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

Journal logoIUCrDATA
ISSN: 2414-3146

(1S,2R,8R)-11-Amino-2,2-di­chloro-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.01,3]dodec-10-en-9-one

CROSSMARK_Color_square_no_text.svg

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 du Solide Appliquée, Faculté des Sciences, Mohammed V University in Rabat, Avenue Ibn Battouta, BP 1014 Rabat, Morocco
*Correspondence e-mail: aitelhad2017@gmail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 11 February 2017; accepted 14 February 2017; online 24 February 2017)

The title compound, C16H23Cl2NO, crystallizes in the monoclinic space group P21 with two independent mol­ecules (A and B) in the asymmetric unit. They have essentially the same conformation. Each mol­ecule is built up from fused six- and seven-membered rings and an additional three-membered ring. The six-membered ring has an envelope conformation, with the C atom belonging to the three-membered ring forming the flap, while the seven-membered ring displays a boat conformation. In the crystal, mol­ecules are linked into chains propagating along the a-axis direction by N—H⋯O hydrogen bonds.

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

Structure description

As part of our studies of the essential oil of the Atlas cedar (Cedrus atlantica) made up mainly (50%) of β-himachalene (Benharref et al., 2013[Benharref, A., Ourhriss, N., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o933-o934.]; 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.]), the reactivity of this sesquiterpene and its derivatives has been studied extensively by our team in order to prepare new products having biological properties (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.]; Zaki et al., 2014[Zaki, M., Benharref, A., El Ammari, L., Saadi, M. & Berraho, M. (2014). Acta Cryst. E70, o444.]; Benharref et al., 2015[Benharref, A., Elkarroumi, J., El Ammari, L., Saadi, M. & Berraho, M. (2015). Acta Cryst. E71, o659-o660.], 2016[Benharref, A., Oukhrib, A., Ait Elhad, M., El Ammari, L., Saadi, M. & Berraho, M. (2016). IUCrData, 1, x160703.]). 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.]).

The asymmetric unit (Fig. 1[link]) includes two crystallographically independent mol­ecules (A and B). A least-squares overlay of the two mol­ecules (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) is shown in Fig. 2[link] and reveals that there is almost no difference between them. In both mol­ecules, the six-membered rings has an envelope conformation as indicated by the total puckering amplitude QT = 0.438 (3) Å and spherical polar angle θ2 = 121.6 (4)° with φ2 = −164.2 (5)°, whereas the seven-membered ring displays a boat conformation with QT = 1.133 (3) Å, θ2 = 88.37 (17)°; φ2 =-49.66 (16)° and φ3 = −86.92 (5).

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2]
Figure 2
The AutoMolFit (PLATON; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) of mol­ecule B (red) on mol­ecule A (black).

In the crystal, mol­ecules are linked via N—H⋯O hydrogen bonds (Table 1[link]), forming chains along [100] as shown in Fig. 3[link]. Owing to the presence of Cl atoms, the absolute configuration could be determined, by refining the Flack parameter as C1(S), C3(R), C8(R) and C17(S), C19(R), C24(R), respectively.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1B⋯O1i 0.86 2.00 2.816 (3) 159
N2—H2B⋯O2i 0.86 2.06 2.873 (3) 159
Symmetry code: (i) x-1, y, z.
[Figure 3]
Figure 3
Crystal structure projection along the b axis of the title compound, showing mol­ecules linked by N—H⋯O hydrogen bonds, forming chains along [100].

Synthesis and crystallization

To a solution of (1S,3R,8R)-2,2-di­chloro-3,7,7,10-tetra­methyl­tri­cyclo [6. 4.0.01,3]dodec-9-en-11-one (1 g, 3.32 mmol) (Benharref et al., 2010[Benharref, A., El Ammari, L. & Berraho, M. (2010). Acta Cryst. E66, o2911.]) in 20 ml of trifuoro­acetic acid at 10°C was added with stirring (500 mg, 7, 8 mmol) of NaN3. After being stirred at room temperature for 24 h, the mixture was neutralized with Na2CO3 and extracted with diethyl ether solution. The combined organic phases were dried on sodium sulfate and concentrated at reduced pressure to give the crude product, which was chromatographed on a silica gel column(cyclo­hexa­ne–ether, 20–80 by volume) to give 630 mg (2 mmol) of the title product, which was recrystallized from diethyl ether.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C16H23Cl2NO
Mr 316.25
Crystal system, space group Monoclinic, P21
Temperature (K) 296
a, b, c (Å) 6.9962 (13), 18.654 (4), 12.426 (3)
β (°) 91.273 (5)
V3) 1621.4 (5)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.40
Crystal size (mm) 0.24 × 0.2 × 0.15
 
Data collection
Diffractometer Bruker X8 APEX
Absorption correction Multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.629, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections 58110, 8375, 6511
Rint 0.053
(sin θ/λ)max−1) 0.676
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.094, 1.02
No. of reflections 8375
No. of parameters 369
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.26, −0.18
Absolute structure Flack x determined using 2672 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 0.010 (18)
Computer programs: APEX2 and SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), 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 publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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); software used to prepare material for publication: publCIF (Westrip, 2010).

(1S,2R,8R)-11-Amino-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-10-en-9-one top
Crystal data top
C16H23Cl2NOF(000) = 672
Mr = 316.25Dx = 1.296 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.9962 (13) ÅCell parameters from 6632 reflections
b = 18.654 (4) Åθ = 1.6–26.4°
c = 12.426 (3) ŵ = 0.40 mm1
β = 91.273 (5)°T = 296 K
V = 1621.4 (5) Å3Prismatic, colourless
Z = 40.24 × 0.2 × 0.15 mm
Data collection top
Bruker X8 APEX
diffractometer
6511 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
φ and ω scansθmax = 28.7°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 98
Tmin = 0.629, Tmax = 0.747k = 2525
58110 measured reflectionsl = 1616
8375 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.0442P)2 + 0.1774P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.26 e Å3
8375 reflectionsΔρmin = 0.18 e Å3
369 parametersAbsolute structure: Flack x determined using 2672 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.010 (18)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3670 (4)0.62609 (15)0.5109 (2)0.0342 (6)
C20.3868 (5)0.69648 (17)0.5700 (2)0.0469 (7)
C30.3294 (5)0.63016 (17)0.6324 (2)0.0452 (7)
C40.4790 (6)0.59418 (18)0.7054 (2)0.0540 (8)
H4A0.45940.60860.77930.065*
H4B0.60540.60990.68520.065*
C50.4675 (6)0.51212 (19)0.6972 (3)0.0610 (10)
H5A0.58830.49230.72280.073*
H5B0.36940.49550.74520.073*
C60.4241 (5)0.48237 (17)0.5853 (2)0.0497 (8)
H6A0.29320.49510.56640.060*
H6B0.42920.43050.59020.060*
C70.5494 (4)0.50495 (15)0.4912 (2)0.0419 (7)
C80.5481 (4)0.58915 (14)0.4760 (2)0.0336 (6)
H80.65080.60760.52320.040*
C90.5984 (4)0.61206 (16)0.3623 (2)0.0375 (6)
C100.4512 (4)0.63564 (15)0.2889 (2)0.0345 (6)
C110.2637 (4)0.63392 (14)0.3179 (2)0.0321 (5)
C120.2033 (4)0.61729 (17)0.4302 (2)0.0374 (6)
H12A0.15630.56840.43300.045*
H12B0.09960.64900.44930.045*
C130.1274 (6)0.6244 (2)0.6731 (3)0.0649 (10)
H13A0.11810.65020.73960.097*
H13B0.09630.57490.68460.097*
H13C0.03970.64450.62080.097*
C140.7561 (6)0.4808 (2)0.5124 (4)0.0719 (11)
H14A0.76040.42940.51770.108*
H14B0.80320.50140.57860.108*
H14C0.83430.49620.45430.108*
C150.4721 (6)0.46588 (19)0.3904 (3)0.0609 (9)
H15A0.54290.48070.32900.091*
H15B0.33950.47750.37910.091*
H15C0.48570.41510.40020.091*
C160.5071 (5)0.65700 (18)0.1765 (2)0.0463 (7)
H16A0.46950.62000.12670.069*
H16B0.64310.66360.17460.069*
H16C0.44420.70100.15690.069*
C170.0333 (4)0.41311 (14)0.0173 (2)0.0318 (6)
C180.0172 (4)0.49436 (15)0.0174 (2)0.0393 (6)
C190.0796 (4)0.45709 (16)0.0835 (2)0.0415 (7)
C200.0609 (6)0.45095 (18)0.1779 (2)0.0522 (8)
H20A0.03260.48780.23030.063*
H20B0.18920.45930.15280.063*
C210.0535 (7)0.3772 (2)0.2327 (3)0.0652 (10)
H21A0.17440.36910.27050.078*
H21B0.04550.37830.28610.078*
C220.0149 (6)0.31356 (18)0.1570 (3)0.0562 (9)
H22A0.11510.31820.12920.067*
H22B0.01940.27030.20040.067*
C230.1448 (5)0.30144 (16)0.0602 (2)0.0447 (7)
C240.1500 (4)0.36961 (14)0.0151 (2)0.0324 (6)
H240.25010.40110.01480.039*
C250.2082 (4)0.35152 (15)0.1298 (2)0.0348 (6)
C260.0656 (4)0.34250 (15)0.2124 (2)0.0342 (6)
C270.1239 (4)0.35081 (14)0.1896 (2)0.0306 (5)
C280.1911 (4)0.37905 (15)0.0838 (2)0.0337 (6)
H28A0.24590.34000.04330.040*
H28B0.29100.41420.09710.040*
C290.2869 (5)0.4639 (2)0.1167 (3)0.0613 (9)
H29A0.30290.50740.15670.092*
H29B0.32010.42370.16080.092*
H29C0.36860.46480.05360.092*
C300.3499 (6)0.2850 (3)0.0979 (4)0.0789 (13)
H30A0.35180.24130.13860.118*
H30B0.39700.32360.14230.118*
H30C0.42960.27990.03650.118*
C310.0658 (6)0.23478 (18)0.0001 (3)0.0628 (10)
H31A0.06710.19440.04780.094*
H31B0.14410.22470.06070.094*
H31C0.06290.24400.02470.094*
C320.1267 (5)0.31821 (19)0.3219 (2)0.0491 (8)
H32A0.08930.26920.33300.074*
H32B0.26310.32220.32660.074*
H32C0.06680.34780.37620.074*
N10.1202 (4)0.64687 (15)0.24803 (19)0.0442 (6)
H1A0.14400.65670.18210.053*
H1B0.00390.64530.26900.053*
N20.2662 (3)0.33465 (14)0.25976 (19)0.0419 (6)
H2A0.24030.31820.32240.050*
H2B0.38320.34070.24200.050*
O10.7681 (3)0.60721 (15)0.3360 (2)0.0583 (6)
O20.3815 (3)0.34305 (14)0.14593 (19)0.0532 (6)
Cl10.20775 (13)0.53695 (4)0.02330 (7)0.0559 (2)
Cl20.18423 (14)0.54562 (5)0.09233 (7)0.0629 (2)
Cl30.61389 (17)0.73707 (5)0.58908 (8)0.0714 (3)
Cl40.21570 (18)0.76477 (5)0.54750 (8)0.0734 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0363 (15)0.0378 (14)0.0286 (12)0.0006 (11)0.0015 (10)0.0034 (10)
C20.064 (2)0.0387 (16)0.0383 (16)0.0063 (14)0.0031 (14)0.0014 (12)
C30.063 (2)0.0415 (16)0.0313 (14)0.0066 (14)0.0002 (13)0.0024 (12)
C40.081 (2)0.0484 (18)0.0322 (15)0.0021 (17)0.0087 (15)0.0000 (13)
C50.095 (3)0.0488 (19)0.0386 (17)0.0041 (18)0.0074 (17)0.0117 (14)
C60.066 (2)0.0350 (15)0.0483 (17)0.0053 (14)0.0016 (15)0.0064 (13)
C70.0438 (18)0.0338 (14)0.0480 (17)0.0002 (12)0.0011 (13)0.0021 (12)
C80.0306 (15)0.0324 (13)0.0375 (14)0.0032 (11)0.0042 (11)0.0023 (11)
C90.0280 (15)0.0396 (15)0.0450 (15)0.0056 (12)0.0046 (12)0.0011 (12)
C100.0317 (15)0.0381 (14)0.0339 (13)0.0042 (11)0.0042 (11)0.0034 (11)
C110.0319 (15)0.0307 (13)0.0337 (13)0.0025 (10)0.0006 (11)0.0022 (10)
C120.0305 (14)0.0486 (16)0.0334 (13)0.0018 (12)0.0043 (11)0.0030 (11)
C130.082 (3)0.072 (2)0.0418 (18)0.012 (2)0.0242 (17)0.0027 (17)
C140.055 (2)0.050 (2)0.111 (3)0.0146 (17)0.002 (2)0.015 (2)
C150.086 (3)0.0411 (18)0.0554 (19)0.0044 (18)0.0070 (18)0.0075 (15)
C160.0466 (19)0.0526 (18)0.0400 (16)0.0035 (14)0.0112 (13)0.0070 (13)
C170.0338 (15)0.0302 (13)0.0314 (13)0.0025 (11)0.0028 (11)0.0043 (10)
C180.0471 (17)0.0319 (14)0.0385 (15)0.0022 (12)0.0060 (12)0.0032 (11)
C190.0534 (19)0.0340 (14)0.0374 (14)0.0024 (13)0.0043 (12)0.0089 (12)
C200.079 (2)0.0444 (17)0.0331 (14)0.0099 (16)0.0053 (14)0.0059 (13)
C210.105 (3)0.055 (2)0.0358 (17)0.013 (2)0.0030 (18)0.0026 (15)
C220.084 (3)0.0430 (18)0.0419 (17)0.0079 (17)0.0071 (17)0.0063 (13)
C230.0509 (19)0.0364 (15)0.0468 (17)0.0008 (13)0.0002 (14)0.0063 (13)
C240.0300 (14)0.0326 (13)0.0346 (13)0.0033 (11)0.0029 (11)0.0023 (10)
C250.0276 (15)0.0336 (13)0.0432 (15)0.0025 (11)0.0049 (11)0.0008 (11)
C260.0316 (15)0.0363 (14)0.0351 (13)0.0040 (11)0.0053 (11)0.0061 (11)
C270.0307 (14)0.0290 (12)0.0323 (12)0.0040 (10)0.0011 (10)0.0028 (10)
C280.0252 (13)0.0375 (14)0.0386 (14)0.0015 (11)0.0040 (11)0.0087 (11)
C290.067 (2)0.059 (2)0.059 (2)0.0056 (19)0.0206 (17)0.0196 (18)
C300.071 (3)0.081 (3)0.084 (3)0.017 (2)0.016 (2)0.030 (2)
C310.091 (3)0.0307 (15)0.067 (2)0.0023 (17)0.012 (2)0.0013 (15)
C320.0436 (18)0.060 (2)0.0441 (17)0.0082 (15)0.0144 (14)0.0128 (15)
N10.0338 (14)0.0620 (17)0.0367 (13)0.0003 (12)0.0009 (10)0.0118 (12)
N20.0331 (13)0.0545 (15)0.0379 (12)0.0010 (11)0.0001 (10)0.0134 (11)
O10.0245 (11)0.0809 (18)0.0700 (15)0.0016 (11)0.0104 (10)0.0140 (13)
O20.0244 (11)0.0735 (16)0.0620 (14)0.0005 (10)0.0066 (9)0.0087 (12)
Cl10.0660 (5)0.0450 (4)0.0565 (4)0.0231 (4)0.0068 (4)0.0036 (4)
Cl20.0772 (6)0.0421 (4)0.0684 (5)0.0142 (4)0.0204 (4)0.0017 (4)
Cl30.0953 (8)0.0444 (4)0.0734 (6)0.0183 (5)0.0224 (5)0.0053 (4)
Cl40.1074 (8)0.0535 (5)0.0593 (5)0.0355 (5)0.0064 (5)0.0030 (4)
Geometric parameters (Å, º) top
C1—C21.509 (4)C17—C181.520 (4)
C1—C81.514 (4)C17—C191.538 (4)
C1—C121.515 (4)C18—C191.506 (4)
C1—C31.540 (4)C18—Cl21.760 (3)
C2—C31.519 (4)C18—Cl11.766 (3)
C2—Cl41.766 (3)C19—C201.518 (4)
C2—Cl31.771 (4)C19—C291.522 (5)
C3—C131.515 (5)C20—C211.536 (5)
C3—C41.525 (4)C20—H20A0.9700
C4—C51.536 (5)C20—H20B0.9700
C4—H4A0.9700C21—C221.534 (5)
C4—H4B0.9700C21—H21A0.9700
C5—C61.521 (4)C21—H21B0.9700
C5—H5A0.9700C22—C231.541 (5)
C5—H5B0.9700C22—H22A0.9700
C6—C71.536 (4)C22—H22B0.9700
C6—H6A0.9700C23—C301.530 (5)
C6—H6B0.9700C23—C311.547 (5)
C7—C141.533 (5)C23—C241.580 (4)
C7—C151.537 (5)C24—C251.529 (4)
C7—C81.582 (4)C24—H240.9800
C8—C91.524 (4)C25—O21.243 (3)
C8—H80.9800C25—C261.425 (4)
C9—O11.241 (3)C26—C271.371 (4)
C9—C101.430 (4)C26—C321.506 (4)
C10—C111.369 (4)C27—N21.343 (3)
C10—C161.512 (4)C27—C281.501 (3)
C11—N11.335 (3)C28—H28A0.9700
C11—C121.499 (4)C28—H28B0.9700
C12—H12A0.9700C29—H29A0.9600
C12—H12B0.9700C29—H29B0.9600
C13—H13A0.9600C29—H29C0.9600
C13—H13B0.9600C30—H30A0.9600
C13—H13C0.9600C30—H30B0.9600
C14—H14A0.9600C30—H30C0.9600
C14—H14B0.9600C31—H31A0.9600
C14—H14C0.9600C31—H31B0.9600
C15—H15A0.9600C31—H31C0.9600
C15—H15B0.9600C32—H32A0.9600
C15—H15C0.9600C32—H32B0.9600
C16—H16A0.9600C32—H32C0.9600
C16—H16B0.9600N1—H1A0.8600
C16—H16C0.9600N1—H1B0.8600
C17—C281.505 (4)N2—H2A0.8600
C17—C241.517 (4)N2—H2B0.8600
C2—C1—C8117.9 (2)C28—C17—C19120.5 (2)
C2—C1—C12118.4 (3)C24—C17—C19117.7 (2)
C8—C1—C12112.7 (2)C18—C17—C1959.03 (18)
C2—C1—C359.76 (19)C19—C18—C1761.08 (18)
C8—C1—C3117.8 (2)C19—C18—Cl2119.3 (2)
C12—C1—C3120.8 (2)C17—C18—Cl2119.6 (2)
C1—C2—C361.13 (19)C19—C18—Cl1121.2 (2)
C1—C2—Cl4119.8 (2)C17—C18—Cl1121.0 (2)
C3—C2—Cl4118.8 (2)Cl2—C18—Cl1108.38 (16)
C1—C2—Cl3120.6 (2)C18—C19—C20118.9 (3)
C3—C2—Cl3121.7 (2)C18—C19—C29118.9 (3)
Cl4—C2—Cl3108.40 (18)C20—C19—C29113.6 (3)
C13—C3—C2119.1 (3)C18—C19—C1759.90 (17)
C13—C3—C4113.8 (3)C20—C19—C17116.4 (3)
C2—C3—C4118.4 (3)C29—C19—C17119.0 (3)
C13—C3—C1120.3 (3)C19—C20—C21112.5 (3)
C2—C3—C159.10 (19)C19—C20—H20A109.1
C4—C3—C1115.5 (3)C21—C20—H20A109.1
C3—C4—C5111.4 (3)C19—C20—H20B109.1
C3—C4—H4A109.3C21—C20—H20B109.1
C5—C4—H4A109.3H20A—C20—H20B107.8
C3—C4—H4B109.3C22—C21—C20115.4 (3)
C5—C4—H4B109.3C22—C21—H21A108.4
H4A—C4—H4B108.0C20—C21—H21A108.4
C6—C5—C4115.7 (3)C22—C21—H21B108.4
C6—C5—H5A108.4C20—C21—H21B108.4
C4—C5—H5A108.4H21A—C21—H21B107.5
C6—C5—H5B108.4C21—C22—C23119.5 (3)
C4—C5—H5B108.4C21—C22—H22A107.4
H5A—C5—H5B107.4C23—C22—H22A107.4
C5—C6—C7119.3 (3)C21—C22—H22B107.4
C5—C6—H6A107.5C23—C22—H22B107.4
C7—C6—H6A107.5H22A—C22—H22B107.0
C5—C6—H6B107.5C30—C23—C22110.8 (3)
C7—C6—H6B107.5C30—C23—C31108.1 (3)
H6A—C6—H6B107.0C22—C23—C31106.6 (3)
C14—C7—C6109.9 (3)C30—C23—C24108.0 (3)
C14—C7—C15108.3 (3)C22—C23—C24111.5 (3)
C6—C7—C15107.1 (3)C31—C23—C24111.9 (3)
C14—C7—C8108.4 (3)C17—C24—C25110.1 (2)
C6—C7—C8111.2 (2)C17—C24—C23114.2 (2)
C15—C7—C8111.9 (3)C25—C24—C23112.6 (2)
C1—C8—C9110.5 (2)C17—C24—H24106.4
C1—C8—C7114.8 (2)C25—C24—H24106.4
C9—C8—C7112.9 (2)C23—C24—H24106.4
C1—C8—H8106.0O2—C25—C26122.6 (2)
C9—C8—H8106.0O2—C25—C24117.3 (2)
C7—C8—H8106.0C26—C25—C24120.0 (2)
O1—C9—C10122.3 (3)C27—C26—C25120.2 (2)
O1—C9—C8117.7 (3)C27—C26—C32121.1 (2)
C10—C9—C8120.0 (2)C25—C26—C32118.5 (2)
C11—C10—C9120.4 (2)N2—C27—C26123.2 (2)
C11—C10—C16121.2 (3)N2—C27—C28113.9 (2)
C9—C10—C16118.2 (2)C26—C27—C28122.9 (2)
N1—C11—C10122.4 (2)C27—C28—C17112.9 (2)
N1—C11—C12114.8 (2)C27—C28—H28A109.0
C10—C11—C12122.8 (2)C17—C28—H28A109.0
C11—C12—C1111.7 (2)C27—C28—H28B109.0
C11—C12—H12A109.3C17—C28—H28B109.0
C1—C12—H12A109.3H28A—C28—H28B107.8
C11—C12—H12B109.3C19—C29—H29A109.5
C1—C12—H12B109.3C19—C29—H29B109.5
H12A—C12—H12B107.9H29A—C29—H29B109.5
C3—C13—H13A109.5C19—C29—H29C109.5
C3—C13—H13B109.5H29A—C29—H29C109.5
H13A—C13—H13B109.5H29B—C29—H29C109.5
C3—C13—H13C109.5C23—C30—H30A109.5
H13A—C13—H13C109.5C23—C30—H30B109.5
H13B—C13—H13C109.5H30A—C30—H30B109.5
C7—C14—H14A109.5C23—C30—H30C109.5
C7—C14—H14B109.5H30A—C30—H30C109.5
H14A—C14—H14B109.5H30B—C30—H30C109.5
C7—C14—H14C109.5C23—C31—H31A109.5
H14A—C14—H14C109.5C23—C31—H31B109.5
H14B—C14—H14C109.5H31A—C31—H31B109.5
C7—C15—H15A109.5C23—C31—H31C109.5
C7—C15—H15B109.5H31A—C31—H31C109.5
H15A—C15—H15B109.5H31B—C31—H31C109.5
C7—C15—H15C109.5C26—C32—H32A109.5
H15A—C15—H15C109.5C26—C32—H32B109.5
H15B—C15—H15C109.5H32A—C32—H32B109.5
C10—C16—H16A109.5C26—C32—H32C109.5
C10—C16—H16B109.5H32A—C32—H32C109.5
H16A—C16—H16B109.5H32B—C32—H32C109.5
C10—C16—H16C109.5C11—N1—H1A120.0
H16A—C16—H16C109.5C11—N1—H1B120.0
H16B—C16—H16C109.5H1A—N1—H1B120.0
C28—C17—C24113.2 (2)C27—N2—H2A120.0
C28—C17—C18118.3 (2)C27—N2—H2B120.0
C24—C17—C18118.1 (2)H2A—N2—H2B120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i0.862.002.816 (3)159
N2—H2B···O2i0.862.062.873 (3)159
Symmetry code: (i) x1, y, z.
 

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

First citationBenharref, A., El Ammari, L. & Berraho, M. (2010). Acta Cryst. E66, o2911.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBenharref, A., Elkarroumi, J., El Ammari, L., Saadi, M. & Berraho, M. (2015). Acta Cryst. E71, o659–o660.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBenharref, A., Oukhrib, A., Ait Elhad, M., El Ammari, L., Saadi, M. & Berraho, M. (2016). IUCrData, 1, x160703.  Google Scholar
First citationBenharref, A., Ourhriss, N., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o933–o934.  CSD CrossRef CAS IUCr Journals Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDaoubi, M., Durán-Patrón, R., Hmamouchi, M., Hernández-Galán, R., Benharref, A. & Collado, I. G. (2004). Pest Manag. Sci. 60, 927–932.  Web of Science CrossRef PubMed CAS Google Scholar
First citationEl Haib, A., Benharref, A., Parrès-Maynadié, S., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101–108.  Web of Science CrossRef CAS Google Scholar
First citationEl Jamili, H., Auhmani, A., Dakir, M., Lassaba, E., Benharref, A., Pierrot, M., Chiaroni, A. & Riche, C. (2002). Tetrahedron Lett. 43, 6645–6648.  CAS Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZaki, M., Benharref, A., El Ammari, L., Saadi, M. & Berraho, M. (2014). Acta Cryst. E70, o444.  CSD CrossRef IUCr Journals Google Scholar

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