Document Detail
rac-Ethyl (2Z)-3-{2-[(Z)-4-eth-oxy-4-oxobut-2-en-2-yl-amino]-cyclo-hexyl-amino}-but-2-enoate.
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The asymmetric unit of the title compound, C(18)H(30)N(2)O(4), contains two independent mol-ecules. In each mol-ecule, the cyclo-hexane ring adopts a chair conformation with equatorial orientation of the substituents, and the conformation is stabilized by two intra-molecular N-H?O hydrogen bonds, forming rings of S(6) graph-set motif. One eth-oxy group and one ethyl group are disordered over two sets of sites with refined occupancy ratios of 0.704 (2):0.296 (2) and 0.505 (3):0.495 (3), respectively. In the crystal, a weak inter-molecular C-H?O hydrogen inter-action is observed, involving the O atom of the major component of the disordered eth-oxy group.
Mohamed Anoir H Brahim B Mustapha Ait A Larbi El F Corrado Rizzoli
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Acta crystallographica. Section E, Structure reports online
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Acta Crystallogr Sect E Struct Rep Online
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Journal Information
Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
Publisher: International Union of Crystallography
Article Information
A full version of this article is available from Crystallography Journals Online.(C) Harrad et al. 2011
open-access:
Received Day: 20 Month: 4 Year: 2011
Accepted Day: 22 Month: 4 Year: 2011
collection publication date: Day: 01 Month: 5 Year: 2011
Electronic publication date: Day: 29 Month: 4 Year: 2011
pmc-release publication date: Day: 29 Month: 4 Year: 2011
Volume: 67 Issue: Pt 5
First Page: o1269 Last Page: o1270
ID: 3089325
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Publisher Id: gk2371
Coden: ACSEBH
Publisher Item Identifier: S5248
rac-Ethyl (2Z)-3-{2-[(Z)-4-eth-oxy-4-oxobut-2-en-2-yl-amino]-cyclo-hexyl-amino}-but-2-enoate
Alternate Title:C18H30N2O4
Mohamed Anoir Harrad
Brahim Boualy
Mustapha Ait Ali
Larbi El Firdoussi
Corrado Rizzoli*
aEquipe de Chimie de Coordination et Catalyse, Faculté des Sciences-Semlalia, BP
Marrakech, Morocco
bDipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Universitá degli Studi di Parma, Viale G. P. Usberti 17/A, I-43124 Parma, Italy
Correspondence: Correspondence e-mail: corrado.rizzoli@unipr.it
Related literature
For the synthesis and applications of β-enamino-esters, see: Spivey et al. (2003); Eddington et al. (2003); Elaridi, Thaqi et al. (2005); Cornils & Herrmann (1996); Venter et al. (2009); Elaridi, Jackson & Robinson (2005); Harrad et al. (2010). For related structures, see: McCann et al. (2001); Huang et al. (2008). For puckering parameters, see: Cremer & Pople (1975). For graph-set notation, see: Bernstein et al. (1995).[Chemical Structure ID: scheme1]
Experimental
Crystal data
C18H30N2O4
Mr = 338.44
Triclinic,
a = 11.1424 (9) ?
b = 12.7445 (6) ?
c = 16.3298 (11) ?
α = 90.904 (6)°
β = 109.222 (6)°
γ = 114.048 (5)°
Cu Kα radiation
μ = 0.65 mm-1
0.18 × 0.15 × 0.10 mm
Data collection
Siemens AED diffractometer
7461 measured reflections
7189 independent reflections
5826 reflections with I & 2σ(I)
Rint = 0.006
3 standard reflections every 100 reflections
intensity decay: 0.02%
Refinement
R[F2 & 2σ(F2)] = 0.034
wR(F2) = 0.106
7189 reflections
467 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.19 e ?-3
Δρmin = -0.14 e ?-3
Data collection: AED (Belletti et al., 1993); cell refinement: AED; data reduction: AED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97 (Keller, 1997); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10./gk2371sup1.cif
Structure factors: contains datablocks I. DOI: 10./gk2371Isup2.hkl
Supplementary material file. DOI: 10./gk2371Isup3.cml
Additional supplementary materials:
crystall 3D checkCIF report
fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2371).
Financial support from the Universitá degli Studi di Parma is gratefully acknowledged.
supplementary crystallographic
information
Experimental
To a stirred mixture of 3-oxo-butyric acid ethyl ester (1.7 mmol),
trans-cyclohexane-1,2-diamine (0.85 mmol) and Ca(CF3COO)2 (0.17 mmol) at room temperature 10 ml of distilled water was added, and the residue
extracted with diethyl ether (3 × 25 ml). The organic layer was dried
over Na2SO4 and the solvent removed under reduced pressure. The title
β-enaminoester was obtained by column chromatography over silica gel using a
mixture of n-hexane/ethyl acetate (5:95 v/v) as eluent
(yield 90%; m. p. 160 °C). Crystals suitable for X-ray analysis were obtained
on slow evaporation of the solvent at room temperature.
Refinement
The amine H atoms were located in a difference Fourier map and refined freely.
All other H atoms were placed at calculated positions and refined using a
riding model approximation, with C—H = 0.93–0.98 ?, and with
Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H
atoms. One ethoxy group (O6/C29–C30) and one ethyl group (C35–C36) are
disordered over two orientations (called A and B) with refined site occupancy
ratios of 0.704 (2):0.296 (2) and 0.505 (3):0.495 (3), respectively. During the
refinement, the O—C and C—C bond distances within the disordered groups
were restrained to be 1.45 (1) and 1.49 (1) ?, respectively, and the
anisotropic displacement parameters of the pairs of the disordered atoms were
set equal by the command EADP (Sheldrick, 2008).
Crystal data
Data collection
Refinement
Special details
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (?2)
Atomic displacement parameters (?2)
Geometric parameters (?, °)
Hydrogen-bond geometry (?, °)
Symmetry codes: (i) x+1, y+1, z.
References
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
Belletti, D., Cantoni, A. & Pasquinelli, G. (1993). AED Internal Report 1/93. Centro di Studio per la Strutturistica Diffrattometrica del CNR, Parma, Italy.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, .
Cornils, B. & Herrmann, W. A. (1996). Editors. Applied Homogeneous Catalysis with Organometallic Compounds. A Comprehensive Handbook, pp. 412–413. Weinheim: VCH.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, .
Eddington, N. D., Cox, D. S., Khurana, M., Salama, N. N., Stables, J. P., Harrison, S. J., Negussie, A., Taylor, R. S., Tran, U. Q., Moore, J. A., Barrow, J. C. & Scott, K. R. (2003). Eur. J. Med. Chem.38, 49–64.
Elaridi, J., Jackson, W. R. & Robinson, A. J. (2005). Tetrahedron Asymmetry, 16, .
Elaridi, J., Thaqi, A., Prosser, A., Jackson, W. R. & Robinson, A. J. (2005). Tetrahedron Asymmetry, 16, .
Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
Harrad, M. A., Outtouch, R., Ait Ali, M., El Firdoussi, L., Karim, A. & Roucoux, A. (2010). Catal. Commun.11, 442–446.
Huang, C.-H., Hsueh, L.-F., Kuo, P.-C., Lee, H. M., Uno, C.-L., Huang, J.-H., Tu, C.-Y., Hu, C.-H., Lee, G.-H. & Hung, C.-H. (2008). Eur. J. Inorg. Chem. pp. .
Keller, E. (1997). SCHAKAL97 University of Freiburg, Germany.
McCann, M., Townsend, S., Devereux, M., McKee, V. & Walker, B. (2001). Polyhedron, 20, .
Nardelli, M. (1995). J. Appl. Cryst.28, 659.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spivey, A. C., Srikaran, R., Diaper, C. M. & Turner, D. J. (2003). Org. Biomol. Chem.1, .
Venter, G. J. S., Steyl, G. & Roodt, A. (2009). Acta Cryst. E65, m1606–m1607.
[Figure ID: Fap1]
The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 30% probability level. Only the major components of disorder are shown.
[Figure ID: Fap2]
Comparison of the conformations of the two independent molecules of the title compound.
[Figure ID: Fap3]
Crystal packing of the title compound with intra- and intermolecular hydrogen bonds shown as dashed lines.
[TableWrap ID: d1e208]
C18H30N2O4
Mr = 338.44
F(000) = 736
Triclinic, P1
Dx = 1.142 Mg m-3
Hall symbol:
Cu Kα radiation, λ = 1.54178 ?
a = 11.1424 (9) ?
Cell parameters from 48 reflections
b = 12.7445 (6) ?
θ = 18.4–29.8°
c = 16.3298 (11) ?
u = 0.65 mm-1
α = 90.904 (6)°
β = 109.222 (6)°
Irregular block, colourless
γ = 114.048 (5)°
0.18 × 0.15 × 0.10 mm
[TableWrap ID: d1e344]
Siemens AED diffractometer
Rint = 0.006
Radiation source: fine-focus sealed tube
θmax = 68.0°, θmin = 2.9°
h = -13→12
θ/2θ scans
k = -15→9
7461 measured reflections
l = -18→19
7189 independent reflections
3 standard reflections every 100 reflections
5826 reflections with I & 2σ(I)
intensity decay: 0.02%
[TableWrap ID: d1e447]
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)] = 0.034
H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106
w = 1/[σ2(Fo2) + (0.0604P)2 + 0.0296P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max & 0.001
7189 reflections
Δρmax = 0.19 e ?-3
467 parameters
Δρmin = -0.14 e ?-3
8 restraints
Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods
Extinction coefficient: 0.0100 (5)
[TableWrap ID: d1e612]
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.
[TableWrap ID: d1e705]
0.65218 (9)
0.84797 (6)
0.08853 (5)
0.0814 (2)
0.58185 (10)
0.74147 (7)
-0.04449 (5)
0.0864 (2)
0.11165 (8)
0.64888 (7)
0.18740 (5)
0.0774 (2)
-0.03250 (9)
0.73472 (8)
0.13437 (6)
0.0912 (3)
-0.19007 (10)
0.18776 (8)
0.38766 (5)
0.0895 (3)
-0.1211 (2)
0.10330 (16)
0.50344 (14)
0.0829 (5)
-0.0647 (6)
0.1425 (4)
0.5121 (4)
0.0829 (5)
0.34330 (8)
0.27768 (7)
0.26921 (6)
0.0846 (2)
0.52581 (9)
0.38869 (8)
0.39309 (7)
0.0963 (3)
0.55037 (10)
0.72198 (8)
0.20595 (6)
0.0684 (2)
0.5994 (13)
0.7854 (12)
0.1927 (8)
0.082 (4)*
0.38841 (10)
0.79819 (8)
0.27442 (7)
0.0727 (2)
0.3211 (14)
0.7281 (12)
0.2553 (8)
0.084 (4)*
-0.13927 (10)
0.13606 (8)
0.24363 (6)
0.0687 (2)
-0.1697 (13)
0.1707 (11)
0.2705 (8)
0.080 (4)*
0.11045 (10)
0.32223 (9)
0.23049 (6)
0.0719 (2)
0.1472 (13)
0.2852 (11)
0.2165 (8)
0.082 (4)*
0.55684 (11)
0.71559 (9)
0.29601 (6)
0.0635 (2)
0.69934 (12)
0.72291 (10)
0.35581 (8)
0.0756 (3)
0.70863 (14)
0.71697 (11)
0.45078 (8)
0.0846 (3)
0.68137 (14)
0.81250 (11)
0.48572 (8)
0.0863 (3)
0.53939 (13)
0.80654 (11)
0.42641 (8)
0.0819 (3)
0.52777 (11)
0.81168 (9)
0.33084 (7)
0.0664 (2)
0.48965 (10)
0.63196 (8)
0.13905 (6)
0.0608 (2)
0.40309 (15)
0.51312 (10)
0.15353 (9)
0.0937 (4)
0.50447 (10)
0.64528 (9)
0.05978 (7)
0.0648 (2)
0.58526 (11)
0.75309 (9)
0.03918 (7)
0.0655 (2)
0.65923 (17)
0.84598 (13)
-0.07360 (9)
0.0971 (4)
0.80899 (19)
0.87259 (17)
-0.04739 (13)
0.1255 (6)
0.34359 (13)
0.88097 (10)
0.25392 (8)
0.0779 (3)
0.45322 (18)
1.00673 (12)
0.28361 (13)
0.1315 (7)
0.20513 (13)
0.85458 (10)
0.20757 (7)
0.0795 (3)
0.09706 (12)
0.73879 (10)
0.17749 (7)
0.0699 (3)
-0.15032 (13)
0.61954 (12)
0.10095 (8)
0.0878 (4)
-0.20206 (15)
0.56635 (16)
0.17051 (10)
0.1087 (5)
-0.13341 (11)
0.16744 (9)
0.15936 (7)
0.0646 (2)
-0.28197 (12)
0.14077 (10)
0.09474 (7)
0.0760 (3)
-0.27846 (14)
0.17667 (11)
0.00643 (8)
0.0837 (3)
-0.18062 (14)
0.30461 (12)
0.01838 (8)
0.0833 (3)
-0.03151 (13)
0.33309 (12)
0.08190 (8)
0.0817 (3)
-0.03252 (11)
0.29689 (9)
0.17064 (7)
0.0652 (2)
-0.07559 (10)
0.07824 (8)
0.29520 (7)
0.0607 (2)
-0.00907 (14)
0.01806 (11)
0.25829 (8)
0.0788 (3)
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0.07126 (9)
0.37959 (7)
0.0654 (2)
-0.12888 (13)
0.12870 (9)
0.42072 (7)
0.0725 (3)
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0.14951 (19)
0.54811 (14)
0.0902 (5)
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0.59710 (16)
0.1157 (7)
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0.2124 (5)
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0.1538 (6)
0.5640 (4)
0.1157 (7)
0.18551 (11)
0.39366 (9)
0.30854 (7)
0.0653 (2)
0.11850 (15)
0.45730 (13)
0.34209 (8)
0.0911 (4)
0.32099 (11)
0.41186 (9)
0.35799 (7)
0.0692 (3)
0.39224 (11)
0.35293 (9)
0.33421 (8)
0.0701 (3)
0.6064 (10)
0.3370 (8)
0.3684 (8)
0.1107 (14)
0.7530 (4)
0.4278 (3)
0.3891 (3)
0.1138 (9)
0.6115 (10)
0.3321 (9)
0.3864 (8)
0.1107 (14)
0.6779 (4)
0.3848 (3)
0.3239 (3)
0.1138 (9)
[TableWrap ID: d1e2377]
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0.0744 (7)
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0.0471 (12)
0.0226 (9)
0.0722 (5)
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0.0336 (4)
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0.0553 (12)
0.0459 (12)
0.0170 (10)
0.1343 (18)
0.1182 (16)
0.1043 (15)
0.0694 (14)
0.0388 (13)
-0.0099 (12)
0.0716 (6)
0.0657 (6)
0.0641 (6)
0.0310 (5)
0.0297 (5)
0.0196 (5)
0.0950 (9)
0.1066 (10)
0.0821 (8)
0.0563 (8)
0.0301 (7)
0.0042 (7)
0.0715 (6)
0.0686 (6)
0.0658 (6)
0.0298 (5)
0.0238 (5)
0.0167 (5)
0.0623 (6)
0.0603 (6)
0.0805 (7)
0.0228 (5)
0.0225 (5)
0.0189 (5)
0.0754 (10)
0.0835 (10)
0.0428 (8)
0.0135 (18)
0.0046 (19)
0.0986 (19)
0.0561 (17)
0.0601 (18)
0.0378 (19)
0.0754 (10)
0.0835 (10)
0.0428 (8)
0.0135 (18)
0.0046 (19)
0.0986 (19)
0.0561 (17)
0.0601 (18)
0.0378 (19)
[TableWrap ID: d1e3229]
1.2273 (12)
1.3584 (13)
1.4482 (15)
1.2272 (13)
1.3605 (13)
1.4520 (16)
1.2294 (13)
1.5327 (14)
1.5368 (15)
1.5277 (16)
1.2264 (14)
1.3558 (13)
1.5121 (19)
1.3448 (13)
1.4538 (13)
1.5264 (17)
0.850 (13)
1.3435 (14)
1.4577 (13)
1.5298 (14)
0.865 (13)
1.3446 (13)
1.4537 (13)
0.847 (13)
1.3727 (14)
1.3392 (14)
1.4979 (14)
1.4639 (13)
0.811 (13)
1.5293 (14)
1.5332 (15)
1.4197 (15)
1.5251 (16)
C29A—C30A
C29A—H29A
C29A—H29B
1.5145 (18)
C30A—H30A
C30A—H30B
C30A—H30C
1.5288 (18)
C29B—C30B
C29B—H29C
C29B—H29D
1.5277 (15)
C30B—H30D
C30B—H30E
C30B—H30F
1.3751 (15)
1.3626 (14)
1.5048 (15)
1.5003 (15)
1.4231 (15)
1.4202 (14)
C35A—C36A
C35A—H35A
C35A—H35B
C36A—H36A
C36A—H36B
C36A—H36C
C35B—C36B
1.3662 (17)
C35B—H35C
1.5119 (18)
C35B—H35D
C36B—H36D
C36B—H36E
C36B—H36F
1.4172 (16)
C10—O2—C11
117.28 (10)
C20—C19—H19
C16—O4—C17
116.58 (9)
C24—C19—H19
C28—O6A—C29A
117.05 (18)
C21—C20—C19
111.11 (10)
C28—O6B—C29B
C21—C20—H20A
C34—O8—C35B
C19—C20—H20A
C34—O8—C35A
C21—C20—H20B
C7—N1—C1
126.83 (9)
C19—C20—H20B
C7—N1—H1N
H20A—C20—H20B
C1—N1—H1N
C22—C21—C20
111.03 (10)
C13—N2—C6
128.79 (10)
C22—C21—H21A
C13—N2—H2N
C20—C21—H21A
C6—N2—H2N
C22—C21—H21B
C25—N3—C19
128.67 (9)
C20—C21—H21B
C25—N3—H3N
H21A—C21—H21B
C19—N3—H3N
C21—C22—C23
111.17 (10)
C31—N4—C24
128.22 (9)
C21—C22—H22A
C31—N4—H4N
C23—C22—H22A
C24—N4—H4N
C21—C22—H22B
N1—C1—C2
111.09 (9)
C23—C22—H22B
N1—C1—C6
110.54 (8)
H22A—C22—H22B
C2—C1—C6
110.93 (8)
C22—C23—C24
111.12 (9)
N1—C1—H1
C22—C23—H23A
C2—C1—H1
C24—C23—H23A
C6—C1—H1
C22—C23—H23B
C3—C2—C1
111.95 (9)
C24—C23—H23B
C3—C2—H2A
H23A—C23—H23B
C1—C2—H2A
N4—C24—C23
110.76 (9)
C3—C2—H2B
N4—C24—C19
110.83 (8)
C1—C2—H2B
C23—C24—C19
111.46 (9)
H2A—C2—H2B
N4—C24—H24
C4—C3—C2
110.45 (10)
C23—C24—H24
C4—C3—H3A
C19—C24—H24
C2—C3—H3A
N3—C25—C27
121.75 (9)
C4—C3—H3B
N3—C25—C26
118.67 (9)
C2—C3—H3B
C27—C25—C26
119.57 (9)
H3A—C3—H3B
C25—C26—H26A
C3—C4—C5
111.02 (10)
C25—C26—H26B
C3—C4—H4A
H26A—C26—H26B
C5—C4—H4A
C25—C26—H26C
C3—C4—H4B
H26A—C26—H26C
C5—C4—H4B
H26B—C26—H26C
H4A—C4—H4B
C25—C27—C28
123.28 (9)
C6—C5—C4
112.53 (10)
C25—C27—H27
C6—C5—H5A
C28—C27—H27
C4—C5—H5A
O5—C28—O6A
120.10 (13)
C6—C5—H5B
O5—C28—O6B
C4—C5—H5B
O5—C28—C27
126.94 (10)
H5A—C5—H5B
O6A—C28—C27
112.70 (12)
N2—C6—C5
111.60 (9)
O6B—C28—C27
N2—C6—C1
109.13 (8)
O6A—C29A—C30A
C5—C6—C1
110.09 (9)
O6A—C29A—H29A
N2—C6—H6
C30A—C29A—H29A
C5—C6—H6
O6A—C29A—H29B
C1—C6—H6
C30A—C29A—H29B
N1—C7—C9
122.42 (9)
H29A—C29A—H29B
N1—C7—C8
118.00 (10)
C29A—C30A—H30A
C9—C7—C8
119.59 (9)
C29A—C30A—H30B
C7—C8—H8A
H30A—C30A—H30B
C7—C8—H8B
C29A—C30A—H30C
H8A—C8—H8B
H30A—C30A—H30C
C7—C8—H8C
H30B—C30A—H30C
H8A—C8—H8C
O6B—C29B—C30B
H8B—C8—H8C
O6B—C29B—H29C
C7—C9—C10
124.40 (9)
C30B—C29B—H29C
C7—C9—H9
O6B—C29B—H29D
C10—C9—H9
C30B—C29B—H29D
O1—C10—O2
121.51 (10)
H29C—C29B—H29D
O1—C10—C9
126.35 (10)
C29B—C30B—H30D
O2—C10—C9
112.14 (9)
C29B—C30B—H30E
O2—C11—C12
112.02 (12)
H30D—C30B—H30E
O2—C11—H11A
C29B—C30B—H30F
C12—C11—H11A
H30D—C30B—H30F
O2—C11—H11B
H30E—C30B—H30F
C12—C11—H11B
N4—C31—C33
122.59 (10)
H11A—C11—H11B
N4—C31—C32
118.16 (10)
C11—C12—H12A
C33—C31—C32
119.25 (10)
C11—C12—H12B
C31—C32—H32A
H12A—C12—H12B
C31—C32—H32B
C11—C12—H12C
H32A—C32—H32B
H12A—C12—H12C
C31—C32—H32C
H12B—C12—H12C
H32A—C32—H32C
N2—C13—C15
122.28 (11)
H32B—C32—H32C
N2—C13—C14
117.39 (11)
C31—C33—C34
123.87 (10)
C15—C13—C14
120.33 (11)
C31—C33—H33
C13—C14—H14A
C34—C33—H33
C13—C14—H14B
O7—C34—O8
121.61 (10)
H14A—C14—H14B
O7—C34—C33
126.26 (10)
C13—C14—H14C
O8—C34—C33
112.13 (10)
H14A—C14—H14C
O8—C35A—C36A
H14B—C14—H14C
O8—C35A—H35A
C13—C15—C16
123.31 (10)
C36A—C35A—H35A
C13—C15—H15
O8—C35A—H35B
C16—C15—H15
C36A—C35A—H35B
O3—C16—O4
120.92 (10)
H35A—C35A—H35B
O3—C16—C15
126.59 (10)
C35A—C36A—H36A
O4—C16—C15
112.49 (10)
C35A—C36A—H36B
O4—C17—C18
112.64 (11)
H36A—C36A—H36B
O4—C17—H17A
C35A—C36A—H36C
C18—C17—H17A
H36A—C36A—H36C
O4—C17—H17B
H36B—C36A—H36C
C18—C17—H17B
O8—C35B—C36B
H17A—C17—H17B
O8—C35B—H35C
C17—C18—H18A
C36B—C35B—H35C
C17—C18—H18B
O8—C35B—H35D
H18A—C18—H18B
C36B—C35B—H35D
C17—C18—H18C
H35C—C35B—H35D
H18A—C18—H18C
C35B—C36B—H36D
H18B—C18—H18C
C35B—C36B—H36E
N3—C19—C20
109.91 (9)
H36D—C36B—H36E
N3—C19—C24
110.78 (8)
C35B—C36B—H36F
C20—C19—C24
110.58 (8)
H36D—C36B—H36F
N3—C19—H19
H36E—C36B—H36F
[TableWrap ID: d1e4829]
D—H···A
D—H···A
N1—H1N···O1
0.850 (13)
2.048 (14)
140.1 (12)
N2—H2N···O3
0.865 (12)
2.009 (12)
138.7 (13)
N3—H3N···O5
0.846 (17)
2.018 (15)
140.3 (12)
N4—H4N···O7
0.811 (17)
2.112 (15)
136.1 (14)
C4—H4A···O6Ai
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