organic compounds
(1S,2R,8R)-11-Amino-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-10-en-9-one
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
The title compound, C16H23Cl2NO, crystallizes in the monoclinic P21 with two independent molecules (A and B) in the 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 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.
Keywords: crystal structure; β-himachalene; Atlas cedar.
CCDC reference: 1532588
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; El Haib et al., 2011), 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; Zaki et al., 2014; Benharref et al., 2015, 2016). 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).
The ) includes two crystallographically independent molecules (A and B). A least-squares overlay of the two molecules (Spek, 2009) is shown in Fig. 2 and reveals that there is almost no difference between them. In both molecules, the six-membered rings has an 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).
(Fig. 1In the crystal, molecules are linked via N—H⋯O hydrogen bonds (Table 1), forming chains along [100] as shown in Fig. 3. Owing to the presence of Cl atoms, the could be determined, by refining the as C1(S), C3(R), C8(R) and C17(S), C19(R), C24(R), respectively.
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) 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 .
details are summarized in Table 2Structural data
CCDC reference: 1532588
https://doi.org/10.1107/S2414314617002553/bt4041sup1.cif
contains datablocks I, block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002553/bt4041Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617002553/bt4041Isup3.cml
Data collection: APEX2 (Bruker, 2009); cell
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).C16H23Cl2NO | F(000) = 672 |
Mr = 316.25 | Dx = 1.296 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9962 (13) Å | Cell parameters from 6632 reflections |
b = 18.654 (4) Å | θ = 1.6–26.4° |
c = 12.426 (3) Å | µ = 0.40 mm−1 |
β = 91.273 (5)° | T = 296 K |
V = 1621.4 (5) Å3 | Prismatic, colourless |
Z = 4 | 0.24 × 0.2 × 0.15 mm |
Bruker X8 APEX diffractometer | 6511 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.053 |
φ and ω scans | θmax = 28.7°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→8 |
Tmin = 0.629, Tmax = 0.747 | k = −25→25 |
58110 measured reflections | l = −16→16 |
8375 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.02 | Δρmax = 0.26 e Å−3 |
8375 reflections | Δρmin = −0.18 e Å−3 |
369 parameters | Absolute structure: Flack x determined using 2672 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.010 (18) |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3670 (4) | 0.62609 (15) | 0.5109 (2) | 0.0342 (6) | |
C2 | 0.3868 (5) | 0.69648 (17) | 0.5700 (2) | 0.0469 (7) | |
C3 | 0.3294 (5) | 0.63016 (17) | 0.6324 (2) | 0.0452 (7) | |
C4 | 0.4790 (6) | 0.59418 (18) | 0.7054 (2) | 0.0540 (8) | |
H4A | 0.4594 | 0.6086 | 0.7793 | 0.065* | |
H4B | 0.6054 | 0.6099 | 0.6852 | 0.065* | |
C5 | 0.4675 (6) | 0.51212 (19) | 0.6972 (3) | 0.0610 (10) | |
H5A | 0.5883 | 0.4923 | 0.7228 | 0.073* | |
H5B | 0.3694 | 0.4955 | 0.7452 | 0.073* | |
C6 | 0.4241 (5) | 0.48237 (17) | 0.5853 (2) | 0.0497 (8) | |
H6A | 0.2932 | 0.4951 | 0.5664 | 0.060* | |
H6B | 0.4292 | 0.4305 | 0.5902 | 0.060* | |
C7 | 0.5494 (4) | 0.50495 (15) | 0.4912 (2) | 0.0419 (7) | |
C8 | 0.5481 (4) | 0.58915 (14) | 0.4760 (2) | 0.0336 (6) | |
H8 | 0.6508 | 0.6076 | 0.5232 | 0.040* | |
C9 | 0.5984 (4) | 0.61206 (16) | 0.3623 (2) | 0.0375 (6) | |
C10 | 0.4512 (4) | 0.63564 (15) | 0.2889 (2) | 0.0345 (6) | |
C11 | 0.2637 (4) | 0.63392 (14) | 0.3179 (2) | 0.0321 (5) | |
C12 | 0.2033 (4) | 0.61729 (17) | 0.4302 (2) | 0.0374 (6) | |
H12A | 0.1563 | 0.5684 | 0.4330 | 0.045* | |
H12B | 0.0996 | 0.6490 | 0.4493 | 0.045* | |
C13 | 0.1274 (6) | 0.6244 (2) | 0.6731 (3) | 0.0649 (10) | |
H13A | 0.1181 | 0.6502 | 0.7396 | 0.097* | |
H13B | 0.0963 | 0.5749 | 0.6846 | 0.097* | |
H13C | 0.0397 | 0.6445 | 0.6208 | 0.097* | |
C14 | 0.7561 (6) | 0.4808 (2) | 0.5124 (4) | 0.0719 (11) | |
H14A | 0.7604 | 0.4294 | 0.5177 | 0.108* | |
H14B | 0.8032 | 0.5014 | 0.5786 | 0.108* | |
H14C | 0.8343 | 0.4962 | 0.4543 | 0.108* | |
C15 | 0.4721 (6) | 0.46588 (19) | 0.3904 (3) | 0.0609 (9) | |
H15A | 0.5429 | 0.4807 | 0.3290 | 0.091* | |
H15B | 0.3395 | 0.4775 | 0.3791 | 0.091* | |
H15C | 0.4857 | 0.4151 | 0.4002 | 0.091* | |
C16 | 0.5071 (5) | 0.65700 (18) | 0.1765 (2) | 0.0463 (7) | |
H16A | 0.4695 | 0.6200 | 0.1267 | 0.069* | |
H16B | 0.6431 | 0.6636 | 0.1746 | 0.069* | |
H16C | 0.4442 | 0.7010 | 0.1569 | 0.069* | |
C17 | −0.0333 (4) | 0.41311 (14) | −0.0173 (2) | 0.0318 (6) | |
C18 | −0.0172 (4) | 0.49436 (15) | −0.0174 (2) | 0.0393 (6) | |
C19 | −0.0796 (4) | 0.45709 (16) | 0.0835 (2) | 0.0415 (7) | |
C20 | 0.0609 (6) | 0.45095 (18) | 0.1779 (2) | 0.0522 (8) | |
H20A | 0.0326 | 0.4878 | 0.2303 | 0.063* | |
H20B | 0.1892 | 0.4593 | 0.1528 | 0.063* | |
C21 | 0.0535 (7) | 0.3772 (2) | 0.2327 (3) | 0.0652 (10) | |
H21A | 0.1744 | 0.3691 | 0.2705 | 0.078* | |
H21B | −0.0455 | 0.3783 | 0.2861 | 0.078* | |
C22 | 0.0149 (6) | 0.31356 (18) | 0.1570 (3) | 0.0562 (9) | |
H22A | −0.1151 | 0.3182 | 0.1292 | 0.067* | |
H22B | 0.0194 | 0.2703 | 0.2004 | 0.067* | |
C23 | 0.1448 (5) | 0.30144 (16) | 0.0602 (2) | 0.0447 (7) | |
C24 | 0.1500 (4) | 0.36961 (14) | −0.0151 (2) | 0.0324 (6) | |
H24 | 0.2501 | 0.4011 | 0.0148 | 0.039* | |
C25 | 0.2082 (4) | 0.35152 (15) | −0.1298 (2) | 0.0348 (6) | |
C26 | 0.0656 (4) | 0.34250 (15) | −0.2124 (2) | 0.0342 (6) | |
C27 | −0.1239 (4) | 0.35081 (14) | −0.1896 (2) | 0.0306 (5) | |
C28 | −0.1911 (4) | 0.37905 (15) | −0.0838 (2) | 0.0337 (6) | |
H28A | −0.2459 | 0.3400 | −0.0433 | 0.040* | |
H28B | −0.2910 | 0.4142 | −0.0971 | 0.040* | |
C29 | −0.2869 (5) | 0.4639 (2) | 0.1167 (3) | 0.0613 (9) | |
H29A | −0.3029 | 0.5074 | 0.1567 | 0.092* | |
H29B | −0.3201 | 0.4237 | 0.1608 | 0.092* | |
H29C | −0.3686 | 0.4648 | 0.0536 | 0.092* | |
C30 | 0.3499 (6) | 0.2850 (3) | 0.0979 (4) | 0.0789 (13) | |
H30A | 0.3518 | 0.2413 | 0.1386 | 0.118* | |
H30B | 0.3970 | 0.3236 | 0.1423 | 0.118* | |
H30C | 0.4296 | 0.2799 | 0.0365 | 0.118* | |
C31 | 0.0658 (6) | 0.23478 (18) | −0.0001 (3) | 0.0628 (10) | |
H31A | 0.0671 | 0.1944 | 0.0478 | 0.094* | |
H31B | 0.1441 | 0.2247 | −0.0607 | 0.094* | |
H31C | −0.0629 | 0.2440 | −0.0247 | 0.094* | |
C32 | 0.1267 (5) | 0.31821 (19) | −0.3219 (2) | 0.0491 (8) | |
H32A | 0.0893 | 0.2692 | −0.3330 | 0.074* | |
H32B | 0.2631 | 0.3222 | −0.3266 | 0.074* | |
H32C | 0.0668 | 0.3478 | −0.3762 | 0.074* | |
N1 | 0.1202 (4) | 0.64687 (15) | 0.24803 (19) | 0.0442 (6) | |
H1A | 0.1440 | 0.6567 | 0.1821 | 0.053* | |
H1B | 0.0039 | 0.6453 | 0.2690 | 0.053* | |
N2 | −0.2662 (3) | 0.33465 (14) | −0.25976 (19) | 0.0419 (6) | |
H2A | −0.2403 | 0.3182 | −0.3224 | 0.050* | |
H2B | −0.3832 | 0.3407 | −0.2420 | 0.050* | |
O1 | 0.7681 (3) | 0.60721 (15) | 0.3360 (2) | 0.0583 (6) | |
O2 | 0.3815 (3) | 0.34305 (14) | −0.14593 (19) | 0.0532 (6) | |
Cl1 | 0.20775 (13) | 0.53695 (4) | −0.02330 (7) | 0.0559 (2) | |
Cl2 | −0.18423 (14) | 0.54562 (5) | −0.09233 (7) | 0.0629 (2) | |
Cl3 | 0.61389 (17) | 0.73707 (5) | 0.58908 (8) | 0.0714 (3) | |
Cl4 | 0.21570 (18) | 0.76477 (5) | 0.54750 (8) | 0.0734 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0363 (15) | 0.0378 (14) | 0.0286 (12) | −0.0006 (11) | 0.0015 (10) | 0.0034 (10) |
C2 | 0.064 (2) | 0.0387 (16) | 0.0383 (16) | 0.0063 (14) | −0.0031 (14) | 0.0014 (12) |
C3 | 0.063 (2) | 0.0415 (16) | 0.0313 (14) | 0.0066 (14) | 0.0002 (13) | −0.0024 (12) |
C4 | 0.081 (2) | 0.0484 (18) | 0.0322 (15) | 0.0021 (17) | −0.0087 (15) | 0.0000 (13) |
C5 | 0.095 (3) | 0.0488 (19) | 0.0386 (17) | 0.0041 (18) | −0.0074 (17) | 0.0117 (14) |
C6 | 0.066 (2) | 0.0350 (15) | 0.0483 (17) | −0.0053 (14) | 0.0016 (15) | 0.0064 (13) |
C7 | 0.0438 (18) | 0.0338 (14) | 0.0480 (17) | −0.0002 (12) | −0.0011 (13) | 0.0021 (12) |
C8 | 0.0306 (15) | 0.0324 (13) | 0.0375 (14) | −0.0032 (11) | −0.0042 (11) | 0.0023 (11) |
C9 | 0.0280 (15) | 0.0396 (15) | 0.0450 (15) | −0.0056 (12) | 0.0046 (12) | 0.0011 (12) |
C10 | 0.0317 (15) | 0.0381 (14) | 0.0339 (13) | −0.0042 (11) | 0.0042 (11) | 0.0034 (11) |
C11 | 0.0319 (15) | 0.0307 (13) | 0.0337 (13) | −0.0025 (10) | 0.0006 (11) | 0.0022 (10) |
C12 | 0.0305 (14) | 0.0486 (16) | 0.0334 (13) | 0.0018 (12) | 0.0043 (11) | 0.0030 (11) |
C13 | 0.082 (3) | 0.072 (2) | 0.0418 (18) | 0.012 (2) | 0.0242 (17) | 0.0027 (17) |
C14 | 0.055 (2) | 0.050 (2) | 0.111 (3) | 0.0146 (17) | 0.002 (2) | 0.015 (2) |
C15 | 0.086 (3) | 0.0411 (18) | 0.0554 (19) | −0.0044 (18) | 0.0070 (18) | −0.0075 (15) |
C16 | 0.0466 (19) | 0.0526 (18) | 0.0400 (16) | −0.0035 (14) | 0.0112 (13) | 0.0070 (13) |
C17 | 0.0338 (15) | 0.0302 (13) | 0.0314 (13) | −0.0025 (11) | 0.0028 (11) | −0.0043 (10) |
C18 | 0.0471 (17) | 0.0319 (14) | 0.0385 (15) | −0.0022 (12) | −0.0060 (12) | −0.0032 (11) |
C19 | 0.0534 (19) | 0.0340 (14) | 0.0374 (14) | −0.0024 (13) | 0.0043 (12) | −0.0089 (12) |
C20 | 0.079 (2) | 0.0444 (17) | 0.0331 (14) | −0.0099 (16) | −0.0053 (14) | −0.0059 (13) |
C21 | 0.105 (3) | 0.055 (2) | 0.0358 (17) | −0.013 (2) | −0.0030 (18) | 0.0026 (15) |
C22 | 0.084 (3) | 0.0430 (18) | 0.0419 (17) | −0.0079 (17) | 0.0071 (17) | 0.0063 (13) |
C23 | 0.0509 (19) | 0.0364 (15) | 0.0468 (17) | −0.0008 (13) | 0.0002 (14) | 0.0063 (13) |
C24 | 0.0300 (14) | 0.0326 (13) | 0.0346 (13) | −0.0033 (11) | −0.0029 (11) | −0.0023 (10) |
C25 | 0.0276 (15) | 0.0336 (13) | 0.0432 (15) | −0.0025 (11) | 0.0049 (11) | −0.0008 (11) |
C26 | 0.0316 (15) | 0.0363 (14) | 0.0351 (13) | −0.0040 (11) | 0.0053 (11) | −0.0061 (11) |
C27 | 0.0307 (14) | 0.0290 (12) | 0.0323 (12) | −0.0040 (10) | 0.0011 (10) | −0.0028 (10) |
C28 | 0.0252 (13) | 0.0375 (14) | 0.0386 (14) | −0.0015 (11) | 0.0040 (11) | −0.0087 (11) |
C29 | 0.067 (2) | 0.059 (2) | 0.059 (2) | 0.0056 (19) | 0.0206 (17) | −0.0196 (18) |
C30 | 0.071 (3) | 0.081 (3) | 0.084 (3) | 0.017 (2) | −0.016 (2) | 0.030 (2) |
C31 | 0.091 (3) | 0.0307 (15) | 0.067 (2) | 0.0023 (17) | 0.012 (2) | −0.0013 (15) |
C32 | 0.0436 (18) | 0.060 (2) | 0.0441 (17) | −0.0082 (15) | 0.0144 (14) | −0.0128 (15) |
N1 | 0.0338 (14) | 0.0620 (17) | 0.0367 (13) | −0.0003 (12) | −0.0009 (10) | 0.0118 (12) |
N2 | 0.0331 (13) | 0.0545 (15) | 0.0379 (12) | −0.0010 (11) | −0.0001 (10) | −0.0134 (11) |
O1 | 0.0245 (11) | 0.0809 (18) | 0.0700 (15) | −0.0016 (11) | 0.0104 (10) | 0.0140 (13) |
O2 | 0.0244 (11) | 0.0735 (16) | 0.0620 (14) | 0.0005 (10) | 0.0066 (9) | −0.0087 (12) |
Cl1 | 0.0660 (5) | 0.0450 (4) | 0.0565 (4) | −0.0231 (4) | −0.0068 (4) | 0.0036 (4) |
Cl2 | 0.0772 (6) | 0.0421 (4) | 0.0684 (5) | 0.0142 (4) | −0.0204 (4) | −0.0017 (4) |
Cl3 | 0.0953 (8) | 0.0444 (4) | 0.0734 (6) | −0.0183 (5) | −0.0224 (5) | −0.0053 (4) |
Cl4 | 0.1074 (8) | 0.0535 (5) | 0.0593 (5) | 0.0355 (5) | 0.0064 (5) | 0.0030 (4) |
C1—C2 | 1.509 (4) | C17—C18 | 1.520 (4) |
C1—C8 | 1.514 (4) | C17—C19 | 1.538 (4) |
C1—C12 | 1.515 (4) | C18—C19 | 1.506 (4) |
C1—C3 | 1.540 (4) | C18—Cl2 | 1.760 (3) |
C2—C3 | 1.519 (4) | C18—Cl1 | 1.766 (3) |
C2—Cl4 | 1.766 (3) | C19—C20 | 1.518 (4) |
C2—Cl3 | 1.771 (4) | C19—C29 | 1.522 (5) |
C3—C13 | 1.515 (5) | C20—C21 | 1.536 (5) |
C3—C4 | 1.525 (4) | C20—H20A | 0.9700 |
C4—C5 | 1.536 (5) | C20—H20B | 0.9700 |
C4—H4A | 0.9700 | C21—C22 | 1.534 (5) |
C4—H4B | 0.9700 | C21—H21A | 0.9700 |
C5—C6 | 1.521 (4) | C21—H21B | 0.9700 |
C5—H5A | 0.9700 | C22—C23 | 1.541 (5) |
C5—H5B | 0.9700 | C22—H22A | 0.9700 |
C6—C7 | 1.536 (4) | C22—H22B | 0.9700 |
C6—H6A | 0.9700 | C23—C30 | 1.530 (5) |
C6—H6B | 0.9700 | C23—C31 | 1.547 (5) |
C7—C14 | 1.533 (5) | C23—C24 | 1.580 (4) |
C7—C15 | 1.537 (5) | C24—C25 | 1.529 (4) |
C7—C8 | 1.582 (4) | C24—H24 | 0.9800 |
C8—C9 | 1.524 (4) | C25—O2 | 1.243 (3) |
C8—H8 | 0.9800 | C25—C26 | 1.425 (4) |
C9—O1 | 1.241 (3) | C26—C27 | 1.371 (4) |
C9—C10 | 1.430 (4) | C26—C32 | 1.506 (4) |
C10—C11 | 1.369 (4) | C27—N2 | 1.343 (3) |
C10—C16 | 1.512 (4) | C27—C28 | 1.501 (3) |
C11—N1 | 1.335 (3) | C28—H28A | 0.9700 |
C11—C12 | 1.499 (4) | C28—H28B | 0.9700 |
C12—H12A | 0.9700 | C29—H29A | 0.9600 |
C12—H12B | 0.9700 | C29—H29B | 0.9600 |
C13—H13A | 0.9600 | C29—H29C | 0.9600 |
C13—H13B | 0.9600 | C30—H30A | 0.9600 |
C13—H13C | 0.9600 | C30—H30B | 0.9600 |
C14—H14A | 0.9600 | C30—H30C | 0.9600 |
C14—H14B | 0.9600 | C31—H31A | 0.9600 |
C14—H14C | 0.9600 | C31—H31B | 0.9600 |
C15—H15A | 0.9600 | C31—H31C | 0.9600 |
C15—H15B | 0.9600 | C32—H32A | 0.9600 |
C15—H15C | 0.9600 | C32—H32B | 0.9600 |
C16—H16A | 0.9600 | C32—H32C | 0.9600 |
C16—H16B | 0.9600 | N1—H1A | 0.8600 |
C16—H16C | 0.9600 | N1—H1B | 0.8600 |
C17—C28 | 1.505 (4) | N2—H2A | 0.8600 |
C17—C24 | 1.517 (4) | N2—H2B | 0.8600 |
C2—C1—C8 | 117.9 (2) | C28—C17—C19 | 120.5 (2) |
C2—C1—C12 | 118.4 (3) | C24—C17—C19 | 117.7 (2) |
C8—C1—C12 | 112.7 (2) | C18—C17—C19 | 59.03 (18) |
C2—C1—C3 | 59.76 (19) | C19—C18—C17 | 61.08 (18) |
C8—C1—C3 | 117.8 (2) | C19—C18—Cl2 | 119.3 (2) |
C12—C1—C3 | 120.8 (2) | C17—C18—Cl2 | 119.6 (2) |
C1—C2—C3 | 61.13 (19) | C19—C18—Cl1 | 121.2 (2) |
C1—C2—Cl4 | 119.8 (2) | C17—C18—Cl1 | 121.0 (2) |
C3—C2—Cl4 | 118.8 (2) | Cl2—C18—Cl1 | 108.38 (16) |
C1—C2—Cl3 | 120.6 (2) | C18—C19—C20 | 118.9 (3) |
C3—C2—Cl3 | 121.7 (2) | C18—C19—C29 | 118.9 (3) |
Cl4—C2—Cl3 | 108.40 (18) | C20—C19—C29 | 113.6 (3) |
C13—C3—C2 | 119.1 (3) | C18—C19—C17 | 59.90 (17) |
C13—C3—C4 | 113.8 (3) | C20—C19—C17 | 116.4 (3) |
C2—C3—C4 | 118.4 (3) | C29—C19—C17 | 119.0 (3) |
C13—C3—C1 | 120.3 (3) | C19—C20—C21 | 112.5 (3) |
C2—C3—C1 | 59.10 (19) | C19—C20—H20A | 109.1 |
C4—C3—C1 | 115.5 (3) | C21—C20—H20A | 109.1 |
C3—C4—C5 | 111.4 (3) | C19—C20—H20B | 109.1 |
C3—C4—H4A | 109.3 | C21—C20—H20B | 109.1 |
C5—C4—H4A | 109.3 | H20A—C20—H20B | 107.8 |
C3—C4—H4B | 109.3 | C22—C21—C20 | 115.4 (3) |
C5—C4—H4B | 109.3 | C22—C21—H21A | 108.4 |
H4A—C4—H4B | 108.0 | C20—C21—H21A | 108.4 |
C6—C5—C4 | 115.7 (3) | C22—C21—H21B | 108.4 |
C6—C5—H5A | 108.4 | C20—C21—H21B | 108.4 |
C4—C5—H5A | 108.4 | H21A—C21—H21B | 107.5 |
C6—C5—H5B | 108.4 | C21—C22—C23 | 119.5 (3) |
C4—C5—H5B | 108.4 | C21—C22—H22A | 107.4 |
H5A—C5—H5B | 107.4 | C23—C22—H22A | 107.4 |
C5—C6—C7 | 119.3 (3) | C21—C22—H22B | 107.4 |
C5—C6—H6A | 107.5 | C23—C22—H22B | 107.4 |
C7—C6—H6A | 107.5 | H22A—C22—H22B | 107.0 |
C5—C6—H6B | 107.5 | C30—C23—C22 | 110.8 (3) |
C7—C6—H6B | 107.5 | C30—C23—C31 | 108.1 (3) |
H6A—C6—H6B | 107.0 | C22—C23—C31 | 106.6 (3) |
C14—C7—C6 | 109.9 (3) | C30—C23—C24 | 108.0 (3) |
C14—C7—C15 | 108.3 (3) | C22—C23—C24 | 111.5 (3) |
C6—C7—C15 | 107.1 (3) | C31—C23—C24 | 111.9 (3) |
C14—C7—C8 | 108.4 (3) | C17—C24—C25 | 110.1 (2) |
C6—C7—C8 | 111.2 (2) | C17—C24—C23 | 114.2 (2) |
C15—C7—C8 | 111.9 (3) | C25—C24—C23 | 112.6 (2) |
C1—C8—C9 | 110.5 (2) | C17—C24—H24 | 106.4 |
C1—C8—C7 | 114.8 (2) | C25—C24—H24 | 106.4 |
C9—C8—C7 | 112.9 (2) | C23—C24—H24 | 106.4 |
C1—C8—H8 | 106.0 | O2—C25—C26 | 122.6 (2) |
C9—C8—H8 | 106.0 | O2—C25—C24 | 117.3 (2) |
C7—C8—H8 | 106.0 | C26—C25—C24 | 120.0 (2) |
O1—C9—C10 | 122.3 (3) | C27—C26—C25 | 120.2 (2) |
O1—C9—C8 | 117.7 (3) | C27—C26—C32 | 121.1 (2) |
C10—C9—C8 | 120.0 (2) | C25—C26—C32 | 118.5 (2) |
C11—C10—C9 | 120.4 (2) | N2—C27—C26 | 123.2 (2) |
C11—C10—C16 | 121.2 (3) | N2—C27—C28 | 113.9 (2) |
C9—C10—C16 | 118.2 (2) | C26—C27—C28 | 122.9 (2) |
N1—C11—C10 | 122.4 (2) | C27—C28—C17 | 112.9 (2) |
N1—C11—C12 | 114.8 (2) | C27—C28—H28A | 109.0 |
C10—C11—C12 | 122.8 (2) | C17—C28—H28A | 109.0 |
C11—C12—C1 | 111.7 (2) | C27—C28—H28B | 109.0 |
C11—C12—H12A | 109.3 | C17—C28—H28B | 109.0 |
C1—C12—H12A | 109.3 | H28A—C28—H28B | 107.8 |
C11—C12—H12B | 109.3 | C19—C29—H29A | 109.5 |
C1—C12—H12B | 109.3 | C19—C29—H29B | 109.5 |
H12A—C12—H12B | 107.9 | H29A—C29—H29B | 109.5 |
C3—C13—H13A | 109.5 | C19—C29—H29C | 109.5 |
C3—C13—H13B | 109.5 | H29A—C29—H29C | 109.5 |
H13A—C13—H13B | 109.5 | H29B—C29—H29C | 109.5 |
C3—C13—H13C | 109.5 | C23—C30—H30A | 109.5 |
H13A—C13—H13C | 109.5 | C23—C30—H30B | 109.5 |
H13B—C13—H13C | 109.5 | H30A—C30—H30B | 109.5 |
C7—C14—H14A | 109.5 | C23—C30—H30C | 109.5 |
C7—C14—H14B | 109.5 | H30A—C30—H30C | 109.5 |
H14A—C14—H14B | 109.5 | H30B—C30—H30C | 109.5 |
C7—C14—H14C | 109.5 | C23—C31—H31A | 109.5 |
H14A—C14—H14C | 109.5 | C23—C31—H31B | 109.5 |
H14B—C14—H14C | 109.5 | H31A—C31—H31B | 109.5 |
C7—C15—H15A | 109.5 | C23—C31—H31C | 109.5 |
C7—C15—H15B | 109.5 | H31A—C31—H31C | 109.5 |
H15A—C15—H15B | 109.5 | H31B—C31—H31C | 109.5 |
C7—C15—H15C | 109.5 | C26—C32—H32A | 109.5 |
H15A—C15—H15C | 109.5 | C26—C32—H32B | 109.5 |
H15B—C15—H15C | 109.5 | H32A—C32—H32B | 109.5 |
C10—C16—H16A | 109.5 | C26—C32—H32C | 109.5 |
C10—C16—H16B | 109.5 | H32A—C32—H32C | 109.5 |
H16A—C16—H16B | 109.5 | H32B—C32—H32C | 109.5 |
C10—C16—H16C | 109.5 | C11—N1—H1A | 120.0 |
H16A—C16—H16C | 109.5 | C11—N1—H1B | 120.0 |
H16B—C16—H16C | 109.5 | H1A—N1—H1B | 120.0 |
C28—C17—C24 | 113.2 (2) | C27—N2—H2A | 120.0 |
C28—C17—C18 | 118.3 (2) | C27—N2—H2B | 120.0 |
C24—C17—C18 | 118.1 (2) | H2A—N2—H2B | 120.0 |
D—H···A | D—H | H···A | D···A | 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. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
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