organic papers
Acta Cryst.(2005). E61, o93±o95 doi:10.1107/S1600536804032003 Rozycka-Sokolowskaet al. C19H20N4
o93
Acta Crystallographica Section EStructure Reports Online
ISSN 1600-5368
5-(
N
,
N
-Diethylamino)-4,6-diphenyl-1,2,3-triazine
Ewa Rozycka-Sokolowska,a
Tomasz Girek,aBernard
Marciniak,a* Volodymyr
Pavlyuk,aJozef Drabowicza,b
and Kyoshi Matsumotoc
aInstitute of Chemistry and Environment
Protec-tion, Pedagogical University of Czestochowa, al. Armii Krajowej 13/15, 42-200 Czestochowa, Poland,bCentre of Molecular and
Macromol-ecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, ul. Sienkiewicza 112, 90-363 Lodz, Poland, and
cGraduate School of Human and Environmental
Studies, Kyoto University, Nihonmatsu-cho Yoshida Sakyo-ku, Kyoto 606-8501, Japan
Correspondence e-mail: crystal@cz.onet.pl
Key indicators
Single-crystal X-ray study
T= 293 K
Mean(C±C) = 0.004 AÊ
Rfactor = 0.035
wRfactor = 0.087 Data-to-parameter ratio = 8.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain ± all rights reserved
In the title compound, C19H20N4, the dihedral angles formed
by the planes of the triazine ring and the two phenyl substituents are 51.54 (1) and 49.27 (1). The phenyl rings form a dihedral angle of 80.81 (1). All bond lengths and angles are normal. The structure is stabilized by van der Waals interactions.
Comment
The derivatives of 1,2,3-triazine are an important class of heterocyclic compounds useful in organic synthesis and as insecticides, pharmaceuticals and dyestuffs. Their chemistry has been reviewed several times since 1956 (Erickson, 1956; Neunhoeffer & Wiley, 1978; Kobylecki & Mckillop, 1976). Their importance in organic synthesis is due to the fact that they can react as dienes on inverse-demand Diels±Alder cycloadditions with electron-rich dienophiles (Prieto et al., 2002). The many applications of these compounds as phar-maceuticals and selective herbicides, which are usually applied as pre- and post-emergent weed control agents to improve the quality of agricultural products (Masquelinet al., 1998), are a result of the wide range of biological activity associated with this interesting heteroaromatic ring system (Tsaiet al., 1998). The Cambridge Structural Database (CSD; Version 5.25 and updates; Allen, 2002) contains eight different derivatives of 1,2,3-triazine [refcodes KOTCIF (Yamaguchi et al., 1992), PIKDAO (Eichhornet al., 1993), PINWEO (Boppet al., 1994), TMPTAZ (Oeser & Schiele, 1972), VOBNAB and VOBNAB01 (Yamaguchi, Itoh, Okada, Ohsawa & Matsu-mura, 1991), VOBPAD, VOBPEH and VOBPEH01 (Yama-guchi, Itoh, Okada & Ohsawa, 1991), and UHUJIQ (Bauet al., 1998)]. Recently, we also published the structure of 5-(N,N-diethylamino)-4,6-tris(4-¯uorophenyl)-1,2,3-triazine (Matsumoto et al., 2002) and we report here the crystal structure of 5-(N,N-diethylamino)-4,6-diphenyl-1,2,3-triazine, (I).
A perspective view of the 4,6-diphenyl-5-(N,N -diethyl-amin)-1,2,3-triazine molecule is shown in Fig. 1. This molecule is built up from an essentially planar triazine ring, two
attached phenyl rings (I and II) and one diethylamino group, which are not coplanar with the triazine ring. The N atom of the diethylamino group lies 0.073 (2) AÊ above the plane formed by the triazine and the phenyl ring C atoms; C16 (ring I) and C17 (ring II) lie 0.094 (2) AÊ above and 0.186 (2) AÊ below this plane, respectively. The angle between the mean plane of phenyl ring I and the triazine mean plane is 51.54 (1), while the angle between the plane of ring II and the triazine plane is 49.27 (1). The angle between the two phenyl rings is 80.81 (1). The values of the bond lengths and valence angles lie in the usual ranges for similar structures included in the CSD.
Molecules pack in the cell, forming sheets parallel to theac
plane (Fig. 2). The crystal structure is stabilized by van der Waals interactions.
Experimental
Diphenylcyclopropenone, used as a starting material, was prepared according to the procedure of Breslow & Posner (1973). To a solution of diphenylcyclopropenone (0.606 g, 3 mmol) in dry dichloromethane (15 ml) under a nitrogen atmosphere was added triethyloxonium tetra¯uoroborate (0.624 g, 3.3 mmol). The resulting solution was stirred for 1 h at room temperature. A solution of diethylamine (0.22 g, 3 mmol) in dichloromethane (10 ml) was then added via
syringe. The reaction mixture was kept at room temperature for another 1 h, diethyl ether (70 ml) was added and the mixture was concentrated to 20 ml. The precipitated white solid was collected on a funnel and dried, giving 1-(N,N -diethylamino)-2,3-diphenylcyclo-propenium tetra¯uoroborate (0.78 g, 72%). To a suspension of this salt (0.69 g, 2 mmol) in dichloromethane (30 ml) was added sodium azide (0.39 g, 6 mmol), and the mixture was further stirred at room temperature for 24 h. The solvent was then evaporated, leaving a yellow solid which was shaken with benzene; a white solid which remained after shaking was ®ltered off and the benzene solution was evaporated again, leaving the crude product. Crystallization from chloroform/ethanol (1:1) afforded yellow crystals (0.4 g, 65%). Analysis calculated for C19H20N4: C 74.97, H 6.62, N 18.41%; found: C
74.92, H 6.64, N 18.19%. M.p. 481±482 K. IR (KBr disk): 2971, 2842, 2776, 2467, 2036, 1468, 1440, 1053;1H NMR (CDCl
3, 200 MHz):0.93
(t,J= 7 Hz, 6H), 2.79 (q,J= 7 Hz, 4H), 7.47±7.51 (m, 6H), 7.67±7.72 (m, 4H);13C NMR (CDCl
3, 54.6z):12.7, 46.0, 128.2, 128.7, 129.5,
136.7, 138.0, 152.6; MS (70 eV) m/z: 304 (100) (M+), 276 (43), 173 (59), 158 (5), 104 (5).
Crystal data C19H20N4
Mr= 304.39
Orthorhombic,Pca21
a= 12.535 (3) AÊ
b= 7.856 (2) AÊ
c= 16.253 (3) AÊ
V= 1600.5 (6) AÊ3
Z= 4
Dx= 1.263 Mg mÿ3
MoKradiation Cell parameters from 20
re¯ections = 10±16
= 0.08 mmÿ1
T= 293 (2) K
Needle, clear pale yellow 0.500.060.02 mm
Data collection Burevestnik DARCH-1
diffractometer !±2scans
Absorption correction: part of the re®nement model (F) (DIFABS; Walker & Stuart, 1983)
Tmin= 0.957,Tmax= 0.998
3080 measured re¯ections 1894 independent re¯ections
1563 re¯ections withI> 2(I)
Rint= 0.020
max= 27.4
h= 0!16
k= 0!10
l=ÿ10!20 3 standard re¯ections every 100 re¯ections intensity decay: 2.3%
Refinement Re®nement onF2
R[F2> 2(F2)] = 0.035
wR(F2) = 0.088
S= 1.06 1894 re¯ections 213 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0374P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.006 max= 0.11 e AÊÿ3 min=ÿ0.14 e AÊÿ3
H atoms were treated as riding (CÐH = 0.93±0.97 AÊ). The two free variables forUiso(H) were re®ned according to SHELXL97 (Shel-drick, 1997). In the absence of signi®cant anomalous dispersion effects, Friedel pairs were merged.
Data collection: DARCH software; cell re®nement: DARCH software; data reduction: DARCH software; program(s) used to solve structure:SHELXS97(Sheldrick, 1990); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication:SHELXL97.
organic papers
o94
Rozycka-Sokolowskaet al. C19H20N4 Acta Cryst.(2005). E61, o93±o95Figure 2
The crystal packing, viewed along thebaxis.
Figure 1
References
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Erickson, J. G. (1956).The Chemistry of Heterocyclic Compounds, Vol. 10. New York: Wiley Interscience.
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Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Spek, A. L. (2000).PLATON. University of Utrecht, The Netherlands. Tsai, Ch.-Y., Chen, Y.-R. & Her, G.-R. (1998).J. Chromatogr. A,813, 379±386. Walker, N. & Stuart, D. (1983).Acta Cryst.A39, 158±166.
Yamaguchi, K., Itoh, T., Okada, M. & Ohsawa, A. (1991).Acta Cryst.C47, 2193±2196.
Yamaguchi, K., Itoh, T., Okada, M. & Ohsawa, A. (1992).Acta Cryst.C48, 964±965.
Yamaguchi, K., Itoh, T., Okada, M., Ohsawa, A. & Matsumura, G. (1991).Acta Cryst.C47, 2256±2258.
organic papers
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Acta Cryst. (2005). E61, o93–o95
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Acta Cryst. (2005). E61, o93–o95 [https://doi.org/10.1107/S1600536804032003]
5-(
N
,
N
-Diethylamino)-4,6-diphenyl-1,2,3-triazine
Ewa Rozycka-Sokolowska, Tomasz Girek, Bernard Marciniak, Volodymyr Pavlyuk, Jozef
Drabowicz and Kyoshi Matsumoto
5-(N,N-Diethylamino)-4,6-diphenyl-1,2,3-triazine
Crystal data
C19H20N4
Mr = 304.39
Orthorhombic, Pca21
Hall symbol: P 2c -2ac
a = 12.535 (3) Å
b = 7.856 (2) Å
c = 16.253 (3) Å
V = 1600.5 (6) Å3
Z = 4
F(000) = 648
Dx = 1.263 Mg m−3
Mo Kα radiation, λ = 0.71069 Å Cell parameters from 20 reflections
θ = 10–16°
µ = 0.08 mm−1
T = 293 K
Needle, clear pale yellow 0.50 × 0.06 × 0.02 mm
Data collection
DARCH-1 diffractometer
Radiation source: BSW x-ray tube Graphite monochromator
ω–2θ scans
Absorption correction: part of the refinement model (ΔF)
(DIFABS; Walker & Stuart, 1983)
Tmin = 0.957, Tmax = 0.998
3080 measured reflections
1894 independent reflections 1563 reflections with I > 2σ(I)
Rint = 0.020
θmax = 27.4°, θmin = 2.5°
h = 0→16
k = 0→10
l = −10→20
3 standard reflections every 100 reflections intensity decay: 2.3%
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.035
wR(F2) = 0.088
S = 1.06 1895 reflections 213 parameters 1 restraint
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) + (0.0374P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.006
Δρmax = 0.11 e Å−3
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Acta Cryst. (2005). E61, o93–o95
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
N1 0.59182 (17) 0.0192 (2) 0.00777 (13) 0.0810 (5)
N2 0.66218 (18) 0.0129 (3) −0.05176 (15) 0.0885 (6)
N3 0.73609 (18) 0.1380 (3) −0.05968 (14) 0.0887 (5)
N4 0.67108 (14) 0.4116 (2) 0.11396 (12) 0.0761 (5)
C1 0.5380 (2) 0.1223 (3) 0.21012 (14) 0.0816 (6)
H1 0.6071 0.1496 0.2262 0.091 (2)*
C2 0.4612 (2) 0.0825 (3) 0.26871 (17) 0.0898 (7)
H2 0.4798 0.0832 0.3241 0.091 (2)*
C3 0.3605 (2) 0.0430 (3) 0.24700 (19) 0.0933 (7)
H3 0.3101 0.0179 0.2872 0.091 (2)*
C4 0.3328 (2) 0.0398 (3) 0.16653 (18) 0.0896 (7)
H4 0.2634 0.0129 0.1511 0.091 (2)*
C5 0.40901 (18) 0.0770 (3) 0.10711 (17) 0.0809 (6)
H5 0.3900 0.0717 0.0519 0.091 (2)*
C6 0.51085 (18) 0.1210 (3) 0.12755 (16) 0.0774 (6)
C7 0.59099 (17) 0.1478 (3) 0.06241 (14) 0.0706 (5)
C8 0.66612 (16) 0.2824 (3) 0.05852 (13) 0.0700 (5)
C9 0.73699 (16) 0.2707 (3) −0.00903 (14) 0.0704 (5)
C10 0.81407 (17) 0.4004 (3) −0.03567 (14) 0.0740 (5)
C11 0.9153 (2) 0.3544 (4) −0.06073 (17) 0.0891 (7)
H11 0.9372 0.2422 −0.0539 0.091 (2)*
C12 0.9838 (2) 0.4682 (5) −0.09500 (18) 0.1002 (9)
H12 1.0512 0.4329 −0.1118 0.091 (2)*
C13 0.9543 (2) 0.6324 (4) −0.10476 (19) 0.0940 (7)
H13 1.0012 0.7104 −0.1281 0.091 (2)*
C14 0.8530 (2) 0.6841 (4) −0.07967 (16) 0.0924 (7)
H14 0.8316 0.7966 −0.0862 0.091 (2)*
C15 0.78562 (19) 0.5672 (3) −0.04542 (15) 0.0794 (6)
H15 0.7183 0.6022 −0.0282 0.091 (2)*
C16 0.57540 (17) 0.4903 (3) 0.14752 (19) 0.0774 (6)
H16A 0.5668 0.4543 0.2042 0.072 (3)*
H16B 0.5139 0.4500 0.1169 0.072 (3)*
C17 0.77252 (17) 0.4671 (3) 0.14785 (17) 0.0773 (6)
H17A 0.8290 0.4021 0.1218 0.072 (3)*
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C18 0.5775 (2) 0.6783 (3) 0.1446 (2) 0.0992 (8)
H18A 0.6394 0.7192 0.1732 0.107 (4)*
H18B 0.5144 0.7226 0.1703 0.107 (4)*
H18C 0.5801 0.7152 0.0883 0.107 (4)*
C19 0.7836 (2) 0.4505 (5) 0.23671 (19) 0.1035 (9)
H19A 0.7336 0.5244 0.2635 0.107 (4)*
H19B 0.8548 0.4812 0.2526 0.107 (4)*
H19C 0.7698 0.3348 0.2525 0.107 (4)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
N1 0.0980 (13) 0.0732 (11) 0.0716 (12) −0.0083 (9) 0.0038 (10) −0.0026 (9) N2 0.0922 (15) 0.0815 (12) 0.0719 (12) −0.0058 (11) 0.0047 (12) −0.0078 (10) N3 0.0907 (13) 0.0771 (12) 0.0782 (13) −0.0063 (11) −0.0001 (10) −0.0082 (11) N4 0.0759 (10) 0.0794 (10) 0.0730 (12) 0.0009 (8) −0.0014 (9) −0.0038 (9) C1 0.0862 (16) 0.0812 (14) 0.0694 (13) −0.0105 (11) −0.0051 (12) 0.0069 (11) C2 0.1099 (19) 0.0897 (16) 0.0698 (15) −0.0139 (14) −0.0016 (13) −0.0002 (13) C3 0.0941 (18) 0.0821 (15) 0.083 (2) −0.0160 (14) 0.0096 (16) 0.0040 (13) C4 0.0875 (14) 0.0892 (15) 0.0798 (2) −0.0088 (11) −0.0011 (14) −0.0086 (14) C5 0.0801 (13) 0.0835 (14) 0.0753 (15) 0.0043 (11) 0.0053 (11) 0.0016 (12) C6 0.0840 (13) 0.0765 (10) 0.0757 (16) 0.0063 (10) 0.0075 (12) 0.0045 (11) C7 0.0744 (12) 0.0748 (11) 0.0625 (12) 0.0085 (9) −0.0067 (9) 0.0018 (10) C8 0.0727 (12) 0.0697 (11) 0.0676 (13) 0.0095 (9) −0.0033 (10) −0.0049 (10) C9 0.0833 (12) 0.0677 (11) 0.0702 (13) −0.0035 (9) −0.0009 (10) −0.0067 (10) C10 0.0803 (12) 0.0844 (13) 0.0724 (13) −0.0018 (10) 0.0050 (10) −0.0018 (10) C11 0.0903 (16) 0.0950 (16) 0.0820 (16) −0.0093 (13) 0.0058 (12) −0.0072 (13) C12 0.0905 (12) 0.0951 (3) 0.0843 (19) −0.0107 (15) 0.0055 (12) −0.0024 (17) C13 0.1012 (19) 0.0966 (18) 0.0842 (17) −0.0174 (14) 0.0009 (14) 0.0062 (14) C14 0.1143 (19) 0.0897 (15) 0.0732 (15) −0.0100 (14) 0.0084 (14) −0.0047 (12) C15 0.0769 (13) 0.0967 (15) 0.0644 (13) −0.0011 (11) 0.0057 (11) 0.0017 (12) C16 0.0694 (11) 0.0812 (12) 0.0816 (15) −0.0013 (9) 0.0081 (11) 0.0034 (11) C17 0.0746 (12) 0.0766 (12) 0.0806 (16) −0.0035 (9) −0.0064 (11) −0.0056 (11) C18 0.0956 (16) 0.0722 (13) 0.130 (2) 0.0086 (11) −0.0009 (17) −0.0041 (15) C19 0.0866 (16) 0.138 (2) 0.0857 (19) 0.0025 (15) −0.0099 (14) −0.0179 (17)
Geometric parameters (Å, º)
N1—N2 1.310 (3) C10—C11 1.381 (3)
N1—C7 1.345 (3) C11—C12 1.359 (4)
N2—N3 1.357 (3) C11—H11 0.9300
N3—C9 1.329 (3) C12—C13 1.351 (4)
N4—C8 1.359 (3) C12—H12 0.9300
N4—C17 1.453 (3) C13—C14 1.394 (4)
N4—C16 1.455 (3) C13—H13 0.9300
C1—C6 1.384 (3) C14—C15 1.366 (4)
C1—C2 1.389 (4) C14—H14 0.9300
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Acta Cryst. (2005). E61, o93–o95
C2—C3 1.348 (4) C16—C18 1.478 (3)
C2—H2 0.9300 C16—H16A 0.9700
C3—C4 1.353 (4) C16—H16B 0.9700
C3—H3 0.9300 C17—C19 1.457 (4)
C4—C5 1.389 (4) C17—H17A 0.9700
C4—H4 0.9300 C17—H17B 0.9700
C5—C6 1.364 (3) C18—H18A 0.9600
C5—H5 0.9300 C18—H18B 0.9600
C6—C7 1.475 (3) C18—H18C 0.9600
C7—C8 1.417 (3) C19—H19A 0.9600
C8—C9 1.415 (3) C19—H19B 0.9600
C9—C10 1.470 (3) C19—H19C 0.9600
C10—C15 1.367 (3)
N2—N1—C7 121.39 (19) C10—C11—H11 119.0
N1—N2—N3 120.17 (19) C13—C12—C11 120.2 (3)
C9—N3—N2 121.0 (2) C13—C12—H12 119.9
C8—N4—C17 121.06 (18) C11—C12—H12 119.9
C8—N4—C16 121.89 (18) C12—C13—C14 119.6 (3)
C17—N4—C16 116.84 (19) C12—C13—H13 120.2
C6—C1—C2 119.5 (2) C14—C13—H13 120.2
C6—C1—H1 120.2 C15—C14—C13 119.1 (3)
C2—C1—H1 120.2 C15—C14—H14 120.4
C3—C2—C1 121.4 (3) C13—C14—H14 120.4
C3—C2—H2 119.3 C14—C15—C10 122.0 (2)
C1—C2—H2 119.3 C14—C15—H15 119.0
C2—C3—C4 119.8 (3) C10—C15—H15 119.0
C2—C3—H3 120.1 N4—C16—C18 113.4 (2)
C4—C3—H3 120.1 N4—C16—H16A 108.9
C3—C4—C5 119.5 (3) C18—C16—H16A 108.9
C3—C4—H4 120.3 N4—C16—H16B 108.9
C5—C4—H4 120.3 C18—C16—H16B 108.9
C6—C5—C4 121.8 (3) H16A—C16—H16B 107.7
C6—C5—H5 119.1 C19—C17—N4 115.6 (2)
C4—C5—H5 119.1 C19—C17—H17A 108.4
C5—C6—C1 117.9 (2) N4—C17—H17A 108.4
C5—C6—C7 119.9 (2) C19—C17—H17B 108.4
C1—C6—C7 121.9 (2) N4—C17—H17B 108.4
N1—C7—C8 121.7 (2) H17A—C17—H17B 107.4
N1—C7—C6 111.83 (19) C16—C18—H18A 109.5
C8—C7—C6 126.2 (2) C16—C18—H18B 109.5
N4—C8—C9 122.27 (19) H18A—C18—H18B 109.5
N4—C8—C7 123.93 (19) C16—C18—H18C 109.5
C9—C8—C7 113.80 (19) H18A—C18—H18C 109.5
N3—C9—C8 121.7 (2) H18B—C18—H18C 109.5
N3—C9—C10 111.5 (2) C17—C19—H19A 109.5
C8—C9—C10 126.62 (19) C17—C19—H19B 109.5
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C15—C10—C9 121.8 (2) C17—C19—H19C 109.5
C11—C10—C9 120.6 (2) H19A—C19—H19C 109.5
C12—C11—C10 122.0 (3) H19B—C19—H19C 109.5
C12—C11—H11 119.0
C7—N1—N2—N3 −0.3 (4) C6—C7—C8—C9 176.9 (2)
N1—N2—N3—C9 −1.8 (4) N2—N3—C9—C8 4.3 (3)
C6—C1—C2—C3 −0.2 (4) N2—N3—C9—C10 −172.4 (2)
C1—C2—C3—C4 0.7 (4) N4—C8—C9—N3 175.4 (2)
C2—C3—C4—C5 0.2 (4) C7—C8—C9—N3 −4.5 (3)
C3—C4—C5—C6 −1.7 (4) N4—C8—C9—C10 −8.4 (3)
C4—C5—C6—C1 2.1 (4) C7—C8—C9—C10 171.7 (2)
C4—C5—C6—C7 175.8 (2) N3—C9—C10—C15 127.8 (2)
C2—C1—C6—C5 −1.2 (3) C8—C9—C10—C15 −48.7 (3)
C2—C1—C6—C7 −174.7 (2) N3—C9—C10—C11 −44.8 (3)
N2—N1—C7—C8 −0.2 (3) C8—C9—C10—C11 138.7 (2)
N2—N1—C7—C6 −175.3 (2) C15—C10—C11—C12 −1.1 (4)
C5—C6—C7—N1 −48.8 (3) C9—C10—C11—C12 171.9 (3)
C1—C6—C7—N1 124.5 (2) C10—C11—C12—C13 0.7 (5)
C5—C6—C7—C8 136.3 (2) C11—C12—C13—C14 −0.2 (5)
C1—C6—C7—C8 −50.3 (3) C12—C13—C14—C15 0.2 (4)
C17—N4—C8—C9 −45.1 (3) C13—C14—C15—C10 −0.6 (4)
C16—N4—C8—C9 140.4 (2) C11—C10—C15—C14 1.1 (4)
C17—N4—C8—C7 134.8 (2) C9—C10—C15—C14 −171.8 (2)
C16—N4—C8—C7 −39.7 (3) C8—N4—C16—C18 −131.5 (3)
N1—C7—C8—N4 −177.5 (2) C17—N4—C16—C18 53.8 (3)
C6—C7—C8—N4 −3.1 (3) C8—N4—C17—C19 −118.7 (3)