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

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ISSN: 2414-3146

4-Amino-5-{[cyclo­hex­yl(meth­yl)amino]­meth­yl}iso­phthalo­nitrile

aDepartment of Chemistry, King Fahd University of Petroleum and Minerals, 31261 Dhahran, Kingdom of , Saudi Arabia, and bLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
*Correspondence e-mail: msharif@kfupm.edu.sa

Edited by J. Simpson, University of Otago, New Zealand (Received 18 September 2019; accepted 8 October 2019; online 22 October 2019)

The title compound, C16H20N4, was synthesized by cyanation of brom­hexine. The compound crystallizes with two unique mol­ecules in the asymmetric unit. The substituted aniline and cyclo­hexane rings are inclined to one another by 37.26 (6)° in one mol­ecule and by 22.84 (7)° in the other. In the crystal packing, intra- and inter­molecular N—H⋯N hydrogen bonds and an inter­molecular C—H⋯N contact were observed.

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

Structure description

The title compound is an aniline derivative with two cyano groups at the ortho and para positions. The other ortho position of the aniline core is occupied by a [cyclo­hex­yl(meth­yl)amino]­methyl substituent. Two unique mol­ecules are present in the asymmetric unit, with intra­molecular N2—H2A⋯N1 and N6—H6A⋯N5 hydrogen bonds (Fig. 1[link] and Table 1[link]). The cyclo­hexyl ring adopts a chair conformation. In the crystal, inter­molecular N—H⋯N and C—H⋯N hydrogen bonds (Table 1[link]) stack the mol­ecules along the a-axis direction (Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯N1 0.909 (15) 2.205 (15) 2.8867 (14) 131.3 (12)
N6—H6A⋯N5 0.871 (15) 2.242 (15) 2.8824 (14) 130.3 (13)
N2—H2B⋯N7i 0.889 (15) 2.122 (15) 2.9894 (15) 164.8 (12)
N6—H6A⋯N4ii 0.871 (15) 2.457 (14) 3.0268 (14) 123.5 (11)
N6—H6B⋯N3i 0.887 (14) 2.526 (15) 3.3780 (17) 161.3 (12)
C16—H16B⋯N8iii 0.99 2.42 3.4095 (18) 177
Symmetry codes: (i) -x, -y+1, -z; (ii) x+1, y-1, z; (iii) x+1, y, z.
[Figure 1]
Figure 1
The asymmetric unit of the title compound, with intra­molecular hydrogen bonds drawn as dashed lines. Displacement ellipsoids are shown at the 30% probability level.
[Figure 2]
Figure 2
The overall packing of the title compound, with hydrogen bonds drawn as dashed lines.

Synthesis and crystallization

The title compound was obtained as the main product while synthesizing the mono- and di­cyano derivatives of the biologically active known mucolytic drug brom­hexine (Bateman, 1971[Bateman, P. P. (1971). Med. J. Aust. 1, 963-965.]; Sharif et al., 2014[Sharif, M., Pews-Davtyan, A., Lukas, J., Schranck, J., Langer, P., Rolfs, A. & Beller, M. (2014). Eur. J. Org. Chem. 2014, 222-230.]; Zanasi et al., 2017[Zanasi, A., Mazzolini, M. & Kantar, A. (2017). Multidiscip. Respir. Med. 12, article No. 7.]).

The reaction was carried out in an Ace pressure tube. A mixture of brom­hexine (2.0 mmol, 752 mg), K4[Fe(CN)6]·3H2O (0.8 mmol, 338 mg), Na2CO3 (2.4 mmol, 254 mg), CuI (0.2 mmol, 38 mg), 1-butyl­imidazole (4.0 mmol, 497 mg) and o-xylene (2.0 ml) was stirred at 433 K for 24 h. Next the reaction mixture was quenched with water and diluted with di­chloro­methane. The organic layer was separated and the aqueous layer was extracted with di­chloro­methane (3 × 20 ml). The combined organic layers were dried on anhydrous Na2SO4. After filtering, the solvent was removed in vacuo and the product was purified by column chromatography (silica gel, ethyl acetate/n-hexa­ne) (yield 62%, 332 mg). Crystals suitable for X-ray analysis were obtained by recrystallization from a mixture of ethyl acetate and n-heptane (1:1 v/v).

1H NMR (300 MHz, CDCl3): δ 1.04–1.54 (m, 6H), 1.73 (t, 4H, J = 13.7 Hz), 2.09 (s, 3H), 2.04 (t, 1H, J = 10.3 Hz), 3.68 (s, 2H), 5.07 (s, 2H, NH2), 7.12–7.18 (m, 2H); 13C NMR (CDCl3): δ 24.7 (2CH2), 25.1 (CH2), 27.0 (2CH2), 35.4 (CH3), 56.4 (CH2), 60.1 (CH), 95.2 (C), 98.3 (C), 114.9 (C), 116.2 (C), 123.2 (C), 134.8 (CH), 135.1 (CH), 152.7 (C); GC—MS (EI, 70 eV): m/z = 268 (M+, 29), 225 (74), 197 (31), 185 (32), 156 (49), 70 (100); HRMS (ESI): calculated for C16H20N4 ([M + H]+) 268,16880 found 268.16810.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C16H20N4
Mr 268.36
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 150
a, b, c (Å) 8.7319 (4), 11.3091 (5), 16.1220 (7)
α, β, γ (°) 69.599 (3), 77.168 (4), 81.042 (4)
V3) 1449.57 (12)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.50 × 0.44 × 0.26
 
Data collection
Diffractometer Stoe IPDS II
Absorption correction
No. of measured, independent and observed [I > 2σ(I)] reflections 27082, 7789, 5101
Rint 0.037
(sin θ/λ)max−1) 0.687
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.091, 0.85
No. of reflections 7789
No. of parameters 379
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.32, −0.22
Computer programs: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), 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 publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

4-Amino-5-{[cyclohexyl(methyl)amino]methyl}isophthalonitrile top
Crystal data top
C16H20N4Z = 4
Mr = 268.36F(000) = 576
Triclinic, P1Dx = 1.230 Mg m3
a = 8.7319 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3091 (5) ÅCell parameters from 508 reflections
c = 16.1220 (7) Åθ = 1.9–29.6°
α = 69.599 (3)°µ = 0.08 mm1
β = 77.168 (4)°T = 150 K
γ = 81.042 (4)°Prism, colourless
V = 1449.57 (12) Å30.50 × 0.44 × 0.26 mm
Data collection top
Stoe IPDS II
diffractometer
5101 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 29.2°, θmin = 1.9°
ω scansh = 1111
27082 measured reflectionsk = 1515
7789 independent reflectionsl = 2222
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0546P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max = 0.001
7789 reflectionsΔρmax = 0.32 e Å3
379 parametersΔρmin = 0.22 e Å3
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
C10.01262 (12)1.01919 (10)0.24558 (7)0.0222 (2)
H1A0.08271.05520.20360.027*
H1B0.05091.07120.28560.027*
C20.13801 (12)1.02839 (10)0.19187 (7)0.0208 (2)
C30.11999 (12)0.95410 (10)0.13430 (7)0.0213 (2)
C40.23642 (12)0.97527 (11)0.08020 (7)0.0236 (2)
C50.36355 (12)1.06504 (11)0.08291 (7)0.0254 (2)
H50.43931.07830.04570.030*
C60.37958 (12)1.13498 (11)0.13990 (7)0.0243 (2)
C70.26577 (12)1.11506 (11)0.19415 (7)0.0225 (2)
H70.27801.16320.23350.027*
C80.10479 (12)0.83245 (11)0.36453 (7)0.0263 (2)
H8A0.15050.88520.40240.039*
H8B0.07130.74770.40240.039*
H8C0.18380.82590.33200.039*
C90.22145 (13)0.90380 (11)0.02018 (7)0.0266 (2)
C100.50693 (13)1.23112 (12)0.14213 (8)0.0285 (3)
C110.16669 (11)0.87861 (10)0.34391 (7)0.0195 (2)
H110.18160.78760.38130.023*
C120.14675 (12)0.95503 (12)0.40779 (7)0.0247 (2)
H12A0.04890.93490.45290.030*
H12B0.13731.04660.37340.030*
C130.28799 (13)0.92430 (13)0.45572 (8)0.0308 (3)
H13A0.27600.97830.49410.037*
H13B0.29020.83480.49520.037*
C140.44315 (13)0.94597 (12)0.38886 (8)0.0289 (3)
H14A0.44741.03760.35520.035*
H14B0.53220.91780.42200.035*
C150.45983 (12)0.87413 (11)0.32331 (8)0.0263 (2)
H15A0.46850.78200.35620.032*
H15B0.55760.89470.27820.032*
C160.31880 (12)0.90780 (12)0.27543 (7)0.0262 (2)
H16A0.31360.99890.23950.031*
H16B0.33150.85850.23380.031*
C170.01014 (13)0.52836 (11)0.24386 (7)0.0239 (2)
H17A0.07790.57340.20000.029*
H17B0.06100.58110.28180.029*
C180.12872 (12)0.51462 (10)0.19315 (7)0.0219 (2)
C190.08922 (12)0.43587 (10)0.13786 (7)0.0211 (2)
C200.19522 (12)0.44230 (11)0.08108 (7)0.0223 (2)
C210.33528 (12)0.51940 (11)0.08063 (7)0.0246 (2)
H210.40360.52300.04130.030*
C220.37496 (12)0.59069 (11)0.13733 (7)0.0246 (2)
C230.26946 (13)0.58799 (11)0.19267 (7)0.0239 (2)
H230.29660.63860.23090.029*
C240.06570 (14)0.34748 (14)0.37635 (8)0.0376 (3)
H24A0.10180.40160.41420.056*
H24B0.02080.26540.41200.056*
H24C0.15510.33480.35370.056*
C250.15260 (13)0.36861 (11)0.02185 (7)0.0241 (2)
C260.52121 (14)0.66902 (12)0.13769 (8)0.0304 (3)
C270.20241 (12)0.42067 (10)0.32479 (7)0.0214 (2)
H270.27180.46420.26700.026*
C280.18887 (14)0.50117 (12)0.38536 (8)0.0284 (2)
H28A0.12320.46070.44440.034*
H28B0.13650.58580.35770.034*
C290.35188 (15)0.51571 (12)0.39894 (9)0.0331 (3)
H29A0.41280.56520.34080.040*
H29B0.34000.56330.44150.040*
C300.44236 (15)0.38784 (13)0.43528 (9)0.0363 (3)
H30A0.55020.40090.43830.044*
H30B0.38910.34290.49700.044*
C310.45189 (14)0.30724 (13)0.37569 (9)0.0342 (3)
H31A0.50530.22290.40270.041*
H31B0.51530.34770.31590.041*
C320.28789 (13)0.29169 (11)0.36465 (8)0.0271 (2)
H32A0.29700.24060.32460.033*
H32B0.22650.24630.42390.033*
N10.03069 (10)0.88957 (8)0.30035 (6)0.02006 (18)
N20.00398 (11)0.86860 (10)0.13082 (7)0.0268 (2)
N30.20948 (13)0.84663 (11)0.02760 (7)0.0370 (3)
N40.60595 (12)1.30916 (12)0.14443 (8)0.0395 (3)
N50.05375 (10)0.40784 (9)0.30093 (6)0.02239 (19)
N60.04566 (11)0.36081 (10)0.13743 (7)0.0273 (2)
N70.11321 (12)0.30789 (10)0.02396 (7)0.0317 (2)
N80.63810 (13)0.72932 (12)0.13812 (8)0.0451 (3)
H2A0.0688 (16)0.8538 (13)0.1710 (10)0.037 (4)*
H2B0.0211 (16)0.8229 (14)0.0941 (10)0.037 (4)*
H6A0.1067 (17)0.3564 (14)0.1746 (10)0.037 (4)*
H6B0.0743 (15)0.3178 (13)0.0990 (9)0.031 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0239 (5)0.0222 (6)0.0228 (5)0.0015 (4)0.0081 (4)0.0080 (4)
C20.0213 (5)0.0223 (5)0.0184 (5)0.0028 (4)0.0047 (4)0.0052 (4)
C30.0220 (5)0.0226 (6)0.0184 (5)0.0049 (4)0.0024 (4)0.0049 (4)
C40.0249 (5)0.0270 (6)0.0193 (5)0.0066 (4)0.0042 (4)0.0062 (4)
C50.0228 (5)0.0308 (6)0.0215 (5)0.0053 (4)0.0075 (4)0.0038 (5)
C60.0201 (5)0.0265 (6)0.0229 (5)0.0018 (4)0.0039 (4)0.0039 (4)
C70.0229 (5)0.0239 (6)0.0195 (5)0.0035 (4)0.0028 (4)0.0058 (4)
C80.0220 (5)0.0297 (6)0.0255 (5)0.0042 (4)0.0050 (4)0.0056 (5)
C90.0274 (5)0.0304 (6)0.0222 (5)0.0070 (5)0.0069 (4)0.0053 (5)
C100.0234 (5)0.0353 (7)0.0271 (6)0.0030 (5)0.0077 (4)0.0086 (5)
C110.0187 (5)0.0195 (5)0.0215 (5)0.0002 (4)0.0061 (4)0.0073 (4)
C120.0214 (5)0.0314 (6)0.0253 (5)0.0009 (4)0.0061 (4)0.0146 (5)
C130.0284 (6)0.0421 (7)0.0284 (6)0.0011 (5)0.0103 (5)0.0171 (5)
C140.0230 (5)0.0301 (6)0.0375 (6)0.0023 (5)0.0126 (5)0.0113 (5)
C150.0186 (5)0.0262 (6)0.0330 (6)0.0003 (4)0.0048 (4)0.0090 (5)
C160.0202 (5)0.0353 (7)0.0251 (5)0.0018 (4)0.0017 (4)0.0139 (5)
C170.0256 (5)0.0235 (6)0.0252 (5)0.0007 (4)0.0100 (4)0.0085 (4)
C180.0235 (5)0.0225 (6)0.0202 (5)0.0024 (4)0.0064 (4)0.0058 (4)
C190.0220 (5)0.0212 (5)0.0195 (5)0.0036 (4)0.0037 (4)0.0050 (4)
C200.0256 (5)0.0227 (6)0.0199 (5)0.0045 (4)0.0043 (4)0.0072 (4)
C210.0244 (5)0.0270 (6)0.0240 (5)0.0033 (4)0.0097 (4)0.0064 (5)
C220.0229 (5)0.0254 (6)0.0251 (5)0.0008 (4)0.0078 (4)0.0066 (5)
C230.0270 (5)0.0232 (6)0.0223 (5)0.0001 (4)0.0064 (4)0.0082 (4)
C240.0301 (6)0.0475 (8)0.0292 (6)0.0124 (6)0.0064 (5)0.0006 (6)
C250.0245 (5)0.0255 (6)0.0223 (5)0.0051 (4)0.0062 (4)0.0056 (5)
C260.0314 (6)0.0335 (7)0.0313 (6)0.0032 (5)0.0134 (5)0.0146 (5)
C270.0215 (5)0.0226 (5)0.0215 (5)0.0016 (4)0.0069 (4)0.0072 (4)
C280.0309 (6)0.0284 (6)0.0315 (6)0.0034 (5)0.0126 (5)0.0151 (5)
C290.0388 (7)0.0327 (7)0.0368 (6)0.0026 (5)0.0173 (5)0.0163 (6)
C300.0362 (6)0.0405 (8)0.0409 (7)0.0015 (5)0.0227 (6)0.0163 (6)
C310.0327 (6)0.0333 (7)0.0414 (7)0.0077 (5)0.0200 (5)0.0146 (6)
C320.0323 (6)0.0232 (6)0.0287 (6)0.0011 (5)0.0136 (5)0.0084 (5)
N10.0187 (4)0.0215 (5)0.0206 (4)0.0019 (3)0.0054 (3)0.0065 (4)
N20.0279 (5)0.0298 (5)0.0276 (5)0.0026 (4)0.0090 (4)0.0153 (4)
N30.0451 (6)0.0405 (7)0.0303 (5)0.0107 (5)0.0088 (5)0.0136 (5)
N40.0289 (5)0.0463 (7)0.0464 (7)0.0073 (5)0.0152 (5)0.0182 (6)
N50.0224 (4)0.0239 (5)0.0209 (4)0.0034 (4)0.0080 (3)0.0042 (4)
N60.0256 (5)0.0316 (6)0.0294 (5)0.0038 (4)0.0096 (4)0.0154 (5)
N70.0367 (5)0.0329 (6)0.0282 (5)0.0056 (4)0.0044 (4)0.0133 (5)
N80.0387 (6)0.0550 (8)0.0541 (7)0.0177 (6)0.0243 (5)0.0326 (6)
Geometric parameters (Å, º) top
C1—N11.4644 (14)C17—H17A0.9900
C1—C21.5107 (14)C17—H17B0.9900
C1—H1A0.9900C18—C231.3714 (15)
C1—H1B0.9900C18—C191.4241 (15)
C2—C71.3686 (15)C19—N61.3405 (14)
C2—C31.4248 (15)C19—C201.4174 (14)
C3—N21.3397 (14)C20—C211.3869 (15)
C3—C41.4226 (14)C20—C251.4301 (16)
C4—C51.3868 (16)C21—C221.3754 (16)
C4—C91.4363 (16)C21—H210.9500
C5—C61.3801 (16)C22—C231.4082 (15)
C5—H50.9500C22—C261.4365 (15)
C6—C71.4079 (14)C23—H230.9500
C6—C101.4328 (16)C24—N51.4533 (15)
C7—H70.9500C24—H24A0.9800
C8—N11.4546 (14)C24—H24B0.9800
C8—H8A0.9800C24—H24C0.9800
C8—H8B0.9800C25—N71.1412 (15)
C8—H8C0.9800C26—N81.1359 (15)
C9—N31.1457 (15)C27—N51.4743 (13)
C10—N41.1397 (15)C27—C321.5226 (15)
C11—N11.4774 (12)C27—C281.5268 (15)
C11—C161.5241 (14)C27—H271.0000
C11—C121.5271 (15)C28—C291.5289 (16)
C11—H111.0000C28—H28A0.9900
C12—C131.5302 (14)C28—H28B0.9900
C12—H12A0.9900C29—C301.5224 (18)
C12—H12B0.9900C29—H29A0.9900
C13—C141.5258 (17)C29—H29B0.9900
C13—H13A0.9900C30—C311.5205 (18)
C13—H13B0.9900C30—H30A0.9900
C14—C151.5137 (17)C30—H30B0.9900
C14—H14A0.9900C31—C321.5255 (16)
C14—H14B0.9900C31—H31A0.9900
C15—C161.5261 (15)C31—H31B0.9900
C15—H15A0.9900C32—H32A0.9900
C15—H15B0.9900C32—H32B0.9900
C16—H16A0.9900N2—H2A0.909 (15)
C16—H16B0.9900N2—H2B0.889 (15)
C17—N51.4603 (14)N6—H6A0.871 (15)
C17—C181.5098 (14)N6—H6B0.887 (14)
N1—C1—C2113.66 (9)C23—C18—C19119.23 (9)
N1—C1—H1A108.8C23—C18—C17119.98 (10)
C2—C1—H1A108.8C19—C18—C17120.45 (9)
N1—C1—H1B108.8N6—C19—C20120.95 (10)
C2—C1—H1B108.8N6—C19—C18121.30 (10)
H1A—C1—H1B107.7C20—C19—C18117.73 (9)
C7—C2—C3119.48 (9)C21—C20—C19121.74 (10)
C7—C2—C1119.49 (10)C21—C20—C25120.11 (10)
C3—C2—C1120.90 (9)C19—C20—C25118.13 (10)
N2—C3—C4121.56 (10)C22—C21—C20119.79 (10)
N2—C3—C2120.66 (9)C22—C21—H21120.1
C4—C3—C2117.77 (9)C20—C21—H21120.1
C5—C4—C3121.53 (10)C21—C22—C23119.32 (10)
C5—C4—C9118.89 (10)C21—C22—C26119.67 (10)
C3—C4—C9119.57 (10)C23—C22—C26121.00 (10)
C6—C5—C4119.72 (10)C18—C23—C22122.11 (10)
C6—C5—H5120.1C18—C23—H23118.9
C4—C5—H5120.1C22—C23—H23118.9
C5—C6—C7119.55 (10)N5—C24—H24A109.5
C5—C6—C10120.99 (10)N5—C24—H24B109.5
C7—C6—C10119.41 (10)H24A—C24—H24B109.5
C2—C7—C6121.94 (10)N5—C24—H24C109.5
C2—C7—H7119.0H24A—C24—H24C109.5
C6—C7—H7119.0H24B—C24—H24C109.5
N1—C8—H8A109.5N7—C25—C20177.23 (12)
N1—C8—H8B109.5N8—C26—C22178.88 (14)
H8A—C8—H8B109.5N5—C27—C32111.22 (9)
N1—C8—H8C109.5N5—C27—C28115.77 (9)
H8A—C8—H8C109.5C32—C27—C28110.22 (9)
H8B—C8—H8C109.5N5—C27—H27106.3
N3—C9—C4179.90 (15)C32—C27—H27106.3
N4—C10—C6178.36 (13)C28—C27—H27106.3
N1—C11—C16111.93 (8)C27—C28—C29110.63 (9)
N1—C11—C12115.86 (8)C27—C28—H28A109.5
C16—C11—C12109.60 (9)C29—C28—H28A109.5
N1—C11—H11106.3C27—C28—H28B109.5
C16—C11—H11106.3C29—C28—H28B109.5
C12—C11—H11106.3H28A—C28—H28B108.1
C11—C12—C13110.45 (9)C30—C29—C28111.73 (10)
C11—C12—H12A109.6C30—C29—H29A109.3
C13—C12—H12A109.6C28—C29—H29A109.3
C11—C12—H12B109.6C30—C29—H29B109.3
C13—C12—H12B109.6C28—C29—H29B109.3
H12A—C12—H12B108.1H29A—C29—H29B107.9
C14—C13—C12111.63 (9)C31—C30—C29111.03 (10)
C14—C13—H13A109.3C31—C30—H30A109.4
C12—C13—H13A109.3C29—C30—H30A109.4
C14—C13—H13B109.3C31—C30—H30B109.4
C12—C13—H13B109.3C29—C30—H30B109.4
H13A—C13—H13B108.0H30A—C30—H30B108.0
C15—C14—C13111.16 (10)C30—C31—C32110.99 (10)
C15—C14—H14A109.4C30—C31—H31A109.4
C13—C14—H14A109.4C32—C31—H31A109.4
C15—C14—H14B109.4C30—C31—H31B109.4
C13—C14—H14B109.4C32—C31—H31B109.4
H14A—C14—H14B108.0H31A—C31—H31B108.0
C14—C15—C16111.16 (9)C27—C32—C31110.27 (10)
C14—C15—H15A109.4C27—C32—H32A109.6
C16—C15—H15A109.4C31—C32—H32A109.6
C14—C15—H15B109.4C27—C32—H32B109.6
C16—C15—H15B109.4C31—C32—H32B109.6
H15A—C15—H15B108.0H32A—C32—H32B108.1
C11—C16—C15110.21 (9)C8—N1—C1111.26 (8)
C11—C16—H16A109.6C8—N1—C11112.12 (8)
C15—C16—H16A109.6C1—N1—C11113.63 (8)
C11—C16—H16B109.6C3—N2—H2A117.3 (9)
C15—C16—H16B109.6C3—N2—H2B123.1 (9)
H16A—C16—H16B108.1H2A—N2—H2B119.4 (13)
N5—C17—C18113.69 (9)C24—N5—C17111.28 (9)
N5—C17—H17A108.8C24—N5—C27115.29 (9)
C18—C17—H17A108.8C17—N5—C27111.64 (9)
N5—C17—H17B108.8C19—N6—H6A119.0 (9)
C18—C17—H17B108.8C19—N6—H6B121.0 (8)
H17A—C17—H17B107.7H6A—N6—H6B120.0 (12)
N1—C1—C2—C7131.11 (11)N6—C19—C20—C21179.99 (11)
N1—C1—C2—C353.09 (13)C18—C19—C20—C211.88 (16)
C7—C2—C3—N2179.99 (10)N6—C19—C20—C251.37 (16)
C1—C2—C3—N24.21 (16)C18—C19—C20—C25176.76 (10)
C7—C2—C3—C40.87 (15)C19—C20—C21—C220.93 (17)
C1—C2—C3—C4174.92 (10)C25—C20—C21—C22179.54 (11)
N2—C3—C4—C5179.08 (11)C20—C21—C22—C232.44 (17)
C2—C3—C4—C50.04 (15)C20—C21—C22—C26179.08 (11)
N2—C3—C4—C90.09 (16)C19—C18—C23—C221.72 (17)
C2—C3—C4—C9179.04 (10)C17—C18—C23—C22171.65 (10)
C3—C4—C5—C60.74 (17)C21—C22—C23—C181.13 (17)
C9—C4—C5—C6179.74 (10)C26—C22—C23—C18179.59 (11)
C4—C5—C6—C70.53 (17)N5—C27—C28—C29175.50 (9)
C4—C5—C6—C10178.04 (11)C32—C27—C28—C2957.20 (13)
C3—C2—C7—C61.12 (16)C27—C28—C29—C3055.22 (14)
C1—C2—C7—C6174.74 (10)C28—C29—C30—C3154.35 (15)
C5—C6—C7—C20.41 (16)C29—C30—C31—C3255.62 (15)
C10—C6—C7—C2177.14 (11)N5—C27—C32—C31171.53 (9)
N1—C11—C12—C13173.93 (9)C28—C27—C32—C3158.69 (12)
C16—C11—C12—C1358.25 (12)C30—C31—C32—C2758.03 (14)
C11—C12—C13—C1455.70 (14)C2—C1—N1—C859.53 (11)
C12—C13—C14—C1553.95 (14)C2—C1—N1—C11172.79 (8)
C13—C14—C15—C1655.06 (13)C16—C11—N1—C8165.75 (9)
N1—C11—C16—C15170.51 (9)C12—C11—N1—C867.60 (12)
C12—C11—C16—C1559.51 (12)C16—C11—N1—C167.01 (11)
C14—C15—C16—C1158.24 (13)C12—C11—N1—C159.64 (12)
N5—C17—C18—C23132.38 (11)C18—C17—N5—C2468.52 (12)
N5—C17—C18—C1954.33 (14)C18—C17—N5—C27161.11 (9)
C23—C18—C19—N6178.74 (11)C32—C27—N5—C2465.28 (13)
C17—C18—C19—N67.93 (17)C28—C27—N5—C2461.52 (14)
C23—C18—C19—C203.15 (16)C32—C27—N5—C17166.45 (9)
C17—C18—C19—C20170.19 (10)C28—C27—N5—C1766.75 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N10.909 (15)2.205 (15)2.8867 (14)131.3 (12)
N6—H6A···N50.871 (15)2.242 (15)2.8824 (14)130.3 (13)
N2—H2B···N7i0.889 (15)2.122 (15)2.9894 (15)164.8 (12)
N6—H6A···N4ii0.871 (15)2.457 (14)3.0268 (14)123.5 (11)
N6—H6B···N3i0.887 (14)2.526 (15)3.3780 (17)161.3 (12)
C16—H16B···N8iii0.992.423.4095 (18)177
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1, z; (iii) x+1, y, z.
 

Funding information

Funding for this research was provided by: Deanship of Scientific Research (DSR) at King Fahd University of Petroleum and Minerals (KFUPM) via project number IN161012.

References

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