organic papers
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Guzeiet al. C26H38N4O5CH4O doi:10.1107/S1600536807012299 Acta Cryst.(2007). E63, o1892–o1894
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
N
-{(Aminocarbonyl)[(
S
)-4-nitrobenzyl]-methyl}-
N
-{[(
R
)-cyclohexyl](cyclohexyl-aminocarbonyl)methyl}propanamide
methanol solvate
Ilia A. Guzei,* Lara C. Spencer, Qi Lin and Helen E. Blackwell
Department of Chemistry, University of Wisconsin–Madison, 1101 University Avenue, Madison, WI 53706, USA
Correspondence e-mail: iguzei@chem.wisc.edu
Key indicators Single-crystal X-ray study
T= 100 K
Mean(C–C) = 0.002 A˚
Rfactor = 0.036
wRfactor = 0.096
Data-to-parameter ratio = 11.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 28 February 2007 Accepted 15 March 2007
#2007 International Union of Crystallography All rights reserved
The title compound, C26H38N4O5CH4O, shows typical
geometric parameters, and four types of hydrogen bonds form a three-dimensional framework.
Comment
Our laboratory is engaged in developing the small molecule macroarray as a general approach for the synthesis and screening of organic compound libraries (Blackwell, 2006). This method entails the spatially addressed solid-phase synthesis of discrete compounds on planar polymeric supports and the title compound, (I), was isolated during this work. We recently reported that our macroarray platform is compatible with the Ugi four-component reaction and have synthesized several libraries using this versatile transformation (Linet al., 2005; Lin & Blackwell, 2006). In each of these libraries, the amine component was l-4-nitrophenylalanine and this
component was attached to the planar solid support through one of two linker systems, either the acid-cleavable Rink linker or the photo-cleavable -methyl-6-nitroveratrylamine linker. While studying this reaction, we observed that the different linker systems gave major products with opposite stereochemistries at the stereogenic center, atom C13 (Fig. 1).
The asymmetric unit consists of one main molecule and one methanol molecule (Fig. 1). The absolute configuration of atom C8 is known to be S from the synthetic procedure, allowing the absolute configuration of atom C13, R, to be determined. The bond distances and angles are within the range of those for similar compounds in the Cambridge Structural Database (CSD; Version 5.28, January 2007 release; Allen, 2002). The two cyclohexane rings are in the chair conformation.
one intramolecular hydrogen bond between atoms N2 and O4 of (I). From this arrangement, a seven-membered ring is formed which can be classified as anS(7) motif according to graph-set analysis (Bernstein et al., 1995). There is an inter-molecular hydrogen bond between atom N2 of (I) and atom O5 of a symmetry-related molecule of (I). Each methanol solvent molecule forms two hydrogen bonds, one between methanol atom O6 and atom O3 of (I), and one between atom N4 of a symmetry-related molecule of (I) and methanol atom O6. These four types of hydrogen bond form a three-dimen-sional network.
Experimental
In an aluminium foil-wrapped Micro Bio-Spin Column (Bio-Rad, No. 732–6204), Fmoc-aminoethyl-photolinker AM resin (201.6 mg, 151.2 mmol; 0.75 mmol g 1) was agitated in 20% piperidine in dimethylformamide (DMF) (3.0 ml) at 298 K for 20 min, twice, followed by washing with DMF and MeOH. The resin was driedin vacuo for 1 h. Five equivalents of Fmoc-l-Nph-OH (N
-fluorenyl-methoxycarbonyl-l-p-nitrophenylalanine) (328.1 mg, 756.0mmol)
and the coupling reagent 2-(1H -benzotriazole-1-yl)-1,1,3,3-tetra-methyluronium hexafluorophosphate (HTBU) (287.3 mg, 756.0mmol) were dissolved in dry DMF (1 ml), to which N,N -diisopropylethylamine (DIPEA) (263.2ml, 1.51mmol) in dry DMF (756ml) was added. The dark-yellow mixture was allowed to stand at 298 K for 5 min before being added to the Micro Bio-Spin Column with the above resin. The column then was agitated for 4 h. The resulting resin was washed with DMF, CH2Cl2and MeOH, followed by subjection to vacuum overnight. The resin tested negative for free amines using a Kaiser colorimetric test. The resin was placed in an aluminium foil-wrapped fritted extract clean reservoir (Alltech, No.
210208), to which a solution containing water (1.33 ml), cyclohexane carboxaldehyde (133ml) and propionic acid (533ml) was added. An aliquot of cyclohexyl isocyanide (333ml) then was added. The vessel was agitated for 45 min at 298 K, and the resin was washed with DMF, MeOH and CH2Cl2, and dried overnight in vacuo. The resin was divided into two portions, placed in glass vials (20 ml) containing MeOH (3 ml), and subjected to photo-cleavage at 365 nm for 16 h. The beads were filtered off and the solution was concentrated to give a colorless oily product. The crude product was subjected to flash silica-gel column chromatography (CH2Cl2–MeOH, 240:1v/vto 60:1
v/v) to yield the product, (I), and its stereoisomer as white solids (overall yield 21%). Crystallization of the major isomer from a solution in methanol gave colorless crystals, which proved to be the title compound, (I).
Crystal data
C26H38N4O5CH4O
Mr= 518.65 Tetragonal,P43
a= 13.1585 (5) A˚
c= 15.8470 (13) A˚
V= 2743.8 (3) A˚3
Z= 4
Mo-Kradiation = 0.09 mm 1
T= 100 (2) K 0.500.400.40 mm
Data collection
Bruker SMART 1000 CCD area-detector diffractometer Absorption correction: multi-scan
(SADABS; Bruker, 2003)
Tmin= 0.88,Tmax= 1.00
48333 measured reflections 3786 independent reflections 3564 reflections withI> 2(I)
Rint= 0.035
Refinement
R[F2> 2(F2)] = 0.036
wR(F2) = 0.096
S= 1.00 3786 reflections 343 parameters
H atoms treated by a mixture of independent and constrained refinement
max= 0.33 e A˚ 3 min= 0.14 e A˚ 3
organic papers
Acta Cryst.(2007). E63, o1892–o1894 Guzeiet al. C
[image:2.610.313.563.69.262.2]26H38N4O5CH4O
o1893
Figure 1The molecular structure of (I), drawn with 50% probability displacement ellipsoids. All H atoms attached to C atoms have been omitted for clarity. Two hydrogen bonds are shown as dashed lines.
Figure 2
Each main molecule forms five hydrogen bonds, shown as dashed lines: one is intramolecular, two are with two symmetry-related main molecules, and two are with two molecules of the methanol solvent. Each methanol forms two hydrogen bonds to two different molecules. All H atoms attached to C atoms have been omitted. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i)y, x+ 2,z+1
4; (ii) x+ 1, y+ 2,z 1
2; (iii) y+ 2,x,z 1
[image:2.610.45.296.72.308.2]Table 1
Hydrogen bonds for compound (I) compared with those for similar compounds in the CSD (A˚ ,).
Xis the number of relevant reference compounds in the CSD.Yis the average
D—H Adistance for relevant reference compounds in the CSD.
D—H A D—H H A D A D—H A X Y
N2—H2A O5i
0.83 (2) 2.23 (2) 3.0040 (19) 156 (2) 16 2.92 (9) N2—H2B O4 0.83 (2) 2.05 (3) 2.735 (2) 139 (2) 32 2.87 (7) N4—H4 O6ii
0.87 (2) 2.00 (3) 2.8597 (16) 171 (3) 56 2.89 (9) O6—H6 O3 0.77 (4) 2.06 (4) 2.8287 (17) 176 (3) 30 2.79 (6)
In the absence of significant anomalous scattering effects, Friedel pairs were merged. All H atoms attached to C atoms were placed in idealized locations and refined as riding, with C—H = 0.95 A˚ for aromatic H, 0.98 A˚ for methyl H, 0.99 A˚ for CH2and 1.00 A˚ for CH, and withUiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for methyl H. H atoms attached to O and N atoms were refined freely.
Data collection:SMART(Bruker, 2003); cell refinement:SAINT
(Bruker, 2003); data reduction: SAINT; program(s) used to solve
structure: SHELXTL (Bruker, 2003); program(s) used to refine structure:SHELXTL; molecular graphics:SHELXTL; software used to prepare material for publication:SHELXTL.
The authors thank the National Science Foundation (grant No. CHE-0449959) for financial support of this work. The manuscript was prepared using the beta test version 1.0.0. of the programpublCIF, to be released by the IUCr, and the program modiCIFer, to be released by the University of Wisconsin-Madison.
References
Allen, F. H. (2002).Acta Cryst.B58, 380–388.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995).Angew. Chem. Int. Ed. Engl.34, 1555–1573.
Blackwell, H. E. (2006).Curr. Opin. Chem. Biol.10, 203–212.
Bruker (2003).SADABS(Version 2.05),SAINT(Version 6.22),SHELXTL
(Version 6.10) andSMART(Version 5.622). Bruker AXS Inc., Madison, Wisconsin, USA.
Lin, Q. & Blackwell, H. E. (2006).Chem. Commun.pp. 2884–2886. Lin, Q., O’Neill, J. C. & Blackwell, H. E. (2005).Org. Lett.7, 4455–4458.
organic papers
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Guzeiet al. Csupporting information
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Acta Cryst. (2007). E63, o1892–o1894
supporting information
Acta Cryst. (2007). E63, o1892–o1894 [https://doi.org/10.1107/S1600536807012299]
N
-{(Aminocarbonyl)[(
S
)-4-nitrobenzyl]methyl}-
N
-{[(
R
)-cyclohexyl](cyclohexyl-aminocarbonyl)methyl}propanamide methanol solvate
Ilia A. Guzei, Lara C. Spencer, Qi Lin and Helen E. Blackwell
N-{(Aminocarbonyl)[(S)-4-nitrobenzyl]methyl}-N-{[(R)- cyclohexyl]
(cyclohexylaminocarbonyl)methyl}propanamide methanol solvate
Crystal data
C26H38N4O5·CH4O
Mr = 518.65
Tetragonal, P43
Hall symbol: P 4cw
a = 13.1585 (5) Å
c = 15.8470 (13) Å
V = 2743.8 (3) Å3
Z = 4
F(000) = 1120
Dx = 1.256 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 8641 reflections
θ = 2.2–28.7°
µ = 0.09 mm−1
T = 100 K
Block, colorless 0.50 × 0.40 × 0.40 mm
Data collection
Bruker SMART1000 CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
0.30° ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2003)
Tmin = 0.88, Tmax = 1.00
48333 measured reflections 3786 independent reflections 3564 reflections with I > 2σ(I)
Rint = 0.035
θmax = 29.1°, θmin = 2.0°
h = −17→17
k = −17→17
l = −21→21
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.036
wR(F2) = 0.096
S = 1.00
3786 reflections 343 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 atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0733P)2 + 0.3284P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.007
Δρmax = 0.33 e Å−3
supporting information
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Acta Cryst. (2007). E63, o1892–o1894
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
O1 1.20267 (12) 0.92796 (17) 0.13752 (13) 0.0505 (5)
O2 1.21398 (11) 1.09261 (17) 0.13973 (12) 0.0473 (5)
O3 0.71139 (10) 1.03642 (10) 0.25459 (8) 0.0222 (3)
O4 0.56771 (9) 1.17929 (9) 0.04743 (8) 0.0188 (2)
O5 0.65987 (8) 0.80631 (9) 0.03406 (8) 0.0177 (2)
N1 1.16702 (13) 1.01335 (18) 0.12702 (12) 0.0376 (5)
N2 0.70357 (12) 1.18116 (11) 0.17807 (10) 0.0201 (3)
H2A 0.7202 (19) 1.217 (2) 0.2185 (18) 0.027 (6)*
H2B 0.6801 (17) 1.2066 (18) 0.1342 (17) 0.020 (5)*
N3 0.57060 (9) 1.01182 (9) 0.08022 (8) 0.0130 (2)
N4 0.51247 (10) 0.80583 (10) −0.04134 (9) 0.0155 (3)
H4 0.4532 (19) 0.8335 (18) −0.0474 (18) 0.025 (6)*
C1 1.06038 (13) 1.02118 (17) 0.09961 (12) 0.0261 (4)
C2 1.00595 (13) 0.93285 (15) 0.08435 (13) 0.0250 (4)
H2C 1.0369 0.8679 0.0897 0.030*
C3 0.90445 (12) 0.94259 (13) 0.06089 (11) 0.0203 (3)
H3 0.8657 0.8834 0.0491 0.024*
C4 0.85879 (12) 1.03807 (12) 0.05447 (10) 0.0169 (3)
C5 0.91712 (13) 1.12492 (13) 0.06896 (11) 0.0218 (3)
H5 0.8868 1.1901 0.0636 0.026*
C6 1.01903 (13) 1.11728 (15) 0.09112 (12) 0.0259 (4)
H6A 1.0591 1.1763 0.1002 0.031*
C7 0.74792 (12) 1.04609 (12) 0.03126 (10) 0.0159 (3)
H7A 0.7335 1.0005 −0.0170 0.019*
H7B 0.7327 1.1166 0.0134 0.019*
C8 0.67844 (11) 1.01710 (11) 0.10623 (10) 0.0134 (3)
H8 0.6977 0.9459 0.1213 0.016*
C9 0.69766 (11) 1.08048 (12) 0.18697 (10) 0.0152 (3)
C10 0.52272 (12) 1.09721 (11) 0.05049 (10) 0.0144 (3)
C11 0.41259 (12) 1.08962 (12) 0.02302 (11) 0.0180 (3)
H11A 0.3713 1.0637 0.0706 0.022*
H11B 0.4071 1.0404 −0.0240 0.022*
C12 0.37028 (14) 1.19195 (14) −0.00541 (13) 0.0236 (3)
H12A 0.3741 1.2405 0.0414 0.035*
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Acta Cryst. (2007). E63, o1892–o1894
H12C 0.4103 1.2174 −0.0531 0.035*
C13 0.52007 (11) 0.91109 (11) 0.08418 (10) 0.0126 (3)
H13 0.4483 0.9203 0.0650 0.015*
C14 0.51695 (11) 0.86840 (11) 0.17426 (10) 0.0137 (3)
H14 0.5883 0.8619 0.1954 0.016*
C15 0.46690 (13) 0.76271 (12) 0.17594 (11) 0.0184 (3)
H15A 0.3971 0.7674 0.1529 0.022*
H15B 0.5062 0.7154 0.1399 0.022*
C16 0.46295 (14) 0.72153 (13) 0.26629 (12) 0.0234 (3)
H16A 0.4279 0.6549 0.2664 0.028*
H16B 0.5331 0.7109 0.2872 0.028*
C17 0.40711 (14) 0.79450 (14) 0.32561 (12) 0.0249 (4)
H17A 0.3348 0.7991 0.3088 0.030*
H17B 0.4100 0.7679 0.3840 0.030*
C18 0.45525 (14) 0.90026 (14) 0.32269 (11) 0.0220 (3)
H18A 0.4153 0.9473 0.3584 0.026*
H18B 0.5251 0.8969 0.3458 0.026*
C19 0.45908 (12) 0.94118 (12) 0.23258 (11) 0.0170 (3)
H19A 0.4929 1.0084 0.2324 0.020*
H19B 0.3890 0.9504 0.2112 0.020*
C20 0.57173 (11) 0.83634 (11) 0.02258 (10) 0.0135 (3)
C21 0.54836 (12) 0.73827 (11) −0.10837 (10) 0.0148 (3)
H21 0.6071 0.6980 −0.0863 0.018*
C22 0.58437 (13) 0.80033 (13) −0.18362 (11) 0.0209 (3)
H22A 0.6403 0.8458 −0.1656 0.025*
H22B 0.5278 0.8434 −0.2041 0.025*
C23 0.62157 (14) 0.73262 (16) −0.25562 (12) 0.0268 (4)
H23A 0.6831 0.6953 −0.2373 0.032*
H23B 0.6402 0.7754 −0.3046 0.032*
C24 0.53947 (14) 0.65675 (15) −0.28192 (12) 0.0254 (4)
H24A 0.4815 0.6938 −0.3073 0.030*
H24B 0.5672 0.6100 −0.3251 0.030*
C25 0.50243 (15) 0.59549 (13) −0.20609 (13) 0.0271 (4)
H25A 0.5587 0.5527 −0.1848 0.032*
H25B 0.4466 0.5499 −0.2241 0.032*
C26 0.46455 (7) 0.66475 (7) −0.13489 (6) 0.0200 (3)
H26A 0.4045 0.7035 −0.1544 0.024*
H26B 0.4438 0.6229 −0.0859 0.024*
O6 0.68356 (7) 1.11280 (7) 0.41983 (6) 0.0255 (3)
H6 0.6930 1.0941 0.3745 0.041 (8)*
C27 0.75769 (7) 1.18107 (7) 0.45291 (6) 0.0297 (4)
H27A 0.7348 1.2067 0.5078 0.045*
H27B 0.7667 1.2381 0.4139 0.045*
supporting information
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Acta Cryst. (2007). E63, o1892–o1894
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.0249 (7) 0.0756 (13) 0.0509 (11) 0.0195 (8) −0.0132 (7) −0.0228 (10)
O2 0.0174 (6) 0.0879 (14) 0.0367 (9) −0.0161 (7) 0.0029 (6) −0.0198 (9)
O3 0.0257 (6) 0.0243 (6) 0.0167 (6) −0.0064 (5) −0.0041 (5) 0.0024 (5)
O4 0.0214 (5) 0.0151 (5) 0.0198 (6) −0.0003 (4) −0.0013 (4) 0.0019 (4)
O5 0.0137 (5) 0.0199 (5) 0.0196 (6) 0.0030 (4) −0.0015 (4) −0.0054 (4)
N1 0.0170 (7) 0.0697 (13) 0.0261 (9) 0.0014 (8) 0.0005 (6) −0.0182 (9)
N2 0.0268 (7) 0.0164 (6) 0.0170 (7) 0.0005 (5) −0.0058 (6) −0.0034 (6)
N3 0.0120 (5) 0.0128 (5) 0.0143 (6) −0.0010 (4) −0.0010 (5) −0.0001 (5)
N4 0.0140 (6) 0.0171 (6) 0.0155 (6) 0.0016 (5) −0.0017 (5) −0.0046 (5)
C1 0.0144 (7) 0.0464 (11) 0.0174 (8) −0.0011 (7) 0.0024 (6) −0.0094 (7)
C2 0.0182 (7) 0.0314 (9) 0.0254 (9) 0.0055 (6) −0.0003 (7) −0.0025 (7)
C3 0.0165 (7) 0.0219 (7) 0.0226 (8) −0.0002 (6) 0.0002 (6) −0.0025 (6)
C4 0.0143 (6) 0.0215 (7) 0.0147 (7) −0.0015 (5) 0.0024 (5) −0.0015 (6)
C5 0.0206 (7) 0.0214 (7) 0.0235 (9) −0.0045 (6) 0.0048 (6) −0.0053 (6)
C6 0.0209 (8) 0.0348 (9) 0.0220 (9) −0.0093 (7) 0.0050 (7) −0.0105 (7)
C7 0.0143 (6) 0.0186 (7) 0.0148 (7) 0.0003 (5) 0.0011 (5) 0.0002 (5)
C8 0.0105 (6) 0.0161 (6) 0.0135 (7) 0.0005 (5) −0.0008 (5) 0.0000 (5)
C9 0.0107 (6) 0.0197 (7) 0.0152 (7) −0.0013 (5) −0.0008 (5) −0.0017 (6)
C10 0.0167 (6) 0.0158 (6) 0.0107 (6) 0.0023 (5) 0.0008 (5) 0.0000 (5)
C11 0.0164 (7) 0.0196 (7) 0.0182 (7) 0.0043 (5) −0.0017 (6) 0.0018 (6)
C12 0.0220 (8) 0.0235 (8) 0.0254 (9) 0.0097 (6) −0.0021 (7) 0.0036 (7)
C13 0.0117 (6) 0.0129 (6) 0.0131 (6) −0.0010 (5) −0.0002 (5) −0.0016 (5)
C14 0.0146 (6) 0.0148 (6) 0.0116 (6) −0.0007 (5) 0.0004 (5) −0.0003 (5)
C15 0.0219 (7) 0.0155 (7) 0.0177 (8) −0.0032 (5) 0.0014 (6) −0.0001 (6)
C16 0.0294 (9) 0.0190 (7) 0.0218 (8) −0.0036 (6) 0.0026 (7) 0.0043 (6)
C17 0.0306 (9) 0.0255 (8) 0.0186 (8) −0.0069 (7) 0.0053 (7) 0.0010 (7)
C18 0.0279 (8) 0.0243 (8) 0.0139 (7) −0.0050 (6) 0.0030 (6) −0.0019 (6)
C19 0.0204 (7) 0.0164 (7) 0.0144 (7) −0.0006 (5) 0.0030 (6) −0.0017 (5)
C20 0.0143 (6) 0.0130 (6) 0.0132 (7) −0.0010 (5) 0.0012 (5) −0.0011 (5)
C21 0.0167 (7) 0.0142 (6) 0.0136 (7) 0.0014 (5) −0.0024 (5) −0.0031 (5)
C22 0.0219 (7) 0.0220 (7) 0.0188 (8) −0.0007 (6) 0.0035 (6) −0.0008 (6)
C23 0.0242 (8) 0.0398 (10) 0.0163 (8) 0.0043 (7) 0.0023 (6) −0.0050 (7)
C24 0.0273 (8) 0.0322 (9) 0.0167 (8) 0.0098 (7) −0.0060 (7) −0.0087 (7)
C25 0.0372 (10) 0.0198 (8) 0.0243 (9) 0.0024 (7) −0.0098 (8) −0.0080 (7)
C26 0.0239 (8) 0.0192 (7) 0.0169 (8) −0.0044 (6) −0.0040 (6) −0.0020 (6)
O6 0.0210 (6) 0.0278 (6) 0.0275 (7) −0.0008 (5) 0.0088 (5) 0.0001 (5)
C27 0.0240 (8) 0.0431 (11) 0.0220 (9) −0.0015 (7) −0.0004 (7) 0.0029 (8)
Geometric parameters (Å, º)
O1—N1 1.229 (3) C13—H13 1.0000
O2—N1 1.229 (3) C14—C19 1.533 (2)
O3—C9 1.232 (2) C14—C15 1.539 (2)
O4—C10 1.233 (2) C14—H14 1.0000
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N1—C1 1.472 (2) C15—H15A 0.9900
N2—C9 1.335 (2) C15—H15B 0.9900
N2—H2A 0.83 (3) C16—C17 1.532 (3)
N2—H2B 0.83 (3) C16—H16A 0.9900
N3—C10 1.3717 (19) C16—H16B 0.9900
N3—C8 1.4793 (19) C17—C18 1.530 (2)
N3—C13 1.4842 (18) C17—H17A 0.9900
N4—C20 1.340 (2) C17—H17B 0.9900
N4—C21 1.463 (2) C18—C19 1.527 (2)
N4—H4 0.87 (2) C18—H18A 0.9900
C1—C6 1.383 (3) C18—H18B 0.9900
C1—C2 1.387 (3) C19—H19A 0.9900
C2—C3 1.392 (2) C19—H19B 0.9900
C2—H2C 0.9500 C21—C22 1.521 (2)
C3—C4 1.396 (2) C21—C26 1.5260 (17)
C3—H3 0.9500 C21—H21 1.0000
C4—C5 1.396 (2) C22—C23 1.528 (2)
C4—C7 1.508 (2) C22—H22A 0.9900
C5—C6 1.390 (2) C22—H22B 0.9900
C5—H5 0.9500 C23—C24 1.529 (3)
C6—H6A 0.9500 C23—H23A 0.9900
C7—C8 1.547 (2) C23—H23B 0.9900
C7—H7A 0.9900 C24—C25 1.527 (3)
C7—H7B 0.9900 C24—H24A 0.9900
C8—C9 1.548 (2) C24—H24B 0.9900
C8—H8 1.0000 C25—C26 1.534 (2)
C10—C11 1.516 (2) C25—H25A 0.9900
C11—C12 1.525 (2) C25—H25B 0.9900
C11—H11A 0.9900 C26—H26A 0.9900
C11—H11B 0.9900 C26—H26B 0.9900
C12—H12A 0.9800 O6—C27 1.4259
C12—H12B 0.9800 O6—H6 0.7695
C12—H12C 0.9800 C27—H27A 0.9800
C13—C14 1.535 (2) C27—H27B 0.9800
C13—C20 1.544 (2) C27—H27C 0.9800
O2—N1—O1 124.18 (19) C14—C15—H15A 109.5
O2—N1—C1 117.9 (2) C16—C15—H15B 109.5
O1—N1—C1 117.9 (2) C14—C15—H15B 109.5
C9—N2—H2A 120.3 (18) H15A—C15—H15B 108.1
C9—N2—H2B 117.8 (17) C17—C16—C15 111.61 (14)
H2A—N2—H2B 121 (2) C17—C16—H16A 109.3
C10—N3—C8 119.85 (12) C15—C16—H16A 109.3
C10—N3—C13 122.71 (12) C17—C16—H16B 109.3
C8—N3—C13 117.38 (12) C15—C16—H16B 109.3
C20—N4—C21 122.88 (13) H16A—C16—H16B 108.0
C20—N4—H4 118.8 (18) C18—C17—C16 110.68 (14)
supporting information
sup-6
Acta Cryst. (2007). E63, o1892–o1894
C6—C1—C2 123.11 (17) C16—C17—H17A 109.5
C6—C1—N1 117.87 (18) C18—C17—H17B 109.5
C2—C1—N1 119.01 (18) C16—C17—H17B 109.5
C1—C2—C3 117.70 (17) H17A—C17—H17B 108.1
C1—C2—H2C 121.1 C19—C18—C17 111.27 (14)
C3—C2—H2C 121.1 C19—C18—H18A 109.4
C2—C3—C4 121.00 (16) C17—C18—H18A 109.4
C2—C3—H3 119.5 C19—C18—H18B 109.4
C4—C3—H3 119.5 C17—C18—H18B 109.4
C5—C4—C3 119.21 (15) H18A—C18—H18B 108.0
C5—C4—C7 120.99 (15) C18—C19—C14 111.09 (13)
C3—C4—C7 119.80 (14) C18—C19—H19A 109.4
C6—C5—C4 120.86 (16) C14—C19—H19A 109.4
C6—C5—H5 119.6 C18—C19—H19B 109.4
C4—C5—H5 119.6 C14—C19—H19B 109.4
C1—C6—C5 118.05 (16) H19A—C19—H19B 108.0
C1—C6—H6A 121.0 O5—C20—N4 124.08 (14)
C5—C6—H6A 121.0 O5—C20—C13 121.52 (14)
C4—C7—C8 111.54 (13) N4—C20—C13 114.38 (13)
C4—C7—H7A 109.3 N4—C21—C22 110.09 (13)
C8—C7—H7A 109.3 N4—C21—C26 110.59 (12)
C4—C7—H7B 109.3 C22—C21—C26 110.46 (12)
C8—C7—H7B 109.3 N4—C21—H21 108.5
H7A—C7—H7B 108.0 C22—C21—H21 108.5
N3—C8—C7 111.38 (12) C26—C21—H21 108.5
N3—C8—C9 114.35 (12) C21—C22—C23 111.85 (14)
C7—C8—C9 113.92 (12) C21—C22—H22A 109.2
N3—C8—H8 105.4 C23—C22—H22A 109.2
C7—C8—H8 105.4 C21—C22—H22B 109.2
C9—C8—H8 105.4 C23—C22—H22B 109.2
O3—C9—N2 123.42 (15) H22A—C22—H22B 107.9
O3—C9—C8 119.30 (14) C22—C23—C24 110.97 (15)
N2—C9—C8 117.19 (14) C22—C23—H23A 109.4
O4—C10—N3 120.71 (14) C24—C23—H23A 109.4
O4—C10—C11 120.36 (13) C22—C23—H23B 109.4
N3—C10—C11 118.92 (13) C24—C23—H23B 109.4
C10—C11—C12 112.05 (14) H23A—C23—H23B 108.0
C10—C11—H11A 109.2 C25—C24—C23 110.84 (15)
C12—C11—H11A 109.2 C25—C24—H24A 109.5
C10—C11—H11B 109.2 C23—C24—H24A 109.5
C12—C11—H11B 109.2 C25—C24—H24B 109.5
H11A—C11—H11B 107.9 C23—C24—H24B 109.5
C11—C12—H12A 109.5 H24A—C24—H24B 108.1
C11—C12—H12B 109.5 C24—C25—C26 111.66 (13)
H12A—C12—H12B 109.5 C24—C25—H25A 109.3
C11—C12—H12C 109.5 C26—C25—H25A 109.3
H12A—C12—H12C 109.5 C24—C25—H25B 109.3
supporting information
sup-7
Acta Cryst. (2007). E63, o1892–o1894
N3—C13—C14 112.23 (12) H25A—C25—H25B 107.9
N3—C13—C20 110.18 (12) C21—C26—C25 110.15 (11)
C14—C13—C20 111.52 (12) C21—C26—H26A 109.6
N3—C13—H13 107.6 C25—C26—H26A 109.6
C14—C13—H13 107.6 C21—C26—H26B 109.6
C20—C13—H13 107.6 C25—C26—H26B 109.6
C19—C14—C13 110.21 (12) H26A—C26—H26B 108.1
C19—C14—C15 109.97 (12) C27—O6—H6 115.7
C13—C14—C15 110.99 (12) O6—C27—H27A 109.5
C19—C14—H14 108.5 O6—C27—H27B 109.5
C13—C14—H14 108.5 H27A—C27—H27B 109.5
C15—C14—H14 108.5 O6—C27—H27C 109.5
C16—C15—C14 110.51 (13) H27A—C27—H27C 109.5
C16—C15—H15A 109.5 H27B—C27—H27C 109.5
O2—N1—C1—C6 −1.0 (3) C10—N3—C13—C14 −121.12 (15)
O1—N1—C1—C6 177.42 (19) C8—N3—C13—C14 61.65 (16)
O2—N1—C1—C2 179.59 (19) C10—N3—C13—C20 113.96 (15)
O1—N1—C1—C2 −2.0 (3) C8—N3—C13—C20 −63.26 (17)
C6—C1—C2—C3 −1.2 (3) N3—C13—C14—C19 59.54 (15)
N1—C1—C2—C3 178.17 (17) C20—C13—C14—C19 −176.28 (12)
C1—C2—C3—C4 −1.1 (3) N3—C13—C14—C15 −178.39 (12)
C2—C3—C4—C5 2.3 (3) C20—C13—C14—C15 −54.21 (16)
C2—C3—C4—C7 −178.31 (16) C19—C14—C15—C16 −57.04 (17)
C3—C4—C5—C6 −1.2 (3) C13—C14—C15—C16 −179.25 (13)
C7—C4—C5—C6 179.38 (16) C14—C15—C16—C17 56.57 (18)
C2—C1—C6—C5 2.2 (3) C15—C16—C17—C18 −55.4 (2)
N1—C1—C6—C5 −177.15 (17) C16—C17—C18—C19 55.3 (2)
C4—C5—C6—C1 −1.0 (3) C17—C18—C19—C14 −56.91 (18)
C5—C4—C7—C8 −105.39 (18) C13—C14—C19—C18 −179.87 (13)
C3—C4—C7—C8 75.21 (19) C15—C14—C19—C18 57.46 (17)
C10—N3—C8—C7 −62.27 (18) C21—N4—C20—O5 −4.3 (2)
C13—N3—C8—C7 115.03 (14) C21—N4—C20—C13 177.49 (13)
C10—N3—C8—C9 68.65 (18) N3—C13—C20—O5 67.30 (18)
C13—N3—C8—C9 −114.04 (14) C14—C13—C20—O5 −58.02 (18)
C4—C7—C8—N3 −172.47 (12) N3—C13—C20—N4 −114.45 (14)
C4—C7—C8—C9 56.38 (17) C14—C13—C20—N4 120.23 (14)
N3—C8—C9—O3 101.56 (16) C20—N4—C21—C22 −94.66 (18)
C7—C8—C9—O3 −128.76 (15) C20—N4—C21—C26 142.99 (14)
N3—C8—C9—N2 −81.82 (17) N4—C21—C22—C23 −179.41 (14)
C7—C8—C9—N2 47.86 (18) C26—C21—C22—C23 −56.98 (17)
C8—N3—C10—O4 −2.1 (2) C21—C22—C23—C24 55.6 (2)
C13—N3—C10—O4 −179.26 (14) C22—C23—C24—C25 −54.3 (2)
C8—N3—C10—C11 179.13 (14) C23—C24—C25—C26 55.64 (19)
C13—N3—C10—C11 2.0 (2) N4—C21—C26—C25 179.10 (13)
O4—C10—C11—C12 −0.7 (2) C22—C21—C26—C25 56.96 (15)
supporting information
sup-8
Acta Cryst. (2007). E63, o1892–o1894
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N2—H2A···O5i 0.83 (3) 2.23 (3) 3.0040 (19) 156 (2)
N2—H2B···O4 0.83 (3) 2.05 (3) 2.735 (2) 139 (2)
N4—H4···O6ii 0.87 (2) 2.00 (3) 2.8597 (16) 171 (3)
O6—H6···O3 0.77 2.06 2.8287 (17) 176