adopts an envelope conformation. There are intermolecular CÐH O and CÐH interac-tions.
Comment
3-Substituted cyclobutane carboxylic acid derivatives exhibit anti-in¯ammatory and antidepressant activities (Dehmlow & Schmidt, 1990), and liquid crystal properties (Coghi et al., 1976). A recent communication showed that compounds incorporating 1,3,4-trisubstituted pyrrolidine ring scaffolds were potent CCR5 antagonists (Lynch et al., 2002). The pyrrolidine ring is a structure very often encountered in the alkaloid ®eld (Martin & Brossi, 1987). Furthermore, numerous chiral non-racemic substituted pyrrolidines and pyrrolidones are used as intermediates, chiral ligands or auxiliaries in asymmetric synthesis (Hurynet al., 1991). The development of new methods for the preparation of enantiomerically pure, highly substituted pyrrolidines and pyrrolidones is then of increasing interest. Taking into account the importance of cyclobutane and pyrrolidine, we have undertaken an X-ray diffraction study of the title compound, (I).
Fig. 1 shows the molecular structure and conformation of (I), with the atomic numbering scheme. The four-atom bridge (N1/C9/C10/C5) linking the cyclobutane and pyrrolidine rings is not planar, the N1ÐC9ÐC10ÐC5 torsion angle being
ÿ54.1 (4), which corresponds to the (ÿ)synclinal
con®gura-tion. Although close to planar, the cyclobutane ring is more puckered than that in a related compound; the C8/C5/C6 plane forms a dihedral angle of 19.8 (3) with the C6/C7/C8
plane in (I) [11.55 (3) in the related compound; OÈzdemiret
al., 2004]. However, the bond lengths in the cyclobutane ring are similar to those in the related compound. In (I), the pyrrolidine ring is close to an envelope conformation, with atom N1 deviating by 0.257 (4) AÊ from the C1±C4 plane, and puckering parameters (Cremer & Pople, 1975) Q2 =
0.408 (5) AÊ and'2= 354.1 (7).
The crystal structure does not exhibit intramolecular or± interactions. There are, however, CÐH O and CÐH
intermolecular interactions (Table 2). Atom O1 and the centroid, Cg3, of the C12±C17 benzene ring act as a double acceptor for CÐH O and CÐH interactions, respec-tively.
Experimental
A mixture of 1-phenyl-1-mesityl-3-(2-chloro-1-oxoethyl)cyclobutane (5.29 g, 20 mmol) and pyrrolidine (2.874 g, 40 mmol) in dry benzene (50 ml) was re¯uxed with continuous stirring. The course of the reaction was monitored by IR spectroscopy. The product was formed after about half an hour. After cooling to room temperature and ®ltration of the pyrrolidine salt, benzene was removed under reduced pressure through a rotary evaporator. The oily product was treated with diethyl ether and dried over magnesium sulfate. Shiny crystals of (I) suitable for X-ray analysis were obtained from a diethyl ether solution by deep freezing at 253 K (yield 78%, m.p. 412 K). IR (KBr): 1724 cmÿ1(C O).1H NMR (DMSO-d
6, p.p.m.): 1.59 (s, 3H, CH3on
cyclobutane), 1.85 (s, 3H,p-CH3on mesitylene), 2.24±2.74 (br, 10H,
o-CH3on mesitylene plus ±CH2± on pyrollidine), 2.78±3.04 (br, 8H,
±CH2ÐNÐCH2± plus ±CH2± in cyclobutane), 3.31 (q,j= 7.8 Hz, 1H,
>CH±), 3.58 (s, 2H, ±COÐCH2ÐN), 6.77 (s, 2H, aromatics on
mesitylene).
Crystal data
C20H29NO
Mr= 299.44 Tetragonal,P42=n
a= 21.2110 (9) AÊ
c= 7.8940 (4) AÊ
V= 3551.6 (3) AÊ3
Z= 8
Dx= 1.120 Mg mÿ3
MoKradiation
Cell parameters from 18 614 re¯ections
= 1.4±26.0 = 0.07 mmÿ1
T= 293 (2) K Prism, yellow 0.420.290.20 mm
Data collection
Stoe IPDS-II diffractometer
!scans
Absorption correction: none 23 972 measured re¯ections 3390 independent re¯ections 1642 re¯ections withI> 2(I)
Rint= 0.068
max= 26.0
h=ÿ26!26
k=ÿ26!26
l=ÿ9!8
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.068
wR(F2) = 0.194
S= 1.01 3390 re¯ections 202 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0947P)2] whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.74 e AÊÿ3
min=ÿ0.24 e AÊÿ3
Extinction correction:SHELXL97 Extinction coef®cient: 0.0042 (12)
Table 1
Selected geometric parameters (AÊ,).
O1ÐC10 1.186 (4)
N1ÐC1 1.401 (5)
N1ÐC9 1.450 (4)
N1ÐC4 1.561 (5)
C5ÐC10 1.498 (5)
C5ÐC6 1.527 (5)
C5ÐC8 1.540 (4)
C6ÐC7 1.565 (4)
C7ÐC12 1.525 (4)
C7ÐC11 1.534 (4)
C7ÐC8 1.554 (4)
C9ÐC10 1.572 (5)
C13ÐC18 1.508 (4)
C15ÐC19 1.521 (4)
C17ÐC20 1.521 (4)
C1ÐN1ÐC9 114.5 (3)
C1ÐN1ÐC4 105.5 (3)
C9ÐN1ÐC4 108.3 (3)
N1ÐC1ÐC2 104.7 (3)
C1ÐC2ÐC3 106.1 (4)
C4ÐC3ÐC2 106.7 (3)
C3ÐC4ÐN1 98.0 (3)
C6ÐC5ÐC8 88.8 (2)
C5ÐC6ÐC7 90.4 (3)
C12ÐC7ÐC11 111.2 (2) C11ÐC7ÐC8 111.9 (3) C11ÐC7ÐC6 111.3 (2)
C8ÐC7ÐC6 86.9 (2)
C5ÐC8ÐC7 90.3 (3)
O1ÐC10ÐC5 122.9 (3) O1ÐC10ÐC9 119.0 (3)
N1ÐC9ÐC10ÐC5 ÿ54.1 (4)
Table 2
Hydrogen-bonding geometry (AÊ,).
Cg3 is the centroid of the C12±C17 benzene ring.
DÐH A DÐH H A D A DÐH A
C6ÐH6B O1i 0.97 2.65 3.594 (4) 164 C9ÐH9A O1i 0.97 2.69 3.450 (5) 136 C9ÐH9B Cg3ii 0.97 3.05 3.994 (4) 165 C11ÐH11A Cg3iii 0.96 2.96 3.818 (3) 149
Symmetry codes: (i)ÿx;1ÿy;1ÿz; (ii)ÿx;ÿy;2ÿz; (iii)ÿ1
2ÿy;x;12ÿz.
H atoms were positioned geometrically and treated as riding, with CÐH bond lengths of 0.93±0.98 AÊ, and withUiso(H) = 1.2Ueq(C)
[1.5Ueq(C) for methyl]. In the ®nal difference Fourier map, the
maximum residual density was located 1.27 AÊ from atom H1A, and the minimum was 0.26 AÊ from H18C.
Data collection: X-AREA (Stoe & Cie, 2002); cell re®nement:
X-AREA; data reduction:X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP-3for Windows(Farrugia, 1997); software used to prepare material for publication:WinGX(Farrugia, 1999).
References
Coghi, L., Lanfredi, A. M. M. & Tiripicchio, A. (1976).J. Chem. Soc. Perkin Trans.2, pp. 1808±1810.
Cremer, D. & Pople, J. A. (1975).J. Am. Chem. Soc.97, 1354±1358. Dehmlow, E. V. & Schmidt, S. (1990).Liebigs Ann. Chem.p. 411. Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Farrugia, L. J. (1999).J. Appl. Cryst.32, 837±838.
Huryn, D. M., Trost, B. M. & Fleming, I. (1991). Editors.Comprehensive Organic Synthesis, Vol. 1, pp. 64±74. Oxford: Pergamon.
Lynch, C. L., Gentry, A. L., Hale, J. J., Mills, S. G., MacCoss, M., Malkowitz, L., Springer, M. S., Gould, S. L., DeMartino, J. A., Siciliano, S. J., Cascieri, M. A., Doss, G., Carella, A., Carver, G., Holmes, K., Schleif, W. A., Danzeisen, R., Hazuda, D., Kessler, J., Lineberger, J., Miller, M. & Emini, E. A. (2002).Bioorg. Med. Chem. Lett.12, 677±679.
Martin, S. F. & Brossi, A. (1987). Editors.The Alkaloids, Vol. 30, ch. 3. Orlando: Academic Press.
OÈzdemir, N., DincËer, M., Yõlmaz, IÇ. & CËukurovalõ, A. (2004).Acta Cryst.E60, o145±o147.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.
Stoe & Cie (2002).X-AREA(Version 1.18) andX-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.
Figure 1
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Acta Cryst. (2004). E60, o1523–o1524
supporting information
Acta Cryst. (2004). E60, o1523–o1524 [https://doi.org/10.1107/S1600536804019002]
1-(3-Mesityl-3-methylcyclobutyl)-2-(pyrrolidin-1-yl)ethan-1-one
Muharrem Din
ç
er, Nam
ı
k
Ö
zdemir, Alaaddin
Ç
ukuroval
ı
,
İ
brahim Y
ı
lmaz and Orhan
B
ü
y
ü
kg
ü
ng
ö
r
1-(3-Mesityl-3-methylcyclobutyl)-2-(pyrrolidin-1-yl)ethan-1-one
Crystal data
C20H29NO Mr = 299.44 Tetragonal, P42/n Hall symbol: -P 4bc a = 21.2110 (9) Å c = 7.8940 (4) Å V = 3551.6 (3) Å3 Z = 8
F(000) = 1312
Dx = 1.120 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 18614 reflections θ = 1.4–26.0°
µ = 0.07 mm−1 T = 293 K Prism, yellow
0.42 × 0.29 × 0.20 mm
Data collection
Stoe IPDS-II diffractometer
Radiation source: sealed X-ray tube Plane graphite monochromator Detector resolution: 6.67 pixels mm-1 ω scans
23972 measured reflections
3390 independent reflections 1642 reflections with I > 2σ(I) Rint = 0.068
θmax = 26.0°, θmin = 1.4° h = −26→26
k = −26→26 l = −9→8
Refinement
Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.068 wR(F2) = 0.194 S = 1.01 3390 reflections 202 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) + (0.0947P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001
Δρmax = 0.74 e Å−3 Δρmin = −0.24 e Å−3
Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction coefficient: 0.0042 (12)
Special details
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
O1 0.01735 (10) 0.47663 (10) 0.2651 (3) 0.0611 (7)
N1 0.10207 (11) 0.61478 (11) 0.3020 (4) 0.0556 (8)
C1 0.13574 (19) 0.59939 (18) 0.1550 (6) 0.0725 (12)
H1A 0.1073 0.5919 0.0609 0.087*
H1B 0.1612 0.5620 0.1726 0.087*
C2 0.17553 (18) 0.6543 (2) 0.1226 (7) 0.0885 (15)
H2A 0.1557 0.6821 0.0408 0.106*
H2B 0.2162 0.6414 0.0788 0.106*
C3 0.18316 (17) 0.68755 (18) 0.2922 (6) 0.0772 (13)
H3A 0.2275 0.6923 0.3197 0.093*
H3B 0.1639 0.7290 0.2885 0.093*
C4 0.15090 (16) 0.64699 (17) 0.4221 (6) 0.0721 (12)
H4A 0.1307 0.6718 0.5098 0.087*
H4B 0.1795 0.6168 0.4731 0.087*
C5 −0.03070 (14) 0.57584 (15) 0.2227 (5) 0.0545 (10)
H5 −0.0151 0.6062 0.1391 0.065*
C6 −0.06678 (14) 0.60881 (14) 0.3649 (5) 0.0500 (9)
H6A −0.0583 0.6537 0.3722 0.060*
H6B −0.0618 0.5888 0.4745 0.060*
C7 −0.13078 (13) 0.59287 (13) 0.2759 (4) 0.0438 (8)
C8 −0.09309 (14) 0.54568 (16) 0.1646 (5) 0.0521 (9)
H8A −0.0978 0.5021 0.1995 0.063*
H8B −0.1011 0.5503 0.0442 0.063*
C9 0.07508 (16) 0.56114 (17) 0.3900 (5) 0.0641 (10)
H9A 0.0585 0.5744 0.4988 0.077*
H9B 0.1074 0.5296 0.4098 0.077*
C10 0.02067 (15) 0.53218 (16) 0.2794 (6) 0.0664 (11)
C11 −0.15517 (15) 0.64903 (15) 0.1724 (5) 0.0572 (10)
H11A −0.1219 0.6650 0.1022 0.086*
H11B −0.1693 0.6816 0.2479 0.086*
H11C −0.1897 0.6356 0.1024 0.086*
C12 −0.18235 (12) 0.56590 (13) 0.3894 (4) 0.0376 (7)
C13 −0.22210 (12) 0.51696 (13) 0.3304 (4) 0.0367 (7)
C14 −0.26606 (12) 0.48986 (13) 0.4398 (4) 0.0387 (7)
H14 −0.2913 0.4572 0.4000 0.046*
C15 −0.27349 (13) 0.50965 (13) 0.6041 (4) 0.0412 (8)
C16 −0.23747 (13) 0.55985 (14) 0.6577 (4) 0.0423 (8)
H16 −0.2430 0.5750 0.7673 0.051*
C17 −0.19308 (13) 0.58874 (13) 0.5540 (4) 0.0408 (8)
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Acta Cryst. (2004). E60, o1523–o1524
H18A −0.1887 0.5128 0.0884 0.078*
H18B −0.2608 0.4972 0.0998 0.078*
H18C −0.2108 0.4469 0.1560 0.078*
C19 −0.32105 (14) 0.47823 (16) 0.7211 (5) 0.0537 (9)
H19A −0.3100 0.4868 0.8368 0.081*
H19B −0.3207 0.4335 0.7021 0.081*
H19C −0.3624 0.4946 0.6982 0.081*
C20 −0.15962 (16) 0.64603 (16) 0.6271 (5) 0.0603 (10)
H20A −0.1864 0.6661 0.7090 0.090*
H20B −0.1502 0.6752 0.5377 0.090*
H20C −0.1212 0.6330 0.6808 0.090*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.0586 (14) 0.0445 (14) 0.080 (2) −0.0028 (10) 0.0041 (13) 0.0026 (12)
N1 0.0336 (13) 0.0410 (14) 0.092 (3) −0.0030 (11) 0.0088 (14) 0.0061 (14)
C1 0.070 (2) 0.069 (2) 0.078 (3) 0.010 (2) 0.016 (2) 0.009 (2)
C2 0.053 (2) 0.090 (3) 0.123 (4) 0.001 (2) 0.010 (2) −0.022 (3)
C3 0.051 (2) 0.063 (2) 0.117 (4) −0.0159 (17) 0.003 (2) −0.011 (2)
C4 0.048 (2) 0.056 (2) 0.112 (4) 0.0006 (16) 0.004 (2) −0.001 (2)
C5 0.0394 (16) 0.0500 (18) 0.074 (3) −0.0049 (14) 0.0064 (16) 0.0134 (17)
C6 0.0421 (16) 0.0454 (17) 0.063 (3) −0.0071 (13) −0.0036 (16) 0.0102 (16)
C7 0.0402 (15) 0.0443 (16) 0.047 (2) −0.0026 (13) −0.0023 (14) 0.0052 (14)
C8 0.0408 (16) 0.062 (2) 0.053 (2) −0.0056 (14) 0.0102 (15) 0.0031 (17)
C9 0.060 (2) 0.065 (2) 0.067 (3) 0.0021 (17) 0.0082 (19) 0.0113 (19)
C10 0.0424 (18) 0.0439 (19) 0.113 (4) −0.0050 (14) 0.0090 (19) 0.011 (2)
C11 0.0478 (18) 0.0558 (19) 0.068 (3) −0.0067 (15) −0.0026 (17) 0.0194 (18)
C12 0.0353 (14) 0.0377 (15) 0.040 (2) 0.0019 (11) −0.0021 (13) 0.0025 (13)
C13 0.0329 (14) 0.0411 (15) 0.036 (2) −0.0004 (12) −0.0002 (13) −0.0005 (13)
C14 0.0339 (14) 0.0402 (15) 0.042 (2) 0.0003 (12) 0.0007 (13) −0.0019 (13)
C15 0.0351 (15) 0.0473 (17) 0.041 (2) 0.0062 (12) 0.0023 (13) 0.0046 (14)
C16 0.0414 (16) 0.0488 (17) 0.037 (2) 0.0064 (14) −0.0010 (14) −0.0053 (14)
C17 0.0366 (15) 0.0396 (15) 0.046 (2) 0.0006 (12) −0.0037 (14) −0.0021 (14)
C18 0.0475 (18) 0.063 (2) 0.045 (2) −0.0058 (15) 0.0011 (15) −0.0086 (16)
C19 0.0478 (18) 0.065 (2) 0.048 (2) −0.0020 (15) 0.0109 (16) 0.0066 (17)
C20 0.061 (2) 0.057 (2) 0.064 (3) −0.0095 (16) −0.0026 (18) −0.0182 (18)
Geometric parameters (Å, º)
O1—C10 1.186 (4) C9—C10 1.572 (5)
N1—C1 1.401 (5) C9—H9A 0.9700
N1—C9 1.450 (4) C9—H9B 0.9700
N1—C4 1.561 (5) C11—H11A 0.9600
C1—C2 1.461 (6) C11—H11B 0.9600
C1—H1A 0.9700 C11—H11C 0.9600
C1—H1B 0.9700 C12—C17 1.405 (4)
C2—H2A 0.9700 C13—C14 1.395 (4)
C2—H2B 0.9700 C13—C18 1.508 (4)
C3—C4 1.503 (6) C14—C15 1.373 (4)
C3—H3A 0.9700 C14—H14 0.9300
C3—H3B 0.9700 C15—C16 1.377 (4)
C4—H4A 0.9700 C15—C19 1.521 (4)
C4—H4B 0.9700 C16—C17 1.390 (4)
C5—C10 1.498 (5) C16—H16 0.9300
C5—C6 1.527 (5) C17—C20 1.521 (4)
C5—C8 1.540 (4) C18—H18A 0.9600
C5—H5 0.9800 C18—H18B 0.9600
C6—C7 1.565 (4) C18—H18C 0.9600
C6—H6A 0.9700 C19—H19A 0.9600
C6—H6B 0.9700 C19—H19B 0.9600
C7—C12 1.525 (4) C19—H19C 0.9600
C7—C11 1.534 (4) C20—H20A 0.9600
C7—C8 1.554 (4) C20—H20B 0.9600
C8—H8A 0.9700 C20—H20C 0.9600
C8—H8B 0.9700
C1—N1—C9 114.5 (3) N1—C9—C10 109.3 (3)
C1—N1—C4 105.5 (3) N1—C9—H9A 109.8
C9—N1—C4 108.3 (3) C10—C9—H9A 109.8
N1—C1—C2 104.7 (3) N1—C9—H9B 109.8
N1—C1—H1A 110.8 C10—C9—H9B 109.8
C2—C1—H1A 110.8 H9A—C9—H9B 108.3
N1—C1—H1B 110.8 O1—C10—C5 122.9 (3)
C2—C1—H1B 110.8 O1—C10—C9 119.0 (3)
H1A—C1—H1B 108.9 C5—C10—C9 117.3 (3)
C1—C2—C3 106.1 (4) C7—C11—H11A 109.5
C1—C2—H2A 110.5 C7—C11—H11B 109.5
C3—C2—H2A 110.5 H11A—C11—H11B 109.5
C1—C2—H2B 110.5 C7—C11—H11C 109.5
C3—C2—H2B 110.5 H11A—C11—H11C 109.5
H2A—C2—H2B 108.7 H11B—C11—H11C 109.5
C4—C3—C2 106.7 (3) C17—C12—C13 117.4 (3)
C4—C3—H3A 110.4 C17—C12—C7 122.0 (3)
C2—C3—H3A 110.4 C13—C12—C7 120.6 (3)
C4—C3—H3B 110.4 C14—C13—C12 119.7 (3)
C2—C3—H3B 110.4 C14—C13—C18 116.3 (3)
H3A—C3—H3B 108.6 C12—C13—C18 124.0 (3)
C3—C4—N1 98.0 (3) C15—C14—C13 122.4 (3)
C3—C4—H4A 112.2 C15—C14—H14 118.8
N1—C4—H4A 112.2 C13—C14—H14 118.8
C3—C4—H4B 112.2 C14—C15—C16 117.6 (3)
N1—C4—H4B 112.2 C14—C15—C19 121.0 (3)
H4A—C4—H4B 109.8 C16—C15—C19 121.4 (3)
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C10—C5—C8 117.2 (3) C15—C16—H16 118.8
C6—C5—C8 88.8 (2) C17—C16—H16 118.8
C10—C5—H5 111.3 C16—C17—C12 120.2 (3)
C6—C5—H5 111.3 C16—C17—C20 116.4 (3)
C8—C5—H5 111.3 C12—C17—C20 123.4 (3)
C5—C6—C7 90.4 (3) C13—C18—H18A 109.5
C5—C6—H6A 113.6 C13—C18—H18B 109.5
C7—C6—H6A 113.6 H18A—C18—H18B 109.5
C5—C6—H6B 113.6 C13—C18—H18C 109.5
C7—C6—H6B 113.6 H18A—C18—H18C 109.5
H6A—C6—H6B 110.9 H18B—C18—H18C 109.5
C12—C7—C11 111.2 (2) C15—C19—H19A 109.5
C12—C7—C8 117.4 (2) C15—C19—H19B 109.5
C11—C7—C8 111.9 (3) H19A—C19—H19B 109.5
C12—C7—C6 116.1 (3) C15—C19—H19C 109.5
C11—C7—C6 111.3 (2) H19A—C19—H19C 109.5
C8—C7—C6 86.9 (2) H19B—C19—H19C 109.5
C5—C8—C7 90.3 (3) C17—C20—H20A 109.5
C5—C8—H8A 113.6 C17—C20—H20B 109.5
C7—C8—H8A 113.6 H20A—C20—H20B 109.5
C5—C8—H8B 113.6 C17—C20—H20C 109.5
C7—C8—H8B 113.6 H20A—C20—H20C 109.5
H8A—C8—H8B 110.9 H20B—C20—H20C 109.5
C9—N1—C1—C2 −161.0 (3) N1—C9—C10—C5 −54.1 (4)
C4—N1—C1—C2 −41.9 (4) C11—C7—C12—C17 −88.4 (3)
N1—C1—C2—C3 23.5 (4) C8—C7—C12—C17 141.0 (3)
C1—C2—C3—C4 4.3 (4) C6—C7—C12—C17 40.2 (4)
C2—C3—C4—N1 −26.8 (4) C11—C7—C12—C13 90.6 (3)
C1—N1—C4—C3 42.8 (3) C8—C7—C12—C13 −40.0 (4)
C9—N1—C4—C3 165.8 (3) C6—C7—C12—C13 −140.7 (3)
C10—C5—C6—C7 −134.1 (3) C17—C12—C13—C14 −5.4 (4)
C8—C5—C6—C7 −14.3 (2) C7—C12—C13—C14 175.5 (2)
C5—C6—C7—C12 133.3 (3) C17—C12—C13—C18 174.6 (3)
C5—C6—C7—C11 −98.1 (3) C7—C12—C13—C18 −4.5 (4)
C5—C6—C7—C8 14.2 (2) C12—C13—C14—C15 1.3 (4)
C10—C5—C8—C7 132.5 (3) C18—C13—C14—C15 −178.7 (3)
C6—C5—C8—C7 14.4 (3) C13—C14—C15—C16 2.7 (4)
C12—C7—C8—C5 −132.0 (3) C13—C14—C15—C19 −178.8 (3)
C11—C7—C8—C5 97.7 (3) C14—C15—C16—C17 −2.5 (4)
C6—C7—C8—C5 −14.1 (2) C19—C15—C16—C17 179.1 (3)
C1—N1—C9—C10 −68.6 (4) C15—C16—C17—C12 −1.7 (4)
C4—N1—C9—C10 174.1 (3) C15—C16—C17—C20 176.5 (3)
C6—C5—C10—O1 110.3 (4) C13—C12—C17—C16 5.6 (4)
C8—C5—C10—O1 7.7 (6) C7—C12—C17—C16 −175.3 (3)
C6—C5—C10—C9 −58.9 (4) C13—C12—C17—C20 −172.5 (3)
C8—C5—C10—C9 −161.4 (3) C7—C12—C17—C20 6.5 (4)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C6—H6B···O1i 0.97 2.65 3.594 (4) 164
C9—H9A···O1i 0.97 2.69 3.450 (5) 136
C9—H9B···Cg3ii 0.97 3.05 3.994 (4) 165
C11—H11A···Cg3iii 0.96 2.96 3.818 (3) 149