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2,6-Bis[(S)-1-phenyl-eth-yl]-1H,5H-pyrrolo-[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone.
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PMID:  22412753     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
In the title compound, C(26)H(20)N(2)O(4), the central isoindole core is almost planar (r.m.s. deviation = 0.043 Å). The phenyl rings lie to either side of the plane [dihedral angles = 88.64 (5) and 67.74 (6)°] and the dihedral angle between the phenyl rings is 63.39 (7)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions; notably, one carbonyl O atom accepts three such bonds.
Authors:
Alaa A-M Abdel-Aziz; Adel S El-Azab; Amer M Alanazi; Seik Weng Ng; Edward R T Tiekink
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Publication Detail:
Type:  Journal Article     Date:  2012-02-29
Journal Detail:
Title:  Acta crystallographica. Section E, Structure reports online     Volume:  68     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr Sect E Struct Rep Online     Publication Date:  2012 Mar 
Date Detail:
Created Date:  2012-03-13     Completed Date:  2012-10-02     Revised Date:  2013-02-27    
Medline Journal Info:
Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr Sect E Struct Rep Online     Country:  United States    
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Languages:  eng     Pagination:  o907     Citation Subset:  -    
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Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
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A full version of this article is available from Crystallography Journals Online.© Abdel-Aziz et al. 2012
open-access:
Received Day: 20 Month: 2 Year: 2012
Accepted Day: 20 Month: 2 Year: 2012
collection publication date: Day: 01 Month: 3 Year: 2012
Electronic publication date: Day: 29 Month: 2 Year: 2012
pmc-release publication date: Day: 29 Month: 2 Year: 2012
Volume: 68 Issue: Pt 3
First Page: o907 Last Page: o907
ID: 3297950
PubMed Id: 22412753
Publisher Id: bt5823
DOI: 10.1107/S1600536812007684
Coden: ACSEBH
Publisher Item Identifier: S1600536812007684

2,6-Bis[(S)-1-phenyl­eth­yl]-1H,5H-pyrrolo­[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone Alternate Title:C26H20N2O4
Alaa A.-M. Abdel-Azizab
Adel S. El-Azabac
Amer M. Alanazia
Seik Weng Ngde
Edward R. T. Tiekinkd*
aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
bDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt
cDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt
dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence: Correspondence e-mail: edward.tiekink@gmail.com
Additional correspondence author, e-mail: alaa_moenes@yahoo.com.

Related literature  

For the biological activity of cyclic imides including that of the title compound, see: Abdel-Aziz (2007); Abdel-Aziz, El-Azab et al. (2011); Abdel-Aziz, ElTahir et al. (2011).[Chemical Structure ID: scheme1]


Experimental  
Crystal data  

  • C26H20N2O4
  • Mr = 424.44
  • Monoclinic,
  • a = 5.6401 (1) Å
  • b = 16.1040 (2) Å
  • c = 11.3759 (2) Å
  • β = 99.762 (2)°
  • V = 1018.29 (3) Å3
  • Z = 2
  • Cu Kα radiation
  • μ = 0.77 mm−1
  • T = 100 K
  • 0.30 × 0.25 × 0.20 mm

Data collection  

  • Agilent SuperNova Dual diffractometer with an Atlas detector
  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) Tmin = 0.656, Tmax = 1.000
  • 7858 measured reflections
  • 4093 independent reflections
  • 4091 reflections with I > 2σ(I)
  • Rint = 0.018

Refinement  

  • R[F2 > 2σ(F2)] = 0.033
  • wR(F2) = 0.099
  • S = 1.11
  • 4093 reflections
  • 289 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983), 1898 Friedel pairs
  • Flack parameter: 0.08 (12)

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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: publCIF (Westrip, 2010).


Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007684/bt5823sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007684/bt5823Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007684/bt5823Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


Notes

fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5823).

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding the work through the research group project (No. RGP-VPP-163). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information
Comment

Recent work has shown that cyclic imides possess important biological potential, such as anti-hyperlipidemic, anti-diabetic, anti-tumour and anti-inflammatory activities (Abdel-Aziz, 2007; Abdel-Aziz, El-Azab et al., 2011; Abdel-Aziz, ElTahir et al., 2011). The title cyclic imide, 2,6-bis((S)-1-phenylethyl)pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone (I), was investigated during these trials and herein the crystal structure determination is described.

In (I), Fig. 1, the 12 atoms comprising the isoindole core are co-planar with a r.m.s. deviation for the fitted atoms of 0.043 Å. The maximum deviations from this least-squares plane are 0.043 (1) Å for the C15 and C16 atoms, and -0.058 (1) Å for the N2 atom. The phenyl rings lie to either side of the plane, forming dihedral angles of 88.64 (5)° [C1–C6] and 67.74 (6)° [C21–C26]; the dihedral angle between the phenyl rings = 63.39 (7)°.

Molecules are assembled in the crystal structure by C–H···O interactions, Fig. 2 and Table 1. Notably, one carbonyl-O atom is involved in a trifurcated H bond.

Experimental

A solution of (+)-(S)-1-phenylethanamine (10 mmol) and benzene-1,2,4,5-tetracarboxylic dianhydride (10 mmol) in glacial acetic acid (10 ml) was heated under reflux for 12 h. After the evaporation of the reaction mixture to dryness under reduced pressure, the residue was neutralized using sodium bicarbonate solution (4%) until effervescence ceased. The precipitate obtained was washed with water, dried and recrystallized from MeOH/CHCl3 (1:1 v/v). Yield 59%. M.pt: > 623 K. 1H NMR (CDCl3): δ 8.20 (s, 2H, Ar—H), 7.53–7.51 (d, 4H, J = 7.0 Hz, Ar—H), 7.38–7.35 (t, 4H, J = 7.0 Hz, Ar—H), 7.32–7.28 (q, 2H, J = 8.0 Hz, Ar—H), 5.62–5.61 (d, 2H, J = 6.0 Hz, 2CH), 1.98–1.96 (d, 6H, J = 6.0 Hz, 2CH3). 13C NMR (CDCl3): δ 166.02, 139.52, 137.05, 128.64, 128.07, 127.49, 118.19, 50.52, 17.41.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C—H = 0.95 to 1.00 Å, Uiso(H) = 1.2–1.5Ueq(C)] and were included in the refinement in the riding model approximation. The absolute configuration was determined from 1898 Friedel pairs, and was that of the starting reactant.

Figures
Crystal data
Data collection
Refinement
Special details
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, º)
Hydrogen-bond geometry (Å, º)

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


References
Abdel-Aziz, A. A.-M. (2007). Eur. J. Med. Chem.42, 614–626.
Abdel-Aziz, A. A.-M., El-Azab, A. S., Attia, S. M., Al-Obaid, A. M., Al-Omar, M. A. & El-Subbagh, H. I. (2011). Eur. J. Med. Chem.46, 4324–4329.
Abdel-Aziz, A. A.-M., ElTahir, K. E. H. & Asiri, Y. A. (2011). Eur. J. Med. Chem.46, 1648–1655.
Agilent (2011). CrysAlis PRO Agilent Technologies, Yarnton, Oxfordshire, England.
Brandenburg, K. (2006). DIAMOND Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Figures

[Figure ID: Fap1]
Fig. 1. 

The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.



[Figure ID: Fap2]
Fig. 2. 

A view in projection down the a axis of the unit-cell contents for (I). The C—H···O interactions are shown as orange dashed lines.



Tables
[TableWrap ID: d1e172]
C26H20N2O4 F(000) = 444
Mr = 424.44 Dx = 1.384 Mg m3
Monoclinic, P21 Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2yb Cell parameters from 6911 reflections
a = 5.6401 (1) Å θ = 2.7–76.5°
b = 16.1040 (2) Å µ = 0.77 mm1
c = 11.3759 (2) Å T = 100 K
β = 99.762 (2)° Prism, colourless
V = 1018.29 (3) Å3 0.30 × 0.25 × 0.20 mm
Z = 2

[TableWrap ID: d1e299]
Agilent SuperNova Dual diffractometer with an Atlas detector 4093 independent reflections
Radiation source: SuperNova (Cu) X-ray Source 4091 reflections with I > 2σ(I)
Mirror monochromator Rint = 0.018
Detector resolution: 10.4041 pixels mm-1 θmax = 76.7°, θmin = 3.9°
ω scan h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) k = −20→20
Tmin = 0.656, Tmax = 1.000 l = −14→13
7858 measured reflections

[TableWrap ID: d1e419]
Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033 H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0781P)2 + 0.0806P] where P = (Fo2 + 2Fc2)/3
S = 1.11 (Δ/σ)max < 0.001
4093 reflections Δρmax = 0.24 e Å3
289 parameters Δρmin = −0.25 e Å3
1 restraint Absolute structure: Flack (1983), 1898 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.08 (12)

[TableWrap ID: d1e581]
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, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(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.

[TableWrap ID: d1e680]
x y z Uiso*/Ueq
O1 −0.21322 (17) 0.49962 (6) 0.84958 (9) 0.0190 (2)
O2 0.52962 (18) 0.42601 (6) 1.05125 (9) 0.0204 (2)
O3 −0.18870 (17) 0.21623 (6) 0.51186 (8) 0.0194 (2)
O4 0.55058 (17) 0.13790 (6) 0.71548 (9) 0.0198 (2)
N1 0.1580 (2) 0.48014 (7) 0.97059 (10) 0.0157 (2)
N2 0.1824 (2) 0.15891 (7) 0.59322 (10) 0.0154 (2)
C1 0.1785 (2) 0.63194 (8) 0.97086 (11) 0.0156 (3)
C2 0.0123 (3) 0.69641 (9) 0.96693 (13) 0.0197 (3)
H2 −0.1151 0.6924 1.0116 0.024*
C3 0.0320 (3) 0.76653 (9) 0.89804 (14) 0.0224 (3)
H3 −0.0829 0.8099 0.8954 0.027*
C4 0.2184 (3) 0.77357 (9) 0.83304 (13) 0.0214 (3)
H4 0.2327 0.8219 0.7870 0.026*
C5 0.3837 (2) 0.70929 (10) 0.83595 (12) 0.0212 (3)
H5 0.5106 0.7133 0.7909 0.025*
C6 0.3636 (2) 0.63922 (9) 0.90455 (12) 0.0184 (3)
H6 0.4776 0.5956 0.9063 0.022*
C7 0.1695 (2) 0.55439 (8) 1.04732 (11) 0.0158 (3)
H7 0.3270 0.5517 1.1029 0.019*
C8 −0.0248 (3) 0.55292 (10) 1.12469 (13) 0.0211 (3)
H8A −0.0150 0.5007 1.1696 0.032*
H8B −0.1831 0.5573 1.0740 0.032*
H8C −0.0017 0.5998 1.1804 0.032*
C9 −0.0287 (2) 0.46074 (8) 0.87821 (11) 0.0153 (3)
C10 0.0478 (2) 0.38325 (8) 0.82149 (12) 0.0146 (3)
C11 0.2743 (2) 0.36088 (8) 0.88183 (11) 0.0142 (3)
C12 0.3478 (2) 0.42320 (8) 0.97899 (12) 0.0150 (3)
C13 0.4002 (2) 0.29243 (8) 0.85060 (11) 0.0147 (3)
H13 0.5538 0.2767 0.8927 0.018*
C14 0.2814 (2) 0.24907 (8) 0.75224 (12) 0.0141 (2)
C15 0.0553 (2) 0.27140 (8) 0.69167 (11) 0.0144 (3)
C16 −0.0710 (2) 0.33948 (9) 0.72418 (12) 0.0151 (3)
H16 −0.2258 0.3547 0.6831 0.018*
C17 −0.0107 (2) 0.21467 (8) 0.58745 (12) 0.0150 (3)
C18 0.3646 (2) 0.17566 (8) 0.68996 (11) 0.0146 (2)
C19 0.2125 (2) 0.09707 (8) 0.50044 (12) 0.0158 (3)
H19 0.3719 0.0698 0.5268 0.019*
C20 0.2275 (3) 0.14171 (9) 0.38372 (12) 0.0201 (3)
H20A 0.3534 0.1843 0.3978 0.030*
H20B 0.0726 0.1680 0.3533 0.030*
H20C 0.2662 0.1016 0.3251 0.030*
C21 0.0229 (2) 0.02911 (8) 0.49308 (12) 0.0164 (3)
C22 −0.1846 (3) 0.02927 (9) 0.40638 (12) 0.0189 (3)
H22 −0.2102 0.0727 0.3491 0.023*
C23 −0.3546 (3) −0.03401 (9) 0.40349 (13) 0.0207 (3)
H23 −0.4949 −0.0336 0.3440 0.025*
C24 −0.3199 (3) −0.09748 (9) 0.48692 (14) 0.0218 (3)
H24 −0.4374 −0.1399 0.4857 0.026*
C25 −0.1120 (3) −0.09870 (9) 0.57237 (14) 0.0249 (3)
H25 −0.0862 −0.1425 0.6291 0.030*
C26 0.0579 (3) −0.03601 (10) 0.57488 (12) 0.0217 (3)
H26 0.2000 −0.0375 0.6332 0.026*

[TableWrap ID: d1e1400]
U11 U22 U33 U12 U13 U23
O1 0.0176 (4) 0.0184 (5) 0.0201 (5) 0.0040 (4) 0.0006 (3) −0.0031 (4)
O2 0.0200 (5) 0.0155 (5) 0.0229 (5) −0.0003 (4) −0.0038 (4) −0.0023 (4)
O3 0.0173 (5) 0.0189 (5) 0.0201 (5) 0.0021 (4) −0.0022 (4) −0.0031 (4)
O4 0.0201 (5) 0.0184 (5) 0.0195 (4) 0.0061 (4) −0.0005 (4) −0.0008 (4)
N1 0.0179 (5) 0.0116 (6) 0.0170 (5) 0.0003 (4) 0.0013 (4) −0.0026 (4)
N2 0.0164 (5) 0.0135 (5) 0.0156 (5) 0.0013 (4) 0.0009 (4) −0.0017 (4)
C1 0.0153 (6) 0.0133 (6) 0.0173 (6) −0.0007 (5) −0.0001 (4) −0.0050 (5)
C2 0.0197 (6) 0.0158 (7) 0.0245 (7) 0.0008 (5) 0.0064 (5) −0.0033 (5)
C3 0.0242 (7) 0.0131 (6) 0.0280 (7) 0.0039 (5) −0.0011 (6) −0.0022 (5)
C4 0.0260 (7) 0.0161 (7) 0.0199 (6) −0.0032 (5) −0.0022 (5) −0.0006 (5)
C5 0.0212 (7) 0.0234 (7) 0.0188 (6) −0.0040 (6) 0.0032 (5) −0.0036 (5)
C6 0.0162 (6) 0.0180 (7) 0.0207 (6) 0.0017 (5) 0.0023 (5) −0.0042 (5)
C7 0.0182 (6) 0.0119 (6) 0.0168 (6) −0.0008 (5) 0.0014 (4) −0.0041 (5)
C8 0.0243 (7) 0.0191 (6) 0.0208 (6) −0.0041 (5) 0.0060 (5) −0.0033 (5)
C9 0.0183 (6) 0.0127 (6) 0.0146 (6) −0.0019 (5) 0.0023 (5) 0.0004 (5)
C10 0.0161 (6) 0.0115 (6) 0.0163 (6) 0.0001 (5) 0.0030 (5) 0.0006 (5)
C11 0.0154 (6) 0.0125 (6) 0.0141 (6) −0.0028 (5) 0.0012 (5) 0.0012 (5)
C12 0.0173 (6) 0.0108 (6) 0.0169 (6) −0.0020 (5) 0.0024 (5) 0.0011 (5)
C13 0.0146 (6) 0.0136 (6) 0.0155 (6) −0.0009 (5) 0.0015 (4) 0.0013 (5)
C14 0.0159 (6) 0.0112 (6) 0.0155 (5) −0.0007 (5) 0.0030 (4) 0.0037 (5)
C15 0.0150 (6) 0.0129 (6) 0.0149 (6) −0.0019 (5) 0.0014 (4) 0.0004 (4)
C16 0.0145 (6) 0.0133 (6) 0.0166 (6) 0.0009 (5) 0.0004 (4) 0.0011 (4)
C17 0.0163 (6) 0.0125 (6) 0.0160 (6) −0.0002 (5) 0.0025 (4) −0.0013 (5)
C18 0.0156 (6) 0.0143 (6) 0.0139 (6) −0.0013 (5) 0.0028 (4) 0.0018 (5)
C19 0.0169 (6) 0.0144 (6) 0.0163 (6) 0.0015 (5) 0.0033 (4) −0.0046 (5)
C20 0.0235 (6) 0.0193 (7) 0.0180 (6) −0.0019 (5) 0.0045 (5) −0.0021 (5)
C21 0.0196 (6) 0.0133 (6) 0.0162 (6) 0.0019 (5) 0.0027 (5) −0.0035 (5)
C22 0.0204 (6) 0.0148 (6) 0.0205 (6) 0.0022 (5) 0.0007 (5) 0.0004 (5)
C23 0.0184 (6) 0.0190 (7) 0.0232 (7) 0.0014 (5) −0.0011 (5) −0.0039 (5)
C24 0.0239 (6) 0.0157 (7) 0.0260 (7) −0.0019 (5) 0.0046 (5) −0.0024 (5)
C25 0.0316 (7) 0.0196 (7) 0.0223 (7) −0.0027 (6) 0.0012 (6) 0.0040 (5)
C26 0.0238 (7) 0.0203 (7) 0.0189 (6) −0.0003 (6) −0.0024 (5) 0.0005 (5)

[TableWrap ID: d1e2019]
O1—C9 1.2111 (17) C10—C16 1.3855 (19)
O2—C12 1.2017 (16) C10—C11 1.3915 (18)
O3—C17 1.2062 (16) C11—C13 1.3897 (19)
O4—C18 1.2049 (16) C11—C12 1.4984 (18)
N1—C9 1.3911 (16) C13—C14 1.3909 (18)
N1—C12 1.4004 (17) C13—H13 0.9500
N1—C7 1.4754 (16) C14—C15 1.3902 (18)
N2—C18 1.3986 (16) C14—C18 1.4941 (18)
N2—C17 1.4046 (16) C15—C16 1.3913 (18)
N2—C19 1.4815 (16) C15—C17 1.4930 (17)
C1—C6 1.3928 (18) C16—H16 0.9500
C1—C2 1.3945 (18) C19—C21 1.5222 (19)
C1—C7 1.5276 (18) C19—C20 1.5249 (18)
C2—C3 1.390 (2) C19—H19 1.0000
C2—H2 0.9500 C20—H20A 0.9800
C3—C4 1.389 (2) C20—H20B 0.9800
C3—H3 0.9500 C20—H20C 0.9800
C4—C5 1.390 (2) C21—C26 1.394 (2)
C4—H4 0.9500 C21—C22 1.3970 (18)
C5—C6 1.388 (2) C22—C23 1.396 (2)
C5—H5 0.9500 C22—H22 0.9500
C6—H6 0.9500 C23—C24 1.386 (2)
C7—C8 1.5175 (18) C23—H23 0.9500
C7—H7 1.0000 C24—C25 1.391 (2)
C8—H8A 0.9800 C24—H24 0.9500
C8—H8B 0.9800 C25—C26 1.389 (2)
C8—H8C 0.9800 C25—H25 0.9500
C9—C10 1.5012 (18) C26—H26 0.9500
C9—N1—C12 112.10 (11) C11—C13—C14 113.97 (11)
C9—N1—C7 125.51 (11) C11—C13—H13 123.0
C12—N1—C7 122.27 (11) C14—C13—H13 123.0
C18—N2—C17 111.95 (11) C15—C14—C13 123.06 (12)
C18—N2—C19 122.19 (11) C15—C14—C18 107.76 (11)
C17—N2—C19 125.31 (11) C13—C14—C18 129.16 (12)
C6—C1—C2 118.78 (13) C14—C15—C16 122.69 (12)
C6—C1—C7 118.53 (11) C14—C15—C17 108.64 (11)
C2—C1—C7 122.67 (12) C16—C15—C17 128.56 (12)
C3—C2—C1 120.37 (13) C10—C16—C15 114.41 (11)
C3—C2—H2 119.8 C10—C16—H16 122.8
C1—C2—H2 119.8 C15—C16—H16 122.8
C4—C3—C2 120.44 (13) O3—C17—N2 126.28 (12)
C4—C3—H3 119.8 O3—C17—C15 128.21 (12)
C2—C3—H3 119.8 N2—C17—C15 105.50 (10)
C3—C4—C5 119.48 (13) O4—C18—N2 125.85 (13)
C3—C4—H4 120.3 O4—C18—C14 128.01 (12)
C5—C4—H4 120.3 N2—C18—C14 106.14 (11)
C6—C5—C4 120.03 (13) N2—C19—C21 111.00 (10)
C6—C5—H5 120.0 N2—C19—C20 109.47 (11)
C4—C5—H5 120.0 C21—C19—C20 115.67 (11)
C5—C6—C1 120.89 (13) N2—C19—H19 106.7
C5—C6—H6 119.6 C21—C19—H19 106.7
C1—C6—H6 119.6 C20—C19—H19 106.7
N1—C7—C8 111.52 (11) C19—C20—H20A 109.5
N1—C7—C1 109.15 (10) C19—C20—H20B 109.5
C8—C7—C1 116.11 (11) H20A—C20—H20B 109.5
N1—C7—H7 106.5 C19—C20—H20C 109.5
C8—C7—H7 106.5 H20A—C20—H20C 109.5
C1—C7—H7 106.5 H20B—C20—H20C 109.5
C7—C8—H8A 109.5 C26—C21—C22 118.67 (13)
C7—C8—H8B 109.5 C26—C21—C19 119.05 (12)
H8A—C8—H8B 109.5 C22—C21—C19 122.29 (12)
C7—C8—H8C 109.5 C23—C22—C21 120.35 (13)
H8A—C8—H8C 109.5 C23—C22—H22 119.8
H8B—C8—H8C 109.5 C21—C22—H22 119.8
O1—C9—N1 126.36 (13) C24—C23—C22 120.37 (12)
O1—C9—C10 127.63 (12) C24—C23—H23 119.8
N1—C9—C10 106.01 (11) C22—C23—H23 119.8
C16—C10—C11 122.80 (12) C23—C24—C25 119.57 (13)
C16—C10—C9 129.12 (12) C23—C24—H24 120.2
C11—C10—C9 108.05 (11) C25—C24—H24 120.2
C13—C11—C10 123.07 (12) C26—C25—C24 120.09 (13)
C13—C11—C12 129.09 (12) C26—C25—H25 120.0
C10—C11—C12 107.84 (11) C24—C25—H25 120.0
O2—C12—N1 125.16 (13) C25—C26—C21 120.93 (13)
O2—C12—C11 128.83 (13) C25—C26—H26 119.5
N1—C12—C11 106.01 (10) C21—C26—H26 119.5
C6—C1—C2—C3 −0.06 (19) C13—C14—C15—C16 0.31 (19)
C7—C1—C2—C3 178.47 (13) C18—C14—C15—C16 −177.85 (11)
C1—C2—C3—C4 −0.5 (2) C13—C14—C15—C17 176.77 (11)
C2—C3—C4—C5 0.9 (2) C18—C14—C15—C17 −1.39 (14)
C3—C4—C5—C6 −0.8 (2) C11—C10—C16—C15 −0.13 (18)
C4—C5—C6—C1 0.2 (2) C9—C10—C16—C15 177.67 (12)
C2—C1—C6—C5 0.21 (19) C14—C15—C16—C10 0.26 (18)
C7—C1—C6—C5 −178.38 (12) C17—C15—C16—C10 −175.45 (12)
C9—N1—C7—C8 66.11 (16) C18—N2—C17—O3 177.94 (13)
C12—N1—C7—C8 −118.32 (13) C19—N2—C17—O3 6.4 (2)
C9—N1—C7—C1 −63.51 (15) C18—N2—C17—C15 −0.74 (14)
C12—N1—C7—C1 112.06 (13) C19—N2—C17—C15 −172.31 (12)
C6—C1—C7—N1 −57.40 (14) C14—C15—C17—O3 −177.32 (13)
C2—C1—C7—N1 124.07 (13) C16—C15—C17—O3 −1.1 (2)
C6—C1—C7—C8 175.54 (12) C14—C15—C17—N2 1.33 (13)
C2—C1—C7—C8 −2.99 (18) C16—C15—C17—N2 177.52 (12)
C12—N1—C9—O1 −179.01 (13) C17—N2—C18—O4 −179.55 (12)
C7—N1—C9—O1 −3.1 (2) C19—N2—C18—O4 −7.7 (2)
C12—N1—C9—C10 0.25 (14) C17—N2—C18—C14 −0.08 (14)
C7—N1—C9—C10 176.20 (11) C19—N2—C18—C14 171.80 (11)
O1—C9—C10—C16 0.9 (2) C15—C14—C18—O4 −179.61 (13)
N1—C9—C10—C16 −178.40 (13) C13—C14—C18—O4 2.4 (2)
O1—C9—C10—C11 178.91 (13) C15—C14—C18—N2 0.93 (14)
N1—C9—C10—C11 −0.33 (13) C13—C14—C18—N2 −177.07 (12)
C16—C10—C11—C13 −0.58 (19) C18—N2—C19—C21 120.96 (13)
C9—C10—C11—C13 −178.79 (12) C17—N2—C19—C21 −68.29 (16)
C16—C10—C11—C12 178.50 (12) C18—N2—C19—C20 −110.14 (13)
C9—C10—C11—C12 0.29 (13) C17—N2—C19—C20 60.61 (16)
C9—N1—C12—O2 −179.90 (13) N2—C19—C21—C26 −81.30 (15)
C7—N1—C12—O2 4.0 (2) C20—C19—C21—C26 153.20 (13)
C9—N1—C12—C11 −0.07 (14) N2—C19—C21—C22 99.25 (14)
C7—N1—C12—C11 −176.18 (11) C20—C19—C21—C22 −26.25 (18)
C13—C11—C12—O2 −1.3 (2) C26—C21—C22—C23 1.0 (2)
C10—C11—C12—O2 179.68 (13) C19—C21—C22—C23 −179.51 (12)
C13—C11—C12—N1 178.86 (12) C21—C22—C23—C24 0.3 (2)
C10—C11—C12—N1 −0.15 (13) C22—C23—C24—C25 −1.2 (2)
C10—C11—C13—C14 1.07 (18) C23—C24—C25—C26 0.9 (2)
C12—C11—C13—C14 −177.80 (12) C24—C25—C26—C21 0.5 (2)
C11—C13—C14—C15 −0.94 (18) C22—C21—C26—C25 −1.4 (2)
C11—C13—C14—C18 176.79 (12) C19—C21—C26—C25 179.11 (13)

[TableWrap ID: d1e3181]
D—H···A D—H H···A D···A D—H···A
C6—H6···O1i 0.95 2.50 3.4129 (16) 162
C7—H7···O4ii 1.00 2.49 3.1840 (16) 126
C20—H20C···O1iii 0.98 2.56 3.4948 (17) 161
C23—H23···O1iv 0.95 2.57 3.4847 (18) 161


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