organic compounds
9-(3,5-Dimethylbenzylidene)-8-(3,5-dimethylphenyl)-1,3,5,7-tetraphenyl-2,4,7,8-tetrahydro-4,7-methanoazulene acetonitrile disolvate
aDepartment of Chemistry & Chemistry Research Center, United States Air Force Academy, Colorado Springs, CO 80840, USA
*Correspondence e-mail: gary.balaich@usafa.edu
The title Diels–Alder product, C52H44·2CH3CN, was obtained in trace quantity as the `endo' isomer during the synthesis of 1,3-diphenyl-6-(3,5-dimethylphenyl)fulvene. One of the two co-crystallized acetonitrile molecules is linked to the main molecule by a weak C—H⋯N hydrogen bond.
Keywords: cystal structure; azulene; benzylidene; crystal structure.
CCDC reference: 1835896
Structure description
The title compound is formed by Diels–Alder reaction of the fulvene component of one molecule of 1,3-diphenyl-6-(3,5-dimethylphenyl)fulvene and the exocyclic double bond of a second fulvene molecule, resulting in an `endo' product. The molecular structure is shown in Fig. 1. The bond lengths are typical of those observed in related (Peloquin et al., 2012). A weak C34—H34⋯N1 hydrogen bond (Table 1) links the main molecule to one of the two acetonitrile solvent molecules.
Synthesis and crystallization
To a vigorously stirred suspension of 1,3-diphenylcyclopentadiene (1.36 g, 6.21 mmol) in absolute EtOH (50 ml) under N2 was added 3,5-dimethylbenzaldehyde (1.00 g, 7.45 mmol) and pyrrolidine (0.82 ml, 9.94 mmol), and the reaction mixture was maintained at room temperature for 8 h. The reaction mixture was cooled to −5°C for 12 h, the resulting precipitate isolated by vacuum filtration, and dried in vacuo to yield a red solid (0.215 g, 10%). The solvent was removed from the filtrate in vacuo. The resulting residue was dissolved in Et2O (20 ml), washed with saturated NaHSO3, dried over MgSO4, and cooled to −5°C for 48 hrs. An additional crop of red solid material was isolated by vacuum filtration (0.339 g, total combined yield 0.554 g, 26%). Crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation of an acetonitrile solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1835896
https://doi.org/10.1107/S2414314618005539/sj4173sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618005539/sj4173Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618005539/sj4173Isup3.cml
Data collection: APEX2 (Bruker, 2017); cell
SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C52H44·2C2H3N | Z = 2 |
Mr = 750.98 | F(000) = 800 |
Triclinic, P1 | Dx = 1.160 Mg m−3 |
a = 10.4026 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.6115 (4) Å | Cell parameters from 3666 reflections |
c = 16.5769 (6) Å | θ = 2.7–23.0° |
α = 105.502 (2)° | µ = 0.07 mm−1 |
β = 105.796 (2)° | T = 100 K |
γ = 94.038 (2)° | Prism, dark red |
V = 2150.30 (12) Å3 | 0.19 × 0.18 × 0.18 mm |
Bruker APEXII CCD diffractometer | 5894 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.059 |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | θmax = 26.8°, θmin = 1.7° |
Tmin = 0.804, Tmax = 0.914 | h = −13→13 |
32078 measured reflections | k = −17→17 |
8992 independent reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0524P)2 + 0.8994P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
8992 reflections | Δρmax = 0.26 e Å−3 |
529 parameters | Δρmin = −0.24 e Å−3 |
0 restraints |
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 | 0.62899 (18) | 0.47941 (15) | 0.14895 (12) | 0.0208 (4) | |
C2 | 0.6900 (2) | 0.59098 (15) | 0.17214 (13) | 0.0233 (4) | |
H2A | 0.643654 | 0.622662 | 0.127142 | 0.028* | |
H2B | 0.787475 | 0.597427 | 0.177324 | 0.028* | |
C3 | 0.66858 (18) | 0.64125 (15) | 0.25942 (13) | 0.0216 (4) | |
C4 | 0.60350 (18) | 0.56787 (14) | 0.28198 (12) | 0.0195 (4) | |
C5 | 0.57835 (18) | 0.46750 (14) | 0.21387 (12) | 0.0203 (4) | |
C6 | 0.51239 (18) | 0.36835 (14) | 0.22266 (12) | 0.0194 (4) | |
H6 | 0.580932 | 0.320384 | 0.224780 | 0.023* | |
C7 | 0.63983 (19) | 0.40180 (15) | 0.07072 (12) | 0.0221 (4) | |
C8 | 0.6316 (2) | 0.42727 (16) | −0.00655 (13) | 0.0262 (5) | |
H8 | 0.617660 | 0.494949 | −0.008448 | 0.031* | |
C9 | 0.6433 (2) | 0.35588 (17) | −0.08068 (14) | 0.0318 (5) | |
H9 | 0.634451 | 0.374417 | −0.133041 | 0.038* | |
C10 | 0.6677 (2) | 0.25814 (17) | −0.07852 (14) | 0.0351 (5) | |
H10 | 0.677284 | 0.209527 | −0.128810 | 0.042* | |
C11 | 0.6780 (2) | 0.23184 (17) | −0.00221 (15) | 0.0377 (6) | |
H11 | 0.695009 | 0.164728 | −0.000227 | 0.045* | |
C12 | 0.6638 (2) | 0.30217 (16) | 0.07139 (14) | 0.0293 (5) | |
H12 | 0.670427 | 0.282428 | 0.123007 | 0.035* | |
C13 | 0.71457 (19) | 0.75077 (15) | 0.30998 (13) | 0.0228 (4) | |
C14 | 0.8398 (2) | 0.80224 (16) | 0.31707 (15) | 0.0315 (5) | |
H14 | 0.896653 | 0.766764 | 0.287011 | 0.038* | |
C15 | 0.8825 (2) | 0.90480 (17) | 0.36757 (16) | 0.0374 (6) | |
H15 | 0.967772 | 0.938845 | 0.371234 | 0.045* | |
C16 | 0.8021 (2) | 0.95767 (16) | 0.41248 (15) | 0.0335 (5) | |
H16 | 0.832662 | 1.027197 | 0.448174 | 0.040* | |
C17 | 0.6769 (2) | 0.90832 (16) | 0.40489 (14) | 0.0311 (5) | |
H17 | 0.620503 | 0.944311 | 0.434985 | 0.037* | |
C18 | 0.6332 (2) | 0.80677 (15) | 0.35372 (14) | 0.0270 (5) | |
H18 | 0.546002 | 0.774372 | 0.348177 | 0.032* | |
C19 | 0.38835 (19) | 0.31274 (15) | 0.14540 (12) | 0.0216 (4) | |
C20 | 0.29397 (19) | 0.36707 (15) | 0.10607 (12) | 0.0238 (4) | |
H20 | 0.311035 | 0.440359 | 0.124881 | 0.029* | |
C21 | 0.1756 (2) | 0.31651 (16) | 0.04003 (13) | 0.0279 (5) | |
C22 | 0.1519 (2) | 0.20943 (17) | 0.01294 (14) | 0.0332 (5) | |
H22 | 0.070889 | 0.174148 | −0.031758 | 0.040* | |
C23 | 0.2445 (2) | 0.15275 (16) | 0.05000 (14) | 0.0312 (5) | |
C24 | 0.3626 (2) | 0.20562 (15) | 0.11579 (13) | 0.0269 (5) | |
H24 | 0.426966 | 0.167545 | 0.140923 | 0.032* | |
C25 | 0.0735 (2) | 0.37751 (18) | 0.00006 (16) | 0.0411 (6) | |
H25A | 0.093454 | 0.449349 | 0.037407 | 0.062* | |
H25B | −0.017614 | 0.347532 | −0.004506 | 0.062* | |
H25C | 0.078555 | 0.375134 | −0.058587 | 0.062* | |
C26 | 0.2178 (3) | 0.03637 (17) | 0.02230 (16) | 0.0471 (7) | |
H26A | 0.199817 | 0.013230 | 0.069850 | 0.071* | |
H26B | 0.297117 | 0.009100 | 0.009420 | 0.071* | |
H26C | 0.139204 | 0.011188 | −0.030373 | 0.071* | |
C27 | 0.47673 (18) | 0.39042 (14) | 0.31296 (12) | 0.0198 (4) | |
C28 | 0.36308 (19) | 0.45486 (14) | 0.30875 (12) | 0.0204 (4) | |
H28 | 0.269753 | 0.426725 | 0.287361 | 0.024* | |
C29 | 0.40990 (19) | 0.55538 (15) | 0.33861 (12) | 0.0208 (4) | |
C30 | 0.56498 (18) | 0.57118 (14) | 0.36412 (12) | 0.0194 (4) | |
H30 | 0.610396 | 0.633564 | 0.415039 | 0.023* | |
C31 | 0.59450 (18) | 0.46958 (14) | 0.38120 (12) | 0.0193 (4) | |
C32 | 0.69876 (18) | 0.45072 (15) | 0.43931 (12) | 0.0204 (4) | |
H32 | 0.697236 | 0.380820 | 0.439198 | 0.025* | |
C33 | 0.44909 (19) | 0.29195 (14) | 0.33668 (12) | 0.0209 (4) | |
C34 | 0.5261 (2) | 0.21256 (15) | 0.32410 (13) | 0.0249 (4) | |
H34 | 0.598925 | 0.220035 | 0.300825 | 0.030* | |
C35 | 0.4982 (2) | 0.12266 (16) | 0.34500 (13) | 0.0290 (5) | |
H35 | 0.550963 | 0.069071 | 0.335040 | 0.035* | |
C36 | 0.3940 (2) | 0.11082 (16) | 0.38019 (14) | 0.0306 (5) | |
H36 | 0.373663 | 0.048802 | 0.393312 | 0.037* | |
C37 | 0.3198 (2) | 0.19009 (16) | 0.39607 (14) | 0.0292 (5) | |
H37 | 0.249673 | 0.183301 | 0.421778 | 0.035* | |
C38 | 0.34690 (19) | 0.27988 (15) | 0.37467 (13) | 0.0238 (4) | |
H38 | 0.295060 | 0.333805 | 0.386105 | 0.029* | |
C39 | 0.33417 (19) | 0.64335 (15) | 0.33960 (13) | 0.0216 (4) | |
C40 | 0.2347 (2) | 0.64701 (16) | 0.26484 (13) | 0.0265 (5) | |
H40 | 0.209202 | 0.589441 | 0.213367 | 0.032* | |
C41 | 0.1732 (2) | 0.73391 (17) | 0.26525 (15) | 0.0318 (5) | |
H41 | 0.107113 | 0.736006 | 0.213577 | 0.038* | |
C42 | 0.2068 (2) | 0.81772 (17) | 0.33996 (15) | 0.0332 (5) | |
H42 | 0.165791 | 0.877817 | 0.339330 | 0.040* | |
C43 | 0.3008 (2) | 0.81329 (16) | 0.41577 (14) | 0.0287 (5) | |
H43 | 0.321562 | 0.869367 | 0.468090 | 0.034* | |
C44 | 0.3647 (2) | 0.72731 (15) | 0.41550 (13) | 0.0243 (4) | |
H44 | 0.429979 | 0.725404 | 0.467562 | 0.029* | |
C45 | 0.81598 (18) | 0.52355 (14) | 0.50365 (12) | 0.0209 (4) | |
C46 | 0.87823 (19) | 0.50031 (15) | 0.58076 (13) | 0.0236 (4) | |
H46 | 0.845059 | 0.437801 | 0.588632 | 0.028* | |
C47 | 0.98684 (19) | 0.56552 (16) | 0.64614 (13) | 0.0262 (5) | |
C48 | 1.03670 (19) | 0.65565 (16) | 0.63328 (13) | 0.0259 (5) | |
H48 | 1.110829 | 0.701187 | 0.677859 | 0.031* | |
C49 | 0.98033 (19) | 0.68044 (15) | 0.55664 (13) | 0.0256 (5) | |
C50 | 0.87020 (19) | 0.61401 (15) | 0.49205 (13) | 0.0236 (4) | |
H50 | 0.831347 | 0.630440 | 0.439310 | 0.028* | |
C51 | 1.0514 (2) | 0.5376 (2) | 0.72843 (15) | 0.0426 (6) | |
H51A | 0.997946 | 0.475463 | 0.728623 | 0.064* | |
H51B | 1.054786 | 0.594710 | 0.779978 | 0.064* | |
H51C | 1.143378 | 0.524448 | 0.730204 | 0.064* | |
C52 | 1.0402 (2) | 0.77656 (17) | 0.54269 (16) | 0.0389 (6) | |
H52A | 1.090664 | 0.825899 | 0.599695 | 0.058* | |
H52B | 0.967505 | 0.807697 | 0.512110 | 0.058* | |
H52C | 1.101452 | 0.758471 | 0.507218 | 0.058* | |
C53 | 0.6664 (3) | 0.9128 (2) | 0.15696 (19) | 0.0587 (8) | |
H53A | 0.627272 | 0.895627 | 0.199880 | 0.088* | |
H53B | 0.752146 | 0.885960 | 0.160801 | 0.088* | |
H53C | 0.603605 | 0.881801 | 0.097701 | 0.088* | |
C54 | 0.6906 (2) | 1.0242 (2) | 0.17549 (16) | 0.0403 (6) | |
C55 | 0.9502 (3) | 0.8449 (2) | 0.80174 (18) | 0.0521 (7) | |
H55A | 1.026712 | 0.842034 | 0.850591 | 0.078* | |
H55B | 0.954771 | 0.797311 | 0.746906 | 0.078* | |
H55C | 0.865336 | 0.824845 | 0.812274 | 0.078* | |
C56 | 0.9560 (2) | 0.9494 (2) | 0.79496 (16) | 0.0466 (7) | |
N1 | 0.7109 (2) | 1.11149 (19) | 0.18894 (16) | 0.0535 (6) | |
N2 | 0.9628 (2) | 1.0317 (2) | 0.79074 (16) | 0.0636 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0183 (10) | 0.0239 (11) | 0.0204 (10) | 0.0052 (8) | 0.0035 (8) | 0.0088 (8) |
C2 | 0.0233 (10) | 0.0245 (11) | 0.0243 (10) | 0.0039 (8) | 0.0076 (8) | 0.0103 (9) |
C3 | 0.0178 (10) | 0.0224 (11) | 0.0247 (10) | 0.0034 (8) | 0.0055 (8) | 0.0083 (8) |
C4 | 0.0154 (9) | 0.0203 (10) | 0.0219 (10) | 0.0039 (8) | 0.0035 (8) | 0.0066 (8) |
C5 | 0.0164 (9) | 0.0206 (10) | 0.0230 (10) | 0.0034 (8) | 0.0030 (8) | 0.0077 (8) |
C6 | 0.0185 (10) | 0.0195 (10) | 0.0205 (10) | 0.0037 (8) | 0.0062 (8) | 0.0063 (8) |
C7 | 0.0188 (10) | 0.0255 (11) | 0.0218 (10) | 0.0023 (8) | 0.0073 (8) | 0.0058 (8) |
C8 | 0.0267 (11) | 0.0283 (12) | 0.0257 (11) | 0.0061 (9) | 0.0100 (9) | 0.0089 (9) |
C9 | 0.0337 (12) | 0.0395 (14) | 0.0243 (11) | 0.0066 (10) | 0.0115 (9) | 0.0096 (10) |
C10 | 0.0426 (14) | 0.0324 (13) | 0.0294 (12) | 0.0035 (11) | 0.0181 (10) | 0.0008 (10) |
C11 | 0.0533 (15) | 0.0248 (12) | 0.0415 (14) | 0.0106 (11) | 0.0251 (12) | 0.0083 (10) |
C12 | 0.0354 (12) | 0.0283 (12) | 0.0280 (11) | 0.0091 (10) | 0.0128 (9) | 0.0102 (9) |
C13 | 0.0248 (10) | 0.0198 (11) | 0.0245 (10) | 0.0033 (8) | 0.0071 (8) | 0.0079 (8) |
C14 | 0.0271 (11) | 0.0241 (12) | 0.0438 (13) | 0.0026 (9) | 0.0157 (10) | 0.0063 (10) |
C15 | 0.0284 (12) | 0.0291 (13) | 0.0522 (15) | −0.0043 (10) | 0.0158 (11) | 0.0064 (11) |
C16 | 0.0401 (13) | 0.0189 (11) | 0.0397 (13) | 0.0001 (10) | 0.0133 (10) | 0.0054 (9) |
C17 | 0.0402 (13) | 0.0217 (12) | 0.0371 (12) | 0.0065 (10) | 0.0203 (10) | 0.0090 (10) |
C18 | 0.0274 (11) | 0.0221 (11) | 0.0353 (12) | 0.0023 (9) | 0.0141 (9) | 0.0104 (9) |
C19 | 0.0223 (10) | 0.0219 (11) | 0.0200 (10) | 0.0010 (8) | 0.0073 (8) | 0.0050 (8) |
C20 | 0.0267 (11) | 0.0206 (11) | 0.0224 (10) | 0.0029 (8) | 0.0069 (8) | 0.0044 (8) |
C21 | 0.0251 (11) | 0.0309 (12) | 0.0241 (11) | 0.0017 (9) | 0.0029 (9) | 0.0078 (9) |
C22 | 0.0301 (12) | 0.0338 (13) | 0.0251 (11) | −0.0050 (10) | −0.0011 (9) | 0.0037 (10) |
C23 | 0.0379 (13) | 0.0245 (12) | 0.0253 (11) | −0.0016 (10) | 0.0064 (9) | 0.0026 (9) |
C24 | 0.0324 (12) | 0.0219 (11) | 0.0244 (11) | 0.0053 (9) | 0.0077 (9) | 0.0047 (9) |
C25 | 0.0334 (13) | 0.0383 (14) | 0.0409 (14) | 0.0052 (11) | −0.0047 (11) | 0.0105 (11) |
C26 | 0.0613 (17) | 0.0261 (13) | 0.0385 (14) | −0.0019 (12) | 0.0006 (12) | 0.0012 (11) |
C27 | 0.0194 (10) | 0.0199 (10) | 0.0199 (10) | 0.0023 (8) | 0.0066 (8) | 0.0052 (8) |
C28 | 0.0188 (10) | 0.0216 (11) | 0.0203 (10) | 0.0020 (8) | 0.0070 (8) | 0.0047 (8) |
C29 | 0.0193 (10) | 0.0227 (11) | 0.0206 (10) | 0.0032 (8) | 0.0068 (8) | 0.0063 (8) |
C30 | 0.0199 (10) | 0.0169 (10) | 0.0211 (10) | 0.0021 (8) | 0.0070 (8) | 0.0047 (8) |
C31 | 0.0199 (10) | 0.0199 (10) | 0.0204 (10) | 0.0025 (8) | 0.0110 (8) | 0.0050 (8) |
C32 | 0.0211 (10) | 0.0171 (10) | 0.0232 (10) | 0.0027 (8) | 0.0084 (8) | 0.0047 (8) |
C33 | 0.0219 (10) | 0.0181 (10) | 0.0185 (9) | −0.0012 (8) | 0.0025 (8) | 0.0032 (8) |
C34 | 0.0281 (11) | 0.0217 (11) | 0.0256 (11) | 0.0039 (9) | 0.0093 (9) | 0.0069 (9) |
C35 | 0.0395 (13) | 0.0215 (11) | 0.0257 (11) | 0.0081 (9) | 0.0090 (9) | 0.0068 (9) |
C36 | 0.0370 (13) | 0.0216 (11) | 0.0296 (12) | −0.0030 (10) | 0.0047 (10) | 0.0091 (9) |
C37 | 0.0262 (11) | 0.0305 (12) | 0.0312 (12) | −0.0020 (9) | 0.0078 (9) | 0.0119 (10) |
C38 | 0.0213 (10) | 0.0232 (11) | 0.0248 (10) | 0.0018 (8) | 0.0058 (8) | 0.0056 (9) |
C39 | 0.0192 (10) | 0.0205 (10) | 0.0273 (11) | 0.0015 (8) | 0.0105 (8) | 0.0076 (8) |
C40 | 0.0242 (11) | 0.0287 (12) | 0.0267 (11) | 0.0055 (9) | 0.0087 (9) | 0.0072 (9) |
C41 | 0.0250 (11) | 0.0403 (14) | 0.0340 (12) | 0.0123 (10) | 0.0074 (9) | 0.0171 (11) |
C42 | 0.0304 (12) | 0.0266 (12) | 0.0488 (14) | 0.0121 (10) | 0.0171 (11) | 0.0142 (11) |
C43 | 0.0288 (11) | 0.0218 (11) | 0.0356 (12) | 0.0038 (9) | 0.0149 (10) | 0.0036 (9) |
C44 | 0.0240 (10) | 0.0219 (11) | 0.0279 (11) | 0.0038 (9) | 0.0102 (9) | 0.0065 (9) |
C45 | 0.0188 (10) | 0.0210 (11) | 0.0230 (10) | 0.0038 (8) | 0.0089 (8) | 0.0039 (8) |
C46 | 0.0205 (10) | 0.0231 (11) | 0.0280 (11) | 0.0037 (8) | 0.0087 (8) | 0.0071 (9) |
C47 | 0.0194 (10) | 0.0327 (12) | 0.0257 (11) | 0.0064 (9) | 0.0061 (8) | 0.0074 (9) |
C48 | 0.0167 (10) | 0.0274 (12) | 0.0270 (11) | 0.0012 (8) | 0.0054 (8) | −0.0008 (9) |
C49 | 0.0205 (10) | 0.0233 (11) | 0.0315 (11) | 0.0019 (8) | 0.0094 (9) | 0.0048 (9) |
C50 | 0.0213 (10) | 0.0248 (11) | 0.0247 (10) | 0.0029 (8) | 0.0071 (8) | 0.0074 (9) |
C51 | 0.0296 (13) | 0.0536 (16) | 0.0386 (14) | −0.0004 (11) | −0.0031 (10) | 0.0195 (12) |
C52 | 0.0347 (13) | 0.0340 (13) | 0.0420 (14) | −0.0084 (10) | 0.0069 (10) | 0.0099 (11) |
C53 | 0.070 (2) | 0.0522 (18) | 0.0521 (17) | −0.0051 (15) | 0.0122 (15) | 0.0229 (14) |
C54 | 0.0357 (13) | 0.0501 (17) | 0.0417 (14) | 0.0102 (12) | 0.0161 (11) | 0.0192 (13) |
C55 | 0.0455 (16) | 0.0554 (18) | 0.0453 (16) | −0.0020 (13) | 0.0127 (12) | 0.0019 (13) |
C56 | 0.0338 (14) | 0.061 (2) | 0.0344 (14) | −0.0010 (13) | 0.0034 (11) | 0.0066 (13) |
N1 | 0.0609 (15) | 0.0514 (15) | 0.0639 (15) | 0.0208 (12) | 0.0363 (12) | 0.0217 (12) |
N2 | 0.0529 (15) | 0.0726 (19) | 0.0565 (16) | 0.0047 (14) | 0.0003 (12) | 0.0230 (14) |
C1—C2 | 1.509 (3) | C28—C29 | 1.329 (3) |
C1—C5 | 1.361 (3) | C29—C30 | 1.536 (3) |
C1—C7 | 1.475 (3) | C29—C39 | 1.478 (3) |
C2—H2A | 0.9900 | C30—H30 | 1.0000 |
C2—H2B | 0.9900 | C30—C31 | 1.519 (2) |
C2—C3 | 1.509 (3) | C31—C32 | 1.331 (3) |
C3—C4 | 1.356 (2) | C32—H32 | 0.9500 |
C3—C13 | 1.472 (3) | C32—C45 | 1.471 (3) |
C4—C5 | 1.474 (3) | C33—C34 | 1.395 (3) |
C4—C30 | 1.511 (3) | C33—C38 | 1.396 (3) |
C5—C6 | 1.531 (2) | C34—H34 | 0.9500 |
C6—H6 | 1.0000 | C34—C35 | 1.390 (3) |
C6—C19 | 1.524 (3) | C35—H35 | 0.9500 |
C6—C27 | 1.596 (3) | C35—C36 | 1.382 (3) |
C7—C8 | 1.396 (3) | C36—H36 | 0.9500 |
C7—C12 | 1.398 (3) | C36—C37 | 1.380 (3) |
C8—H8 | 0.9500 | C37—H37 | 0.9500 |
C8—C9 | 1.389 (3) | C37—C38 | 1.392 (3) |
C9—H9 | 0.9500 | C38—H38 | 0.9500 |
C9—C10 | 1.380 (3) | C39—C40 | 1.397 (3) |
C10—H10 | 0.9500 | C39—C44 | 1.397 (3) |
C10—C11 | 1.383 (3) | C40—H40 | 0.9500 |
C11—H11 | 0.9500 | C40—C41 | 1.383 (3) |
C11—C12 | 1.386 (3) | C41—H41 | 0.9500 |
C12—H12 | 0.9500 | C41—C42 | 1.382 (3) |
C13—C14 | 1.395 (3) | C42—H42 | 0.9500 |
C13—C18 | 1.397 (3) | C42—C43 | 1.385 (3) |
C14—H14 | 0.9500 | C43—H43 | 0.9500 |
C14—C15 | 1.390 (3) | C43—C44 | 1.385 (3) |
C15—H15 | 0.9500 | C44—H44 | 0.9500 |
C15—C16 | 1.382 (3) | C45—C46 | 1.396 (3) |
C16—H16 | 0.9500 | C45—C50 | 1.400 (3) |
C16—C17 | 1.381 (3) | C46—H46 | 0.9500 |
C17—H17 | 0.9500 | C46—C47 | 1.384 (3) |
C17—C18 | 1.383 (3) | C47—C48 | 1.389 (3) |
C18—H18 | 0.9500 | C47—C51 | 1.507 (3) |
C19—C20 | 1.395 (3) | C48—H48 | 0.9500 |
C19—C24 | 1.389 (3) | C48—C49 | 1.387 (3) |
C20—H20 | 0.9500 | C49—C50 | 1.395 (3) |
C20—C21 | 1.390 (3) | C49—C52 | 1.509 (3) |
C21—C22 | 1.388 (3) | C50—H50 | 0.9500 |
C21—C25 | 1.514 (3) | C51—H51A | 0.9800 |
C22—H22 | 0.9500 | C51—H51B | 0.9800 |
C22—C23 | 1.392 (3) | C51—H51C | 0.9800 |
C23—C24 | 1.394 (3) | C52—H52A | 0.9800 |
C23—C26 | 1.509 (3) | C52—H52B | 0.9800 |
C24—H24 | 0.9500 | C52—H52C | 0.9800 |
C25—H25A | 0.9800 | C53—H53A | 0.9800 |
C25—H25B | 0.9800 | C53—H53B | 0.9800 |
C25—H25C | 0.9800 | C53—H53C | 0.9800 |
C26—H26A | 0.9800 | C53—C54 | 1.452 (4) |
C26—H26B | 0.9800 | C54—N1 | 1.142 (3) |
C26—H26C | 0.9800 | C55—H55A | 0.9800 |
C27—C28 | 1.519 (3) | C55—H55B | 0.9800 |
C27—C31 | 1.533 (3) | C55—H55C | 0.9800 |
C27—C33 | 1.524 (2) | C55—C56 | 1.455 (4) |
C28—H28 | 0.9500 | C56—N2 | 1.140 (3) |
C5—C1—C2 | 108.57 (17) | C29—C28—C27 | 111.86 (16) |
C5—C1—C7 | 130.12 (18) | C29—C28—H28 | 124.1 |
C7—C1—C2 | 121.10 (16) | C28—C29—C30 | 109.16 (17) |
C1—C2—H2A | 110.9 | C28—C29—C39 | 129.03 (17) |
C1—C2—H2B | 110.9 | C39—C29—C30 | 121.42 (16) |
C1—C2—C3 | 104.33 (15) | C4—C30—C29 | 107.43 (15) |
H2A—C2—H2B | 108.9 | C4—C30—H30 | 114.2 |
C3—C2—H2A | 110.9 | C4—C30—C31 | 104.56 (15) |
C3—C2—H2B | 110.9 | C29—C30—H30 | 114.2 |
C4—C3—C2 | 107.99 (17) | C31—C30—C29 | 101.13 (14) |
C4—C3—C13 | 127.47 (18) | C31—C30—H30 | 114.2 |
C13—C3—C2 | 124.52 (16) | C30—C31—C27 | 103.66 (15) |
C3—C4—C5 | 110.18 (17) | C32—C31—C27 | 126.94 (17) |
C3—C4—C30 | 131.60 (18) | C32—C31—C30 | 129.37 (17) |
C5—C4—C30 | 118.04 (16) | C31—C32—H32 | 115.6 |
C1—C5—C4 | 108.93 (16) | C31—C32—C45 | 128.72 (18) |
C1—C5—C6 | 128.46 (18) | C45—C32—H32 | 115.6 |
C4—C5—C6 | 122.53 (16) | C34—C33—C27 | 122.01 (17) |
C5—C6—H6 | 107.1 | C34—C33—C38 | 117.59 (17) |
C5—C6—C27 | 110.84 (15) | C38—C33—C27 | 120.38 (18) |
C19—C6—C5 | 113.78 (15) | C33—C34—H34 | 119.4 |
C19—C6—H6 | 107.1 | C35—C34—C33 | 121.18 (19) |
C19—C6—C27 | 110.62 (15) | C35—C34—H34 | 119.4 |
C27—C6—H6 | 107.1 | C34—C35—H35 | 119.8 |
C8—C7—C1 | 120.45 (18) | C36—C35—C34 | 120.4 (2) |
C8—C7—C12 | 117.38 (18) | C36—C35—H35 | 119.8 |
C12—C7—C1 | 122.12 (17) | C35—C36—H36 | 120.4 |
C7—C8—H8 | 119.3 | C37—C36—C35 | 119.28 (19) |
C9—C8—C7 | 121.49 (19) | C37—C36—H36 | 120.4 |
C9—C8—H8 | 119.3 | C36—C37—H37 | 119.8 |
C8—C9—H9 | 119.9 | C36—C37—C38 | 120.5 (2) |
C10—C9—C8 | 120.2 (2) | C38—C37—H37 | 119.8 |
C10—C9—H9 | 119.9 | C33—C38—H38 | 119.5 |
C9—C10—H10 | 120.4 | C37—C38—C33 | 121.0 (2) |
C9—C10—C11 | 119.2 (2) | C37—C38—H38 | 119.5 |
C11—C10—H10 | 120.4 | C40—C39—C29 | 121.53 (18) |
C10—C11—H11 | 119.6 | C40—C39—C44 | 118.30 (18) |
C10—C11—C12 | 120.8 (2) | C44—C39—C29 | 120.13 (17) |
C12—C11—H11 | 119.6 | C39—C40—H40 | 119.8 |
C7—C12—H12 | 119.5 | C41—C40—C39 | 120.4 (2) |
C11—C12—C7 | 120.91 (19) | C41—C40—H40 | 119.8 |
C11—C12—H12 | 119.5 | C40—C41—H41 | 119.6 |
C14—C13—C3 | 122.04 (18) | C42—C41—C40 | 120.8 (2) |
C14—C13—C18 | 117.55 (18) | C42—C41—H41 | 119.6 |
C18—C13—C3 | 120.41 (17) | C41—C42—H42 | 120.3 |
C13—C14—H14 | 119.6 | C41—C42—C43 | 119.4 (2) |
C15—C14—C13 | 120.8 (2) | C43—C42—H42 | 120.3 |
C15—C14—H14 | 119.6 | C42—C43—H43 | 119.9 |
C14—C15—H15 | 119.7 | C42—C43—C44 | 120.2 (2) |
C16—C15—C14 | 120.6 (2) | C44—C43—H43 | 119.9 |
C16—C15—H15 | 119.7 | C39—C44—H44 | 119.6 |
C15—C16—H16 | 120.4 | C43—C44—C39 | 120.82 (19) |
C17—C16—C15 | 119.2 (2) | C43—C44—H44 | 119.6 |
C17—C16—H16 | 120.4 | C46—C45—C32 | 117.90 (17) |
C16—C17—H17 | 119.8 | C46—C45—C50 | 117.86 (17) |
C16—C17—C18 | 120.3 (2) | C50—C45—C32 | 124.23 (17) |
C18—C17—H17 | 119.8 | C45—C46—H46 | 119.0 |
C13—C18—H18 | 119.3 | C47—C46—C45 | 122.04 (18) |
C17—C18—C13 | 121.41 (19) | C47—C46—H46 | 119.0 |
C17—C18—H18 | 119.3 | C46—C47—C48 | 118.63 (18) |
C20—C19—C6 | 121.36 (17) | C46—C47—C51 | 120.43 (19) |
C24—C19—C6 | 120.25 (17) | C48—C47—C51 | 120.92 (18) |
C24—C19—C20 | 118.28 (18) | C47—C48—H48 | 119.4 |
C19—C20—H20 | 119.2 | C49—C48—C47 | 121.27 (18) |
C21—C20—C19 | 121.58 (18) | C49—C48—H48 | 119.4 |
C21—C20—H20 | 119.2 | C48—C49—C50 | 119.05 (18) |
C20—C21—C25 | 120.40 (19) | C48—C49—C52 | 120.19 (18) |
C22—C21—C20 | 118.70 (19) | C50—C49—C52 | 120.74 (18) |
C22—C21—C25 | 120.89 (18) | C45—C50—H50 | 119.5 |
C21—C22—H22 | 119.4 | C49—C50—C45 | 121.09 (18) |
C21—C22—C23 | 121.27 (19) | C49—C50—H50 | 119.5 |
C23—C22—H22 | 119.4 | C47—C51—H51A | 109.5 |
C22—C23—C24 | 118.70 (19) | C47—C51—H51B | 109.5 |
C22—C23—C26 | 121.51 (19) | C47—C51—H51C | 109.5 |
C24—C23—C26 | 119.8 (2) | H51A—C51—H51B | 109.5 |
C19—C24—C23 | 121.45 (19) | H51A—C51—H51C | 109.5 |
C19—C24—H24 | 119.3 | H51B—C51—H51C | 109.5 |
C23—C24—H24 | 119.3 | C49—C52—H52A | 109.5 |
C21—C25—H25A | 109.5 | C49—C52—H52B | 109.5 |
C21—C25—H25B | 109.5 | C49—C52—H52C | 109.5 |
C21—C25—H25C | 109.5 | H52A—C52—H52B | 109.5 |
H25A—C25—H25B | 109.5 | H52A—C52—H52C | 109.5 |
H25A—C25—H25C | 109.5 | H52B—C52—H52C | 109.5 |
H25B—C25—H25C | 109.5 | H53A—C53—H53B | 109.5 |
C23—C26—H26A | 109.5 | H53A—C53—H53C | 109.5 |
C23—C26—H26B | 109.5 | H53B—C53—H53C | 109.5 |
C23—C26—H26C | 109.5 | C54—C53—H53A | 109.5 |
H26A—C26—H26B | 109.5 | C54—C53—H53B | 109.5 |
H26A—C26—H26C | 109.5 | C54—C53—H53C | 109.5 |
H26B—C26—H26C | 109.5 | N1—C54—C53 | 178.7 (3) |
C28—C27—C6 | 108.65 (14) | H55A—C55—H55B | 109.5 |
C28—C27—C31 | 100.54 (15) | H55A—C55—H55C | 109.5 |
C28—C27—C33 | 114.32 (15) | H55B—C55—H55C | 109.5 |
C31—C27—C6 | 105.60 (14) | C56—C55—H55A | 109.5 |
C33—C27—C6 | 112.36 (15) | C56—C55—H55B | 109.5 |
C33—C27—C31 | 114.40 (15) | C56—C55—H55C | 109.5 |
C27—C28—H28 | 124.1 | N2—C56—C55 | 178.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34···N1i | 0.95 | 2.63 | 3.417 (3) | 140 |
Symmetry code: (i) x, y−1, z. |
Funding information
Funding for this research was provided by: Defense Threat Reduction Agency (DTRA) - Joint Science and Technology Transfer Office for Chemical and Biological Defense (MIPR No. HDTRA13964) ; Air Force Office of Scientific Research (AFOSR) .
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