organic papers
o1846
Daqing Shiet al. C22H15N3 DOI: 10.1107/S1600536803024267 Acta Cryst.(2003). E59, o1846±o1848 Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
8,9-Diphenylimidazo[1,2-
c
]quinazoline
Daqing Shi,a* Juxian Wang,a
Chunling Shi,aLiangce Rong,a
Xiangshan Wang,aHongwen Hub
and Kaibei Yuc
aDepartment of Chemistry, Xuzhou Normal
University, Xuzhou 221116, People's Republic of China,bDepartment of Chemistry, Nanjing University, Nanjing 210093, People's Republic of China, andcChinese Academy of Sciences, Chengdu 610041, People's Republic of China
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study
T= 291 K
Mean(C±C) = 0.003 AÊ
Rfactor = 0.042
wRfactor = 0.094
Data-to-parameter ratio = 13.0
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, C22H15N3, was synthesized by the
reaction of 4,5-diphenyl-2-(2-nitrophenyl)imidazole with triethyl orthoformate, induced by a low-valent titanium reagent (TiCl4/Zn). There are two independent molecules of
similar conformation in the asymmetric unit. X-ray analysis reveals that the imidazole ring and pyrimidine ring are essentially coplanar.
Comment
Quinazolines are an important class of compounds found in many naturally occurring products (e.g. hinckdentine A; Blackman et al., 1987; Billimmoria & Cava, 1994) and employed as potent cytotoxic agents (Ibrahim et al., 1988; Riouet al., 1991; Branaet al., 1994; Helisseyet al., 1994). Low-valent titanium reagents have an exceedingly high ability to promote reductive coupling of carbonyl compounds and are attracting increasing interest in organic synthesis (McMurry, 1983; Shiet al., 1993, 1997, 1998, 2003). We report here the crystal structure of 8,9-diphenylimidazo[1,2-c]quinazoline, (I), synthesized by the reaction of 4,5-diphenyl-2-(2-nitro-phenyl)imidazole with triethyl orthoformate, induced by a low-valent titanium reagent (TiCl4/Zn).
In (I), there are two independent molecules of similar conformation in the asymmetric unit (Fig. 1 and Table 1). The dihedral angle between the pyrimidine (N3/C1/C6/C7/N2/C8) and imidazole rings (N1/C7/N2/C9/C10) is 0.71 (1), indicating
that these two rings are nearly coplanar. N1ÐC7 and N3ÐC8 [1.321 (2) and 1.283 (2) AÊ] are double bonds, while the other CÐN bond distances are in the range 1.380 (2)±1.398 (2) AÊ, corresponding to single bonds. Atoms N3 and N30are involved
in weak intermolecular CÐH N interactions (Fig. 2 and Table 2).
Experimental
The title compound, (I), was prepared by the reaction of 4,5-di-phenyl-2-(2-nitrophenyl)imidazole with triethyl orthoformate, induced by a low-valent titanium reagent (TiCl4/Zn) (m.p. 466±
468 K). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.
Crystal data
C22H15N3
Mr= 321.37 Monoclinic, P21=c
a= 13.262 (2) AÊ b= 10.814 (1) AÊ c= 23.462 (4) AÊ
= 98.40 (1)
V= 3328.6 (8) AÊ3
Z= 8
Dx= 1.283 Mg mÿ3
MoKradiation Cell parameters from 31
re¯ections
= 3.1±13.4
= 0.08 mmÿ1
T= 291 (2) K Block, colourless 0.440.420.40 mm
Data collection
SiemensP4 diffractometer
!scans
Absorption correction: none 6709 measured re¯ections 5856 independent re¯ections 2804 re¯ections withI> 2(I) Rint= 0.015
max= 25.0
h= 0!15 k= 0!12 l=ÿ27!27 3 standard re¯ections
every 97 re¯ections intensity decay: 1.5%
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.042
wR(F2) = 0.094
S= 0.80 5856 re¯ections 452 parameters
H-atom parameters constrained
w= 1/[2(Fo2) + (0.0408P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.17 e AÊÿ3
min=ÿ0.14 e AÊÿ3
Extinction correction:SHELXTL Extinction coef®cient: 0.0034 (2)
Table 1
Selected geometric parameters (AÊ,). N1ÐC7 1.321 (2) N1ÐC10 1.391 (2) N2ÐC7 1.380 (2) N2ÐC8 1.383 (2) N2ÐC9 1.398 (2) N3ÐC8 1.283 (2) N3ÐC1 1.392 (2) C6ÐC7 1.428 (3) C9ÐC10 1.375 (3)
N10ÐC70 1.320 (2)
N10ÐC100 1.394 (2)
N20ÐC80 1.384 (2)
N20ÐC70 1.387 (2)
N20ÐC90 1.394 (2)
N30ÐC80 1.283 (2)
N30ÐC10 1.398 (3)
C60ÐC70 1.433 (3)
C90ÐC100 1.371 (2)
C7ÐN1ÐC10 105.23 (16) C7ÐN2ÐC8 121.24 (19) C7ÐN2ÐC9 107.41 (16) C8ÐN2ÐC9 131.32 (18) C8ÐN3ÐC1 118.26 (18) N3ÐC1ÐC2 118.4 (2) N3ÐC1ÐC6 122.7 (2) N1ÐC7ÐN2 111.46 (18)
N1ÐC7ÐC6 130.98 (19) N2ÐC7ÐC6 117.55 (18) N3ÐC8ÐN2 123.3 (2) C10ÐC9ÐN2 104.49 (16) N2ÐC9ÐC17 121.50 (18) C9ÐC10ÐN1 111.38 (17) N1ÐC10ÐC11 119.13 (18)
C8ÐN3ÐC1ÐC2 ÿ178.7 (2) C8ÐN3ÐC1ÐC6 0.4 (3) N3ÐC1ÐC2ÐC3 179.4 (2) N3ÐC1ÐC6ÐC5 ÿ178.2 (2) N3ÐC1ÐC6ÐC7 1.4 (3) C10ÐN1ÐC7ÐN2 ÿ0.6 (2) C10ÐN1ÐC7ÐC6 178.7 (2)
C8ÐN2ÐC7ÐN1 179.63 (18) C9ÐN2ÐC7ÐN1 1.3 (2) C9ÐN2ÐC7ÐC6 ÿ178.07 (18) C5ÐC6ÐC7ÐN1 ÿ1.3 (4) C1ÐC6ÐC7ÐN1 179.1 (2) C5ÐC6ÐC7ÐN2 177.9 (2) C9ÐN2ÐC8ÐN3 179.5 (2)
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
C8ÐH8 N30 0.93 2.59 3.267 (3) 130
C80ÐH80 N3 0.93 2.63 3.280 (3) 128
H atoms were positioned geometrically and were treated as riding on their parent C atoms, with CÐH distances in the range 0.93± 0.97 AÊ; theUiso(H) values were set equal to1.2Ueq(C).
Data collection: XSCANS (Siemens, 1994); cell re®nement:
XSCANS; data reduction:SHELXTL(Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to re®ne structure:SHELXTL; molecular graphics:SHELXTL; software used to prepare material for publication:SHELXTL.
The authors thank the Foundation of the `Surpassing Project' of Jiangsu Province and the Natural Science Found-ation of the EducFound-ation Committee of Jiangsu Province (grant No. 03KJB150136) for ®nancial support.
References
Billimmoria, A. D. & Cava, M. P. (1994).J. Org. Chem.59, 6777±6782. Blackman, A., Hambley, T. W., Picker, R., Taylor, W. C. & Thirasana, N.
(1987).Tetrahedron Lett.28, 5561±5564.
Brana, M. F., Castellano, J. M., Keilhauer, G., Machuca, A., Martin, Y., Redondo, C., Schlick, E. & Walker, N. (1994).Anti-Cancer Drugs Des.9, 527±538.
Helissey, P., Cros, S. & Giorgi-Renault, S. (1994).Anti-Cancer Drugs Des.9, 51±57.
Acta Cryst.(2003). E59, o1846±o1848 Daqing Shiet al. C22H15N3
o1847
organic papers
Figure 1
The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Figure 2
organic papers
o1848
Daqing Shiet al. C22H15N3 Acta Cryst.(2003). E59, o1846±o1848Ibrahim, E., Montgomerie, A. M., Senddon, A. H., Proctor, G. R. & Green, B. (1988).Eur. J. Med. Chem.23, 183±188.
McMurry, J. E. (1983).Acc. Chem. Res.16, 405±411.
Riou, J. F., Helissey, P., Grondard, L. & Giorgi-Renault, S. (1991). Mol. Pharmacol.40, 699±706.
Sheldrick, G. M. (1997).SHELXTL.Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
Shi, D. Q., Chen, J. X., Chai, W. Y., Chen, W. X. & Kao, T. Y. (1993). Tetrahedron Lett.34, 2963±2964.
Shi, D. Q., Lu, Z. S., Mu, L. L. & Dai G. Y. (1998).Synth. Commun.28, 1073± 1078.
Shi, D. Q., Mu, L. L., Lu, Z. S. & Dai, G. Y. (1997).Synth. Commun.27, 4121± 4129.
Shi, D. Q., Rong, L. C., Wang, J. X., Zhuang, Q. Y., Wang, X. S. & Hu, H. W. (2003).Tetrahedron Lett.44, 3199±3201.
supporting information
sup-1 Acta Cryst. (2003). E59, o1846–o1848
supporting information
Acta Cryst. (2003). E59, o1846–o1848 [https://doi.org/10.1107/S1600536803024267]
8,9-Diphenylimidazo[1,2-
c
]quinazoline
Daqing Shi, Juxian Wang, Chunling Shi, Liangce Rong, Xiangshan Wang, Hongwen Hu and
Kaibei Yu
8,9-diphenylimidazo[1,2-c]quinazoline
Crystal data
C22H15N3
Mr = 321.37 Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 13.262 (2) Å
b = 10.814 (1) Å
c = 23.462 (4) Å
β = 98.40 (1)°
V = 3328.6 (8) Å3
Z = 8
F(000) = 1344
Dx = 1.283 Mg m−3
Melting point = 466–468 K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 31 reflections
θ = 3.1–13.4°
µ = 0.08 mm−1
T = 291 K Block, colourless 0.44 × 0.42 × 0.40 mm
Data collection
Siemens P4 diffractometer
Radiation source: normal-focus sealed tube Graphite monochromator
ω scans
6709 measured reflections 5856 independent reflections 2804 reflections with I > 2σ(I)
Rint = 0.015
θmax = 25.0°, θmin = 1.6°
h = 0→15
k = 0→12
l = −27→27
3 standard reflections every 97 reflections intensity decay: 1.5%
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.042
wR(F2) = 0.094
S = 0.80 5856 reflections 452 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) + (0.0408P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.17 e Å−3
Δρmin = −0.14 e Å−3
Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
supporting information
sup-2 Acta Cryst. (2003). E59, o1846–o1848
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 0.09817 (13) 1.01090 (15) 0.62894 (7) 0.0445 (5) N2 0.15065 (13) 0.82854 (15) 0.59964 (7) 0.0424 (5) N3 0.15915 (14) 0.63997 (16) 0.64961 (8) 0.0534 (5) C1 0.12270 (16) 0.7002 (2) 0.69491 (10) 0.0472 (6) C2 0.10956 (17) 0.6314 (2) 0.74374 (10) 0.0588 (7)
H2 0.1246 0.5473 0.7451 0.071*
C3 0.07475 (19) 0.6869 (2) 0.78952 (10) 0.0646 (7)
H3 0.0653 0.6401 0.8216 0.077*
C4 0.05334 (18) 0.8130 (2) 0.78843 (10) 0.0626 (7)
H4 0.0301 0.8501 0.8198 0.075*
C5 0.06642 (16) 0.8825 (2) 0.74135 (9) 0.0535 (6)
H5 0.0529 0.9669 0.7410 0.064*
C6 0.10001 (15) 0.8271 (2) 0.69384 (9) 0.0440 (6) C7 0.11382 (15) 0.89340 (19) 0.64291 (9) 0.0411 (5) C8 0.17297 (16) 0.70385 (19) 0.60530 (10) 0.0504 (6)
H8 0.1993 0.6643 0.5755 0.060*
C9 0.16099 (15) 0.91233 (19) 0.55547 (8) 0.0413 (5) C10 0.12703 (15) 1.02286 (18) 0.57452 (8) 0.0405 (5) C11 0.11670 (15) 1.14394 (18) 0.54554 (9) 0.0420 (5) C12 0.10640 (17) 1.1550 (2) 0.48587 (10) 0.0565 (7)
H12 0.1059 1.0847 0.4631 0.068*
C13 0.09686 (19) 1.2707 (2) 0.46049 (11) 0.0677 (7)
H13 0.0921 1.2775 0.4207 0.081*
C14 0.09438 (18) 1.3758 (2) 0.49336 (12) 0.0676 (7)
H14 0.0879 1.4532 0.4759 0.081*
C15 0.10155 (17) 1.3656 (2) 0.55224 (12) 0.0616 (7)
H15 0.0989 1.4360 0.5747 0.074*
C16 0.11271 (16) 1.25084 (19) 0.57781 (9) 0.0494 (6)
H16 0.1177 1.2449 0.6177 0.059*
C17 0.20703 (16) 0.87552 (19) 0.50465 (8) 0.0428 (5) C18 0.29418 (17) 0.9354 (2) 0.49284 (9) 0.0521 (6)
H18 0.3225 0.9987 0.5169 0.062*
C19 0.3391 (2) 0.9017 (2) 0.44576 (10) 0.0678 (8)
H19 0.3971 0.9426 0.4378 0.081*
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sup-3 Acta Cryst. (2003). E59, o1846–o1848
H20 0.3280 0.7851 0.3788 0.096*
C21 0.2129 (2) 0.7467 (2) 0.42211 (10) 0.0762 (9)
H21 0.1864 0.6820 0.3984 0.091*
C22 0.16606 (18) 0.7805 (2) 0.46868 (9) 0.0584 (6)
H22 0.1074 0.7399 0.4759 0.070*
N1′ 0.40582 (13) 0.12548 (15) 0.60705 (7) 0.0438 (5) N2′ 0.35495 (12) 0.31016 (15) 0.63417 (7) 0.0405 (4) N3′ 0.33677 (14) 0.49298 (16) 0.57947 (8) 0.0585 (5) C1′ 0.36842 (16) 0.4280 (2) 0.53372 (10) 0.0513 (6) C2′ 0.36893 (19) 0.4906 (2) 0.48170 (11) 0.0714 (8)
H2′ 0.3506 0.5736 0.4787 0.086*
C3′ 0.3963 (2) 0.4301 (3) 0.43536 (11) 0.0820 (9)
H3′ 0.3956 0.4720 0.4007 0.098*
C4′ 0.4254 (2) 0.3062 (3) 0.43931 (11) 0.0723 (8)
H4′ 0.4443 0.2662 0.4074 0.087*
C5′ 0.42624 (17) 0.2435 (2) 0.49000 (9) 0.0583 (6)
H5′ 0.4464 0.1611 0.4927 0.070*
C6′ 0.39694 (16) 0.3031 (2) 0.53766 (9) 0.0462 (6) C7′ 0.38985 (15) 0.2416 (2) 0.59102 (8) 0.0410 (5) C8′ 0.32979 (16) 0.4338 (2) 0.62612 (10) 0.0520 (6)
H8′ 0.3066 0.4762 0.6561 0.062*
C9′ 0.34543 (15) 0.22973 (18) 0.67948 (8) 0.0388 (5) C10′ 0.37805 (15) 0.11753 (18) 0.66199 (8) 0.0399 (5) C11′ 0.38588 (16) −0.00260 (19) 0.69202 (9) 0.0429 (5) C12′ 0.38904 (17) −0.0123 (2) 0.75154 (9) 0.0582 (7)
H12′ 0.3883 0.0590 0.7737 0.070*
C13′ 0.3932 (2) −0.1261 (2) 0.77775 (11) 0.0724 (8)
H13′ 0.3938 −0.1310 0.8174 0.087*
C14′ 0.39634 (18) −0.2330 (2) 0.74614 (12) 0.0676 (7)
H14′ 0.3990 −0.3097 0.7642 0.081*
C15′ 0.39547 (18) −0.2250 (2) 0.68757 (11) 0.0617 (7)
H15′ 0.3982 −0.2967 0.6659 0.074*
C16′ 0.39048 (16) −0.11062 (19) 0.66061 (9) 0.0496 (6)
H16′ 0.3902 −0.1062 0.6210 0.059*
C17′ 0.30408 (16) 0.27214 (19) 0.73127 (8) 0.0410 (5) C18′ 0.21965 (17) 0.2149 (2) 0.74781 (9) 0.0545 (6)
H18′ 0.1875 0.1512 0.7254 0.065*
C19′ 0.18269 (19) 0.2514 (2) 0.79721 (10) 0.0665 (7)
H19′ 0.1269 0.2109 0.8084 0.080*
C20′ 0.2280 (2) 0.3473 (3) 0.82984 (11) 0.0722 (8)
H20′ 0.2025 0.3721 0.8629 0.087*
C21′ 0.3107 (2) 0.4062 (2) 0.81356 (10) 0.0689 (7)
H21′ 0.3410 0.4716 0.8354 0.083*
C22′ 0.34926 (17) 0.3685 (2) 0.76463 (9) 0.0536 (6)
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sup-4 Acta Cryst. (2003). E59, o1846–o1848
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
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sup-5 Acta Cryst. (2003). E59, o1846–o1848
C18′ 0.0528 (16) 0.0643 (16) 0.0480 (14) −0.0028 (13) 0.0124 (12) −0.0044 (12) C19′ 0.0628 (18) 0.085 (2) 0.0563 (16) −0.0003 (16) 0.0230 (14) 0.0014 (16) C20′ 0.084 (2) 0.087 (2) 0.0509 (16) 0.0153 (17) 0.0270 (15) −0.0057 (16) C21′ 0.090 (2) 0.0670 (17) 0.0497 (15) 0.0078 (16) 0.0099 (15) −0.0169 (14) C22′ 0.0567 (16) 0.0524 (15) 0.0517 (14) −0.0004 (13) 0.0080 (12) −0.0075 (12)
Geometric parameters (Å, º)
N1—C7 1.321 (2) N1′—C7′ 1.320 (2)
N1—C10 1.391 (2) N1′—C10′ 1.394 (2)
N2—C7 1.380 (2) N2′—C8′ 1.384 (2)
N2—C8 1.383 (2) N2′—C7′ 1.387 (2)
N2—C9 1.398 (2) N2′—C9′ 1.394 (2)
N3—C8 1.283 (2) N3′—C8′ 1.283 (2)
N3—C1 1.392 (2) N3′—C1′ 1.398 (3)
C1—C2 1.398 (3) C1′—C2′ 1.397 (3)
C1—C6 1.405 (3) C1′—C6′ 1.401 (3)
C2—C3 1.368 (3) C2′—C3′ 1.363 (3)
C2—H2 0.9300 C2′—H2′ 0.9300
C3—C4 1.392 (3) C3′—C4′ 1.393 (3)
C3—H3 0.9300 C3′—H3′ 0.9300
C4—C5 1.368 (3) C4′—C5′ 1.368 (3)
C4—H4 0.9300 C4′—H4′ 0.9300
C5—C6 1.394 (3) C5′—C6′ 1.394 (3)
C5—H5 0.9300 C5′—H5′ 0.9300
C6—C7 1.428 (3) C6′—C7′ 1.433 (3)
C8—H8 0.9300 C8′—H8′ 0.9300
C9—C10 1.375 (3) C9′—C10′ 1.371 (2)
C9—C17 1.472 (3) C9′—C17′ 1.477 (3)
C10—C11 1.472 (3) C10′—C11′ 1.474 (3)
C11—C16 1.387 (3) C11′—C16′ 1.387 (3)
C11—C12 1.392 (3) C11′—C12′ 1.395 (3)
C12—C13 1.383 (3) C12′—C13′ 1.373 (3)
C12—H12 0.9300 C12′—H12′ 0.9300
C13—C14 1.377 (3) C13′—C14′ 1.377 (3)
C13—H13 0.9300 C13′—H13′ 0.9300
C14—C15 1.375 (3) C14′—C15′ 1.375 (3)
C14—H14 0.9300 C14′—H14′ 0.9300
C15—C16 1.377 (3) C15′—C16′ 1.387 (3)
C15—H15 0.9300 C15′—H15′ 0.9300
C16—H16 0.9300 C16′—H16′ 0.9300
C17—C18 1.388 (3) C17′—C18′ 1.384 (3)
C17—C22 1.389 (3) C17′—C22′ 1.386 (3)
C18—C19 1.378 (3) C18′—C19′ 1.381 (3)
C18—H18 0.9300 C18′—H18′ 0.9300
C19—C20 1.371 (3) C19′—C20′ 1.374 (3)
C19—H19 0.9300 C19′—H19′ 0.9300
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sup-6 Acta Cryst. (2003). E59, o1846–o1848
C20—H20 0.9300 C20′—H20′ 0.9300
C21—C22 1.383 (3) C21′—C22′ 1.385 (3)
C21—H21 0.9300 C21′—H21′ 0.9300
C22—H22 0.9300 C22′—H22′ 0.9300
C7—N1—C10 105.23 (16) C7′—N1′—C10′ 105.62 (16) C7—N2—C8 121.24 (19) C8′—N2′—C7′ 121.04 (18) C7—N2—C9 107.41 (16) C8′—N2′—C9′ 131.30 (18) C8—N2—C9 131.32 (18) C7′—N2′—C9′ 107.49 (16) C8—N3—C1 118.26 (18) C8′—N3′—C1′ 118.11 (19)
N3—C1—C2 118.4 (2) C2′—C1′—N3′ 117.9 (2)
N3—C1—C6 122.7 (2) C2′—C1′—C6′ 119.3 (2)
C2—C1—C6 118.9 (2) N3′—C1′—C6′ 122.8 (2)
C3—C2—C1 120.5 (2) C3′—C2′—C1′ 120.0 (2)
C3—C2—H2 119.8 C3′—C2′—H2′ 120.0
C1—C2—H2 119.8 C1′—C2′—H2′ 120.0
C2—C3—C4 120.4 (2) C2′—C3′—C4′ 120.8 (2)
C2—C3—H3 119.8 C2′—C3′—H3′ 119.6
C4—C3—H3 119.8 C4′—C3′—H3′ 119.6
C5—C4—C3 120.2 (2) C5′—C4′—C3′ 120.1 (3)
C5—C4—H4 119.9 C5′—C4′—H4′ 120.0
C3—C4—H4 119.9 C3′—C4′—H4′ 120.0
C4—C5—C6 120.2 (2) C4′—C5′—C6′ 120.0 (2)
C4—C5—H5 119.9 C4′—C5′—H5′ 120.0
C6—C5—H5 119.9 C6′—C5′—H5′ 120.0
C5—C6—C1 119.9 (2) C5′—C6′—C1′ 119.8 (2)
C5—C6—C7 123.2 (2) C5′—C6′—C7′ 123.2 (2)
C1—C6—C7 116.9 (2) C1′—C6′—C7′ 116.9 (2)
N1—C7—N2 111.46 (18) N1′—C7′—N2′ 110.92 (17) N1—C7—C6 130.98 (19) N1′—C7′—C6′ 131.5 (2) N2—C7—C6 117.55 (18) N2′—C7′—C6′ 117.48 (19)
N3—C8—N2 123.3 (2) N3′—C8′—N2′ 123.5 (2)
N3—C8—H8 118.4 N3′—C8′—H8′ 118.2
N2—C8—H8 118.4 N2′—C8′—H8′ 118.2
C10—C9—N2 104.49 (16) C10′—C9′—N2′ 104.84 (16) C10—C9—C17 133.86 (19) C10′—C9′—C17′ 133.81 (19) N2—C9—C17 121.50 (18) N2′—C9′—C17′ 121.31 (18) C9—C10—N1 111.38 (17) C9′—C10′—N1′ 111.09 (17) C9—C10—C11 129.48 (18) C9′—C10′—C11′ 129.79 (18) N1—C10—C11 119.13 (18) N1′—C10′—C11′ 119.11 (17) C16—C11—C12 118.1 (2) C16′—C11′—C12′ 118.1 (2) C16—C11—C10 119.83 (19) C16′—C11′—C10′ 119.58 (19) C12—C11—C10 122.01 (19) C12′—C11′—C10′ 122.28 (19) C13—C12—C11 120.0 (2) C13′—C12′—C11′ 120.6 (2)
C13—C12—H12 120.0 C13′—C12′—H12′ 119.7
C11—C12—H12 120.0 C11′—C12′—H12′ 119.7
C14—C13—C12 120.9 (2) C12′—C13′—C14′ 120.9 (2)
supporting information
sup-7 Acta Cryst. (2003). E59, o1846–o1848
C12—C13—H13 119.5 C14′—C13′—H13′ 119.6
C15—C14—C13 119.5 (2) C15′—C14′—C13′ 119.3 (2)
C15—C14—H14 120.3 C15′—C14′—H14′ 120.4
C13—C14—H14 120.3 C13′—C14′—H14′ 120.4
C14—C15—C16 119.8 (2) C14′—C15′—C16′ 120.3 (2)
C14—C15—H15 120.1 C14′—C15′—H15′ 119.9
C16—C15—H15 120.1 C16′—C15′—H15′ 119.9
C15—C16—C11 121.6 (2) C15′—C16′—C11′ 120.8 (2)
C15—C16—H16 119.2 C15′—C16′—H16′ 119.6
C11—C16—H16 119.2 C11′—C16′—H16′ 119.6
C18—C17—C22 119.2 (2) C18′—C17′—C22′ 118.6 (2) C18—C17—C9 119.46 (19) C18′—C17′—C9′ 120.30 (19) C22—C17—C9 121.4 (2) C22′—C17′—C9′ 121.1 (2) C19—C18—C17 120.4 (2) C19′—C18′—C17′ 120.6 (2)
C19—C18—H18 119.8 C19′—C18′—H18′ 119.7
C17—C18—H18 119.8 C17′—C18′—H18′ 119.7
C20—C19—C18 119.7 (3) C20′—C19′—C18′ 120.3 (2)
C20—C19—H19 120.1 C20′—C19′—H19′ 119.9
C18—C19—H19 120.1 C18′—C19′—H19′ 119.9
C21—C20—C19 120.6 (2) C21′—C20′—C19′ 119.9 (2)
C21—C20—H20 119.7 C21′—C20′—H20′ 120.1
C19—C20—H20 119.7 C19′—C20′—H20′ 120.1
C20—C21—C22 120.4 (2) C20′—C21′—C22′ 120.1 (2)
C20—C21—H21 119.8 C20′—C21′—H21′ 119.9
C22—C21—H21 119.8 C22′—C21′—H21′ 119.9
C21—C22—C17 119.7 (2) C21′—C22′—C17′ 120.5 (2)
C21—C22—H22 120.2 C21′—C22′—H22′ 119.7
C17—C22—H22 120.2 C17′—C22′—H22′ 119.7
supporting information
sup-8 Acta Cryst. (2003). E59, o1846–o1848
C5—C6—C7—N1 −1.3 (4) C5′—C6′—C7′—N1′ −1.1 (4) C1—C6—C7—N1 179.1 (2) C1′—C6′—C7′—N1′ 176.2 (2) C5—C6—C7—N2 177.9 (2) C5′—C6′—C7′—N2′ −176.9 (2) C1—C6—C7—N2 −1.6 (3) C1′—C6′—C7′—N2′ 0.3 (3) C1—N3—C8—N2 −2.0 (3) C1′—N3′—C8′—N2′ 2.1 (3) C7—N2—C8—N3 1.7 (3) C7′—N2′—C8′—N3′ −0.1 (3) C9—N2—C8—N3 179.5 (2) C9′—N2′—C8′—N3′ −174.7 (2) C7—N2—C9—C10 −1.4 (2) C8′—N2′—C9′—C10′ 176.9 (2) C8—N2—C9—C10 −179.5 (2) C7′—N2′—C9′—C10′ 1.8 (2) C7—N2—C9—C17 174.68 (19) C8′—N2′—C9′—C17′ −1.3 (3) C8—N2—C9—C17 −3.4 (3) C7′—N2′—C9′—C17′ −176.47 (18) N2—C9—C10—N1 1.1 (2) N2′—C9′—C10′—N1′ −1.0 (2) C17—C9—C10—N1 −174.3 (2) C17′—C9′—C10′—N1′ 176.9 (2) N2—C9—C10—C11 −177.8 (2) N2′—C9′—C10′—C11′ 179.6 (2) C17—C9—C10—C11 6.8 (4) C17′—C9′—C10′—C11′ −2.5 (4) C7—N1—C10—C9 −0.4 (2) C7′—N1′—C10′—C9′ −0.3 (2) C7—N1—C10—C11 178.66 (18) C7′—N1′—C10′—C11′ 179.23 (18) C9—C10—C11—C16 −159.3 (2) C9′—C10′—C11′—C16′ 160.2 (2) N1—C10—C11—C16 21.9 (3) N1′—C10′—C11′—C16′ −19.2 (3) C9—C10—C11—C12 23.5 (3) C9′—C10′—C11′—C12′ −19.9 (4) N1—C10—C11—C12 −155.3 (2) N1′—C10′—C11′—C12′ 160.7 (2) C16—C11—C12—C13 2.7 (3) C16′—C11′—C12′—C13′ −2.1 (3) C10—C11—C12—C13 180.0 (2) C10′—C11′—C12′—C13′ 178.0 (2) C11—C12—C13—C14 −1.9 (4) C11′—C12′—C13′—C14′ 1.3 (4) C12—C13—C14—C15 0.0 (4) C12′—C13′—C14′—C15′ 0.1 (4) C13—C14—C15—C16 1.0 (4) C13′—C14′—C15′—C16′ −0.6 (4) C14—C15—C16—C11 −0.2 (4) C14′—C15′—C16′—C11′ −0.3 (4) C12—C11—C16—C15 −1.7 (3) C12′—C11′—C16′—C15′ 1.6 (3) C10—C11—C16—C15 −179.0 (2) C10′—C11′—C16′—C15′ −178.5 (2) C10—C9—C17—C18 55.1 (3) C10′—C9′—C17′—C18′ −55.0 (3) N2—C9—C17—C18 −119.7 (2) N2′—C9′—C17′—C18′ 122.7 (2) C10—C9—C17—C22 −126.0 (3) C10′—C9′—C17′—C22′ 124.3 (3) N2—C9—C17—C22 59.2 (3) N2′—C9′—C17′—C22′ −58.1 (3) C22—C17—C18—C19 0.5 (3) C22′—C17′—C18′—C19′ −1.4 (3) C9—C17—C18—C19 179.43 (19) C9′—C17′—C18′—C19′ 177.9 (2) C17—C18—C19—C20 −0.6 (3) C17′—C18′—C19′—C20′ 1.6 (4) C18—C19—C20—C21 −0.3 (4) C18′—C19′—C20′—C21′ −0.6 (4) C19—C20—C21—C22 1.2 (4) C19′—C20′—C21′—C22′ −0.6 (4) C20—C21—C22—C17 −1.3 (4) C20′—C21′—C22′—C17′ 0.8 (4) C18—C17—C22—C21 0.4 (3) C18′—C17′—C22′—C21′ 0.2 (3) C9—C17—C22—C21 −178.5 (2) C9′—C17′—C22′—C21′ −179.0 (2)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C8—H8···N3′ 0.93 2.59 3.267 (3) 130
