organic papers
o2750
Kuboet al. C21H28N2O doi:10.1107/S1600536805023792 Acta Cryst.(2005). E61, o2750–o2752 Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
2-Amino-5-[4-(octylamino)phenyl]cyclo-hepta-2,4,6-trien-1-one
Kanji Kubo,a* Taisuke Matsumoto,bKouki Katahirac and Akira Morib
aSchool of Dentistry, Health Sciences University
of Hokkaido, 1757 Kanazawa, Ishikari-Tobetsu, Hokkaido 061-0293, Japan,bInstitute for
Materials Chemistry and Engineering, Kyushu University, Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan, andcGraduate School of Engineering Sciences, Kyushu University, Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan
Correspondence e-mail: kubo-k@hoku-iryo-u.ac.jp
Key indicators
Single-crystal X-ray study
T= 123 K
Mean(C–C) = 0.004 A˚
Rfactor = 0.071
wRfactor = 0.202
Data-to-parameter ratio = 16.3
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
The title compound, also known as 2-amino-5-[4-(octylamino)phenyl]tropone, C21H28N2O, contains two
crys-tallographically independent molecules in the asymmetric unit. The NH2group of the 2-aminotropone unit and the NH
group of the aminobenzene unit participate in intermolecular hydrogen bonding with the O atoms of neighbouring mol-ecules. An intermolecular –interaction is observed in the crystal structure.
Comment
Self-assembled systems are of great significance, particularly for their potential application to nanomaterials such as liquid crystals and gelators (Kubo, Tsuji et al., 2004). Numerous studies have been dedicated to the structural investigation and the determination of the molecular aggregation mechanisms. Troponoids, a remarkable class of non-benzenoid -conju-gated systems, have also been used as a building block of molecular assemblies such as liquid crystals and organogela-tors (Kubo, Mori et al., 2004). Tropone and tropolone frequently play an important role as entities determining the specific properties of molecular assemblies.
Recently, we have prepared liquid crystals with a troponoid core such as tropone itself (Mori & Takeshita, 1995), nitro-tropone (Kubo, Tsurutaet al., 2002), bitropone (Kubo, Sutoh
et al., 2002), and phenyltropone (Mori et al., 2002). The
troponoid cores enhanced formation of smectic phases when compared with the corresponding benzenoids. The crystal structure analyses of some troponoid-core liquid crystals have been carried out (Yamamoto et al., 2001; Kubo et al., 2001,
[image:1.610.216.449.603.724.2]Received 21 July 2005 Accepted 25 July 2005 Online 30 July 2005
Figure 1
2005; Kubo, Sutohet al., 2002). These crystal structures involve intermolecular–interactions and intermolecular hydrogen bonds. We now report the crystal structure of 2-amino-5-[4-(octylamino)phenyl]tropone, (I), which was determined in order to elucidate the substituent effect of 5-phenyltropone on the crystal packing.
There are two molecules, (Ia) and (Ib), in the asymmetric unit (Fig. 1). In both, the octyl chain has an all-trans confor-mation, thus forming an almost planar zigzag; the deviations of atoms from the least-squares plane defined by atoms C14–C21 for (Ia) and C34–C42 for (Ib) are all within 0.045 (3) and 0.021 (3) A˚ , respectively. The planarity of the seven-membered ring is fairly good; the deviations of atoms from the least-squares plane defined by atoms C1–C7 for (Ia) and C22– C28 for (Ib) are within 0.013 (3) and 0.007 (3) A˚ . The C—C bond lengths of the seven-membered ring, apart from the C1—C2 and C22—C23 bonds, show no apparent bond alter-nation, in contrast to what has been observed for tropolone (Shimanouchi & Sasada, 1973), but similar to 2-amino-5-hexyloxytropone (Yamamotoet al., 2001). The average value of the C—C bond lengths, apart from the C1—C2 and C22— C23 bonds, is 1.394 A˚ , which agrees with that of tropolone (1.385 A˚ ) and the standard aromatic C—C bond length of 1.392 A˚ (Lide, 1990). The C1—C2 and C22—C23 bonds are significantly longer than all other bonds in the ring. The dihedral angles between the least-squares planes A(defined by atoms C1–C7) and B (defined by C8–C13) of (Ia) and between the least-squares planesC(defined by C22–C28) and
D (defined by C29–C34) of (Ib) are 36.4 (1) and 38.1 (1), respectively, resembling those of 40.6 (2)in
2-methoxy-5-(4-methoxyphenyl)cyclohepta-2,4,6-trien-1-one (Gulbis et al., 1992), and distinct from that (0) in biphenyl (Charbonneau &
Delugeard, 1977).
An intermolecular – interaction between pairs of tropone planes (head-to-tail) is observed for (Ia) (Fig. 2). The distances between the tropone planes are within the range associated with–interactions (3.3–3.8 A˚ ; Proutet al., 1973; Kuboet al., 2001).
There is an intramolecular N—H O hydrogen bond in the 2-aminotropone unit (Table 2). Furthermore the NH2group of
the 2-aminotropone unit of (1b) and the NH group of the
hydrogen bonds. The N O distances are close to the inter-molecular N—H O distance [N O = 2.877 (4) A˚ ] of 2-amino-5-hexyloxytropone (Yamamotoet al., 2001). Thus, the crystal structure of (I) has intermolecular–interactions and intermolecular N—H O hydrogen bonds.
Experimental
A hexamethylphosphoric triamide (3 ml) solution of 2-amino-5-(4-aminophenyl)tropone (40 mg, 0.19 mmol) and NaH (60%, 14 mg, 0.57 mmol) was stirred at 273 K for 1 h. 1-Bromohexane (75 mg, 0.46 mmol) was added and the reaction mixture was stirred at 333 K for 12 h. The mixture was poured into 2MHCl and shaken with ethyl acetate. The organic layer was washed with saturated NaCl solution and dried over MgSO4. The solvent was evaporated and the residue chromatographed on a silica-gel column (hexane–ethyl acetate, 5:1 (v/v) to give (I) (20 mg, 27%). Crystals of (I) were grown from hexane and ethyl acetate solution (1:1v/v) by slow evaporation.
Crystal data
C21H28N2O Mr= 324.46
Triclinic,P1
a= 7.691 (2) A˚
b= 14.882 (4) A˚
c= 16.948 (5) A˚
= 77.200 (14)
= 77.262 (14)
= 80.658 (14) V= 1832.0 (9) A˚3
Z= 4
Dx= 1.176 Mg m
3
MoKradiation Cell parameters from 2903
reflections
= 3.1–27.5
= 0.07 mm1 T= 123.1 K Platelet, yellow 0.120.100.03 mm
Data collection
Rigaku Saturn diffractometer
!scans
Absorption correction: multi-scan (Jacobson, 1998)
Tmin= 0.991,Tmax= 0.998
22067 measured reflections 8302 independent reflections
3759 reflections withI> 2(I)
Rint= 0.064
max= 27.5 h=9!9
k=19!19
l=21!21
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.071
wR(F2) = 0.202 S= 1.00 8285 reflections 508 parameters
H atoms treated by a mixture of
w= 1/[0.0015Fo2+(Fo2)]/(4Fo2)
(/)max< 0.001 max= 0.53 e A˚
3 min=0.49 e A˚ 3
Extinction correction: Larson (1970), equation 22 Extinction coefficient:
[image:2.610.53.489.72.221.2]2
Figure 2
The–interaction of molecule (Ia). [Symmetry code: (i)1x,y, 2z.]
Figure 3
Table 1
Selected geometric parameters (A˚ ,).
O1—C1 1.279 (3) O2—C22 1.274 (3) N1—C2 1.345 (3) N2—C11 1.362 (3) N2—C14 1.451 (3) N3—C23 1.352 (3) N4—C32 1.385 (3) N4—C35 1.439 (4) C1—C2 1.472 (3) C1—C7 1.414 (3) C2—C3 1.382 (3) C3—C4 1.390 (3)
C4—C5 1.391 (3) C5—C6 1.418 (3) C5—C8 1.482 (3) C6—C7 1.375 (3) C22—C23 1.473 (4) C22—C28 1.423 (3) C23—C24 1.389 (4) C24—C25 1.382 (3) C25—C26 1.397 (3) C26—C27 1.404 (4) C26—C29 1.486 (3) C27—C28 1.379 (4) C1 C3i
3.570 (4) C1 C4i
3.459 (4) C2 C4i 3.522 (4)
C3 C1i
3.570 (4) C3 C7i
3.591 (4) C7 C3i 3.591 (4) O1—C1—C2 116.0 (2)
O1—C1—C7 120.4 (2) C2—C1—C7 123.6 (2) N1—C2—C1 113.5 (2) N1—C2—C3 120.3 (2) C1—C2—C3 126.2 (2) C2—C3—C4 132.3 (2) C3—C4—C5 130.9 (2) C4—C5—C6 123.3 (2) C5—C6—C7 130.7 (2) C1—C7—C6 132.8 (2)
O2—C22—C23 117.0 (2) O2—C22—C28 120.0 (2) C23—C22—C28 123.0 (2) N3—C23—C22 112.9 (2) N3—C23—C24 120.4 (2) C22—C23—C24 126.7 (2) C23—C24—C25 132.3 (2) C24—C25—C26 130.6 (2) C25—C26—C27 123.6 (2) C26—C27—C28 131.4 (2) C22—C28—C27 132.4 (2) C11—N2—C14—C15 172.2 (2)
C32—N4—C35—C36 169.9 (2) N2—C14—C15—C16 179.9 (2) C14—C15—C16—C17 171.3 (2) C15—C16—C17—C18 178.8 (2) C16—C17—C18—C19 179.2 (2) C17—C18—C19—C20 177.0 (2)
C18—C19—C20—C21 179.7 (2) N4—C35—C36—C37 174.9 (2) C35—C36—C37—C38 177.3 (2) C36—C37—C38—C39 179.0 (2) C37—C38—C39—C40 178.1 (2) C38—C39—C40—C41 179.2 (2) C39—C40—C41—C42 178.3 (2)
Symmetry code: (i)x1;y;zþ2.
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N1—H1 O1 0.89 (3) 2.13 (2) 2.570 (2) 109 (2) N2—H11 O2ii
0.93 (3) 2.07 (3) 2.993 (3) 168 (2) N3—H29 O2 0.87 (3) 2.11 (2) 2.579 (3) 113 (2) N3—H30 O1i
0.97 (3) 1.90 (3) 2.845 (3) 165 (3) N4—H39 O1iii
0.98 (3) 2.02 (3) 2.993 (4) 170 (2)
Symmetry codes: (i)x1;y;zþ2; (ii)xþ1;þy;þz; (iii)xþ1;þyþ1;þz.
H atoms bonded to C atoms were included in the refinement at calculated positions as riding atoms, with C—H = 0.95 A˚ andUiso(H) = 1.2Ueq(C). The H atoms of the NH2and NH groups were located in a difference synthesis and refined isotropically. Some low-angle reflections were excluded from the refinement, as they were probably obscured by the beam-stop.
Data collection: CRYSTALCLEAR (Rigaku, 1999); cell refine-ment:CRYSTALCLEAR; data reduction:CrystalStructure(Rigaku/ MSC, 2004); program(s) used to solve structure:SIR97(Altomareet al., 1999); program(s) used to refine structure:CRYSTALS (Better-idgeet al., 2003); molecular graphics:ORTEPIII(Burnett & Johnson, 1996) andMERCURY(Version 1.3; Brunoet al., 2002); software used to prepare material for publication:CrystalStructure.
References
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999).J. Appl. Cryst.32, 115–119.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003).J. Appl. Cryst.36, 1487.
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M. K., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002).Acta Cryst.B58, 389–397.
Burnett, M. N. & Johnson, C. K. (1996).ORTEPIII. Report ORNL-6895. Ridge National Laboratory, Tennessee, USA.
Charbonneau, G. P. & Delugeard, Y. (1977).Acta Cryst.B33, 1586–1588. Gulbis, J. M., Mackay, M. F., Banwell, M. G. & Lambert, J. N. (1992).Acta
Cryst.C48, 332–334.
Jacobson, R. (1998). Private communication to Rigaku Corporation, Tokyo, Japan.
Kubo, K., Mori, A., Ujiie, S. & Tschierske, C. (2004).J. Oleo. Sci.53, 575–579. Kubo, K., Mori, A., Ujiie, S. & Tschierske, C. (2005).J. Oleo. Sci.54, 179–183. Kubo, K., Sutoh, T., Mori, A. & Ujiie, S. (2002).Bull. Chem. Soc. Jpn,75, 1353–
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Batteries New Technol. Med.3, 475–478.
Kubo, K. Yamamoto, E. & Mori, A. (2001).Acta Cryst.C57, 611–613. Larson, A. C. (1970).Crystallographic Computing,edited by F. R. Ahmed, S.
R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard.
Lide, D. R. (1990).Handbook of Chemistry and Physics, 71st ed. Boston: CRC Press.
Mori, A. & Takeshita, H. (1995).J. Synth. Org. Chem Jpn.53, 197–206. Mori, A., Takeshita, H., Katahira, K., Kida, K., Jin, C. & Ujiie, S. (2002).Liq.
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Prout, C. K., Orley, T. M., Tickle, I. J. & Wright, J. D. (1973).J. Chem. Soc. Perkin Trans. 2, pp. 523–527.
Rigaku (1999).CRYSTALCLEAR. Rigaku Corporation, 3-9-12 Akishima, Tokyo 196-8666, Japan.
Rigaku/MSC (2004).CrystalStructure. Version 3.7.0. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA.
Shimanouchi, H. & Sasada, Y. (1973).Acta Cryst.B29, 81–90.
Yamamoto, E., Kubo, K., Kato, N. & Mori, A. (2001).Acta Cryst.E57, o279– o281.
organic papers
o2752
Kuboet al. Csupporting information
Acta Cryst. (2005). E61, o2750–o2752 [https://doi.org/10.1107/S1600536805023792]
2-Amino-5-[4-(octylamino)phenyl]cyclohepta-2,4,6-trien-1-one
Kanji Kubo, Taisuke Matsumoto, Kouki Katahira and Akira Mori
2-Amino-5-[4-(octylamino)phenyl]cyclohepta-2,4,6-trien-1-one
Crystal data
C21H28N2O Mr = 324.46
Triclinic, P1 Hall symbol: -P 1 a = 7.691 (2) Å b = 14.882 (4) Å c = 16.948 (5) Å α = 77.200 (14)° β = 77.262 (14)° γ = 80.658 (14)° V = 1832.0 (9) Å3
Z = 4
F(000) = 704.00 Dx = 1.176 Mg m−3
Mo Kα radiation, λ = 0.71070 Å Cell parameters from 2903 reflections θ = 3.1–27.5°
µ = 0.07 mm−1 T = 123 K Platelet, yellow 0.12 × 0.10 × 0.03 mm
Data collection
Rigaku Saturn diffractometer
Detector resolution: 7.31 pixels mm-1 ω scans
Absorption correction: multi-scan (Jacobson, 1998)
Tmin = 0.991, Tmax = 0.998 22067 measured reflections
8302 independent reflections 3759 reflections with I > 2σ(I) Rint = 0.064
θmax = 27.5° h = −9→9 k = −19→19 l = −21→21
Refinement
Refinement on F2 R[F2 > 2σ(F2)] = 0.071 wR(F2) = 0.202 S = 1.00 8285 reflections 508 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[0.0015Fo2 + σ(Fo2)]/(4Fo2) (Δ/σ)max < 0.001
Δρmax = 0.53 e Å−3 Δρmin = −0.49 e Å−3
Extinction correction: Larson (1970), eq. 22 Extinction coefficient: 156 (60)
Special details
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
supporting information
sup-2 Acta Cryst. (2005). E61, o2750–o2752
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
C40 0.9623 (4) 1.1326 (2) 0.5568 (2) 0.0480 (9) C41 1.0564 (4) 1.1906 (2) 0.4788 (2) 0.0546 (10) C42 1.2145 (4) 1.2326 (2) 0.4903 (2) 0.0646 (11) H1 −0.840 (3) −0.088 (2) 0.939 (2) 0.056 (9)* H2 −0.901 (4) 0.013 (2) 0.937 (2) 0.053 (9)*
H3 −0.7016 0.1186 0.9191 0.046*
H4 −0.4461 0.1745 0.8810 0.046*
H5 −0.0997 −0.0494 0.8437 0.046*
H6 −0.2693 −0.1587 0.8785 0.046*
H7 −0.2196 0.2146 0.9146 0.045*
H8 0.0091 0.3072 0.8783 0.046*
H9 0.2699 0.1542 0.7071 0.044*
H10 0.0415 0.0601 0.7462 0.046*
H11 0.277 (3) 0.3474 (19) 0.7977 (17) 0.036 (7)*
H12 0.5250 0.2255 0.7244 0.048*
H13 0.4445 0.3005 0.6583 0.048*
H14 0.5209 0.4161 0.7117 0.047*
H15 0.6010 0.3412 0.7779 0.047*
H16 0.8401 0.2998 0.6826 0.048*
H17 0.7546 0.3619 0.6113 0.048*
H18 0.7873 0.4931 0.6557 0.052*
H19 0.8689 0.4317 0.7285 0.052*
H20 1.1195 0.3873 0.6370 0.050*
H21 1.0381 0.4498 0.5646 0.051*
H22 1.0569 0.5802 0.6163 0.061*
H23 1.1466 0.5164 0.6855 0.061*
H24 1.3923 0.4779 0.5880 0.063*
H25 1.3027 0.5422 0.5189 0.063*
H26 1.3713 0.6680 0.5454 0.086*
H27 1.5315 0.5992 0.5725 0.086*
H28 1.3664 0.6254 0.6380 0.086*
H29 −0.672 (4) 0.320 (2) 0.9586 (19) 0.047 (8)* H30 −0.524 (4) 0.279 (2) 1.011 (2) 0.087 (13)*
H31 −0.2785 0.3710 0.9748 0.050*
H32 −0.1259 0.4878 0.9257 0.050*
H33 −0.4484 0.6652 0.7936 0.055*
H34 −0.6722 0.5897 0.8060 0.053*
H35 −0.0695 0.6227 0.9487 0.046*
H36 0.1326 0.7309 0.9164 0.046*
H37 0.0363 0.8034 0.6836 0.053*
H38 −0.1742 0.6991 0.7177 0.051*
H39 0.298 (3) 0.828 (2) 0.825 (2) 0.051 (9)*
H40 0.3541 0.8372 0.6635 0.052*
H41 0.2225 0.9266 0.6731 0.053*
H42 0.4223 0.9742 0.7367 0.053*
H43 0.5563 0.8880 0.7188 0.053*
H44 0.5911 0.9500 0.5786 0.056*
supporting information
sup-4 Acta Cryst. (2005). E61, o2750–o2752
H46 0.6693 1.0720 0.6657 0.055*
H47 0.7975 0.9853 0.6442 0.055*
H48 0.8383 1.0550 0.5058 0.056*
H49 0.7147 1.1424 0.5288 0.056*
H50 0.9231 1.1705 0.5971 0.055*
H51 1.0462 1.0824 0.5755 0.055*
H52 0.9718 1.2396 0.4591 0.062*
H53 1.0994 1.1522 0.4390 0.062*
H54 1.1737 1.2918 0.5042 0.075*
H55 1.3013 1.2390 0.4405 0.075*
H56 1.2672 1.1932 0.5333 0.075*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C28 0.0357 (14) 0.0251 (13) 0.070 (2) 0.0052 (11) −0.0221 (14) −0.0180 (14) C29 0.0308 (13) 0.0261 (13) 0.059 (2) 0.0041 (11) −0.0136 (13) −0.0164 (13) C30 0.0274 (12) 0.0261 (13) 0.062 (2) 0.0042 (10) −0.0109 (13) −0.0117 (13) C31 0.0286 (12) 0.0275 (13) 0.060 (2) 0.0010 (10) −0.0153 (13) −0.0121 (13) C32 0.0346 (13) 0.0238 (12) 0.061 (2) 0.0008 (11) −0.0126 (13) −0.0140 (13) C33 0.0446 (15) 0.0287 (13) 0.058 (2) −0.0024 (12) −0.0117 (15) −0.0122 (14) C34 0.0393 (14) 0.0296 (13) 0.060 (2) 0.0007 (11) −0.0180 (14) −0.0147 (14) C35 0.0452 (15) 0.0315 (14) 0.055 (2) −0.0016 (12) −0.0086 (15) −0.0101 (14) C36 0.0445 (16) 0.0283 (13) 0.060 (2) −0.0028 (12) −0.0052 (15) −0.0091 (14) C37 0.0492 (17) 0.0346 (15) 0.056 (2) −0.0041 (13) −0.0043 (15) −0.0085 (14) C38 0.0510 (17) 0.0306 (14) 0.055 (2) −0.0066 (13) −0.0018 (15) −0.0086 (14) C39 0.0536 (18) 0.0359 (15) 0.051 (2) −0.0044 (14) −0.0007 (15) −0.0045 (14) C40 0.0541 (17) 0.0315 (14) 0.053 (2) −0.0082 (13) 0.0034 (15) −0.0074 (14) C41 0.0597 (19) 0.0410 (17) 0.055 (2) −0.0035 (15) −0.0020 (17) −0.0040 (15) C42 0.064 (2) 0.0512 (19) 0.071 (2) −0.0105 (17) 0.0027 (19) −0.0083 (19)
Geometric parameters (Å, º)
O1—C1 1.279 (3) N3—H29 0.87 (3)
O2—C22 1.274 (3) N3—H30 0.97 (3)
N1—C2 1.345 (3) N4—H39 0.98 (3)
N2—C11 1.362 (3) C3—H3 0.950
N2—C14 1.451 (3) C4—H4 0.950
N3—C23 1.352 (3) C6—H5 0.950
N4—C32 1.385 (3) C7—H6 0.950
N4—C35 1.439 (4) C9—H7 0.950
C1—C2 1.472 (3) C10—H8 0.950
C1—C7 1.414 (3) C12—H9 0.950
C2—C3 1.382 (3) C13—H10 0.950
C3—C4 1.390 (3) C14—H12 0.950
C4—C5 1.391 (3) C14—H13 0.950
C5—C6 1.418 (3) C15—H14 0.950
C5—C8 1.482 (3) C15—H15 0.950
C6—C7 1.375 (3) C16—H16 0.950
C8—C9 1.411 (4) C16—H17 0.950
C8—C13 1.397 (3) C17—H18 0.950
C9—C10 1.374 (3) C17—H19 0.950
C10—C11 1.409 (3) C18—H20 0.950
C11—C12 1.400 (4) C18—H21 0.950
C12—C13 1.386 (3) C19—H22 0.950
C14—C15 1.521 (4) C19—H23 0.950
C15—C16 1.521 (3) C20—H24 0.950
C16—C17 1.525 (4) C20—H25 0.950
C17—C18 1.506 (3) C21—H26 0.950
C18—C19 1.530 (4) C21—H27 0.950
C19—C20 1.513 (4) C21—H28 0.950
C20—C21 1.519 (5) C24—H31 0.950
supporting information
sup-6 Acta Cryst. (2005). E61, o2750–o2752
C22—C28 1.423 (3) C27—H33 0.950
C23—C24 1.389 (4) C28—H34 0.950
C24—C25 1.382 (3) C30—H35 0.950
C25—C26 1.397 (3) C31—H36 0.950
C26—C27 1.404 (4) C33—H37 0.950
C26—C29 1.486 (3) C34—H38 0.950
C27—C28 1.379 (4) C35—H40 0.950
C29—C30 1.405 (4) C35—H41 0.950
C29—C34 1.405 (4) C36—H42 0.950
C30—C31 1.382 (3) C36—H43 0.950
C31—C32 1.406 (4) C37—H44 0.950
C32—C33 1.392 (5) C37—H45 0.950
C33—C34 1.387 (4) C38—H46 0.950
C35—C36 1.512 (4) C38—H47 0.950
C36—C37 1.521 (4) C39—H48 0.950
C37—C38 1.524 (4) C39—H49 0.950
C38—C39 1.521 (4) C40—H50 0.950
C39—C40 1.525 (4) C40—H51 0.950
C40—C41 1.514 (4) C41—H52 0.950
C41—C42 1.520 (5) C41—H53 0.950
N1—H1 0.89 (3) C42—H54 0.950
N1—H2 0.83 (3) C42—H55 0.950
N2—H11 0.93 (3) C42—H56 0.950
O1···N3i 2.845 (3) C10···H19iii 3.166
O1···N4ii 2.993 (4) C10···H31 3.262
O1···C31ii 3.520 (3) C11···H3v 2.805
O2···N2iii 2.993 (3) C11···H4v 3.574
O2···C10iii 3.550 (3) C11···H16iii 3.291 O2···C25iii 3.529 (3) C11···H19iii 3.455
N1···N1iv 3.210 (3) C11···H20iii 3.022
N1···N4ii 3.580 (4) C12···H2v 3.46 (3)
N1···C5i 3.523 (4) C12···H3v 3.132
N1···C8iii 3.455 (3) C12···H16iii 3.218 N1···C13iii 3.407 (3) C12···H20iii 3.425
N2···O2v 2.993 (3) C12···H42ix 3.204
N2···C4v 3.597 (3) C12···H50ii 3.522
N3···O1i 2.845 (3) C12···H56ii 3.523
N3···C1i 3.573 (3) C13···H2v 2.94 (3)
N3···C26vi 3.486 (4) C13···H3v 3.564
N3···C30vi 3.358 (3) C13···H16iii 3.198
N4···O1vii 2.993 (4) C13···H41ix 3.488
N4···N1vii 3.580 (4) C13···H42ix 3.348
N4···C1vii 3.531 (4) C13···H50ii 3.180
C1···N3i 3.573 (3) C13···H51ii 3.446
C1···N4ii 3.531 (4) C14···H4v 3.119
C1···C3i 3.570 (4) C14···H20iii 3.223
C1···C36ii 3.495 (4) C14···H46ix 3.504
C2···C4i 3.522 (4) C15···H4v 3.354
C3···C1i 3.570 (4) C15···H24iii 3.074
C3···C7i 3.591 (4) C16···H24iii 3.512
C3···C11iii 3.372 (3) C16···H25xii 3.294 C3···C12iii 3.423 (4) C16···H50ix 3.194
C4···N2iii 3.597 (3) C18···H13v 3.531
C4···C1i 3.459 (4) C18···H21xii 3.342
C4···C2i 3.522 (4) C18···H54ix 3.215
C4···C14iii 3.563 (3) C19···H14v 3.561
C5···N1i 3.523 (4) C19···H38v 3.567
C7···C3i 3.591 (4) C19···H52xiii 3.537
C8···N1v 3.455 (3) C20···H13v 3.516
C10···O2v 3.550 (3) C20···H14v 3.142
C11···C3v 3.372 (3) C20···H17xii 3.308
C12···C3v 3.423 (4) C20···H24viii 3.166 C13···N1v 3.407 (3) C20···H25viii 3.172 C14···C4v 3.563 (3) C20···H27viii 3.413
C15···C22v 3.422 (4) C21···H14v 3.372
C20···C20viii 3.530 (4) C21···H18v 3.506 C22···C15iii 3.422 (4) C21···H24viii 3.439 C23···C25vi 3.454 (4) C21···H25viii 3.442 C25···O2v 3.529 (3) C21···H52xiii 3.439 C25···C23vi 3.454 (4) C21···H55xiv 3.297 C26···N3vi 3.486 (4) C22···H11iii 2.79 (3) C28···C31iii 3.385 (3) C22···H14iii 3.047 C30···N3vi 3.358 (3) C22···H15iii 2.931 C31···O1vii 3.520 (3) C22···H32vi 3.567
C31···C28v 3.385 (3) C22···H35vi 3.475
C36···C1vii 3.495 (4) C22···H35vi 3.475
O1···H4i 3.398 C23···H7 3.301
O1···H7i 2.803 C23···H11iii 3.42 (3)
O1···H29i 3.35 (3) C23···H15iii 2.859
O1···H30i 1.90 (3) C23···H35vi 3.503
O1···H31i 3.236 C24···H7 3.153
O1···H33ix 3.473 C24···H8 3.018
O1···H36ii 2.766 C24···H15iii 3.380
O1···H39ii 2.02 (3) C24···H19iii 3.568
O1···H42ii 3.425 C24···H36xv 3.397
O1···H43ii 3.363 C25···H8 3.200
O2···H8iii 2.800 C25···H19iii 3.304
O2···H11iii 2.07 (3) C26···H19iii 3.352
O2···H14iii 3.232 C26···H30vi 3.34 (4)
O2···H15iii 3.270 C27···H30vi 3.50 (4)
O2···H23x 3.386 C27···H39iii 3.59 (2)
O2···H32iii 2.716 C28···H14iii 3.179
O2···H35iii 3.530 C28···H15iii 3.544
supporting information
sup-8 Acta Cryst. (2005). E61, o2750–o2752
N1···H1iv 3.46 (3) C28···H31vi 3.500
N1···H2iv 2.68 (2) C28···H36iii 3.433
N1···H5iii 3.041 C29···H6xi 3.048
N1···H7i 3.284 C29···H29vi 3.53 (3)
N1···H10iii 3.572 C29···H30vi 3.41 (3)
N1···H39ii 3.07 (3) C29···H34v 3.568
N1···H42ii 3.513 C30···H6xi 2.931
N2···H3v 3.221 C30···H29vi 2.93 (2)
N2···H4v 3.095 C30···H30vi 3.39 (3)
N2···H20iii 2.882 C30···H34v 3.099
N2···H23iii 3.400 C31···H1vii 3.42 (3)
N2···H29v 3.33 (3) C31···H5xi 3.394
N3···H4 2.821 C31···H6xi 2.910
N3···H6i 3.340 C31···H31xv 3.226
N3···H7 2.940 C31···H34v 2.821
N3···H11iii 3.27 (3) C32···H1vii 3.58 (3)
N3···H15iii 3.136 C32···H5xi 2.981
N3···H35vi 2.934 C32···H6xi 3.040
N4···H1vii 3.04 (3) C32···H33v 3.535
N4···H5xi 2.952 C32···H34v 3.010
N4···H10xi 3.350 C33···H5xi 3.485
N4···H33v 3.271 C33···H6xi 3.124
C1···H4i 3.463 C33···H28iii 3.513
C1···H7i 3.485 C33···H34v 3.453
C1···H30i 2.72 (3) C33···H52xvi 3.338
C1···H39ii 2.68 (3) C33···H53xvi 3.226
C1···H42ii 2.974 C34···H6xi 3.117
C1···H43ii 3.178 C34···H22iii 3.272
C2···H39ii 3.22 (3) C34···H23iii 3.454
C2···H42ii 3.035 C34···H43iii 3.484
C3···H12iii 3.455 C34···H52xvi 3.550
C3···H42ii 3.485 C34···H53xvi 3.537
C4···H12iii 2.892 C35···H10xi 3.223
C4···H15iii 3.534 C36···H9xi 3.405
C4···H30 3.57 (4) C36···H10xi 3.516
C5···H2v 3.26 (3) C37···H9xi 3.384
C5···H12iii 3.380 C37···H53xiii 3.244
C5···H46ii 3.418 C38···H12xi 3.567
C6···H1v 3.40 (3) C38···H53xiii 3.211
C6···H2v 3.24 (3) C39···H48xiii 3.337
C6···H46ii 3.532 C39···H51xiii 3.572
C6···H47ii 3.596 C39···H53xiii 3.562
C7···H3i 3.383 C40···H10vii 3.310
C7···H30i 3.09 (3) C40···H16xi 3.511
C7···H39ii 3.59 (3) C40···H48xiii 3.236
C7···H42ii 3.316 C41···H22xiii 3.494
C7···H43ii 3.124 C41···H37xvi 2.972
C8···H16iii 3.261 C41···H44xiii 3.251
C9···H1i 3.24 (3) C41···H47xiii 3.590
C9···H2v 3.13 (3) C41···H48xiii 3.576
C9···H3v 3.447 C42···H22xiii 3.595
C9···H15iii 3.179 C42···H27xiv 3.271
C9···H16iii 3.289 C42···H38xvi 3.514
C9···H31 3.294 C42···H44xiii 3.208
C10···H3v 2.984 C42···H45v 3.583
C10···H16iii 3.316
C11—N2—C14 126.2 (2) C14—C15—H14 107.9
C32—N4—C35 123.4 (3) C14—C15—H15 107.7
O1—C1—C2 116.0 (2) C16—C15—H14 107.8
O1—C1—C7 120.4 (2) C16—C15—H15 107.7
C2—C1—C7 123.6 (2) H14—C15—H15 109.5
N1—C2—C1 113.5 (2) C15—C16—H16 109.1
N1—C2—C3 120.3 (2) C15—C16—H17 109.0
C1—C2—C3 126.2 (2) C17—C16—H16 109.0
C2—C3—C4 132.3 (2) C17—C16—H17 109.2
C3—C4—C5 130.9 (2) H16—C16—H17 109.5
C4—C5—C6 123.3 (2) C16—C17—H18 107.9
C4—C5—C8 118.2 (2) C16—C17—H19 108.1
C6—C5—C8 118.4 (2) C18—C17—H18 108.0
C5—C6—C7 130.7 (2) C18—C17—H19 108.0
C1—C7—C6 132.8 (2) H18—C17—H19 109.5
C5—C8—C9 120.6 (2) C17—C18—H20 108.5
C5—C8—C13 123.2 (2) C17—C18—H21 108.6
C9—C8—C13 116.2 (2) C19—C18—H20 108.4
C8—C9—C10 122.1 (2) C19—C18—H21 108.6
C9—C10—C11 120.9 (2) H20—C18—H21 109.5
N2—C11—C10 118.4 (2) C18—C19—H22 108.4
N2—C11—C12 123.7 (2) C18—C19—H23 108.6
C10—C11—C12 117.9 (2) C20—C19—H22 108.3
C11—C12—C13 120.3 (2) C20—C19—H23 108.6
C8—C13—C12 122.7 (2) H22—C19—H23 109.5
N2—C14—C15 107.8 (2) C19—C20—H24 108.2
C14—C15—C16 116.1 (2) C19—C20—H25 108.6
C15—C16—C17 111.0 (2) C21—C20—H24 108.2
C16—C17—C18 115.3 (2) C21—C20—H25 108.5
C17—C18—C19 113.3 (2) H24—C20—H25 109.5
C18—C19—C20 113.4 (2) C20—C21—H26 109.3
C19—C20—C21 113.8 (3) C20—C21—H27 109.7
O2—C22—C23 117.0 (2) C20—C21—H28 109.4
O2—C22—C28 120.0 (2) H26—C21—H27 109.5
C23—C22—C28 123.0 (2) H26—C21—H28 109.5
N3—C23—C22 112.9 (2) H27—C21—H28 109.5
N3—C23—C24 120.4 (2) C23—C24—H31 113.8
supporting information
sup-10 Acta Cryst. (2005). E61, o2750–o2752
C23—C24—C25 132.3 (2) C24—C25—H32 114.7
C24—C25—C26 130.6 (2) C26—C25—H32 114.7
C25—C26—C27 123.6 (2) C26—C27—H33 114.3
C25—C26—C29 118.0 (2) C28—C27—H33 114.3
C27—C26—C29 118.4 (2) C22—C28—H34 113.8
C26—C27—C28 131.4 (2) C27—C28—H34 113.8
C22—C28—C27 132.4 (2) C29—C30—H35 119.1
C26—C29—C30 121.7 (2) C31—C30—H35 119.2
C26—C29—C34 121.7 (3) C30—C31—H36 119.5
C30—C29—C34 116.6 (2) C32—C31—H36 119.5
C29—C30—C31 121.6 (2) C32—C33—H37 119.7
C30—C31—C32 121.0 (3) C34—C33—H37 119.7
N4—C32—C31 119.0 (3) C29—C34—H38 118.9
N4—C32—C33 123.0 (2) C33—C34—H38 119.0
C31—C32—C33 118.0 (2) N4—C35—H40 109.5
C32—C33—C34 120.7 (2) N4—C35—H41 109.4
C29—C34—C33 122.1 (3) C36—C35—H40 109.5
N4—C35—C36 109.6 (2) C36—C35—H41 109.4
C35—C36—C37 116.0 (3) H40—C35—H41 109.5
C36—C37—C38 112.1 (2) C35—C36—H42 107.8
C37—C38—C39 114.8 (3) C35—C36—H43 107.8
C38—C39—C40 113.0 (2) C37—C36—H42 107.9
C39—C40—C41 114.4 (3) C37—C36—H43 107.8
C40—C41—C42 114.1 (3) H42—C36—H43 109.5
C2—N1—H1 115.8 (18) C36—C37—H44 108.8
C2—N1—H2 120 (2) C36—C37—H45 108.8
H1—N1—H2 121 (3) C38—C37—H44 108.8
C11—N2—H11 116.4 (15) C38—C37—H45 108.8
C14—N2—H11 117.4 (15) H44—C37—H45 109.5
C23—N3—H29 113.2 (18) C37—C38—H46 108.1
C23—N3—H30 125 (2) C37—C38—H47 108.1
H29—N3—H30 118 (2) C39—C38—H46 108.1
C32—N4—H39 108.6 (17) C39—C38—H47 108.1
C35—N4—H39 122.6 (16) H46—C38—H47 109.5
C2—C3—H3 113.8 C38—C39—H48 108.6
C4—C3—H3 113.9 C38—C39—H49 108.6
C3—C4—H4 114.5 C40—C39—H48 108.6
C5—C4—H4 114.6 C40—C39—H49 108.6
C5—C6—H5 114.7 H48—C39—H49 109.5
C7—C6—H5 114.6 C39—C40—H50 108.2
C1—C7—H6 113.6 C39—C40—H51 108.2
C6—C7—H6 113.6 C41—C40—H50 108.2
C8—C9—H7 119.0 C41—C40—H51 108.3
C10—C9—H7 118.9 H50—C40—H51 109.5
C9—C10—H8 119.6 C40—C41—H52 108.4
C11—C10—H8 119.5 C40—C41—H53 108.3
C11—C12—H9 119.8 C42—C41—H52 108.4
C8—C13—H10 118.7 H52—C41—H53 109.5
C12—C13—H10 118.6 C41—C42—H54 109.4
N2—C14—H12 109.9 C41—C42—H55 109.6
N2—C14—H13 109.9 C41—C42—H56 109.5
C15—C14—H12 110.0 H54—C42—H55 109.5
C15—C14—H13 109.8 H54—C42—H56 109.5
H12—C14—H13 109.5 H55—C42—H56 109.5
C11—N2—C14—C15 −172.2 (2) C16—C17—C18—C19 −179.2 (2) C14—N2—C11—C10 175.9 (2) C17—C18—C19—C20 −177.0 (2) C14—N2—C11—C12 −2.0 (4) C18—C19—C20—C21 −179.7 (2) C32—N4—C35—C36 −169.9 (2) O2—C22—C23—N3 1.7 (4) C35—N4—C32—C31 165.8 (2) O2—C22—C23—C24 178.3 (3) C35—N4—C32—C33 −15.7 (3) O2—C22—C28—C27 −179.9 (2) O1—C1—C2—N1 −1.6 (4) C23—C22—C28—C27 0.3 (5) O1—C1—C2—C3 178.6 (3) C28—C22—C23—N3 −178.5 (3) O1—C1—C7—C6 178.4 (3) C28—C22—C23—C24 −1.9 (5) C2—C1—C7—C6 0.5 (5) N3—C23—C24—C25 177.8 (3) C7—C1—C2—N1 176.4 (3) C22—C23—C24—C25 1.4 (6) C7—C1—C2—C3 −3.4 (5) C23—C24—C25—C26 0.2 (5) N1—C2—C3—C4 −176.8 (3) C24—C25—C26—C27 −0.1 (4) C1—C2—C3—C4 2.9 (6) C24—C25—C26—C29 178.2 (3) C2—C3—C4—C5 0.9 (6) C25—C26—C27—C28 −1.4 (5) C3—C4—C5—C6 −2.6 (5) C25—C26—C29—C30 −36.6 (4) C3—C4—C5—C8 179.1 (3) C25—C26—C29—C34 141.8 (2) C4—C5—C6—C7 0.4 (5) C27—C26—C29—C30 141.8 (2) C4—C5—C8—C9 34.2 (4) C27—C26—C29—C34 −39.8 (4) C4—C5—C8—C13 −144.6 (2) C29—C26—C27—C28 −179.8 (3) C6—C5—C8—C9 −144.2 (3) C26—C27—C28—C22 1.7 (6) C6—C5—C8—C13 37.0 (4) C26—C29—C30—C31 179.7 (2) C8—C5—C6—C7 178.7 (3) C26—C29—C34—C33 −178.5 (2) C5—C6—C7—C1 1.4 (6) C30—C29—C34—C33 −0.0 (3) C5—C8—C9—C10 −179.6 (2) C34—C29—C30—C31 1.2 (3) C5—C8—C13—C12 179.0 (2) C29—C30—C31—C32 −2.2 (3) C9—C8—C13—C12 0.1 (3) C30—C31—C32—N4 −179.5 (2) C13—C8—C9—C10 −0.7 (4) C30—C31—C32—C33 1.9 (3) C8—C9—C10—C11 0.8 (4) N4—C32—C33—C34 −179.2 (2) C9—C10—C11—N2 −178.1 (2) C31—C32—C33—C34 −0.7 (3) C9—C10—C11—C12 −0.1 (3) C32—C33—C34—C29 −0.2 (4) N2—C11—C12—C13 177.4 (2) N4—C35—C36—C37 −174.9 (2) C10—C11—C12—C13 −0.5 (4) C35—C36—C37—C38 −177.3 (2) C11—C12—C13—C8 0.5 (4) C36—C37—C38—C39 −179.0 (2) N2—C14—C15—C16 179.9 (2) C37—C38—C39—C40 −178.1 (2) C14—C15—C16—C17 171.3 (2) C38—C39—C40—C41 179.2 (2) C15—C16—C17—C18 178.8 (2) C39—C40—C41—C42 178.3 (2)
supporting information
sup-12 Acta Cryst. (2005). E61, o2750–o2752
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N1—H1···O1 0.89 (3) 2.13 (2) 2.570 (2) 109 (2) N2—H11···O2v 0.93 (3) 2.07 (3) 2.993 (3) 168 (2) N3—H29···O2 0.87 (3) 2.11 (2) 2.579 (3) 113 (2) N3—H30···O1i 0.97 (3) 1.90 (3) 2.845 (3) 165 (3) N4—H39···O1vii 0.98 (3) 2.02 (3) 2.993 (4) 170 (2)