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

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ISSN: 2414-3146

9-(3,5-Di­methyl­benzyl­­idene)-8-(3,5-di­methyl­phen­yl)-1,3,5,7-tetra­phenyl-2,4,7,8-tetra­hydro-4,7-methano­azulene aceto­nitrile disolvate

CROSSMARK_Color_square_no_text.svg

aDepartment of Chemistry & Chemistry Research Center, United States Air Force Academy, Colorado Springs, CO 80840, USA
*Correspondence e-mail: gary.balaich@usafa.edu

Edited by J. Simpson, University of Otago, New Zealand (Received 23 March 2018; accepted 9 April 2018; online 17 April 2018)

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.

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

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[link]. The bond lengths are typical of those observed in related fulvenes (Peloquin et al., 2012[Peloquin, A. J., Stone, R. S., Avila, S. E., Rudico, E. R., Horn, C. B., Gardner, K. A., Ball, D. W., Johnson, J. E. B., Iacono, S. T. & Balaich, G. J. (2012). J. Org. Chem. 77, 6371-6376.]). A weak C34—H34⋯N1 hydrogen bond (Table 1[link]) links the main mol­ecule to one of the two aceto­nitrile solvent mol­ecules.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C34—H34⋯N1i 0.95 2.63 3.417 (3) 140
Symmetry code: (i) x, y-1, z.
[Figure 1]
Figure 1
The asymmetric unit of of the title compound. Displacement ellipsoids are shown at the 50% probability level.

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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C52H44·2C2H3N
Mr 750.98
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 10.4026 (3), 13.6115 (4), 16.5769 (6)
α, β, γ (°) 105.502 (2), 105.796 (2), 94.038 (2)
V3) 2150.30 (12)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.19 × 0.18 × 0.18
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2017[Bruker, (2017). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.804, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections 32078, 8992, 5894
Rint 0.059
(sin θ/λ)max−1) 0.634
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.140, 1.02
No. of reflections 8992
No. of parameters 529
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.26, −0.24
Computer programs: APEX2 and SAINT (Bruker, 2017[Bruker, (2017). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 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.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2017); cell refinement: 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).

9-(3,5-Dimethylbenzylidene)-8-(3,5-dimethylphenyl)-1,3,5,7-tetraphenyl-2,4,7,8-tetrahydro-4,7-methanoazulene acetonitrile disolvate top
Crystal data top
C52H44·2C2H3NZ = 2
Mr = 750.98F(000) = 800
Triclinic, P1Dx = 1.160 Mg m3
a = 10.4026 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.6115 (4) ÅCell parameters from 3666 reflections
c = 16.5769 (6) Åθ = 2.7–23.0°
α = 105.502 (2)°µ = 0.07 mm1
β = 105.796 (2)°T = 100 K
γ = 94.038 (2)°Prism, dark red
V = 2150.30 (12) Å30.19 × 0.18 × 0.18 mm
Data collection top
Bruker APEXII CCD
diffractometer
5894 reflections with I > 2σ(I)
φ and ω scansRint = 0.059
Absorption correction: multi-scan
(SADABS; Bruker, 2017)
θmax = 26.8°, θmin = 1.7°
Tmin = 0.804, Tmax = 0.914h = 1313
32078 measured reflectionsk = 1717
8992 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-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 reflectionsΔρmax = 0.26 e Å3
529 parametersΔρmin = 0.24 e Å3
0 restraints
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
C10.62899 (18)0.47941 (15)0.14895 (12)0.0208 (4)
C20.6900 (2)0.59098 (15)0.17214 (13)0.0233 (4)
H2A0.6436540.6226620.1271420.028*
H2B0.7874750.5974270.1773240.028*
C30.66858 (18)0.64125 (15)0.25942 (13)0.0216 (4)
C40.60350 (18)0.56787 (14)0.28198 (12)0.0195 (4)
C50.57835 (18)0.46750 (14)0.21387 (12)0.0203 (4)
C60.51239 (18)0.36835 (14)0.22266 (12)0.0194 (4)
H60.5809320.3203840.2247800.023*
C70.63983 (19)0.40180 (15)0.07072 (12)0.0221 (4)
C80.6316 (2)0.42727 (16)0.00655 (13)0.0262 (5)
H80.6176600.4949490.0084480.031*
C90.6433 (2)0.35588 (17)0.08068 (14)0.0318 (5)
H90.6344510.3744170.1330410.038*
C100.6677 (2)0.25814 (17)0.07852 (14)0.0351 (5)
H100.6772840.2095270.1288100.042*
C110.6780 (2)0.23184 (17)0.00221 (15)0.0377 (6)
H110.6950090.1647280.0002270.045*
C120.6638 (2)0.30217 (16)0.07139 (14)0.0293 (5)
H120.6704270.2824280.1230070.035*
C130.71457 (19)0.75077 (15)0.30998 (13)0.0228 (4)
C140.8398 (2)0.80224 (16)0.31707 (15)0.0315 (5)
H140.8966530.7667640.2870110.038*
C150.8825 (2)0.90480 (17)0.36757 (16)0.0374 (6)
H150.9677720.9388450.3712340.045*
C160.8021 (2)0.95767 (16)0.41248 (15)0.0335 (5)
H160.8326621.0271970.4481740.040*
C170.6769 (2)0.90832 (16)0.40489 (14)0.0311 (5)
H170.6205030.9443110.4349850.037*
C180.6332 (2)0.80677 (15)0.35372 (14)0.0270 (5)
H180.5460020.7743720.3481770.032*
C190.38835 (19)0.31274 (15)0.14540 (12)0.0216 (4)
C200.29397 (19)0.36707 (15)0.10607 (12)0.0238 (4)
H200.3110350.4403590.1248810.029*
C210.1756 (2)0.31651 (16)0.04003 (13)0.0279 (5)
C220.1519 (2)0.20943 (17)0.01294 (14)0.0332 (5)
H220.0708890.1741480.0317580.040*
C230.2445 (2)0.15275 (16)0.05000 (14)0.0312 (5)
C240.3626 (2)0.20562 (15)0.11579 (13)0.0269 (5)
H240.4269660.1675450.1409230.032*
C250.0735 (2)0.37751 (18)0.00006 (16)0.0411 (6)
H25A0.0934540.4493490.0374070.062*
H25B0.0176140.3475320.0045060.062*
H25C0.0785550.3751340.0585870.062*
C260.2178 (3)0.03637 (17)0.02230 (16)0.0471 (7)
H26A0.1998170.0132300.0698500.071*
H26B0.2971170.0091000.0094200.071*
H26C0.1392040.0111880.0303730.071*
C270.47673 (18)0.39042 (14)0.31296 (12)0.0198 (4)
C280.36308 (19)0.45486 (14)0.30875 (12)0.0204 (4)
H280.2697530.4267250.2873610.024*
C290.40990 (19)0.55538 (15)0.33861 (12)0.0208 (4)
C300.56498 (18)0.57118 (14)0.36412 (12)0.0194 (4)
H300.6103960.6335640.4150390.023*
C310.59450 (18)0.46958 (14)0.38120 (12)0.0193 (4)
C320.69876 (18)0.45072 (15)0.43931 (12)0.0204 (4)
H320.6972360.3808200.4391980.025*
C330.44909 (19)0.29195 (14)0.33668 (12)0.0209 (4)
C340.5261 (2)0.21256 (15)0.32410 (13)0.0249 (4)
H340.5989250.2200350.3008250.030*
C350.4982 (2)0.12266 (16)0.34500 (13)0.0290 (5)
H350.5509630.0690710.3350400.035*
C360.3940 (2)0.11082 (16)0.38019 (14)0.0306 (5)
H360.3736630.0488020.3933120.037*
C370.3198 (2)0.19009 (16)0.39607 (14)0.0292 (5)
H370.2496730.1833010.4217780.035*
C380.34690 (19)0.27988 (15)0.37467 (13)0.0238 (4)
H380.2950600.3338050.3861050.029*
C390.33417 (19)0.64335 (15)0.33960 (13)0.0216 (4)
C400.2347 (2)0.64701 (16)0.26484 (13)0.0265 (5)
H400.2092020.5894410.2133670.032*
C410.1732 (2)0.73391 (17)0.26525 (15)0.0318 (5)
H410.1071130.7360060.2135770.038*
C420.2068 (2)0.81772 (17)0.33996 (15)0.0332 (5)
H420.1657910.8778170.3393300.040*
C430.3008 (2)0.81329 (16)0.41577 (14)0.0287 (5)
H430.3215620.8693670.4680900.034*
C440.3647 (2)0.72731 (15)0.41550 (13)0.0243 (4)
H440.4299790.7254040.4675620.029*
C450.81598 (18)0.52355 (14)0.50365 (12)0.0209 (4)
C460.87823 (19)0.50031 (15)0.58076 (13)0.0236 (4)
H460.8450590.4378010.5886320.028*
C470.98684 (19)0.56552 (16)0.64614 (13)0.0262 (5)
C481.03670 (19)0.65565 (16)0.63328 (13)0.0259 (5)
H481.1108290.7011870.6778590.031*
C490.98033 (19)0.68044 (15)0.55664 (13)0.0256 (5)
C500.87020 (19)0.61401 (15)0.49205 (13)0.0236 (4)
H500.8313470.6304400.4393100.028*
C511.0514 (2)0.5376 (2)0.72843 (15)0.0426 (6)
H51A0.9979460.4754630.7286230.064*
H51B1.0547860.5947100.7799780.064*
H51C1.1433780.5244480.7302040.064*
C521.0402 (2)0.77656 (17)0.54269 (16)0.0389 (6)
H52A1.0906640.8258990.5996950.058*
H52B0.9675050.8076970.5121100.058*
H52C1.1014520.7584710.5072180.058*
C530.6664 (3)0.9128 (2)0.15696 (19)0.0587 (8)
H53A0.6272720.8956270.1998800.088*
H53B0.7521460.8859600.1608010.088*
H53C0.6036050.8818010.0977010.088*
C540.6906 (2)1.0242 (2)0.17549 (16)0.0403 (6)
C550.9502 (3)0.8449 (2)0.80174 (18)0.0521 (7)
H55A1.0267120.8420340.8505910.078*
H55B0.9547710.7973110.7469060.078*
H55C0.8653360.8248450.8122740.078*
C560.9560 (2)0.9494 (2)0.79496 (16)0.0466 (7)
N10.7109 (2)1.11149 (19)0.18894 (16)0.0535 (6)
N20.9628 (2)1.0317 (2)0.79074 (16)0.0636 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0183 (10)0.0239 (11)0.0204 (10)0.0052 (8)0.0035 (8)0.0088 (8)
C20.0233 (10)0.0245 (11)0.0243 (10)0.0039 (8)0.0076 (8)0.0103 (9)
C30.0178 (10)0.0224 (11)0.0247 (10)0.0034 (8)0.0055 (8)0.0083 (8)
C40.0154 (9)0.0203 (10)0.0219 (10)0.0039 (8)0.0035 (8)0.0066 (8)
C50.0164 (9)0.0206 (10)0.0230 (10)0.0034 (8)0.0030 (8)0.0077 (8)
C60.0185 (10)0.0195 (10)0.0205 (10)0.0037 (8)0.0062 (8)0.0063 (8)
C70.0188 (10)0.0255 (11)0.0218 (10)0.0023 (8)0.0073 (8)0.0058 (8)
C80.0267 (11)0.0283 (12)0.0257 (11)0.0061 (9)0.0100 (9)0.0089 (9)
C90.0337 (12)0.0395 (14)0.0243 (11)0.0066 (10)0.0115 (9)0.0096 (10)
C100.0426 (14)0.0324 (13)0.0294 (12)0.0035 (11)0.0181 (10)0.0008 (10)
C110.0533 (15)0.0248 (12)0.0415 (14)0.0106 (11)0.0251 (12)0.0083 (10)
C120.0354 (12)0.0283 (12)0.0280 (11)0.0091 (10)0.0128 (9)0.0102 (9)
C130.0248 (10)0.0198 (11)0.0245 (10)0.0033 (8)0.0071 (8)0.0079 (8)
C140.0271 (11)0.0241 (12)0.0438 (13)0.0026 (9)0.0157 (10)0.0063 (10)
C150.0284 (12)0.0291 (13)0.0522 (15)0.0043 (10)0.0158 (11)0.0064 (11)
C160.0401 (13)0.0189 (11)0.0397 (13)0.0001 (10)0.0133 (10)0.0054 (9)
C170.0402 (13)0.0217 (12)0.0371 (12)0.0065 (10)0.0203 (10)0.0090 (10)
C180.0274 (11)0.0221 (11)0.0353 (12)0.0023 (9)0.0141 (9)0.0104 (9)
C190.0223 (10)0.0219 (11)0.0200 (10)0.0010 (8)0.0073 (8)0.0050 (8)
C200.0267 (11)0.0206 (11)0.0224 (10)0.0029 (8)0.0069 (8)0.0044 (8)
C210.0251 (11)0.0309 (12)0.0241 (11)0.0017 (9)0.0029 (9)0.0078 (9)
C220.0301 (12)0.0338 (13)0.0251 (11)0.0050 (10)0.0011 (9)0.0037 (10)
C230.0379 (13)0.0245 (12)0.0253 (11)0.0016 (10)0.0064 (9)0.0026 (9)
C240.0324 (12)0.0219 (11)0.0244 (11)0.0053 (9)0.0077 (9)0.0047 (9)
C250.0334 (13)0.0383 (14)0.0409 (14)0.0052 (11)0.0047 (11)0.0105 (11)
C260.0613 (17)0.0261 (13)0.0385 (14)0.0019 (12)0.0006 (12)0.0012 (11)
C270.0194 (10)0.0199 (10)0.0199 (10)0.0023 (8)0.0066 (8)0.0052 (8)
C280.0188 (10)0.0216 (11)0.0203 (10)0.0020 (8)0.0070 (8)0.0047 (8)
C290.0193 (10)0.0227 (11)0.0206 (10)0.0032 (8)0.0068 (8)0.0063 (8)
C300.0199 (10)0.0169 (10)0.0211 (10)0.0021 (8)0.0070 (8)0.0047 (8)
C310.0199 (10)0.0199 (10)0.0204 (10)0.0025 (8)0.0110 (8)0.0050 (8)
C320.0211 (10)0.0171 (10)0.0232 (10)0.0027 (8)0.0084 (8)0.0047 (8)
C330.0219 (10)0.0181 (10)0.0185 (9)0.0012 (8)0.0025 (8)0.0032 (8)
C340.0281 (11)0.0217 (11)0.0256 (11)0.0039 (9)0.0093 (9)0.0069 (9)
C350.0395 (13)0.0215 (11)0.0257 (11)0.0081 (9)0.0090 (9)0.0068 (9)
C360.0370 (13)0.0216 (11)0.0296 (12)0.0030 (10)0.0047 (10)0.0091 (9)
C370.0262 (11)0.0305 (12)0.0312 (12)0.0020 (9)0.0078 (9)0.0119 (10)
C380.0213 (10)0.0232 (11)0.0248 (10)0.0018 (8)0.0058 (8)0.0056 (9)
C390.0192 (10)0.0205 (10)0.0273 (11)0.0015 (8)0.0105 (8)0.0076 (8)
C400.0242 (11)0.0287 (12)0.0267 (11)0.0055 (9)0.0087 (9)0.0072 (9)
C410.0250 (11)0.0403 (14)0.0340 (12)0.0123 (10)0.0074 (9)0.0171 (11)
C420.0304 (12)0.0266 (12)0.0488 (14)0.0121 (10)0.0171 (11)0.0142 (11)
C430.0288 (11)0.0218 (11)0.0356 (12)0.0038 (9)0.0149 (10)0.0036 (9)
C440.0240 (10)0.0219 (11)0.0279 (11)0.0038 (9)0.0102 (9)0.0065 (9)
C450.0188 (10)0.0210 (11)0.0230 (10)0.0038 (8)0.0089 (8)0.0039 (8)
C460.0205 (10)0.0231 (11)0.0280 (11)0.0037 (8)0.0087 (8)0.0071 (9)
C470.0194 (10)0.0327 (12)0.0257 (11)0.0064 (9)0.0061 (8)0.0074 (9)
C480.0167 (10)0.0274 (12)0.0270 (11)0.0012 (8)0.0054 (8)0.0008 (9)
C490.0205 (10)0.0233 (11)0.0315 (11)0.0019 (8)0.0094 (9)0.0048 (9)
C500.0213 (10)0.0248 (11)0.0247 (10)0.0029 (8)0.0071 (8)0.0074 (9)
C510.0296 (13)0.0536 (16)0.0386 (14)0.0004 (11)0.0031 (10)0.0195 (12)
C520.0347 (13)0.0340 (13)0.0420 (14)0.0084 (10)0.0069 (10)0.0099 (11)
C530.070 (2)0.0522 (18)0.0521 (17)0.0051 (15)0.0122 (15)0.0229 (14)
C540.0357 (13)0.0501 (17)0.0417 (14)0.0102 (12)0.0161 (11)0.0192 (13)
C550.0455 (16)0.0554 (18)0.0453 (16)0.0020 (13)0.0127 (12)0.0019 (13)
C560.0338 (14)0.061 (2)0.0344 (14)0.0010 (13)0.0034 (11)0.0066 (13)
N10.0609 (15)0.0514 (15)0.0639 (15)0.0208 (12)0.0363 (12)0.0217 (12)
N20.0529 (15)0.0726 (19)0.0565 (16)0.0047 (14)0.0003 (12)0.0230 (14)
Geometric parameters (Å, º) top
C1—C21.509 (3)C28—C291.329 (3)
C1—C51.361 (3)C29—C301.536 (3)
C1—C71.475 (3)C29—C391.478 (3)
C2—H2A0.9900C30—H301.0000
C2—H2B0.9900C30—C311.519 (2)
C2—C31.509 (3)C31—C321.331 (3)
C3—C41.356 (2)C32—H320.9500
C3—C131.472 (3)C32—C451.471 (3)
C4—C51.474 (3)C33—C341.395 (3)
C4—C301.511 (3)C33—C381.396 (3)
C5—C61.531 (2)C34—H340.9500
C6—H61.0000C34—C351.390 (3)
C6—C191.524 (3)C35—H350.9500
C6—C271.596 (3)C35—C361.382 (3)
C7—C81.396 (3)C36—H360.9500
C7—C121.398 (3)C36—C371.380 (3)
C8—H80.9500C37—H370.9500
C8—C91.389 (3)C37—C381.392 (3)
C9—H90.9500C38—H380.9500
C9—C101.380 (3)C39—C401.397 (3)
C10—H100.9500C39—C441.397 (3)
C10—C111.383 (3)C40—H400.9500
C11—H110.9500C40—C411.383 (3)
C11—C121.386 (3)C41—H410.9500
C12—H120.9500C41—C421.382 (3)
C13—C141.395 (3)C42—H420.9500
C13—C181.397 (3)C42—C431.385 (3)
C14—H140.9500C43—H430.9500
C14—C151.390 (3)C43—C441.385 (3)
C15—H150.9500C44—H440.9500
C15—C161.382 (3)C45—C461.396 (3)
C16—H160.9500C45—C501.400 (3)
C16—C171.381 (3)C46—H460.9500
C17—H170.9500C46—C471.384 (3)
C17—C181.383 (3)C47—C481.389 (3)
C18—H180.9500C47—C511.507 (3)
C19—C201.395 (3)C48—H480.9500
C19—C241.389 (3)C48—C491.387 (3)
C20—H200.9500C49—C501.395 (3)
C20—C211.390 (3)C49—C521.509 (3)
C21—C221.388 (3)C50—H500.9500
C21—C251.514 (3)C51—H51A0.9800
C22—H220.9500C51—H51B0.9800
C22—C231.392 (3)C51—H51C0.9800
C23—C241.394 (3)C52—H52A0.9800
C23—C261.509 (3)C52—H52B0.9800
C24—H240.9500C52—H52C0.9800
C25—H25A0.9800C53—H53A0.9800
C25—H25B0.9800C53—H53B0.9800
C25—H25C0.9800C53—H53C0.9800
C26—H26A0.9800C53—C541.452 (4)
C26—H26B0.9800C54—N11.142 (3)
C26—H26C0.9800C55—H55A0.9800
C27—C281.519 (3)C55—H55B0.9800
C27—C311.533 (3)C55—H55C0.9800
C27—C331.524 (2)C55—C561.455 (4)
C28—H280.9500C56—N21.140 (3)
C5—C1—C2108.57 (17)C29—C28—C27111.86 (16)
C5—C1—C7130.12 (18)C29—C28—H28124.1
C7—C1—C2121.10 (16)C28—C29—C30109.16 (17)
C1—C2—H2A110.9C28—C29—C39129.03 (17)
C1—C2—H2B110.9C39—C29—C30121.42 (16)
C1—C2—C3104.33 (15)C4—C30—C29107.43 (15)
H2A—C2—H2B108.9C4—C30—H30114.2
C3—C2—H2A110.9C4—C30—C31104.56 (15)
C3—C2—H2B110.9C29—C30—H30114.2
C4—C3—C2107.99 (17)C31—C30—C29101.13 (14)
C4—C3—C13127.47 (18)C31—C30—H30114.2
C13—C3—C2124.52 (16)C30—C31—C27103.66 (15)
C3—C4—C5110.18 (17)C32—C31—C27126.94 (17)
C3—C4—C30131.60 (18)C32—C31—C30129.37 (17)
C5—C4—C30118.04 (16)C31—C32—H32115.6
C1—C5—C4108.93 (16)C31—C32—C45128.72 (18)
C1—C5—C6128.46 (18)C45—C32—H32115.6
C4—C5—C6122.53 (16)C34—C33—C27122.01 (17)
C5—C6—H6107.1C34—C33—C38117.59 (17)
C5—C6—C27110.84 (15)C38—C33—C27120.38 (18)
C19—C6—C5113.78 (15)C33—C34—H34119.4
C19—C6—H6107.1C35—C34—C33121.18 (19)
C19—C6—C27110.62 (15)C35—C34—H34119.4
C27—C6—H6107.1C34—C35—H35119.8
C8—C7—C1120.45 (18)C36—C35—C34120.4 (2)
C8—C7—C12117.38 (18)C36—C35—H35119.8
C12—C7—C1122.12 (17)C35—C36—H36120.4
C7—C8—H8119.3C37—C36—C35119.28 (19)
C9—C8—C7121.49 (19)C37—C36—H36120.4
C9—C8—H8119.3C36—C37—H37119.8
C8—C9—H9119.9C36—C37—C38120.5 (2)
C10—C9—C8120.2 (2)C38—C37—H37119.8
C10—C9—H9119.9C33—C38—H38119.5
C9—C10—H10120.4C37—C38—C33121.0 (2)
C9—C10—C11119.2 (2)C37—C38—H38119.5
C11—C10—H10120.4C40—C39—C29121.53 (18)
C10—C11—H11119.6C40—C39—C44118.30 (18)
C10—C11—C12120.8 (2)C44—C39—C29120.13 (17)
C12—C11—H11119.6C39—C40—H40119.8
C7—C12—H12119.5C41—C40—C39120.4 (2)
C11—C12—C7120.91 (19)C41—C40—H40119.8
C11—C12—H12119.5C40—C41—H41119.6
C14—C13—C3122.04 (18)C42—C41—C40120.8 (2)
C14—C13—C18117.55 (18)C42—C41—H41119.6
C18—C13—C3120.41 (17)C41—C42—H42120.3
C13—C14—H14119.6C41—C42—C43119.4 (2)
C15—C14—C13120.8 (2)C43—C42—H42120.3
C15—C14—H14119.6C42—C43—H43119.9
C14—C15—H15119.7C42—C43—C44120.2 (2)
C16—C15—C14120.6 (2)C44—C43—H43119.9
C16—C15—H15119.7C39—C44—H44119.6
C15—C16—H16120.4C43—C44—C39120.82 (19)
C17—C16—C15119.2 (2)C43—C44—H44119.6
C17—C16—H16120.4C46—C45—C32117.90 (17)
C16—C17—H17119.8C46—C45—C50117.86 (17)
C16—C17—C18120.3 (2)C50—C45—C32124.23 (17)
C18—C17—H17119.8C45—C46—H46119.0
C13—C18—H18119.3C47—C46—C45122.04 (18)
C17—C18—C13121.41 (19)C47—C46—H46119.0
C17—C18—H18119.3C46—C47—C48118.63 (18)
C20—C19—C6121.36 (17)C46—C47—C51120.43 (19)
C24—C19—C6120.25 (17)C48—C47—C51120.92 (18)
C24—C19—C20118.28 (18)C47—C48—H48119.4
C19—C20—H20119.2C49—C48—C47121.27 (18)
C21—C20—C19121.58 (18)C49—C48—H48119.4
C21—C20—H20119.2C48—C49—C50119.05 (18)
C20—C21—C25120.40 (19)C48—C49—C52120.19 (18)
C22—C21—C20118.70 (19)C50—C49—C52120.74 (18)
C22—C21—C25120.89 (18)C45—C50—H50119.5
C21—C22—H22119.4C49—C50—C45121.09 (18)
C21—C22—C23121.27 (19)C49—C50—H50119.5
C23—C22—H22119.4C47—C51—H51A109.5
C22—C23—C24118.70 (19)C47—C51—H51B109.5
C22—C23—C26121.51 (19)C47—C51—H51C109.5
C24—C23—C26119.8 (2)H51A—C51—H51B109.5
C19—C24—C23121.45 (19)H51A—C51—H51C109.5
C19—C24—H24119.3H51B—C51—H51C109.5
C23—C24—H24119.3C49—C52—H52A109.5
C21—C25—H25A109.5C49—C52—H52B109.5
C21—C25—H25B109.5C49—C52—H52C109.5
C21—C25—H25C109.5H52A—C52—H52B109.5
H25A—C25—H25B109.5H52A—C52—H52C109.5
H25A—C25—H25C109.5H52B—C52—H52C109.5
H25B—C25—H25C109.5H53A—C53—H53B109.5
C23—C26—H26A109.5H53A—C53—H53C109.5
C23—C26—H26B109.5H53B—C53—H53C109.5
C23—C26—H26C109.5C54—C53—H53A109.5
H26A—C26—H26B109.5C54—C53—H53B109.5
H26A—C26—H26C109.5C54—C53—H53C109.5
H26B—C26—H26C109.5N1—C54—C53178.7 (3)
C28—C27—C6108.65 (14)H55A—C55—H55B109.5
C28—C27—C31100.54 (15)H55A—C55—H55C109.5
C28—C27—C33114.32 (15)H55B—C55—H55C109.5
C31—C27—C6105.60 (14)C56—C55—H55A109.5
C33—C27—C6112.36 (15)C56—C55—H55B109.5
C33—C27—C31114.40 (15)C56—C55—H55C109.5
C27—C28—H28124.1N2—C56—C55178.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C34—H34···N1i0.952.633.417 (3)140
Symmetry code: (i) x, y1, 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) .

References

First citationBruker, (2017). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationMacrae, 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.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationPeloquin, A. J., Stone, R. S., Avila, S. E., Rudico, E. R., Horn, C. B., Gardner, K. A., Ball, D. W., Johnson, J. E. B., Iacono, S. T. & Balaich, G. J. (2012). J. Org. Chem. 77, 6371–6376.  CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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