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Acta Cryst. (2009). E65, o2337    [ doi:10.1107/S1600536809034436 ]

N4,N8,3,6,9,10,11-Heptaphenyl-3,6,9,10,11-pentaazatricyclo[5.2.1.12,5]undecane-4,8-diamine

A. Taheri and S. M. Moosavi

Abstract top

The title compound, C48H43N7, is a polyazapolycyclic compound with a near-C2 symmetric skeleton. In the crystal, a N-H...[pi] interaction occurs.

Comment top

Polyazapolycyclic compounds are constituted of saturated ring systems with multiple N atoms with different kinds of skeletons which be utilized for the syntheses of other derivatives (Nielsen et al., 1992). Among the cage skeletons, 2,4,6,8,10,12-Hexabenzyl-2,4,6,8,10,12-hexaazaisowurtzitane (HBIW) is a famous precursor for 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (HNIW), a highly energetic compound (Nielsen et al., 1990). In the norbornane skeletons triazanorbornanes or triazabicyclo[2,2,1]heptanes have been determined (Nitravati & Sikhibhushan, 1939).

N4,N8,3,6,9,10,11-Heptaphenyl-3,6,9,10,11-pentaazatricyclo[5,2,11,7,12,5]undecane-4,8-diamine is synthesized for the first time via a catalytic reaction of N3,N6,2,5,7-pentaphenyl-2,5,7-triazabicyclo[2,2,1]heptane-3,6-diamine (Taheri & Mossavi, 2009a; Taheri & Mossavi, 2009b) with nickel(II)nitrate as reagent. An ORTEP diagram of the title compound is shown in Figure 1. It consists of a nine-membered ring and two N-atoms bridging between C1 and C3 as well as C4 and C6. The compound is chiral, but only the relative configuration of the chiral centres could be determined. The skeleton is almost C2 symmetric with a two-fold rotation axis running through the midpoint of the C1-C4 bond and N4.

There are no classical hydrogen bonds, just a weak intermolecular interactions, N3—H3···cg [(C71,C72, C73, C74, C75, C76) at x,y,z + z]: H···cg 2.90 Å, angle at H 168.6°.

Related literature top

For the synthesis of the 2,5,7–triazabicyclo[2.2.1]heptane derivative, see: Taheri & Moosavi (2009a,b). For general background to triazanorbornanes, see: Nitravati & Sikhibhushan (1939). For the syntheses of polyazapolycyclic compounds, see: Nielsen et al. (1990, 1992). Cg is the centroid of the C71–C76 ring.

Experimental top

To a stirred solution of N3,N6,2,5,7-pentaphenyl-2,5,7-triazabicyclo[2,2,1]heptane-\ 3,6-diamine(II) (1 mmol) in 20 ml of acetonitril was added 8.9 mg of nickel(II)nitrate (0.5 mmol) slowly at 288 K over 30 min. The reaction mixture was warmed up to 318 K and left for 40 min. The reaction mixture was then allowed to cool to 298 K and stand for 48 h. The precipitation was filtered and washed with cold ethanol to give a white powder 0.61 g (85% yield) of the title compound (m.p. 531 K). Recrystallization in hot dichloromethane yielded the single crystals for data collection. IR (KBr) (υmax/cm-1): 3358 (NH). 1H NMR (CDCl3): δH 6.74–7.24 (35H, m, CHAr),6.30 (2H, s, CH), 5.56 (2H, s, CH), 5.21 (2H, d, 2J=7.0 Hz,NH), 3.89 (2H, d, 2J=7.0 Hz, NH).13C NMR (CDCl3):δC 146.9, 145.6, 145.2, 143.3, 142.5, 130.0, 129.7, 129.5, 129.4,129.1, 129.0, 119.9, 119.0, 118.8, 118.4, 118.3, 118.2, 116.3, 114.6, 114.3, 113.8,113.6, 113.5, 113.2 (CHAr), 81.9 (2CH), 72.3 (2CH), 76.1 (2CH).

Refinement top

All H atoms were located in difference Fourier synthesis. They were refined using a riding model with N-H ranging from 0.81Å - 0.88 Å, C-H ranging from 0.95Å - 1.00 Å and with Uiso(H) set to 1.2 Ueq(C,N).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Only H atoms bond to N and tertiary C atoms are shown. Displacement ellipsoids are at the 50% probability level.
N4,N8,3,6,9,10,11-Heptaphenyl-3,6,9,10,11-\ pentaazatricyclo[5.2.1.12,5]undecane-4,8-diamine top
Crystal data top
C48H43N7Z = 1
Mr = 717.89F(000) = 380
Triclinic, P1Dx = 1.314 Mg m−3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4889 (19) ÅCell parameters from 1186 reflections
b = 9.6252 (19) Åθ = 2.3–22.0°
c = 10.967 (2) ŵ = 0.08 mm−1
α = 113.924 (4)°T = 100 K
β = 94.555 (4)°Prism, red
γ = 93.835 (4)°0.28 × 0.15 × 0.06 mm
V = 907.3 (3) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2787 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
graphiteθmax = 28.0°, θmin = 2.1°
φ and ω scansh = −12→12
9544 measured reflectionsk = −12→12
4343 independent reflectionsl = −14→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: mixed
wR(F2) = 0.121H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.048P)2]
where P = (Fo2 + 2Fc2)/3
4343 reflections(Δ/σ)max < 0.001
496 parametersΔρmax = 0.25 e Å−3
3 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C48H43N7γ = 93.835 (4)°
Mr = 717.89V = 907.3 (3) Å3
Triclinic, P1Z = 1
a = 9.4889 (19) ÅMo Kα radiation
b = 9.6252 (19) ŵ = 0.08 mm−1
c = 10.967 (2) ÅT = 100 K
α = 113.924 (4)°0.28 × 0.15 × 0.06 mm
β = 94.555 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2787 reflections with I > 2σ(I)
9544 measured reflectionsRint = 0.062
4343 independent reflectionsθmax = 28.0°
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.121Δρmax = 0.25 e Å−3
S = 1.03Δρmin = −0.24 e Å−3
4343 reflectionsAbsolute structure: ?
496 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1−0.1525 (3)0.6552 (4)0.2565 (3)0.0243 (8)
N2−0.0946 (3)0.7828 (4)0.4788 (3)0.0251 (8)
N3−0.0754 (4)0.5526 (4)0.5139 (4)0.0310 (9)
H3−0.02310.55890.57870.037*
N40.0672 (3)0.5451 (4)0.2164 (3)0.0232 (7)
N50.1312 (3)0.8199 (4)0.3351 (3)0.0233 (8)
N6−0.0103 (3)0.8702 (4)0.1880 (3)0.0249 (8)
N70.1492 (3)0.7731 (4)0.0288 (3)0.0272 (8)
H70.18150.86900.05340.033*
C1−0.1258 (4)0.8074 (5)0.3592 (4)0.0255 (9)
H1A−0.21200.86290.36460.031*
C2−0.0255 (4)0.6409 (5)0.4445 (4)0.0259 (10)
H2A0.07960.66790.46860.031*
C3−0.0588 (4)0.5602 (5)0.2896 (4)0.0238 (9)
H3A−0.11060.45660.26390.029*
C40.0039 (4)0.8930 (4)0.3268 (4)0.0225 (9)
H4A0.01751.00420.38830.027*
C50.0517 (4)0.7329 (5)0.1059 (4)0.0223 (9)
H5A−0.02380.65040.04620.027*
C60.1311 (4)0.6857 (5)0.2101 (4)0.0255 (9)
H6A0.23150.67250.18970.031*
C11−0.2637 (4)0.5993 (5)0.1503 (4)0.0233 (9)
C12−0.2673 (4)0.4571 (5)0.0480 (5)0.0331 (11)
H12A−0.19550.39380.05060.040*
C13−0.3732 (4)0.4043 (5)−0.0586 (5)0.0353 (11)
H13A−0.37410.3049−0.12820.042*
C14−0.4789 (5)0.4956 (5)−0.0651 (5)0.0381 (12)
H14A−0.55010.4616−0.14000.046*
C15−0.4775 (5)0.6360 (5)0.0396 (4)0.0325 (11)
H15A−0.55020.69850.03740.039*
C16−0.3740 (4)0.6886 (5)0.1473 (4)0.0261 (10)
H16A−0.37680.78510.21960.031*
C21−0.0692 (4)0.9047 (5)0.6055 (4)0.0267 (9)
C22−0.1324 (4)1.0411 (5)0.6308 (4)0.0298 (10)
H22A−0.19221.04970.56110.036*
C23−0.1084 (5)1.1597 (5)0.7535 (5)0.0343 (11)
H23A−0.15071.25100.76790.041*
C24−0.0243 (5)1.1509 (6)0.8581 (5)0.0395 (12)
H24A−0.01001.23400.94420.047*
C250.0386 (5)1.0193 (6)0.8349 (4)0.0361 (11)
H25A0.09881.01260.90540.043*
C260.0159 (5)0.8977 (6)0.7122 (4)0.0341 (11)
H26A0.05870.80710.69930.041*
C31−0.2083 (4)0.4805 (5)0.5026 (5)0.0300 (10)
C32−0.2259 (5)0.3798 (5)0.5641 (5)0.0390 (12)
H32A−0.14750.36670.61640.047*
C33−0.3554 (5)0.2998 (6)0.5492 (5)0.0415 (13)
H33A−0.36470.22820.58820.050*
C34−0.4730 (5)0.3211 (5)0.4788 (5)0.0374 (11)
H34A−0.56270.26570.46990.045*
C35−0.4578 (4)0.4236 (5)0.4217 (5)0.0331 (11)
H35A−0.53860.44000.37420.040*
C36−0.3283 (4)0.5035 (5)0.4315 (5)0.0313 (10)
H36A−0.32000.57350.39070.038*
C410.1493 (4)0.4233 (4)0.1994 (4)0.0236 (9)
C420.1242 (4)0.3272 (4)0.2642 (4)0.0251 (9)
H42A0.05370.34640.32420.030*
C430.2018 (4)0.2039 (5)0.2412 (5)0.0300 (10)
H43A0.18170.13730.28360.036*
C440.3079 (4)0.1759 (5)0.1577 (5)0.0331 (11)
H44A0.36190.09230.14410.040*
C450.3341 (4)0.2711 (5)0.0946 (5)0.0306 (10)
H45A0.40660.25250.03670.037*
C460.2562 (4)0.3936 (4)0.1141 (4)0.0268 (9)
H46A0.27560.45790.06940.032*
C510.2448 (4)0.8775 (5)0.4368 (4)0.0248 (9)
C520.2463 (4)1.0172 (5)0.5463 (4)0.0294 (10)
H52A0.16861.07610.55230.035*
C530.3605 (5)1.0712 (5)0.6467 (5)0.0347 (11)
H53A0.35921.16620.72130.042*
C540.4758 (5)0.9894 (5)0.6402 (5)0.0336 (11)
H54A0.55451.02780.70840.040*
C550.4739 (5)0.8506 (5)0.5322 (5)0.0357 (11)
H55A0.55250.79300.52640.043*
C560.3609 (4)0.7933 (5)0.4323 (5)0.0341 (11)
H56A0.36160.69620.36000.041*
C61−0.1228 (4)0.9217 (5)0.1294 (5)0.0286 (10)
C62−0.1656 (4)0.8543 (5)−0.0059 (5)0.0313 (10)
H62A−0.12000.7705−0.06210.038*
C63−0.2761 (5)0.9077 (6)−0.0627 (5)0.0368 (11)
H63A−0.30520.8600−0.15670.044*
C64−0.3418 (5)1.0297 (6)0.0188 (5)0.0391 (12)
H64A−0.41721.0657−0.01860.047*
C65−0.2976 (5)1.0993 (5)0.1552 (5)0.0375 (12)
H65A−0.34311.18330.21100.045*
C66−0.1882 (4)1.0486 (5)0.2114 (5)0.0329 (11)
H66A−0.15731.09900.30480.039*
C710.1765 (4)0.6732 (5)−0.0973 (4)0.0290 (10)
C720.1245 (4)0.5187 (5)−0.1531 (5)0.0356 (11)
H72A0.06880.4791−0.10380.043*
C730.1538 (5)0.4225 (6)−0.2802 (5)0.0449 (13)
H73A0.11650.3179−0.31740.054*
C740.2338 (5)0.4747 (7)−0.3516 (5)0.0458 (13)
H74A0.25020.4080−0.43970.055*
C750.2917 (5)0.6242 (7)−0.2973 (5)0.0491 (14)
H75A0.35150.6596−0.34650.059*
C760.2640 (5)0.7246 (6)−0.1709 (5)0.0401 (12)
H76A0.30440.8282−0.13440.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0191 (16)0.0197 (18)0.031 (2)0.0057 (14)−0.0021 (15)0.0081 (16)
N20.0234 (18)0.030 (2)0.0216 (19)0.0074 (15)0.0003 (15)0.0098 (17)
N30.0276 (19)0.041 (2)0.033 (2)0.0065 (16)−0.0004 (16)0.0245 (18)
N40.0186 (17)0.0204 (17)0.031 (2)0.0054 (14)0.0036 (14)0.0106 (15)
N50.0195 (17)0.0219 (19)0.025 (2)0.0091 (14)0.0004 (15)0.0056 (16)
N60.0239 (17)0.0233 (19)0.028 (2)0.0095 (14)0.0032 (15)0.0106 (16)
N70.0257 (19)0.0223 (19)0.033 (2)0.0075 (15)0.0063 (16)0.0102 (17)
C10.024 (2)0.026 (2)0.025 (2)0.0081 (17)0.0009 (18)0.0081 (19)
C20.021 (2)0.032 (2)0.030 (3)0.0084 (17)0.0045 (18)0.016 (2)
C30.0173 (19)0.024 (2)0.034 (2)0.0053 (16)0.0023 (18)0.0144 (19)
C40.021 (2)0.021 (2)0.023 (2)0.0075 (16)−0.0003 (17)0.0063 (18)
C50.022 (2)0.022 (2)0.024 (2)0.0079 (16)0.0002 (18)0.0098 (18)
C60.023 (2)0.027 (2)0.025 (2)0.0052 (17)0.0029 (18)0.0095 (19)
C110.018 (2)0.028 (2)0.025 (2)0.0025 (17)0.0008 (17)0.0120 (19)
C120.025 (2)0.036 (3)0.036 (3)0.0055 (19)−0.001 (2)0.013 (2)
C130.030 (2)0.036 (3)0.032 (3)0.003 (2)−0.001 (2)0.006 (2)
C140.031 (2)0.041 (3)0.040 (3)0.001 (2)−0.007 (2)0.016 (2)
C150.028 (2)0.036 (3)0.032 (3)0.0084 (19)−0.001 (2)0.013 (2)
C160.021 (2)0.028 (2)0.027 (2)0.0072 (17)0.0019 (19)0.009 (2)
C210.019 (2)0.034 (2)0.026 (2)−0.0017 (18)0.0021 (17)0.012 (2)
C220.024 (2)0.035 (3)0.032 (3)0.0085 (19)0.0004 (19)0.014 (2)
C230.036 (3)0.028 (3)0.033 (3)0.0059 (19)0.004 (2)0.006 (2)
C240.041 (3)0.042 (3)0.025 (3)0.005 (2)0.003 (2)0.003 (2)
C250.034 (3)0.051 (3)0.026 (3)0.004 (2)0.001 (2)0.019 (2)
C260.032 (2)0.046 (3)0.029 (3)0.008 (2)−0.001 (2)0.021 (2)
C310.027 (2)0.026 (2)0.035 (3)0.0078 (18)0.004 (2)0.010 (2)
C320.031 (2)0.047 (3)0.048 (3)0.007 (2)0.005 (2)0.030 (3)
C330.035 (3)0.052 (3)0.053 (3)0.003 (2)0.006 (2)0.037 (3)
C340.027 (2)0.041 (3)0.046 (3)0.002 (2)0.004 (2)0.020 (2)
C350.026 (2)0.034 (3)0.036 (3)0.0058 (19)0.000 (2)0.011 (2)
C360.032 (2)0.029 (2)0.034 (3)0.0075 (19)0.005 (2)0.014 (2)
C410.018 (2)0.024 (2)0.025 (2)0.0012 (16)−0.0026 (17)0.0072 (18)
C420.022 (2)0.026 (2)0.025 (2)0.0052 (17)−0.0030 (18)0.0090 (19)
C430.027 (2)0.026 (2)0.040 (3)0.0035 (18)0.000 (2)0.017 (2)
C440.025 (2)0.029 (2)0.045 (3)0.0117 (19)0.003 (2)0.014 (2)
C450.026 (2)0.028 (2)0.036 (3)0.0111 (19)0.007 (2)0.010 (2)
C460.022 (2)0.022 (2)0.034 (3)0.0024 (17)−0.0007 (19)0.0103 (19)
C510.022 (2)0.025 (2)0.030 (2)0.0031 (17)0.0013 (18)0.014 (2)
C520.024 (2)0.025 (2)0.032 (3)0.0014 (17)0.003 (2)0.005 (2)
C530.030 (2)0.027 (2)0.036 (3)0.0007 (19)0.000 (2)0.003 (2)
C540.026 (2)0.034 (3)0.036 (3)−0.0005 (19)−0.008 (2)0.012 (2)
C550.028 (2)0.032 (3)0.045 (3)0.0086 (19)−0.002 (2)0.014 (2)
C560.029 (2)0.026 (2)0.041 (3)0.0068 (19)−0.002 (2)0.007 (2)
C610.022 (2)0.028 (2)0.043 (3)0.0075 (17)0.0059 (19)0.021 (2)
C620.034 (2)0.032 (2)0.033 (3)0.0144 (19)0.010 (2)0.016 (2)
C630.035 (3)0.050 (3)0.034 (3)0.015 (2)0.002 (2)0.024 (2)
C640.035 (3)0.048 (3)0.042 (3)0.022 (2)0.008 (2)0.024 (3)
C650.032 (2)0.032 (3)0.057 (3)0.023 (2)0.015 (2)0.023 (2)
C660.032 (2)0.027 (2)0.041 (3)0.0095 (19)0.010 (2)0.013 (2)
C710.023 (2)0.037 (3)0.030 (2)0.0085 (18)0.0001 (19)0.017 (2)
C720.025 (2)0.043 (3)0.039 (3)0.011 (2)0.005 (2)0.015 (2)
C730.031 (3)0.050 (3)0.041 (3)0.015 (2)−0.001 (2)0.005 (3)
C740.035 (3)0.066 (4)0.033 (3)0.022 (3)0.005 (2)0.014 (3)
C750.034 (3)0.087 (4)0.041 (3)0.026 (3)0.013 (2)0.038 (3)
C760.034 (3)0.050 (3)0.042 (3)0.013 (2)0.003 (2)0.024 (3)
Geometric parameters (Å, °) top
N1—C111.407 (5)C32—C331.367 (6)
N1—C11.430 (5)C32—H32A0.9500
N1—C31.444 (5)C33—C341.380 (6)
N2—C211.397 (5)C33—H33A0.9500
N2—C11.437 (5)C34—C351.373 (6)
N2—C21.476 (5)C34—H34A0.9500
N3—C311.370 (5)C35—C361.377 (6)
N3—C21.433 (5)C35—H35A0.9500
N3—H30.8127C36—H36A0.9500
N4—C411.409 (5)C41—C421.396 (6)
N4—C31.475 (5)C41—C461.399 (6)
N4—C61.475 (5)C42—C431.385 (6)
N5—C511.394 (5)C42—H42A0.9500
N5—C61.453 (5)C43—C441.381 (6)
N5—C41.453 (5)C43—H43A0.9500
N6—C611.421 (5)C44—C451.376 (6)
N6—C41.441 (5)C44—H44A0.9500
N6—C51.458 (5)C45—C461.385 (5)
N7—C711.384 (5)C45—H45A0.9500
N7—C51.436 (5)C46—H46A0.9500
N7—H70.8756C51—C521.391 (6)
C1—C41.577 (6)C51—C561.403 (5)
C1—H1A1.0000C52—C531.389 (6)
C2—C31.550 (6)C52—H52A0.9500
C2—H2A1.0000C53—C541.380 (6)
C3—H3A1.0000C53—H53A0.9500
C4—H4A1.0000C54—C551.378 (6)
C5—C61.552 (6)C54—H54A0.9500
C5—H5A1.0000C55—C561.377 (6)
C6—H6A1.0000C55—H55A0.9500
C11—C121.370 (6)C56—H56A0.9500
C11—C161.404 (5)C61—C621.369 (6)
C12—C131.378 (6)C61—C661.409 (6)
C12—H12A0.9500C62—C631.407 (6)
C13—C141.394 (6)C62—H62A0.9500
C13—H13A0.9500C63—C641.379 (6)
C14—C151.371 (6)C63—H63A0.9500
C14—H14A0.9500C64—C651.383 (7)
C15—C161.371 (6)C64—H64A0.9500
C15—H15A0.9500C65—C661.380 (6)
C16—H16A0.9500C65—H65A0.9500
C21—C261.395 (6)C66—H66A0.9500
C21—C221.412 (6)C71—C721.394 (6)
C22—C231.355 (6)C71—C761.400 (6)
C22—H22A0.9500C72—C731.389 (7)
C23—C241.379 (6)C72—H72A0.9500
C23—H23A0.9500C73—C741.343 (7)
C24—C251.374 (7)C73—H73A0.9500
C24—H24A0.9500C74—C751.369 (8)
C25—C261.368 (6)C74—H74A0.9500
C25—H25A0.9500C75—C761.389 (7)
C26—H26A0.9500C75—H75A0.9500
C31—C321.396 (6)C76—H76A0.9500
C31—C361.409 (6)
C11—N1—C1126.6 (3)C21—C26—H26A119.5
C11—N1—C3124.2 (3)N3—C31—C32118.7 (4)
C1—N1—C3108.7 (3)N3—C31—C36122.9 (4)
C21—N2—C1121.5 (3)C32—C31—C36118.5 (4)
C21—N2—C2122.7 (3)C33—C32—C31120.3 (4)
C1—N2—C2109.0 (3)C33—C32—H32A119.8
C31—N3—C2129.2 (4)C31—C32—H32A119.8
C31—N3—H3113.7C32—C33—C34121.3 (5)
C2—N3—H3115.9C32—C33—H33A119.3
C41—N4—C3119.6 (3)C34—C33—H33A119.3
C41—N4—C6120.0 (3)C35—C34—C33118.7 (4)
C3—N4—C6116.3 (3)C35—C34—H34A120.6
C51—N5—C6124.4 (3)C33—C34—H34A120.6
C51—N5—C4126.5 (3)C34—C35—C36121.7 (4)
C6—N5—C4108.6 (3)C34—C35—H35A119.2
C61—N6—C4123.0 (3)C36—C35—H35A119.2
C61—N6—C5119.8 (3)C35—C36—C31119.4 (4)
C4—N6—C5110.7 (3)C35—C36—H36A120.3
C71—N7—C5123.5 (3)C31—C36—H36A120.3
C71—N7—H7115.8C42—C41—C46118.3 (4)
C5—N7—H7119.6C42—C41—N4121.1 (4)
N1—C1—N2102.8 (3)C46—C41—N4120.6 (4)
N1—C1—C4108.6 (3)C43—C42—C41120.2 (4)
N2—C1—C4113.0 (3)C43—C42—H42A119.9
N1—C1—H1A110.7C41—C42—H42A119.9
N2—C1—H1A110.7C44—C43—C42121.2 (4)
C4—C1—H1A110.7C44—C43—H43A119.4
N3—C2—N2112.1 (3)C42—C43—H43A119.4
N3—C2—C3114.4 (3)C45—C44—C43118.9 (4)
N2—C2—C3103.1 (3)C45—C44—H44A120.6
N3—C2—H2A109.0C43—C44—H44A120.6
N2—C2—H2A109.0C44—C45—C46121.0 (4)
C3—C2—H2A109.0C44—C45—H45A119.5
N1—C3—N4110.1 (3)C46—C45—H45A119.5
N1—C3—C2104.1 (3)C45—C46—C41120.4 (4)
N4—C3—C2114.5 (3)C45—C46—H46A119.8
N1—C3—H3A109.3C41—C46—H46A119.8
N4—C3—H3A109.3C52—C51—N5121.7 (4)
C2—C3—H3A109.3C52—C51—C56118.0 (4)
N6—C4—N5101.4 (3)N5—C51—C56120.3 (4)
N6—C4—C1111.7 (3)C53—C52—C51120.5 (4)
N5—C4—C1109.3 (3)C53—C52—H52A119.8
N6—C4—H4A111.3C51—C52—H52A119.8
N5—C4—H4A111.3C54—C53—C52121.3 (4)
C1—C4—H4A111.3C54—C53—H53A119.4
N7—C5—N6108.2 (3)C52—C53—H53A119.4
N7—C5—C6111.1 (3)C55—C54—C53118.2 (4)
N6—C5—C6104.0 (3)C55—C54—H54A120.9
N7—C5—H5A111.1C53—C54—H54A120.9
N6—C5—H5A111.1C56—C55—C54121.7 (4)
C6—C5—H5A111.1C56—C55—H55A119.1
N5—C6—N4112.4 (3)C54—C55—H55A119.1
N5—C6—C5102.5 (3)C55—C56—C51120.3 (4)
N4—C6—C5115.3 (3)C55—C56—H56A119.8
N5—C6—H6A108.8C51—C56—H56A119.8
N4—C6—H6A108.8C62—C61—C66119.2 (4)
C5—C6—H6A108.8C62—C61—N6121.4 (4)
C12—C11—C16118.5 (4)C66—C61—N6119.3 (4)
C12—C11—N1121.0 (3)C61—C62—C63120.8 (4)
C16—C11—N1120.5 (4)C61—C62—H62A119.6
C11—C12—C13121.2 (4)C63—C62—H62A119.6
C11—C12—H12A119.4C64—C63—C62119.6 (4)
C13—C12—H12A119.4C64—C63—H63A120.2
C12—C13—C14120.4 (4)C62—C63—H63A120.2
C12—C13—H13A119.8C63—C64—C65119.8 (4)
C14—C13—H13A119.8C63—C64—H64A120.1
C15—C14—C13118.2 (4)C65—C64—H64A120.1
C15—C14—H14A120.9C66—C65—C64121.0 (4)
C13—C14—H14A120.9C66—C65—H65A119.5
C16—C15—C14121.8 (4)C64—C65—H65A119.5
C16—C15—H15A119.1C65—C66—C61119.7 (4)
C14—C15—H15A119.1C65—C66—H66A120.2
C15—C16—C11119.8 (4)C61—C66—H66A120.2
C15—C16—H16A120.1N7—C71—C72122.2 (4)
C11—C16—H16A120.1N7—C71—C76120.1 (4)
C26—C21—N2122.6 (4)C72—C71—C76117.7 (4)
C26—C21—C22117.1 (4)C73—C72—C71120.3 (5)
N2—C21—C22120.3 (4)C73—C72—H72A119.8
C23—C22—C21120.7 (4)C71—C72—H72A119.8
C23—C22—H22A119.7C74—C73—C72121.2 (5)
C21—C22—H22A119.7C74—C73—H73A119.4
C22—C23—C24121.5 (4)C72—C73—H73A119.4
C22—C23—H23A119.2C73—C74—C75119.8 (5)
C24—C23—H23A119.2C73—C74—H74A120.1
C25—C24—C23118.5 (4)C75—C74—H74A120.1
C25—C24—H24A120.7C74—C75—C76120.8 (5)
C23—C24—H24A120.7C74—C75—H75A119.6
C26—C25—C24121.1 (4)C76—C75—H75A119.6
C26—C25—H25A119.4C75—C76—C71120.0 (5)
C24—C25—H25A119.4C75—C76—H76A120.0
C25—C26—C21121.0 (4)C71—C76—H76A120.0
C25—C26—H26A119.5
C11—N1—C1—N2136.1 (4)C1—N2—C21—C26−152.4 (4)
C3—N1—C1—N2−35.8 (4)C2—N2—C21—C26−4.5 (6)
C11—N1—C1—C4−104.0 (4)C1—N2—C21—C2228.7 (5)
C3—N1—C1—C484.2 (4)C2—N2—C21—C22176.6 (4)
C21—N2—C1—N1−176.5 (3)C26—C21—C22—C230.9 (6)
C2—N2—C1—N131.7 (4)N2—C21—C22—C23179.9 (4)
C21—N2—C1—C466.6 (4)C21—C22—C23—C24−1.1 (7)
C2—N2—C1—C4−85.1 (4)C22—C23—C24—C251.4 (7)
C31—N3—C2—N265.4 (6)C23—C24—C25—C26−1.6 (7)
C31—N3—C2—C3−51.5 (6)C24—C25—C26—C211.5 (7)
C21—N2—C2—N369.0 (5)N2—C21—C26—C25180.0 (4)
C1—N2—C2—N3−139.6 (3)C22—C21—C26—C25−1.1 (6)
C21—N2—C2—C3−167.5 (3)C2—N3—C31—C32169.3 (4)
C1—N2—C2—C3−16.1 (4)C2—N3—C31—C36−10.7 (7)
C11—N1—C3—N490.5 (4)N3—C31—C32—C33−176.7 (4)
C1—N1—C3—N4−97.4 (4)C36—C31—C32—C333.3 (7)
C11—N1—C3—C2−146.3 (4)C31—C32—C33—C34−2.9 (8)
C1—N1—C3—C225.8 (4)C32—C33—C34—C350.7 (7)
C41—N4—C3—N1−160.3 (3)C33—C34—C35—C361.0 (7)
C6—N4—C3—N142.2 (4)C34—C35—C36—C31−0.4 (7)
C41—N4—C3—C282.8 (4)N3—C31—C36—C35178.3 (4)
C6—N4—C3—C2−74.7 (4)C32—C31—C36—C35−1.7 (6)
N3—C2—C3—N1116.4 (3)C3—N4—C41—C42−7.9 (5)
N2—C2—C3—N1−5.6 (4)C6—N4—C41—C42148.8 (4)
N3—C2—C3—N4−123.4 (4)C3—N4—C41—C46170.6 (4)
N2—C2—C3—N4114.7 (4)C6—N4—C41—C46−32.7 (5)
C61—N6—C4—N5179.4 (3)C46—C41—C42—C43−1.5 (6)
C5—N6—C4—N528.0 (4)N4—C41—C42—C43177.0 (4)
C61—N6—C4—C163.0 (5)C41—C42—C43—C442.0 (6)
C5—N6—C4—C1−88.4 (4)C42—C43—C44—C45−1.4 (7)
C51—N5—C4—N6135.2 (4)C43—C44—C45—C460.2 (7)
C6—N5—C4—N6−36.8 (4)C44—C45—C46—C410.2 (6)
C51—N5—C4—C1−106.7 (4)C42—C41—C46—C450.4 (6)
C6—N5—C4—C181.4 (4)N4—C41—C46—C45−178.1 (4)
N1—C1—C4—N646.6 (4)C6—N5—C51—C52171.4 (4)
N2—C1—C4—N6160.0 (3)C4—N5—C51—C520.6 (6)
N1—C1—C4—N5−64.9 (4)C6—N5—C51—C56−9.8 (6)
N2—C1—C4—N548.5 (4)C4—N5—C51—C56179.4 (4)
C71—N7—C5—N6−149.1 (3)N5—C51—C52—C53179.5 (4)
C71—N7—C5—C697.3 (4)C56—C51—C52—C530.6 (6)
C61—N6—C5—N779.5 (4)C51—C52—C53—C540.8 (7)
C4—N6—C5—N7−128.0 (3)C52—C53—C54—C55−1.2 (7)
C61—N6—C5—C6−162.3 (3)C53—C54—C55—C560.1 (7)
C4—N6—C5—C6−9.8 (4)C54—C55—C56—C511.4 (7)
C51—N5—C6—N494.4 (4)C52—C51—C56—C55−1.7 (7)
C4—N5—C6—N4−93.4 (4)N5—C51—C56—C55179.5 (4)
C51—N5—C6—C5−141.3 (4)C4—N6—C61—C62−155.6 (4)
C4—N5—C6—C530.9 (4)C5—N6—C61—C62−6.6 (6)
C41—N4—C6—N5−118.5 (4)C4—N6—C61—C6626.9 (6)
C3—N4—C6—N538.9 (5)C5—N6—C61—C66175.9 (4)
C41—N4—C6—C5124.6 (4)C66—C61—C62—C63−1.7 (6)
C3—N4—C6—C5−78.0 (4)N6—C61—C62—C63−179.3 (4)
N7—C5—C6—N5103.7 (4)C61—C62—C63—C640.2 (7)
N6—C5—C6—N5−12.5 (4)C62—C63—C64—C650.7 (7)
N7—C5—C6—N4−133.9 (3)C63—C64—C65—C660.0 (7)
N6—C5—C6—N4109.9 (4)C64—C65—C66—C61−1.6 (7)
C1—N1—C11—C12171.1 (4)C62—C61—C66—C652.4 (6)
C3—N1—C11—C12−18.2 (6)N6—C61—C66—C65180.0 (4)
C1—N1—C11—C16−9.0 (6)C5—N7—C71—C72−8.1 (6)
C3—N1—C11—C16161.6 (4)C5—N7—C71—C76174.7 (4)
C16—C11—C12—C132.5 (7)N7—C71—C72—C73179.6 (4)
N1—C11—C12—C13−177.6 (4)C76—C71—C72—C73−3.1 (6)
C11—C12—C13—C140.5 (7)C71—C72—C73—C740.9 (7)
C12—C13—C14—C15−2.5 (7)C72—C73—C74—C752.0 (7)
C13—C14—C15—C161.4 (7)C73—C74—C75—C76−2.6 (7)
C14—C15—C16—C111.6 (7)C74—C75—C76—C710.3 (7)
C12—C11—C16—C15−3.6 (6)N7—C71—C76—C75179.8 (4)
N1—C11—C16—C15176.5 (4)C72—C71—C76—C752.5 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3···Cgi0.812.903.699 (4)169
Symmetry codes: (i) x, y, z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3···Cgi0.812.903.699 (4)169
Symmetry codes: (i) x, y, z+1.
Acknowledgements top

We are thankful the Chemistry Group of Imam Hossain University for their cooperation.

references
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