1-Benzoyl-5-phenyl-2-(propan-2-yl)-
1,2,3,4-tetrahydropyrimidin-4-one

Ignez Caracelli,a* Julio Zukerman-Schpector,b

Mônica F. Z. J. Amaral,c Hélio A. Stefanic and

Edward R. T. Tiekinkb

aBioMat-Physics Department, Universidade Estadual Paulista Júlio de Mesquita Filho,

UNESP, 17033-360 Bauru, SP, Brazil, bDepartment of Chemistry, Universidade

Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, and cDepartamento de

Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São

Paulo, SP, Brazil

Correspondence e-mail: ignez@fc.unesp.br

Received 7 September 2009; accepted 8 September 2009

Key indicators: single-crystal X-ray study; T = 98 K; mean �(C–C) = 0.002 Å; R factor =

0.049; wR factor = 0.126; data-to-parameter ratio = 14.5.

The tetrahydropyrimidinone ring in the title compound,

C20H20N2O2, is in a half-boat conformation with the N—C—

N C atom 0.580 (2) Å out of the plane defined by the

remaining five atoms. In the crystal structure, molecules are

connected into centrosymmetric dimers via N—H� � �O inter-

actions. The dimeric aggregates are linked into supra-

molecular chains along the a axis via C—H� � �� interactions.

Related literature

For background to the use of potassium organotrifluoroborate

salts in organic synthesis, see: Caracelli et al. (2007); Stefani et

al. (2007); Vieira et al. (2008). For a related structure, see:

Vega-Teijido et al. (2007). For conformational analysis, see:

Cremer & Pople (1975); Iulek & Zukerman-Schpector (1997).

Experimental

Crystal data

C20H20N2O2

Mr = 320.38
Monoclinic, P21=n
a = 9.346 (4) Å

b = 8.001 (3) Å
c = 22.528 (9) Å
� = 96.843 (9)�

V = 1672.6 (12) Å3

Z = 4

Mo K� radiation
� = 0.08 mm�1

T = 98 K
0.35 � 0.22 � 0.10 mm

Data collection

Rigaku AFC12/SATURN724
diffractometer

Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
Tmin = 0.811, Tmax = 1

5658 measured reflections
3094 independent reflections
2636 reflections with I > 2�(I)
Rint = 0.035

Refinement

R[F 2 > 2�(F 2)] = 0.049
wR(F 2) = 0.126
S = 1.09
3094 reflections

213 parameters
H-atom parameters constrained
��max = 0.22 e �3

��min = �0.20 e �3

Table 1
Hydrogen-bond geometry (Å, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

N3—H1N3� � �O1i 0.93 1.90 2.827 (2) 174
C9—H9� � �Cgii 0.93 2.82 3.632 (2) 147

Symmetry codes: (i) �xþ 2;�y;�z; (ii) �xþ 1;�y;�z. Cg is the centroid of the C14–
C19 ring.

Data collection: CrystalClear (Rigaku, 2005); cell refinement:

CrystalClear; data reduction: CrystalClear; program(s) used to solve

structure: SIR97 (Altomare et al., 1999); program(s) used to refine

structure: SHELXL97 (Sheldrick, 2008); molecular graphics:

ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006);

software used to prepare material for publication: WinGX (Farrugia,

1999).

We thank FAPESP (grant Nos. 07/59404-2 to HAS and 08/

02531-5 to JZS), CNPq (grant Nos. 472237/2008-0 to IC,

300613/2007 to HAS and 307121/2006-0 to JZS) and CAPES

for financial support.

Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: NG2639).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C.,
Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J.
Appl. Cryst. 32, 115–119.

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Caracelli, I., Stefani, H. A., Vieira, A. S., Machado, M. M. P. & Zukerman-

Schpector, J. (2007). Z. Kristallogr. New Cryst. Struct. 222, 345–346.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Iulek, J. & Zukerman-Schpector, J. (1997). Quim. Nova, 20, 433–434.
Rigaku (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Stefani, H. A., Cella, R. & Vieira, A. S. (2007). Tetrahedron, 63, 3623–3658.
Vega-Teijido, M., Zukerman-Schpector, J., Nunes, F. M., Gatti, P. M., Stefani,

H. A. & Caracelli, I. (2007). Z. Kristallogr. 222, 705–712.
Vieira, A. S., Fiorante, P. F., Zukerman-Schpector, J., Alves, D., Botteselle, G.

V. & Stefani, H. A. (2008). Tetrahedron, 64, 7234–7241.

organic compounds

o2466 Caracelli et al. doi:10.1107/S1600536809036356 Acta Cryst. (2009). E65, o2466

Acta Crystallographica Section E

Structure Reports
Online

ISSN 1600-5368

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supplementary materials



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Acta Cryst. (2009). E65, o2466    [ doi:10.1107/S1600536809036356 ]

1-Benzoyl-5-phenyl-2-(propan-2-yl)-1,2,3,4-tetrahydropyrimidin-4-one

I. Caracelli, J. Zukerman-Schpector, M. F. Z. J. Amaral, H. A. Stefani and E. R. T. Tiekink

Comment

As part of our on-going research interest efforts exploring the chemistry of potassium organotrifluoroborate salts, including
their potential use as intermediates in organic synthesis (Caracelli et al., 2007; Stefani et al., 2007; Vieira et al. 2008),
we have started to use the Suzuki–Miyaura cross-coupling reaction as a new tool to synthesize β-amino acids. Herein, the
crystal structure of (I) is described.

The molecular structure of (I), Fig. 1, shows the tetrahydropyrimidinone ring to adopt a half-boat conformation with the
C2 atom being displaced 0.580 (2) Å out of the plane defined by the remaining five atoms. The ring-puckering parameters are
q2 = 0.374 (2) Å, q3 = 0.187 (1) Å, Q = 0.418 (2) Å, and φ2 = 54.0 (2)° (Cremer & Pople, 1975; Iulek & Zukerman-Schpector,

1997). The dihedral angle between the aryl rings is 55.55 (8)°. The deviation of the torsion angle C4—C5—C14—C15
from the ideal value of 60°, which would indicate bisection of the dihydripyrimidinone ring by the plane of the phenyl
ring, is of 15.7°.

In the crystal packing, centrosymmetric dimers are formed being consolidated by eight-membered {O═C—N—H···}2

synthons, Table 1. The carbonyl-O2 atom is involved in an intramolecular C—H···O contact with the C—H2 atom (2.34 Å)
and does not particiate in a significant intermolecular contact. The aggregates thus formed are linked into supramolecular

chains, Fig. 2, aligned along the a axis via C—H···π interactions: C9—H9···Cg(C14–C19)i = 2.82 Å, C9···Cg(C14–C19)i =
3.632 (2) Å with an angle of 147° at H9; symmetry operation i: 1 - x, -y, -z.

Experimental

A 50 ml flask under N2 atmosphere was charged with potassium phenyltrifluoroborate (1.2 mmol), (S)-5-iodopyrimidinone

3 (1.0 mmol, 370 mg), Pd(OAc)2 (9 mol%, 20.02 mg), K2CO3 (2 mmol, 276 mg), and 16 ml of degassed dioxane/H2O

(3/1). The reaction mixture was refluxed at 383 K and the reaction followed by TLC and GC. After completion, the reaction
mixture was cooled and then extracted with ethyl acetate (3 × 50 ml). The organic layers were combined, dried (MgSO4), and

the solvent removed under vacuum to give a viscous oil. The oil was purified via column chromatography using a mixture
of ethyl acetate/hexane (1:1) as the eluent. Single crystals of (I) were obtained by slow evaporation from ethyl acetate.

Refinement

The H atoms were positioned with idealized geometry using a riding model with N—H = 0.93 Å and C—H = 0.93–0.98 Å,
and with Uiso set to 1.2 times (1.5 for methyl) Ueq(parent atom).

http://dx.doi.org/10.1107/S1600536809036356
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http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Zukerman-Schpector,%20J.
http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Amaral,%20M.F.Z.J.
http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Stefani,%20H.A.
http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Tiekink,%20E.R.T.


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Figures

Fig. 1. The molecular structure of (I) showing atom labelling scheme and displacement ellips-
oids at the 50% probability level (arbitrary spheres for the H atoms).

Fig. 2. Supramolecular chain in (I) comprising centrosymmetric dimers mediated by
{O═C—N—H···}2 synthons (hydrogen bonds shown as orange dashed lines) linked by
C—H···π interactions (shown as purple dashed lines).

1-Benzoyl-5-phenyl-2-(propan-2-yl)-1,2,3,4-tetrahydropyrimidin-4-one

Crystal data

C20H20N2O2 F000 = 680

Mr = 320.38 Dx = 1.272 Mg m−3

Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 6484 reflections
a = 9.346 (4) Å θ = 2.5–40.2º
b = 8.001 (3) Å µ = 0.08 mm−1

c = 22.528 (9) Å T = 98 K
β = 96.843 (9)º Prism, colourless

V = 1672.6 (12) Å3 0.35 × 0.22 × 0.10 mm
Z = 4

Data collection

Rigaku AFC12/SATURN724
diffractometer 3094 independent reflections

Radiation source: fine-focus sealed tube 2636 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.035

T = 98 K θmax = 25.5º

ω scans θmin = 2.5º
Absorption correction: multi-scan
ABSCOR (Higashi, 1995) h = −11→8

Tmin = 0.811, Tmax = 1 k = −6→9
5658 measured reflections l = −26→27

Refinement

Refinement on F2 Secondary atom site location: difference Fourier map



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sup-3

Least-squares matrix: full Hydrogen site location: inferred from neighbouring
sites

R[F2 > 2σ(F2)] = 0.049 H-atom parameters constrained

wR(F2) = 0.126
  w = 1/[σ2(Fo

2) + (0.0541P)2 + 0.6346P]
where P = (Fo

2 + 2Fc
2)/3

S = 1.09 (Δ/σ)max < 0.001

3094 reflections Δρmax = 0.22 e Å−3

213 parameters Δρmin = −0.20 e Å−3

Primary atom site location: structure-invariant direct
methods Extinction correction: none

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The
cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between
s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is
used for estimating s.u.'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, convention-

al 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

C2 0.91894 (17) 0.2343 (2) 0.10191 (7) 0.0228 (4)
H2 0.9791 0.1868 0.1364 0.027*
C4 0.81099 (17) 0.1247 (2) 0.00497 (7) 0.0227 (4)
C5 0.68065 (16) 0.2234 (2) 0.01348 (7) 0.0215 (4)
C6 0.66388 (17) 0.2745 (2) 0.06922 (7) 0.0225 (4)
H6 0.5782 0.3264 0.0759 0.027*
C7 0.74672 (18) 0.2425 (2) 0.17669 (7) 0.0250 (4)
C8 0.59340 (18) 0.2378 (2) 0.19000 (7) 0.0249 (4)
C9 0.49283 (19) 0.1281 (2) 0.16115 (8) 0.0289 (4)
H9 0.5177 0.0606 0.1304 0.035*
C10 0.3547 (2) 0.1194 (3) 0.17838 (8) 0.0346 (4)
H10 0.2877 0.0448 0.1596 0.041*
C11 0.3174 (2) 0.2217 (3) 0.22339 (9) 0.0362 (5)
H11 0.2248 0.2171 0.2345 0.043*
C12 0.4177 (2) 0.3315 (2) 0.25215 (8) 0.0346 (4)
H12 0.3917 0.4005 0.2823 0.041*
C13 0.5563 (2) 0.3389 (2) 0.23625 (8) 0.0296 (4)
H13 0.6239 0.4107 0.2562 0.036*
C14 0.56628 (17) 0.2461 (2) −0.03774 (7) 0.0219 (4)
C15 0.60156 (17) 0.2860 (2) −0.09467 (7) 0.0235 (4)
H15 0.6977 0.2993 −0.1005 0.028*
C16 0.49504 (18) 0.3061 (2) −0.14248 (7) 0.0264 (4)



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H16 0.5201 0.3327 −0.1801 0.032*
C17 0.35113 (18) 0.2865 (2) −0.13443 (8) 0.0279 (4)
H17 0.2796 0.3000 −0.1665 0.033*
C18 0.31473 (18) 0.2469 (2) −0.07842 (8) 0.0285 (4)
H18 0.2184 0.2339 −0.0729 0.034*
C19 0.42147 (17) 0.2262 (2) −0.03020 (7) 0.0245 (4)
H19 0.3958 0.1990 0.0073 0.029*
C20 0.98292 (17) 0.4034 (2) 0.08670 (7) 0.0260 (4)
H20 0.9135 0.4597 0.0573 0.031*
C21 1.12258 (19) 0.3783 (2) 0.05890 (8) 0.0323 (4)
H21A 1.1605 0.4851 0.0492 0.048*
H21B 1.1035 0.3125 0.0232 0.048*
H21C 1.1916 0.3215 0.0868 0.048*
C22 1.01001 (18) 0.5154 (2) 0.14175 (8) 0.0318 (4)
H22A 0.9239 0.5223 0.1610 0.048*
H22B 1.0367 0.6252 0.1298 0.048*
H22C 1.0865 0.4692 0.1691 0.048*
N1 0.77103 (14) 0.25198 (17) 0.11728 (6) 0.0226 (3)
N3 0.91274 (14) 0.11564 (18) 0.05278 (6) 0.0232 (3)
H1N3 0.9978 0.0622 0.0463 0.028*
O1 0.82249 (12) 0.04539 (16) −0.04171 (5) 0.0292 (3)
O2 0.84733 (13) 0.23635 (17) 0.21657 (5) 0.0335 (3)

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

C2 0.0202 (8) 0.0296 (9) 0.0179 (8) 0.0028 (7) 0.0000 (6) −0.0023 (7)
C4 0.0207 (8) 0.0246 (8) 0.0227 (8) −0.0016 (7) 0.0022 (6) −0.0002 (7)
C5 0.0201 (8) 0.0254 (8) 0.0191 (8) −0.0008 (7) 0.0022 (6) 0.0008 (7)
C6 0.0198 (7) 0.0273 (8) 0.0203 (8) 0.0023 (7) 0.0018 (6) 0.0029 (7)
C7 0.0308 (9) 0.0247 (9) 0.0192 (8) 0.0059 (7) 0.0015 (7) 0.0028 (7)
C8 0.0307 (9) 0.0265 (9) 0.0180 (8) 0.0051 (7) 0.0047 (6) 0.0049 (7)
C9 0.0337 (9) 0.0316 (9) 0.0220 (8) 0.0023 (8) 0.0061 (7) 0.0021 (7)
C10 0.0345 (10) 0.0382 (11) 0.0318 (10) −0.0026 (8) 0.0072 (7) 0.0062 (8)
C11 0.0342 (10) 0.0420 (11) 0.0346 (10) 0.0079 (9) 0.0129 (8) 0.0104 (9)
C12 0.0454 (11) 0.0349 (10) 0.0257 (9) 0.0146 (9) 0.0137 (8) 0.0055 (8)
C13 0.0383 (10) 0.0281 (9) 0.0226 (8) 0.0056 (8) 0.0041 (7) 0.0020 (7)
C14 0.0223 (8) 0.0227 (8) 0.0206 (8) 0.0007 (7) 0.0026 (6) −0.0009 (6)
C15 0.0220 (8) 0.0266 (8) 0.0220 (8) −0.0008 (7) 0.0030 (6) −0.0003 (7)
C16 0.0306 (9) 0.0292 (9) 0.0191 (8) −0.0001 (7) 0.0024 (7) 0.0012 (7)
C17 0.0272 (8) 0.0317 (9) 0.0228 (8) 0.0052 (8) −0.0049 (6) −0.0012 (7)
C18 0.0199 (8) 0.0370 (10) 0.0283 (9) 0.0023 (7) 0.0012 (7) −0.0021 (8)
C19 0.0232 (8) 0.0311 (9) 0.0194 (8) 0.0012 (7) 0.0037 (6) 0.0007 (7)
C20 0.0243 (8) 0.0282 (9) 0.0242 (8) 0.0011 (7) −0.0026 (6) −0.0001 (7)
C21 0.0334 (9) 0.0343 (10) 0.0297 (9) −0.0054 (8) 0.0060 (7) −0.0005 (8)
C22 0.0281 (9) 0.0325 (10) 0.0338 (10) 0.0004 (8) −0.0006 (7) −0.0090 (8)
N1 0.0212 (7) 0.0292 (8) 0.0169 (7) 0.0030 (6) 0.0008 (5) 0.0012 (6)
N3 0.0196 (6) 0.0270 (7) 0.0223 (7) 0.0034 (6) 0.0003 (5) −0.0030 (6)



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O1 0.0247 (6) 0.0379 (7) 0.0243 (6) 0.0044 (5) 0.0001 (4) −0.0091 (5)
O2 0.0325 (7) 0.0468 (8) 0.0197 (6) 0.0053 (6) −0.0031 (5) 0.0007 (6)

Geometric parameters (Å, °)

C2—N3 1.454 (2) C12—H12 0.9300
C2—N1 1.471 (2) C13—H13 0.9300
C2—C20 1.534 (2) C14—C19 1.393 (2)
C2—H2 0.9800 C14—C15 1.399 (2)
C4—O1 1.244 (2) C15—C16 1.386 (2)
C4—N3 1.351 (2) C15—H15 0.9300
C4—C5 1.483 (2) C16—C17 1.387 (2)
C5—C6 1.347 (2) C16—H16 0.9300
C5—C14 1.488 (2) C17—C18 1.382 (3)
C6—N1 1.396 (2) C17—H17 0.9300
C6—H6 0.9300 C18—C19 1.394 (2)
C7—O2 1.222 (2) C18—H18 0.9300
C7—N1 1.386 (2) C19—H19 0.9300
C7—C8 1.499 (2) C20—C22 1.526 (2)
C8—C9 1.389 (3) C20—C21 1.527 (2)
C8—C13 1.395 (2) C20—H20 0.9800
C9—C10 1.394 (2) C21—H21A 0.9600
C9—H9 0.9300 C21—H21B 0.9600
C10—C11 1.380 (3) C21—H21C 0.9600
C10—H10 0.9300 C22—H22A 0.9600
C11—C12 1.387 (3) C22—H22B 0.9600
C11—H11 0.9300 C22—H22C 0.9600
C12—C13 1.386 (3) N3—H1N3 0.9300

N3—C2—N1 106.75 (12) C16—C15—C14 120.86 (15)
N3—C2—C20 112.78 (14) C16—C15—H15 119.6
N1—C2—C20 111.71 (13) C14—C15—H15 119.6
N3—C2—H2 108.5 C15—C16—C17 120.20 (15)
N1—C2—H2 108.5 C15—C16—H16 119.9
C20—C2—H2 108.5 C17—C16—H16 119.9
O1—C4—N3 121.55 (15) C18—C17—C16 119.55 (15)
O1—C4—C5 122.39 (14) C18—C17—H17 120.2
N3—C4—C5 115.88 (14) C16—C17—H17 120.2
C6—C5—C4 118.07 (15) C17—C18—C19 120.48 (16)
C6—C5—C14 122.20 (15) C17—C18—H18 119.8
C4—C5—C14 119.36 (14) C19—C18—H18 119.8
C5—C6—N1 122.08 (15) C14—C19—C18 120.44 (16)
C5—C6—H6 119.0 C14—C19—H19 119.8
N1—C6—H6 119.0 C18—C19—H19 119.8
O2—C7—N1 120.79 (16) C22—C20—C21 110.07 (14)
O2—C7—C8 121.49 (15) C22—C20—C2 111.56 (15)
N1—C7—C8 117.71 (14) C21—C20—C2 110.53 (14)
C9—C8—C13 120.04 (16) C22—C20—H20 108.2
C9—C8—C7 122.16 (15) C21—C20—H20 108.2
C13—C8—C7 117.61 (16) C2—C20—H20 108.2



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C8—C9—C10 119.94 (17) C20—C21—H21A 109.5
C8—C9—H9 120.0 C20—C21—H21B 109.5
C10—C9—H9 120.0 H21A—C21—H21B 109.5
C11—C10—C9 119.90 (18) C20—C21—H21C 109.5
C11—C10—H10 120.0 H21A—C21—H21C 109.5
C9—C10—H10 120.0 H21B—C21—H21C 109.5
C10—C11—C12 120.21 (17) C20—C22—H22A 109.5
C10—C11—H11 119.9 C20—C22—H22B 109.5
C12—C11—H11 119.9 H22A—C22—H22B 109.5
C13—C12—C11 120.43 (17) C20—C22—H22C 109.5
C13—C12—H12 119.8 H22A—C22—H22C 109.5
C11—C12—H12 119.8 H22B—C22—H22C 109.5
C12—C13—C8 119.46 (18) C7—N1—C6 124.81 (14)
C12—C13—H13 120.3 C7—N1—C2 119.25 (13)
C8—C13—H13 120.3 C6—N1—C2 115.93 (13)
C19—C14—C15 118.46 (15) C4—N3—C2 122.15 (14)
C19—C14—C5 120.67 (15) C4—N3—H1N3 115.7
C15—C14—C5 120.87 (14) C2—N3—H1N3 117.6

O1—C4—C5—C6 165.73 (16) C14—C15—C16—C17 −0.1 (3)
N3—C4—C5—C6 −9.5 (2) C15—C16—C17—C18 0.0 (3)
O1—C4—C5—C14 −7.5 (2) C16—C17—C18—C19 −0.1 (3)
N3—C4—C5—C14 177.25 (14) C15—C14—C19—C18 −0.4 (3)
C4—C5—C6—N1 6.5 (2) C5—C14—C19—C18 −179.68 (16)
C14—C5—C6—N1 179.57 (15) C17—C18—C19—C14 0.3 (3)
O2—C7—C8—C9 −129.50 (19) N3—C2—C20—C22 −171.05 (13)
N1—C7—C8—C9 49.6 (2) N1—C2—C20—C22 68.70 (17)
O2—C7—C8—C13 45.5 (2) N3—C2—C20—C21 −48.23 (18)
N1—C7—C8—C13 −135.33 (17) N1—C2—C20—C21 −168.48 (13)
C13—C8—C9—C10 0.1 (3) O2—C7—N1—C6 −173.99 (16)
C7—C8—C9—C10 175.01 (16) C8—C7—N1—C6 6.9 (2)
C8—C9—C10—C11 1.1 (3) O2—C7—N1—C2 7.3 (2)
C9—C10—C11—C12 −1.0 (3) C8—C7—N1—C2 −171.89 (14)
C10—C11—C12—C13 −0.3 (3) C5—C6—N1—C7 −155.06 (17)
C11—C12—C13—C8 1.5 (3) C5—C6—N1—C2 23.7 (2)
C9—C8—C13—C12 −1.4 (3) N3—C2—N1—C7 132.30 (15)
C7—C8—C13—C12 −176.52 (15) C20—C2—N1—C7 −104.00 (17)
C6—C5—C14—C19 −38.0 (2) N3—C2—N1—C6 −46.57 (18)
C4—C5—C14—C19 134.97 (17) C20—C2—N1—C6 77.13 (17)
C6—C5—C14—C15 142.74 (18) O1—C4—N3—C2 165.52 (15)
C4—C5—C14—C15 −44.3 (2) C5—C4—N3—C2 −19.2 (2)
C19—C14—C15—C16 0.3 (3) N1—C2—N3—C4 46.0 (2)
C5—C14—C15—C16 179.55 (15) C20—C2—N3—C4 −77.04 (19)

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A

N3—H1N3···O1i 0.93 1.90 2.827 (2) 174

C9—H9···Cgii 0.93 2.82 3.632 (2) 147



supplementary materials

sup-7

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z.

Fig. 1



supplementary materials

sup-8

Fig. 2