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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 2| Part 6| June 2017| x170805
https://doi.org/10.1107/S2414314617008057

N-[1,4,4-Tri­methyl­tri­cyclo­[6.3.1.03,9]dodec-8(12)-en-2-yl]acetamide

CROSSMARK_Color_square_no_text.svg
Noureddine Mazoir,a Ahmed Benharref,a Jean-Claude Daran,b Abdelouahd Oukhrib,a Mustapha Ait Elhada and Moha Berrahoa*

aLaboratoire de Chimie des Substances Naturelles, "Unité Associé au CNRST (URAC16)", Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, Université Cadi Ayyad, 40000 Marrakech, Morocco, and bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
*Correspondence e-mail: benharref@uca.ac.ma

Edited by J. Simpson, University of Otago, New Zealand (Received 28 May 2017; accepted 30 May 2017; online 20 June 2017)

The title compound, C17H27NO, crystallizes with three independent mol­ecules in the asymmetric unit with almost identical conformations. Each mol­ecule is built up from a seven-membered ring to which a bridged six-membered ring is fused. In each of the three mol­ecules, the seven-membered rings have a twist-chair conformation, while the cyclo­hexenyl rings display perfect boat conformations. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into zigzag chains running along the b-axis direction.

CCDC reference: 1553210

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The bicyclic sesquiterpene α-himachalene is a constituent (20%) of the essential oil of the Atlas cedar (Cedrus Atlantica) (El Haib et al., 2010[El Haib, A., Benharref, A., Parrès-Maynadié, S., Manoury, E., Daran, J. C., Urrutigoïty, M. & Gouygou, M. (2010). Tetrahedron Asymmetry, 21, 1272-1277.]; Loubidi et al., 2014[Loubidi, M., Agustin, D., Benharref, A. & Poli, R. (2014). C. R. Chim. 17, 549-556.]). The reactivity of this sesquiterpene and its derivatives has been studied extensively by our team (El Jamili et al., 2002[El Jamili, H., Auhmani, A., Dakir, M., Lassaba, E., Benharref, A., Pierrot, M., Chiaroni, A. & Riche, C. (2002). Tetrahedron Lett. 43, 6645-6648.]; El Haib et al., 2011[El Haib, A., Benharref, A., Parrès-Maynadié, S., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101-108.]; Loubidi et al., 2014[Loubidi, M., Agustin, D., Benharref, A. & Poli, R. (2014). C. R. Chim. 17, 549-556.]; Benharref et al., 2016[Benharref, A., Oukhrib, A., Ait Elhad, M., El Ammari, L., Saadi, M. & Berraho, M. (2016). IUCrData, 1, x160703.], 2017[Benharref, A., El Ammari, L., Saadi, M., Mazoir, N., Daran, J.-C. & Berraho, M. (2017). IUCrData, 2, x170584.]) in order to prepare new products with biological properties. Indeed, these compounds have been tested, using the food-poisoning technique, for their potential anti­fungal activity against the phytopathogen Botrytis cinerea (Daoubi et al., 2004[Daoubi, M., Durán-Patrón, R., Hmamouchi, M., Hernández-Galán, R., Benharref, A. & Collado, I. G. (2004). Pest Manag. Sci. 60, 927-932.]). Herein, we report the synthesis and crystal structure of the title compound, synthesized by the reaction of 6α,7α- ep­oxy­himachalene with BF3OEt in aceto­nitrile under argon.

The asymmetric unit of this new compound contains three independent mol­ecules with similar conformations. Each mol­ecule is built up from a seven-membered ring, which is fused to a bridged cyclo­hexenyl ring as shown in Fig. 1[link]. In each of the three mol­ecules, the seven-membered ring displays a twist-chair conformation as indicated by the total puckering amplitude QT = 0.864 (3) Å, a spherical polar angle θ = 39.60 (2)°; φ2 = 342.4 (3)° and φ3 = 301.6 (3)°, whereas the cyclo­hexenyl ring shows a perfect boat conformation with QT = 0.865 (3) Å, a spherical polar angle θ = 88.7 (2)° and φ2 = 125.08 (18)°.

[Figure 1]
Figure 1
The mol­ecular structure of one of the three unique mol­ecules the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The other two mol­ecules are labelled similarly but with the suffix A or B.

In the crystal, the three mol­ecules are linked by N—H⋯O hydrogen bonds, forming zigzag chains running along the b-axis direction (Fig. 2[link] and Table 1[link]). Adjacent chains form sheets of mol­ecules in the bc plane (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O2 0.86 2.04 2.893 (2) 173
N2—H2⋯O3 0.86 2.11 2.956 (3) 167
N3—H3⋯O1i 0.86 2.06 2.909 (2) 169
Symmetry code: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].
[Figure 2]
Figure 2
A view of the three mol­ecules in the asymmetric unit, linked by N—H⋯O hydrogen bonds (see Table 1[link]). A and B mol­ecules should be indicated
[Figure 3]
Figure 3
Overall packing of the title compound viewed along a.

Synthesis and crystallization

2 g (9 mmol) of 8,9-ep­oxy-2methyl­ene-6,6,9-triméthylbi­cyclo [5.4.01,7]undecane (Lassaba et al., 1998[Lassaba, E., El Jamili, H., Chekroun, A., Benharref, A., Chiaroni, A., Riche, C. & Lavergne, J.-P. (1998). Synth. Commun. 28, 2641-2651.]) was dissolved in 30 ml of CH3CN and stirred at 273 K under argon. BF3OEt (3% mmol) was added and the reaction mixture was stirred and monitored by TLC. After the completion of reaction, the solvent was removed and the residue obtained was chromatographed on silica, eluting with hexa­ne–ethyl­acetate (90:10), which allowed the isolation of the title compound (yield: 1.5 g, 5.7 mmol, 64%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C17H27NO
Mr 261.39
Crystal system, space group Orthorhombic, P212121
Temperature (K) 180
a, b, c (Å) 9.0275 (4), 16.9076 (7), 30.7411 (11)
V (Å3) 4692.1 (3)
Z 12
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.50 × 0.25 × 0.12
 
Data collection
Diffractometer Rigaku Oxford Diffraction Xcalibur Eos Gemini ultra
Absorption correction Multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.])
Tmin, Tmax 0.911, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 26928, 9534, 8730
Rint 0.032
(sin θ/λ)max (Å−1) 0.625
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.102, 1.07
No. of reflections 9534
No. of parameters 526
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.37, −0.15
Absolute structure Flack x determined using 3320 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter −0.3 (5)
Computer programs: CrysAlis PRO (Rigaku Oxford Diffraction, 2015[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]), SHELXS2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data

CCDC reference: 1553210

Crystal structure: contains datablocks I, block. DOI: https://doi.org/10.1107/S2414314617008057/sj4115sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008057/sj4115Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617008057/sj4115Isup3.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

N-[1,4,4-Trimethyltricyclo[6.3.1.03,9]dodec-8(12)-en-2-yl]acetamide top
Crystal data top
C17H27NODx = 1.110 Mg m−3
Mr = 261.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9534 reflections
a = 9.0275 (4) Åθ = 3–26.4°
b = 16.9076 (7) ŵ = 0.07 mm−1
c = 30.7411 (11) ÅT = 180 K
V = 4692.1 (3) Å3Rectangular plate, colourless
Z = 120.50 × 0.25 × 0.12 mm
F(000) = 1728
Data collection top
Rigaku Oxford Diffraction Xcalibur Eos Gemini ultra
diffractometer		9534 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source8730 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 16.1978 pixels mm-1θmax = 26.4°, θmin = 3.0°
ω scansh = −10→11
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)		k = −21→20
Tmin = 0.911, Tmax = 1.000l = −38→37
26928 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.047P)2 + 0.5238P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.37 e Å−3
9534 reflectionsΔρmin = −0.15 e Å−3
526 parametersAbsolute structure: Flack x determined using 3320 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: −0.3 (5)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.99 Å (methylene), 0.98 Å (methyl), 1.0Å (methine) with Uiso(H) = 1.2Ueq(CH and CH2) or Uiso(H) = 1.5Ueq(CH3). The coordinates of H atoms attached to N atoms were freely refined with Uiso(H) = 1.2Ueq(N) and the H attached to hydroxyl O atoms were fixed geometrically and treated as riding with O—H = 0.84Å and Uiso(H) = 1.5Ueq(O).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.2729 (2)0.27939 (10)0.21957 (5)0.0355 (4)
O30.8062 (2)0.57328 (10)0.39222 (5)0.0367 (4)
N11.2026 (2)0.26183 (11)0.28991 (6)0.0271 (4)
H11.15100.28110.31090.033*
O21.0471 (2)0.32177 (11)0.36531 (5)0.0435 (4)
N20.9937 (2)0.43161 (11)0.40406 (6)0.0286 (4)
H20.94760.47610.40410.034*
N30.8069 (2)0.69312 (11)0.35888 (6)0.0267 (4)
H30.77220.72010.33740.032*
C8A0.9896 (2)0.38980 (14)0.48235 (7)0.0288 (5)
C10A1.1816 (3)0.49735 (13)0.50212 (7)0.0297 (5)
H10A1.25570.53630.51130.036*
C5A1.3599 (3)0.46297 (14)0.43902 (7)0.0291 (5)
C5B1.1863 (3)0.74100 (14)0.35737 (8)0.0330 (5)
C61.3768 (3)0.18714 (14)0.33651 (7)0.0286 (5)
H61.34530.23190.35450.034*
C1B1.0646 (3)0.85866 (14)0.42509 (8)0.0346 (6)
C16B0.7589 (2)0.61863 (13)0.36388 (7)0.0282 (5)
C17B0.6396 (3)0.59381 (15)0.33209 (8)0.0370 (6)
H17A0.67450.55010.31500.056*
H17B0.61620.63740.31330.056*
H17C0.55250.57820.34780.056*
C6B1.0294 (3)0.77820 (12)0.35998 (7)0.0253 (5)
H6B0.99080.78020.33020.030*
C7A1.0855 (2)0.41177 (12)0.44174 (7)0.0237 (4)
H7A1.14380.36490.43400.028*
C1A1.2051 (3)0.41964 (15)0.52530 (7)0.0310 (5)
C6A1.1968 (2)0.47923 (13)0.45294 (7)0.0250 (4)
H6A1.16400.52650.43720.030*
C71.2724 (2)0.18478 (13)0.29605 (7)0.0252 (5)
H71.33460.17490.27050.030*
C7B0.9144 (2)0.73141 (13)0.38758 (7)0.0249 (5)
H7B0.96730.69010.40360.030*
C12A0.9095 (3)0.46473 (16)0.49821 (8)0.0362 (6)
H12A0.84730.45190.52300.043*
H12B0.84660.48520.47520.043*
C10B1.0316 (3)0.86401 (13)0.37708 (7)0.0313 (5)
H10B1.10750.89520.36210.038*
C41.6173 (3)0.12822 (17)0.30345 (9)0.0412 (6)
H4A1.71440.14470.29340.049*
H4B1.55950.11480.27790.049*
C9B0.9623 (3)0.82009 (16)0.44760 (8)0.0372 (6)
H9B0.96820.81400.47760.045*
C51.5432 (3)0.20015 (15)0.32539 (7)0.0336 (5)
C14B1.1719 (3)0.65226 (15)0.34653 (9)0.0398 (6)
H14A1.10500.64560.32250.060*
H14B1.13430.62450.37140.060*
H14C1.26730.63150.33890.060*
C16A0.9779 (3)0.38418 (15)0.36961 (7)0.0333 (5)
C81.1602 (3)0.11518 (14)0.29940 (8)0.0318 (5)
C3A1.4772 (3)0.41685 (18)0.51402 (8)0.0415 (6)
H3A11.50950.47150.51600.050*
H3A21.56010.38380.52250.050*
C12B0.7612 (3)0.85432 (16)0.39610 (8)0.0396 (6)
H12C0.68800.83280.37630.048*
H12D0.71110.88950.41620.048*
C11A1.0239 (3)0.52780 (16)0.51135 (9)0.0386 (6)
H11A1.01380.53980.54210.046*
H11B1.00640.57600.49500.046*
C2A1.3501 (3)0.40409 (17)0.54694 (8)0.0384 (6)
H2A11.35260.35020.55770.046*
H2A21.36240.43960.57150.046*
C13A0.8812 (3)0.32349 (16)0.47200 (9)0.0426 (6)
H13A0.93470.27820.46160.064*
H13B0.81290.34090.45010.064*
H13C0.82760.30950.49780.064*
C131.0527 (3)0.11491 (17)0.26134 (9)0.0419 (6)
H13D1.10720.11270.23450.063*
H13E0.99400.16220.26200.063*
H13F0.98910.06960.26340.063*
C101.3475 (3)0.11117 (15)0.36304 (8)0.0392 (6)
H101.41940.10620.38680.047*
C8B0.8356 (3)0.78670 (15)0.42139 (7)0.0327 (5)
C17A0.8678 (3)0.41232 (19)0.33585 (9)0.0514 (7)
H17D0.86670.37600.31180.077*
H17E0.89610.46390.32570.077*
H17F0.77080.41490.34860.077*
C121.0776 (3)0.12117 (16)0.34338 (8)0.0394 (6)
H12E1.02570.17130.34510.047*
H12F1.00500.07900.34550.047*
C141.5592 (3)0.27036 (16)0.29424 (8)0.0390 (6)
H14D1.51040.31570.30640.058*
H14E1.51490.25740.26680.058*
H14F1.66230.28200.29010.058*
C91.2618 (3)0.04393 (14)0.29990 (9)0.0401 (6)
H91.25430.00340.27960.048*
C4A1.4388 (3)0.39866 (15)0.46613 (7)0.0338 (5)
H4A11.37700.35180.46580.041*
H4A21.53030.38530.45130.041*
C161.2149 (3)0.30401 (14)0.25332 (7)0.0317 (5)
C9A1.1030 (3)0.36573 (15)0.51578 (7)0.0325 (5)
H9A1.10160.31620.52890.039*
C11.3629 (3)0.04340 (15)0.33164 (9)0.0419 (6)
C15A1.4470 (3)0.54094 (16)0.44141 (9)0.0439 (6)
H15A1.54900.53130.43430.066*
H15B1.44050.56210.47030.066*
H15C1.40600.57810.42110.066*
C2B1.2171 (3)0.87902 (16)0.44012 (9)0.0451 (7)
H2B11.22620.86840.47100.054*
H2B21.23580.93480.43540.054*
C151.6263 (3)0.22284 (19)0.36732 (9)0.0481 (7)
H15D1.72950.23010.36090.072*
H15E1.61520.18140.38840.072*
H15F1.58600.27110.37870.072*
C4B1.2783 (3)0.74766 (15)0.39976 (9)0.0400 (6)
H4B11.21990.72480.42310.048*
H4B21.36550.71480.39630.048*
C14A1.3623 (3)0.43624 (16)0.39113 (8)0.0365 (6)
H14G1.31100.47440.37360.055*
H14H1.31440.38580.38860.055*
H14I1.46300.43190.38140.055*
C3B1.3303 (3)0.82954 (18)0.41482 (11)0.0523 (8)
H3B11.41720.82260.43300.063*
H3B21.36050.85940.38940.063*
C171.1539 (4)0.38749 (16)0.25564 (9)0.0561 (8)
H17G1.22320.42350.24270.084*
H17H1.13830.40180.28550.084*
H17I1.06150.39000.24020.084*
C13B0.7265 (3)0.7406 (2)0.44942 (9)0.0511 (7)
H13G0.77680.69720.46310.077*
H13H0.64780.72060.43150.077*
H13I0.68600.77490.47130.077*
C111.1887 (3)0.11465 (18)0.38117 (8)0.0462 (7)
H11C1.17850.16000.40020.055*
H11D1.16840.06730.39800.055*
C31.6374 (3)0.05218 (19)0.33059 (11)0.0560 (8)
H3A1.72180.02340.31920.067*
H3B1.66090.06730.36020.067*
C11B0.8777 (3)0.90048 (14)0.37048 (8)0.0390 (6)
H11E0.87860.95510.38010.047*
H11F0.85270.89980.33980.047*
C21.5042 (4)−0.00377 (18)0.33162 (13)0.0609 (9)
H2A1.5066−0.03820.30640.073*
H2B1.5087−0.03650.35750.073*
C15B1.2701 (4)0.7791 (2)0.31947 (10)0.0560 (8)
H15G1.26920.83550.32280.084*
H15H1.22310.76500.29250.084*
H15I1.37070.76060.31930.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0459 (10)0.0391 (9)0.0216 (7)0.0015 (8)−0.0010 (7)0.0004 (7)
O30.0387 (10)0.0300 (9)0.0415 (9)−0.0002 (8)−0.0025 (8)0.0102 (7)
N10.0313 (10)0.0275 (9)0.0224 (8)0.0074 (8)0.0003 (8)−0.0010 (7)
O20.0565 (12)0.0402 (10)0.0340 (9)0.0088 (9)−0.0016 (9)−0.0137 (8)
N20.0301 (10)0.0257 (10)0.0301 (9)0.0055 (8)−0.0051 (8)−0.0045 (8)
N30.0273 (10)0.0264 (9)0.0264 (9)0.0000 (8)−0.0048 (8)0.0054 (7)
C8A0.0236 (11)0.0316 (12)0.0311 (11)−0.0007 (10)0.0048 (9)−0.0039 (9)
C10A0.0255 (11)0.0303 (12)0.0332 (12)0.0015 (10)−0.0016 (9)−0.0128 (9)
C5A0.0264 (12)0.0319 (12)0.0289 (11)0.0004 (10)0.0026 (9)−0.0003 (9)
C5B0.0269 (12)0.0324 (12)0.0396 (13)−0.0013 (10)0.0030 (10)−0.0017 (10)
C60.0302 (12)0.0330 (12)0.0226 (10)0.0043 (10)0.0018 (9)0.0035 (9)
C1B0.0418 (14)0.0254 (11)0.0366 (13)0.0078 (11)−0.0141 (11)−0.0079 (10)
C16B0.0231 (11)0.0295 (11)0.0319 (11)−0.0003 (10)0.0035 (9)0.0024 (9)
C17B0.0320 (13)0.0358 (13)0.0432 (13)−0.0086 (11)−0.0018 (11)0.0028 (11)
C6B0.0302 (12)0.0237 (11)0.0221 (9)0.0015 (9)−0.0019 (9)0.0016 (8)
C7A0.0240 (11)0.0214 (10)0.0256 (10)0.0043 (9)−0.0006 (8)−0.0039 (8)
C1A0.0303 (12)0.0417 (13)0.0210 (10)0.0070 (11)0.0037 (9)−0.0059 (9)
C6A0.0252 (11)0.0226 (10)0.0273 (10)0.0017 (9)−0.0008 (9)−0.0011 (8)
C70.0265 (11)0.0248 (10)0.0242 (10)0.0046 (9)0.0023 (9)0.0014 (8)
C7B0.0245 (11)0.0258 (11)0.0245 (10)0.0045 (9)−0.0035 (8)0.0017 (8)
C12A0.0245 (12)0.0459 (15)0.0383 (13)0.0031 (11)0.0033 (10)−0.0119 (11)
C10B0.0376 (14)0.0233 (11)0.0329 (12)−0.0001 (10)−0.0074 (10)0.0015 (9)
C40.0266 (13)0.0525 (16)0.0446 (14)0.0081 (12)0.0025 (11)0.0027 (12)
C9B0.0435 (15)0.0421 (14)0.0260 (11)0.0123 (13)−0.0071 (11)−0.0072 (10)
C50.0288 (13)0.0429 (14)0.0291 (11)0.0019 (11)−0.0017 (10)0.0040 (10)
C14B0.0318 (14)0.0392 (14)0.0484 (15)0.0080 (12)−0.0007 (12)−0.0116 (11)
C16A0.0352 (13)0.0351 (13)0.0294 (11)0.0017 (11)0.0000 (10)−0.0072 (10)
C80.0279 (12)0.0304 (12)0.0370 (12)0.0010 (10)0.0053 (10)0.0019 (10)
C3A0.0280 (13)0.0565 (17)0.0399 (13)0.0077 (13)−0.0060 (11)−0.0006 (12)
C12B0.0362 (14)0.0440 (14)0.0386 (13)0.0182 (12)−0.0085 (11)−0.0160 (11)
C11A0.0313 (13)0.0401 (14)0.0446 (14)0.0076 (12)0.0015 (11)−0.0183 (11)
C2A0.0382 (14)0.0492 (15)0.0277 (11)0.0109 (12)−0.0032 (10)−0.0054 (11)
C13A0.0349 (14)0.0417 (15)0.0513 (15)−0.0085 (12)0.0064 (12)−0.0058 (12)
C130.0334 (13)0.0435 (15)0.0488 (15)−0.0061 (12)0.0011 (11)−0.0051 (12)
C100.0380 (14)0.0459 (15)0.0336 (12)0.0066 (12)0.0019 (11)0.0174 (11)
C8B0.0305 (13)0.0423 (14)0.0251 (10)0.0077 (11)0.0002 (9)−0.0019 (10)
C17A0.0530 (17)0.0627 (19)0.0384 (14)0.0055 (15)−0.0157 (13)−0.0141 (13)
C120.0340 (14)0.0393 (14)0.0448 (14)0.0000 (12)0.0141 (11)0.0097 (11)
C140.0326 (13)0.0481 (15)0.0361 (12)−0.0103 (12)−0.0035 (11)0.0053 (11)
C90.0409 (15)0.0241 (12)0.0552 (16)−0.0012 (11)0.0120 (13)0.0033 (11)
C4A0.0243 (12)0.0423 (14)0.0346 (12)0.0062 (11)0.0049 (10)−0.0018 (10)
C160.0376 (13)0.0311 (12)0.0264 (11)0.0018 (11)−0.0066 (10)0.0004 (9)
C9A0.0350 (13)0.0364 (13)0.0262 (11)0.0022 (11)0.0079 (9)0.0032 (9)
C10.0379 (15)0.0310 (13)0.0567 (16)0.0054 (12)0.0079 (13)0.0180 (12)
C15A0.0369 (14)0.0412 (15)0.0537 (15)−0.0080 (12)0.0031 (13)0.0015 (12)
C2B0.0493 (16)0.0342 (13)0.0519 (15)−0.0029 (13)−0.0228 (13)−0.0033 (12)
C150.0397 (15)0.0674 (19)0.0372 (13)0.0018 (14)−0.0103 (12)0.0048 (13)
C4B0.0267 (13)0.0362 (13)0.0571 (16)0.0038 (11)−0.0092 (11)−0.0017 (12)
C14A0.0344 (13)0.0430 (14)0.0321 (12)0.0017 (12)0.0091 (10)0.0032 (10)
C3B0.0338 (15)0.0462 (16)0.077 (2)−0.0071 (13)−0.0166 (15)−0.0071 (15)
C170.092 (2)0.0357 (15)0.0405 (14)0.0197 (16)0.0053 (15)0.0097 (12)
C13B0.0403 (16)0.077 (2)0.0364 (14)0.0018 (15)0.0126 (12)−0.0001 (14)
C110.0485 (16)0.0532 (17)0.0367 (13)0.0033 (14)0.0145 (12)0.0176 (12)
C30.0401 (16)0.061 (2)0.068 (2)0.0253 (15)−0.0007 (15)0.0083 (16)
C11B0.0510 (16)0.0275 (12)0.0386 (13)0.0123 (12)−0.0172 (12)−0.0046 (10)
C20.058 (2)0.0407 (17)0.084 (2)0.0197 (15)0.0040 (17)0.0197 (15)
C15B0.0428 (17)0.064 (2)0.0610 (18)−0.0049 (16)0.0189 (14)0.0049 (15)
Geometric parameters (Å, º) top
O1—C161.234 (3)C3A—C2A1.545 (4)
O3—C16B1.237 (3)C3A—H3A10.9700
N1—C161.336 (3)C3A—H3A20.9700
N1—C71.459 (3)C12B—C11B1.528 (4)
N1—H10.8600C12B—C8B1.537 (3)
O2—C16A1.233 (3)C12B—H12C0.9700
N2—C16A1.336 (3)C12B—H12D0.9700
N2—C7A1.463 (3)C11A—H11A0.9700
N2—H20.8600C11A—H11B0.9700
N3—C16B1.341 (3)C2A—H2A10.9700
N3—C7B1.463 (3)C2A—H2A20.9700
N3—H30.8600C13A—H13A0.9600
C8A—C9A1.506 (3)C13A—H13B0.9600
C8A—C13A1.522 (3)C13A—H13C0.9600
C8A—C12A1.538 (3)C13—H13D0.9600
C8A—C7A1.564 (3)C13—H13E0.9600
C10A—C1A1.510 (3)C13—H13F0.9600
C10A—C11A1.540 (3)C10—C11.505 (4)
C10A—C6A1.549 (3)C10—C111.539 (4)
C10A—H10A0.9800C10—H100.9800
C5A—C15A1.537 (3)C8B—C13B1.524 (4)
C5A—C14A1.540 (3)C17A—H17D0.9600
C5A—C4A1.544 (3)C17A—H17E0.9600
C5A—C6A1.558 (3)C17A—H17F0.9600
C5B—C15B1.531 (4)C12—C111.539 (4)
C5B—C14B1.542 (3)C12—H12E0.9700
C5B—C4B1.549 (4)C12—H12F0.9700
C5B—C6B1.552 (3)C14—H14D0.9600
C6—C101.544 (3)C14—H14E0.9600
C6—C51.557 (3)C14—H14F0.9600
C6—C71.561 (3)C9—C11.336 (4)
C6—H60.9800C9—H90.9300
C1B—C9B1.326 (4)C4A—H4A10.9700
C1B—C2B1.492 (4)C4A—H4A20.9700
C1B—C10B1.508 (3)C16—C171.517 (4)
C16B—C17B1.514 (3)C9A—H9A0.9300
C17B—H17A0.9600C1—C21.504 (4)
C17B—H17B0.9600C15A—H15A0.9600
C17B—H17C0.9600C15A—H15B0.9600
C6B—C10B1.543 (3)C15A—H15C0.9600
C6B—C7B1.557 (3)C2B—C3B1.533 (4)
C6B—H6B0.9800C2B—H2B10.9700
C7A—C6A1.558 (3)C2B—H2B20.9700
C7A—H7A0.9800C15—H15D0.9600
C1A—C9A1.329 (4)C15—H15E0.9600
C1A—C2A1.492 (3)C15—H15F0.9600
C6A—H6A0.9800C4B—C3B1.533 (4)
C7—C81.556 (3)C4B—H4B10.9700
C7—H70.9800C4B—H4B20.9700
C7B—C8B1.568 (3)C14A—H14G0.9600
C7B—H7B0.9800C14A—H14H0.9600
C12A—C11A1.539 (4)C14A—H14I0.9600
C12A—H12A0.9700C3B—H3B10.9700
C12A—H12B0.9700C3B—H3B20.9700
C10B—C11B1.533 (4)C17—H17G0.9600
C10B—H10B0.9800C17—H17H0.9600
C4—C51.543 (4)C17—H17I0.9600
C4—C31.543 (4)C13B—H13G0.9600
C4—H4A0.9700C13B—H13H0.9600
C4—H4B0.9700C13B—H13I0.9600
C9B—C8B1.509 (3)C11—H11C0.9700
C9B—H9B0.9300C11—H11D0.9700
C5—C141.532 (3)C3—C21.530 (5)
C5—C151.540 (3)C3—H3A0.9700
C14B—H14A0.9600C3—H3B0.9700
C14B—H14B0.9600C11B—H11E0.9700
C14B—H14C0.9600C11B—H11F0.9700
C16A—C17A1.514 (4)C2—H2A0.9700
C8—C91.514 (3)C2—H2B0.9700
C8—C131.520 (3)C15B—H15G0.9600
C8—C121.547 (3)C15B—H15H0.9600
C3A—C4A1.543 (3)C15B—H15I0.9600
C16—N1—C7123.34 (18)C1A—C2A—C3A109.58 (19)
C16—N1—H1118.3C1A—C2A—H2A1109.8
C7—N1—H1118.3C3A—C2A—H2A1109.8
C16A—N2—C7A123.41 (19)C1A—C2A—H2A2109.8
C16A—N2—H2118.3C3A—C2A—H2A2109.8
C7A—N2—H2118.3H2A1—C2A—H2A2108.2
C16B—N3—C7B124.11 (18)C8A—C13A—H13A109.5
C16B—N3—H3117.9C8A—C13A—H13B109.5
C7B—N3—H3117.9H13A—C13A—H13B109.5
C9A—C8A—C13A112.4 (2)C8A—C13A—H13C109.5
C9A—C8A—C12A109.02 (19)H13A—C13A—H13C109.5
C13A—C8A—C12A111.75 (19)H13B—C13A—H13C109.5
C9A—C8A—C7A103.46 (17)C8—C13—H13D109.5
C13A—C8A—C7A111.35 (18)C8—C13—H13E109.5
C12A—C8A—C7A108.52 (19)H13D—C13—H13E109.5
C1A—C10A—C11A109.5 (2)C8—C13—H13F109.5
C1A—C10A—C6A106.04 (17)H13D—C13—H13F109.5
C11A—C10A—C6A109.11 (19)H13E—C13—H13F109.5
C1A—C10A—H10A110.7C1—C10—C11110.4 (2)
C11A—C10A—H10A110.7C1—C10—C6106.18 (19)
C6A—C10A—H10A110.7C11—C10—C6108.6 (2)
C15A—C5A—C14A106.9 (2)C1—C10—H10110.5
C15A—C5A—C4A110.0 (2)C11—C10—H10110.5
C14A—C5A—C4A107.63 (19)C6—C10—H10110.5
C15A—C5A—C6A108.62 (19)C9B—C8B—C13B112.3 (2)
C14A—C5A—C6A109.12 (19)C9B—C8B—C12B108.8 (2)
C4A—C5A—C6A114.34 (19)C13B—C8B—C12B112.6 (2)
C15B—C5B—C14B106.6 (2)C9B—C8B—C7B103.50 (18)
C15B—C5B—C4B110.1 (2)C13B—C8B—C7B111.3 (2)
C14B—C5B—C4B107.3 (2)C12B—C8B—C7B107.83 (18)
C15B—C5B—C6B108.7 (2)C16A—C17A—H17D109.5
C14B—C5B—C6B109.17 (19)C16A—C17A—H17E109.5
C4B—C5B—C6B114.59 (19)H17D—C17A—H17E109.5
C10—C6—C5113.5 (2)C16A—C17A—H17F109.5
C10—C6—C7107.23 (19)H17D—C17A—H17F109.5
C5—C6—C7114.29 (17)H17E—C17A—H17F109.5
C10—C6—H6107.1C11—C12—C8109.9 (2)
C5—C6—H6107.1C11—C12—H12E109.7
C7—C6—H6107.1C8—C12—H12E109.7
C9B—C1B—C2B126.5 (2)C11—C12—H12F109.7
C9B—C1B—C10B113.7 (2)C8—C12—H12F109.7
C2B—C1B—C10B118.1 (2)H12E—C12—H12F108.2
O3—C16B—N3123.5 (2)C5—C14—H14D109.5
O3—C16B—C17B121.9 (2)C5—C14—H14E109.5
N3—C16B—C17B114.6 (2)H14D—C14—H14E109.5
C16B—C17B—H17A109.5C5—C14—H14F109.5
C16B—C17B—H17B109.5H14D—C14—H14F109.5
H17A—C17B—H17B109.5H14E—C14—H14F109.5
C16B—C17B—H17C109.5C1—C9—C8115.3 (2)
H17A—C17B—H17C109.5C1—C9—H9122.4
H17B—C17B—H17C109.5C8—C9—H9122.4
C10B—C6B—C5B112.75 (19)C3A—C4A—C5A118.6 (2)
C10B—C6B—C7B107.50 (18)C3A—C4A—H4A1107.7
C5B—C6B—C7B115.53 (17)C5A—C4A—H4A1107.7
C10B—C6B—H6B106.9C3A—C4A—H4A2107.7
C5B—C6B—H6B106.9C5A—C4A—H4A2107.7
C7B—C6B—H6B106.9H4A1—C4A—H4A2107.1
N2—C7A—C6A111.84 (17)O1—C16—N1124.2 (2)
N2—C7A—C8A111.92 (17)O1—C16—C17120.5 (2)
C6A—C7A—C8A110.75 (17)N1—C16—C17115.3 (2)
N2—C7A—H7A107.4C1A—C9A—C8A115.9 (2)
C6A—C7A—H7A107.4C1A—C9A—H9A122.1
C8A—C7A—H7A107.4C8A—C9A—H9A122.1
C9A—C1A—C2A125.9 (2)C9—C1—C2125.6 (3)
C9A—C1A—C10A113.3 (2)C9—C1—C10113.6 (2)
C2A—C1A—C10A119.1 (2)C2—C1—C10118.8 (3)
C10A—C6A—C5A112.72 (18)C5A—C15A—H15A109.5
C10A—C6A—C7A107.68 (17)C5A—C15A—H15B109.5
C5A—C6A—C7A114.81 (17)H15A—C15A—H15B109.5
C10A—C6A—H6A107.1C5A—C15A—H15C109.5
C5A—C6A—H6A107.1H15A—C15A—H15C109.5
C7A—C6A—H6A107.1H15B—C15A—H15C109.5
N1—C7—C8113.79 (18)C1B—C2B—C3B109.4 (2)
N1—C7—C6109.92 (17)C1B—C2B—H2B1109.8
C8—C7—C6111.06 (17)C3B—C2B—H2B1109.8
N1—C7—H7107.3C1B—C2B—H2B2109.8
C8—C7—H7107.3C3B—C2B—H2B2109.8
C6—C7—H7107.3H2B1—C2B—H2B2108.2
N3—C7B—C6B109.80 (16)C5—C15—H15D109.5
N3—C7B—C8B111.28 (18)C5—C15—H15E109.5
C6B—C7B—C8B111.14 (18)H15D—C15—H15E109.5
N3—C7B—H7B108.2C5—C15—H15F109.5
C6B—C7B—H7B108.2H15D—C15—H15F109.5
C8B—C7B—H7B108.2H15E—C15—H15F109.5
C8A—C12A—C11A109.77 (18)C3B—C4B—C5B118.9 (2)
C8A—C12A—H12A109.7C3B—C4B—H4B1107.6
C11A—C12A—H12A109.7C5B—C4B—H4B1107.6
C8A—C12A—H12B109.7C3B—C4B—H4B2107.6
C11A—C12A—H12B109.7C5B—C4B—H4B2107.6
H12A—C12A—H12B108.2H4B1—C4B—H4B2107.0
C1B—C10B—C11B109.4 (2)C5A—C14A—H14G109.5
C1B—C10B—C6B106.23 (18)C5A—C14A—H14H109.5
C11B—C10B—C6B108.7 (2)H14G—C14A—H14H109.5
C1B—C10B—H10B110.8C5A—C14A—H14I109.5
C11B—C10B—H10B110.8H14G—C14A—H14I109.5
C6B—C10B—H10B110.8H14H—C14A—H14I109.5
C5—C4—C3118.1 (2)C2B—C3B—C4B116.2 (2)
C5—C4—H4A107.8C2B—C3B—H3B1108.2
C3—C4—H4A107.8C4B—C3B—H3B1108.2
C5—C4—H4B107.8C2B—C3B—H3B2108.2
C3—C4—H4B107.8C4B—C3B—H3B2108.2
H4A—C4—H4B107.1H3B1—C3B—H3B2107.4
C1B—C9B—C8B115.7 (2)C16—C17—H17G109.5
C1B—C9B—H9B122.2C16—C17—H17H109.5
C8B—C9B—H9B122.2H17G—C17—H17H109.5
C14—C5—C15106.5 (2)C16—C17—H17I109.5
C14—C5—C4107.3 (2)H17G—C17—H17I109.5
C15—C5—C4110.6 (2)H17H—C17—H17I109.5
C14—C5—C6109.7 (2)C8B—C13B—H13G109.5
C15—C5—C6108.7 (2)C8B—C13B—H13H109.5
C4—C5—C6113.8 (2)H13G—C13B—H13H109.5
C5B—C14B—H14A109.5C8B—C13B—H13I109.5
C5B—C14B—H14B109.5H13G—C13B—H13I109.5
H14A—C14B—H14B109.5H13H—C13B—H13I109.5
C5B—C14B—H14C109.5C10—C11—C12109.66 (19)
H14A—C14B—H14C109.5C10—C11—H11C109.7
H14B—C14B—H14C109.5C12—C11—H11C109.7
O2—C16A—N2123.0 (2)C10—C11—H11D109.7
O2—C16A—C17A121.9 (2)C12—C11—H11D109.7
N2—C16A—C17A115.2 (2)H11C—C11—H11D108.2
C9—C8—C13113.1 (2)C2—C3—C4115.7 (2)
C9—C8—C12109.6 (2)C2—C3—H3A108.3
C13—C8—C12111.4 (2)C4—C3—H3A108.3
C9—C8—C7102.04 (17)C2—C3—H3B108.3
C13—C8—C7111.51 (19)C4—C3—H3B108.3
C12—C8—C7108.78 (19)H3A—C3—H3B107.4
C4A—C3A—C2A115.5 (2)C12B—C11B—C10B110.48 (19)
C4A—C3A—H3A1108.4C12B—C11B—H11E109.6
C2A—C3A—H3A1108.4C10B—C11B—H11E109.6
C4A—C3A—H3A2108.4C12B—C11B—H11F109.6
C2A—C3A—H3A2108.4C10B—C11B—H11F109.6
H3A1—C3A—H3A2107.5H11E—C11B—H11F108.1
C11B—C12B—C8B109.9 (2)C1—C2—C3109.8 (2)
C11B—C12B—H12C109.7C1—C2—H2A109.7
C8B—C12B—H12C109.7C3—C2—H2A109.7
C11B—C12B—H12D109.7C1—C2—H2B109.7
C8B—C12B—H12D109.7C3—C2—H2B109.7
H12C—C12B—H12D108.2H2A—C2—H2B108.2
C12A—C11A—C10A109.92 (19)C5B—C15B—H15G109.5
C12A—C11A—H11A109.7C5B—C15B—H15H109.5
C10A—C11A—H11A109.7H15G—C15B—H15H109.5
C12A—C11A—H11B109.7C5B—C15B—H15I109.5
C10A—C11A—H11B109.7H15G—C15B—H15I109.5
H11A—C11A—H11B108.2H15H—C15B—H15I109.5
C7B—N3—C16B—O3−3.5 (3)C7A—N2—C16A—C17A174.9 (2)
C7B—N3—C16B—C17B175.87 (19)N1—C7—C8—C9173.33 (19)
C15B—C5B—C6B—C10B−72.3 (3)C6—C7—C8—C9−62.0 (2)
C14B—C5B—C6B—C10B171.80 (19)N1—C7—C8—C1352.3 (2)
C4B—C5B—C6B—C10B51.4 (3)C6—C7—C8—C13177.01 (19)
C15B—C5B—C6B—C7B163.6 (2)N1—C7—C8—C12−70.9 (2)
C14B—C5B—C6B—C7B47.6 (3)C6—C7—C8—C1253.7 (2)
C4B—C5B—C6B—C7B−72.7 (2)C8A—C12A—C11A—C10A3.0 (3)
C16A—N2—C7A—C6A128.1 (2)C1A—C10A—C11A—C12A−55.8 (3)
C16A—N2—C7A—C8A−106.9 (2)C6A—C10A—C11A—C12A59.9 (3)
C9A—C8A—C7A—N2175.83 (18)C9A—C1A—C2A—C3A110.7 (3)
C13A—C8A—C7A—N254.9 (2)C10A—C1A—C2A—C3A−53.5 (3)
C12A—C8A—C7A—N2−68.5 (2)C4A—C3A—C2A—C1A−30.7 (3)
C9A—C8A—C7A—C6A−58.6 (2)C5—C6—C10—C1−74.6 (3)
C13A—C8A—C7A—C6A−179.54 (19)C7—C6—C10—C152.6 (2)
C12A—C8A—C7A—C6A57.1 (2)C5—C6—C10—C11166.7 (2)
C11A—C10A—C1A—C9A54.5 (2)C7—C6—C10—C11−66.1 (2)
C6A—C10A—C1A—C9A−63.1 (2)C1B—C9B—C8B—C13B177.7 (2)
C11A—C10A—C1A—C2A−139.4 (2)C1B—C9B—C8B—C12B−56.9 (3)
C6A—C10A—C1A—C2A103.0 (2)C1B—C9B—C8B—C7B57.6 (3)
C1A—C10A—C6A—C5A−72.7 (2)C11B—C12B—C8B—C9B52.1 (2)
C11A—C10A—C6A—C5A169.4 (2)C11B—C12B—C8B—C13B177.3 (2)
C1A—C10A—C6A—C7A54.9 (2)C11B—C12B—C8B—C7B−59.6 (2)
C11A—C10A—C6A—C7A−62.9 (2)N3—C7B—C8B—C9B179.91 (18)
C15A—C5A—C6A—C10A−70.3 (2)C6B—C7B—C8B—C9B−57.4 (2)
C14A—C5A—C6A—C10A173.54 (19)N3—C7B—C8B—C13B59.1 (2)
C4A—C5A—C6A—C10A53.0 (3)C6B—C7B—C8B—C13B−178.22 (19)
C15A—C5A—C6A—C7A165.91 (19)N3—C7B—C8B—C12B−64.9 (2)
C14A—C5A—C6A—C7A49.7 (2)C6B—C7B—C8B—C12B57.8 (2)
C4A—C5A—C6A—C7A−70.8 (2)C9—C8—C12—C1149.7 (3)
N2—C7A—C6A—C10A129.69 (18)C13—C8—C12—C11175.5 (2)
C8A—C7A—C6A—C10A4.1 (2)C7—C8—C12—C11−61.1 (3)
N2—C7A—C6A—C5A−103.9 (2)C13—C8—C9—C1177.0 (2)
C8A—C7A—C6A—C5A130.54 (19)C12—C8—C9—C1−58.0 (3)
C16—N1—C7—C8−112.4 (2)C7—C8—C9—C157.1 (3)
C16—N1—C7—C6122.3 (2)C2A—C3A—C4A—C5A83.0 (3)
C10—C6—C7—N1135.11 (19)C15A—C5A—C4A—C3A53.1 (3)
C5—C6—C7—N1−98.2 (2)C14A—C5A—C4A—C3A169.2 (2)
C10—C6—C7—C88.3 (2)C6A—C5A—C4A—C3A−69.4 (3)
C5—C6—C7—C8135.0 (2)C7—N1—C16—O17.7 (4)
C16B—N3—C7B—C6B136.5 (2)C7—N1—C16—C17−171.3 (2)
C16B—N3—C7B—C8B−100.0 (2)C2A—C1A—C9A—C8A−161.7 (2)
C10B—C6B—C7B—N3126.08 (18)C10A—C1A—C9A—C8A3.3 (3)
C5B—C6B—C7B—N3−107.1 (2)C13A—C8A—C9A—C1A177.5 (2)
C10B—C6B—C7B—C8B2.5 (2)C12A—C8A—C9A—C1A−58.0 (3)
C5B—C6B—C7B—C8B129.40 (19)C7A—C8A—C9A—C1A57.3 (2)
C9A—C8A—C12A—C11A51.1 (3)C8—C9—C1—C2−159.1 (2)
C13A—C8A—C12A—C11A176.0 (2)C8—C9—C1—C104.8 (3)
C7A—C8A—C12A—C11A−60.9 (2)C11—C10—C1—C953.5 (3)
C9B—C1B—C10B—C11B54.7 (3)C6—C10—C1—C9−64.0 (3)
C2B—C1B—C10B—C11B−138.9 (2)C11—C10—C1—C2−141.5 (2)
C9B—C1B—C10B—C6B−62.5 (3)C6—C10—C1—C2101.0 (3)
C2B—C1B—C10B—C6B103.8 (2)C9B—C1B—C2B—C3B110.3 (3)
C5B—C6B—C10B—C1B−72.8 (2)C10B—C1B—C2B—C3B−54.0 (3)
C7B—C6B—C10B—C1B55.7 (2)C15B—C5B—C4B—C3B55.3 (3)
C5B—C6B—C10B—C11B169.54 (19)C14B—C5B—C4B—C3B171.0 (2)
C7B—C6B—C10B—C11B−62.0 (2)C6B—C5B—C4B—C3B−67.6 (3)
C2B—C1B—C9B—C8B−163.1 (2)C1B—C2B—C3B—C4B−30.3 (4)
C10B—C1B—C9B—C8B1.9 (3)C5B—C4B—C3B—C2B82.4 (3)
C3—C4—C5—C14171.3 (2)C1—C10—C11—C12−56.6 (3)
C3—C4—C5—C1555.5 (3)C6—C10—C11—C1259.4 (3)
C3—C4—C5—C6−67.2 (3)C8—C12—C11—C104.6 (3)
C10—C6—C5—C14172.6 (2)C5—C4—C3—C285.2 (4)
C7—C6—C5—C1449.2 (3)C8B—C12B—C11B—C10B1.3 (3)
C10—C6—C5—C15−71.2 (3)C1B—C10B—C11B—C12B−54.3 (3)
C7—C6—C5—C15165.4 (2)C6B—C10B—C11B—C12B61.3 (2)
C10—C6—C5—C452.5 (3)C9—C1—C2—C3114.8 (3)
C7—C6—C5—C4−70.9 (3)C10—C1—C2—C3−48.3 (4)
C7A—N2—C16A—O2−4.9 (4)C4—C3—C2—C1−35.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.862.042.893 (2)173
N2—H2···O30.862.112.956 (3)167
N3—H3···O1i0.862.062.909 (2)169
Symmetry code: (i) −x+2, y+1/2, −z+1/2.
 

Acknowledgements

The authors thank the Laboratoire de Chimie de Coordination, UPR-CNRS 8241 Toulouse, for the X-ray measurements.

References

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ISSN: 2414-3146
Volume 2| Part 6| June 2017| x170805
https://doi.org/10.1107/S2414314617008057
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