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

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ISSN: 2414-3146

t-3-Benzyl-r-2,c-6-di­phenyl­piperidin-4-one

CROSSMARK_Color_square_no_text.svg

aResearch and Development Centre, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, bDepartment of Chemistry, Thiruvalluvar Arts and Science College, Kurinjipadi 607 302, Tamilnadu, India, cPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and dDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India
*Correspondence e-mail: sivakumar.phd2015@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 21 January 2016; accepted 1 February 2016; online 10 February 2016)

The asymmetric unit of the title compound, C24H23NO, contains two crystallographically independent mol­ecules (A and B). In both mol­ecules, the piperidine rings adopt a chair conformation and the phenyl rings and the benzyl group substituents are attached equatorially. The dihedral angle between the phenyl rings is 60.80 (10)° in mol­ecule A and 68.43 (9)° in mol­ecule B. The phenyl ring of the benzyl group makes dihedral angles of 76.95 (9) and 42.25 (10)° with the phenyl rings in mol­ecule A, and dihedral angles of 81.38 (11) and 30.19 (11)° in mol­ecule B. In the crystal, the two mol­ecules are linked by N—H⋯O hydrogen bonds, forming –ABAB– chains along [100]. In addition, five C—H⋯π inter­actions are also present, linking the chains to form a three-dimensional structure.

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

Structure description

The asymmetric unit of the title compound, (Fig. 1[link] and Fig. 2[link]), contains two crystallographically independent mol­ecules (A and B). In both mol­ecules, the piperidine ring adopts a chair conformation with puckering parameters q2 = 0.0236 (18) Å, q3 = −0.5892 (18) Å, Q = 0.5895 (18) Å, θ = 178.12 (17)° and φ = 141 (4)° for mol­ecule A and q2 = 0.0396 (18) Å, q3 = −0.5886 (18) Å, Q = 0.5898 (18) Å, θ = 176.34 (17)° and φ = 133 (3)° for mol­ecule B.

[Figure 1]
Figure 1
A view of mol­ecule A, with displacement ellipsoids drawn at the 40% probability level and atom labelling.
[Figure 2]
Figure 2
A view of mol­ecule B, with displacement ellipsoids drawn at the 40% probability level and atom labelling.

An AutoMolFit of mol­ecule A on mol­ecule B gives the best fit (Fig. 3[link]; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Weighted and unit weight r.m.s. fit are 0.248 and 0.219 Å, respectively (for all 26 non-H atoms). Comparison of the bonds of the fitted residues gives, r.m.s. bond fit = 0.0033 Å. Comparison of the bond angles of the fitted residues gives r.m.s. angle fit = 0.683°.

[Figure 3]
Figure 3
AutoMolFit diagram of mol­ecule A (black) on mol­ecule B (red).

The phenyl rings at positions 2,6 and the benzyl group at position 3 are attached equatorially. The dihedral angle between the two phenyl rings at positions 2 and 6 is 60.80 (10)° in mol­ecule A, and 68.43 (9)° in mol­ecule B. The phenyl ring of the benzyl group makes dihedral angles of 76.95 (9) and 42.25 (10)° with the two phenyl rings in mol­ecule A, and 81.38 (11) and 30.19 (11)° in mol­ecule B.

In the crystal, the mol­ecules are linked by N—H⋯O hydrogen bonds forming –A–B–A–B– chains along the a-axis direction (Fig. 4[link]). In addition, there are a number of C—H⋯π inter­actions present, linking the chains to form a three-dimensional structure (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3, Cg6 and Cg7 are the centroids of phenyl rings C21A–C26A, C31A–C36A, C21B–C26B and C31B–C36B, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1A⋯O4Bi 0.88 (2) 2.41 (2) 3.234 (2) 158 (2)
N1B—H1B⋯O4Aii 0.90 (2) 2.48 (2) 3.315 (2) 153 (2)
C2A—H2ACg6iii 1.00 2.95 3.9315 (19) 167
C2B—H2BCg2iv 1.00 3.00 3.9733 (19) 166
C25B—H25BCg3v 0.95 2.78 3.626 (2) 150
C64A—H64ACg3ii 0.95 2.78 3.661 (2) 155
C64B—H64BCg7i 0.95 2.93 3.796 (2) 153
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (v) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].
[Figure 4]
Figure 4
The crystal packing of the title compound, viewed along the b axis (mol­ecule A is black and mol­ecule B is red). Hydrogen bonds are shown as dashed lines (see Table 1[link]). H atoms not involved in hydrogen bonding have been omitted for clarity.

Jayabharathi et al., (2008[Jayabharathi, J., Thangamani, A., Balamurugan, S., Thiruvalluvar, A. & Linden, A. (2008). Acta Cryst. E64, o1181.]) have reported the crystal structure of t-3-benzyl-r-2,c-6-bis­(4-meth­oxy­phen­yl)piperidin-4-one, in which the piperidine ring adopts a chair conformation, with equatorial orientation of all substituents. Gayathri et al., (2009[Gayathri, P., Jayabharathi, J., Rajarajan, G., Thiruvalluvar, A. & Butcher, R. J. (2009). Acta Cryst. E65, o3083.]) have reported the crystal structure of t-3-pentyl-r-2,c-6-di­phenyl­piperidin-4-one, in which the piperidine ring adopts a chair conformation, with equatorial orientation of all substituents.

Synthesis and crystallization

A mixture of ammonium acetate (0.1 mol, 7.71 g), benzaldehyde (0.2 mol, 20.3 ml) and benzyl acetone (0.1 mol, 15.0 ml) in distilled ethanol was heated first to boiling. After cooling, the viscous liquid obtained was dissolved in ether (200 ml) and shaken with 100 ml concentrated hydro­chloric acid. The precipitated hydro­chloride of t(3)-benzyl-r(2),c(6)-di­phenyl­piperidin-4-one was removed by filtration and washed first with 40 ml mixture of ethanol and ether (1:1) and then with ether to remove most of the coloured impurities. The base was liberated from an alcoholic solution by adding aqueous ammonia and then diluted with water. The title compound was recrystallized from ethanol to give colourless plate-like crystals (yield 2.5 g).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C24H23NO
Mr 341.43
Crystal system, space group Monoclinic, P21/n
Temperature (K) 178
a, b, c (Å) 9.8918 (5), 30.6042 (12), 12.3878 (6)
β (°) 92.426 (2)
V3) 3746.8 (3)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.40 × 0.36 × 0.16
 
Data collection
Diffractometer Bruker Kappa APEXIII CCD area-detector
Absorption correction Multi-scan (SADABS; Bruker, 2015[Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.81, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections 58653, 10617, 6350
Rint 0.078
(sin θ/λ)max−1) 0.698
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.150, 1.05
No. of reflections 10617
No. of parameters 477
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.28, −0.22
Computer programs: APEX3 (Bruker, 2015[Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2015[Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (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.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

t-3-Benzyl-r-2,c-6-diphenylpiperidin-4-one top
Crystal data top
C24H23NOF(000) = 1456
Mr = 341.43Dx = 1.211 Mg m3
Monoclinic, P21/nMelting point: 471 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.8918 (5) ÅCell parameters from 7035 reflections
b = 30.6042 (12) Åθ = 2.6–22.8°
c = 12.3878 (6) ŵ = 0.07 mm1
β = 92.426 (2)°T = 178 K
V = 3746.8 (3) Å3Plate, colourless
Z = 80.40 × 0.36 × 0.16 mm
Data collection top
Bruker Kappa APEXIII CCD area-detector
diffractometer
10617 independent reflections
Radiation source: fine-focus sealed tube6350 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1Rint = 0.078
φ and ω scansθmax = 29.7°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
h = 1313
Tmin = 0.81, Tmax = 0.99k = 4242
58653 measured reflectionsl = 1417
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)] = 0.066Hydrogen site location: mixed
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0506P)2 + 1.0513P]
where P = (Fo2 + 2Fc2)/3
10617 reflections(Δ/σ)max = 0.001
477 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O4A0.66207 (13)0.14287 (4)0.97486 (11)0.0395 (5)
N1A0.29441 (15)0.17242 (5)0.87397 (13)0.0294 (5)
C2A0.33073 (17)0.12682 (5)0.89839 (14)0.0255 (5)
C3A0.42875 (17)0.12561 (5)0.99936 (14)0.0258 (5)
C4A0.54612 (18)0.15567 (6)0.97724 (14)0.0287 (5)
O4B0.64521 (13)0.35463 (4)0.14639 (11)0.0398 (4)
C5A0.50630 (18)0.20176 (6)0.94862 (15)0.0310 (6)
C6A0.40932 (18)0.20027 (5)0.84847 (14)0.0281 (5)
C13A0.4738 (2)0.07909 (6)1.02805 (14)0.0316 (6)
C21A0.20186 (17)0.10166 (5)0.91607 (13)0.0256 (5)
C22A0.10267 (19)0.11842 (6)0.98114 (15)0.0327 (6)
C23A0.0152 (2)0.09519 (7)0.99688 (16)0.0376 (6)
C24A0.0346 (2)0.05489 (7)0.94932 (16)0.0385 (7)
C25A0.0624 (2)0.03799 (6)0.88431 (16)0.0371 (6)
C26A0.17976 (19)0.06132 (6)0.86759 (15)0.0314 (6)
C31A0.53595 (17)0.07396 (5)1.14082 (14)0.0260 (5)
C32A0.4699 (2)0.08900 (6)1.22942 (16)0.0368 (6)
C33A0.5230 (2)0.08269 (7)1.33323 (17)0.0462 (7)
C34A0.6440 (2)0.06114 (7)1.35011 (17)0.0440 (7)
C35A0.7111 (2)0.04598 (6)1.26319 (17)0.0393 (6)
C36A0.65797 (18)0.05231 (5)1.15920 (15)0.0315 (6)
C61A0.35679 (18)0.24486 (5)0.81445 (15)0.0292 (6)
C62A0.3975 (2)0.26388 (6)0.72053 (17)0.0437 (7)
C63A0.3443 (3)0.30352 (7)0.68587 (19)0.0560 (9)
C64A0.2511 (2)0.32475 (7)0.74529 (19)0.0490 (8)
C65A0.2101 (2)0.30642 (7)0.83958 (19)0.0484 (8)
C66A0.2627 (2)0.26665 (6)0.87408 (18)0.0425 (7)
N1B0.28747 (15)0.32434 (5)0.24447 (13)0.0290 (5)
C2B0.31937 (17)0.36986 (5)0.21806 (14)0.0260 (5)
C3B0.40928 (17)0.37099 (5)0.11867 (14)0.0254 (5)
C4B0.52943 (18)0.34139 (6)0.14279 (14)0.0282 (5)
C5B0.49399 (19)0.29549 (6)0.17362 (15)0.0323 (6)
C6B0.40709 (17)0.29780 (5)0.27294 (14)0.0280 (5)
C13B0.45080 (19)0.41762 (6)0.09216 (15)0.0311 (6)
C21B0.18873 (17)0.39485 (5)0.19832 (13)0.0258 (5)
C22B0.08347 (18)0.37718 (6)0.13450 (14)0.0308 (6)
C23B0.03523 (19)0.40058 (6)0.11528 (15)0.0347 (6)
C24B0.0486 (2)0.44195 (6)0.15741 (16)0.0370 (6)
C25B0.0544 (2)0.45969 (6)0.22133 (16)0.0378 (6)
C26B0.17202 (19)0.43595 (6)0.24253 (15)0.0323 (6)
C31B0.52074 (18)0.42469 (6)0.01175 (15)0.0306 (6)
C32B0.4822 (2)0.40348 (7)0.10618 (16)0.0419 (7)
C33B0.5413 (3)0.41335 (9)0.20217 (18)0.0574 (9)
C34B0.6411 (3)0.44425 (10)0.2052 (3)0.0717 (11)
C35B0.6830 (3)0.46507 (9)0.1112 (3)0.0744 (13)
C36B0.6227 (2)0.45573 (7)0.0158 (2)0.0507 (8)
C61B0.36041 (18)0.25385 (5)0.31273 (15)0.0291 (5)
C62B0.3830 (2)0.24185 (6)0.41921 (16)0.0392 (7)
C63B0.3325 (2)0.20300 (7)0.45824 (18)0.0478 (7)
C64B0.2605 (2)0.17535 (7)0.39071 (18)0.0444 (7)
C65B0.2378 (2)0.18668 (7)0.28414 (19)0.0486 (8)
C66B0.2869 (2)0.22564 (6)0.24535 (17)0.0424 (7)
H1A0.2395 (19)0.1715 (6)0.8167 (16)0.032 (5)*
H2A0.376920.113990.835500.0306*
H3A0.380180.137761.061850.0310*
H5A0.587610.219140.933060.0372*
H5B0.461130.215591.009710.0372*
H6A0.457400.186950.787150.0338*
H13A0.394490.059461.020030.0379*
H13B0.540560.069500.975620.0379*
H22A0.115940.146031.015010.0392*
H23A0.082640.107101.040590.0451*
H24A0.114670.038760.961260.0461*
H25A0.048710.010300.850920.0445*
H26A0.245840.049530.822360.0376*
H32A0.386240.103991.218850.0441*
H33A0.475740.093271.393090.0554*
H34A0.680700.056811.421410.0528*
H35A0.794660.031021.274350.0471*
H36A0.705710.041691.099640.0378*
H62A0.462880.249610.678980.0523*
H63A0.372630.316070.620440.0672*
H64A0.214910.352020.721430.0588*
H65A0.145610.321050.881250.0580*
H66A0.233870.254170.939450.0510*
H1B0.235 (2)0.3253 (7)0.3023 (18)0.050 (7)*
H2B0.370690.383230.281030.0312*
H3B0.356000.358850.055140.0305*
H5C0.443170.280960.113140.0387*
H5D0.577360.278490.190600.0387*
H6B0.460290.312640.332800.0336*
H13C0.511340.428360.152100.0373*
H13D0.368510.436060.090580.0373*
H22B0.092850.348930.103900.0369*
H23B0.107550.388050.072930.0417*
H24B0.128970.458210.142300.0444*
H25B0.045010.488120.250880.0453*
H26B0.242090.448070.288020.0387*
H32B0.413840.381690.105230.0503*
H33B0.512470.398600.266580.0688*
H34B0.681060.451240.271440.0860*
H35B0.753870.486000.112120.0891*
H36B0.651350.470740.048310.0608*
H62B0.433970.260560.466640.0470*
H63B0.347990.195500.532150.0573*
H64B0.226480.148570.417270.0533*
H65B0.188060.167590.236830.0583*
H66B0.270050.233180.171620.0509*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O4A0.0305 (7)0.0438 (8)0.0443 (9)0.0043 (6)0.0016 (6)0.0055 (6)
N1A0.0308 (8)0.0251 (7)0.0316 (9)0.0028 (6)0.0066 (7)0.0049 (6)
C2A0.0304 (9)0.0229 (8)0.0231 (9)0.0009 (7)0.0001 (7)0.0003 (7)
C3A0.0297 (9)0.0248 (8)0.0229 (9)0.0011 (7)0.0003 (7)0.0011 (7)
C4A0.0313 (10)0.0341 (9)0.0204 (9)0.0003 (8)0.0031 (7)0.0024 (7)
O4B0.0283 (7)0.0468 (8)0.0442 (8)0.0015 (6)0.0012 (6)0.0078 (6)
C5A0.0312 (10)0.0277 (9)0.0337 (10)0.0050 (7)0.0020 (8)0.0011 (8)
C6A0.0315 (10)0.0244 (8)0.0286 (10)0.0020 (7)0.0021 (8)0.0002 (7)
C13A0.0411 (11)0.0263 (9)0.0272 (10)0.0031 (8)0.0014 (8)0.0001 (7)
C21A0.0304 (9)0.0258 (8)0.0202 (9)0.0003 (7)0.0018 (7)0.0053 (7)
C22A0.0362 (10)0.0321 (10)0.0297 (10)0.0016 (8)0.0008 (8)0.0009 (8)
C23A0.0330 (10)0.0501 (12)0.0300 (10)0.0028 (9)0.0052 (8)0.0054 (9)
C24A0.0346 (11)0.0454 (12)0.0351 (11)0.0084 (9)0.0013 (9)0.0143 (9)
C25A0.0449 (12)0.0290 (9)0.0371 (11)0.0091 (9)0.0010 (9)0.0027 (8)
C26A0.0367 (10)0.0264 (9)0.0312 (10)0.0031 (8)0.0036 (8)0.0009 (7)
C31A0.0293 (9)0.0212 (8)0.0276 (10)0.0026 (7)0.0016 (8)0.0032 (7)
C32A0.0347 (10)0.0420 (11)0.0338 (11)0.0067 (9)0.0043 (9)0.0042 (9)
C33A0.0590 (14)0.0516 (13)0.0283 (11)0.0007 (11)0.0068 (10)0.0012 (9)
C34A0.0560 (14)0.0418 (11)0.0329 (12)0.0073 (10)0.0124 (10)0.0072 (9)
C35A0.0340 (10)0.0316 (10)0.0511 (13)0.0010 (8)0.0117 (10)0.0077 (9)
C36A0.0315 (10)0.0249 (9)0.0383 (11)0.0001 (7)0.0041 (8)0.0017 (8)
C61A0.0331 (10)0.0243 (9)0.0299 (10)0.0047 (7)0.0023 (8)0.0008 (7)
C62A0.0594 (14)0.0316 (10)0.0407 (12)0.0011 (10)0.0106 (10)0.0053 (9)
C63A0.0872 (19)0.0361 (12)0.0454 (14)0.0026 (12)0.0110 (13)0.0135 (10)
C64A0.0661 (15)0.0275 (10)0.0525 (14)0.0041 (10)0.0089 (12)0.0060 (10)
C65A0.0529 (14)0.0333 (11)0.0591 (15)0.0089 (10)0.0041 (11)0.0025 (10)
C66A0.0503 (13)0.0331 (10)0.0447 (12)0.0049 (9)0.0094 (10)0.0048 (9)
N1B0.0293 (8)0.0259 (7)0.0324 (9)0.0046 (6)0.0077 (7)0.0047 (6)
C2B0.0285 (9)0.0254 (8)0.0239 (9)0.0026 (7)0.0004 (7)0.0011 (7)
C3B0.0274 (9)0.0259 (8)0.0230 (9)0.0000 (7)0.0007 (7)0.0019 (7)
C4B0.0290 (10)0.0335 (9)0.0223 (9)0.0015 (8)0.0030 (7)0.0020 (7)
C5B0.0307 (10)0.0295 (9)0.0370 (11)0.0068 (8)0.0053 (8)0.0002 (8)
C6B0.0305 (10)0.0246 (8)0.0289 (10)0.0023 (7)0.0000 (8)0.0001 (7)
C13B0.0345 (10)0.0280 (9)0.0308 (10)0.0021 (8)0.0028 (8)0.0009 (7)
C21B0.0291 (9)0.0259 (8)0.0229 (9)0.0020 (7)0.0059 (7)0.0038 (7)
C22B0.0356 (10)0.0308 (9)0.0260 (10)0.0006 (8)0.0030 (8)0.0003 (7)
C23B0.0299 (10)0.0477 (11)0.0264 (10)0.0000 (9)0.0003 (8)0.0048 (8)
C24B0.0338 (10)0.0422 (11)0.0356 (11)0.0100 (9)0.0078 (9)0.0101 (9)
C25B0.0423 (11)0.0288 (9)0.0430 (12)0.0092 (8)0.0111 (9)0.0008 (8)
C26B0.0338 (10)0.0298 (9)0.0334 (10)0.0019 (8)0.0041 (8)0.0026 (8)
C31B0.0260 (9)0.0305 (9)0.0354 (11)0.0068 (7)0.0043 (8)0.0092 (8)
C32B0.0374 (11)0.0545 (13)0.0340 (11)0.0056 (10)0.0033 (9)0.0087 (10)
C33B0.0589 (15)0.0794 (17)0.0346 (13)0.0313 (14)0.0113 (11)0.0167 (12)
C34B0.0725 (19)0.0713 (18)0.075 (2)0.0380 (15)0.0477 (16)0.0439 (16)
C35B0.0626 (17)0.0534 (15)0.111 (3)0.0014 (13)0.0478 (18)0.0283 (17)
C36B0.0422 (12)0.0402 (12)0.0706 (16)0.0054 (10)0.0148 (12)0.0075 (11)
C61B0.0297 (9)0.0252 (9)0.0324 (10)0.0059 (7)0.0024 (8)0.0036 (7)
C62B0.0477 (12)0.0332 (10)0.0364 (12)0.0031 (9)0.0022 (9)0.0042 (8)
C63B0.0610 (14)0.0415 (12)0.0405 (12)0.0029 (10)0.0008 (11)0.0137 (10)
C64B0.0461 (12)0.0313 (10)0.0559 (14)0.0024 (9)0.0022 (10)0.0115 (10)
C65B0.0564 (14)0.0355 (11)0.0533 (14)0.0110 (10)0.0057 (11)0.0017 (10)
C66B0.0524 (13)0.0366 (11)0.0375 (12)0.0057 (10)0.0055 (10)0.0045 (9)
Geometric parameters (Å, º) top
O4A—C4A1.214 (2)C64A—H64A0.9500
N1A—C2A1.469 (2)C65A—H65A0.9500
N1A—C6A1.466 (2)C66A—H66A0.9500
N1A—H1A0.876 (19)N1B—H1B0.90 (2)
C2A—C3A1.550 (2)C2B—C3B1.549 (2)
C2A—C21A1.513 (2)C2B—C21B1.513 (2)
C3A—C4A1.515 (2)C3B—C4B1.514 (2)
C3A—C13A1.529 (2)C3B—C13B1.525 (2)
C4A—C5A1.503 (3)C4B—C5B1.501 (3)
O4B—C4B1.214 (2)C5B—C6B1.532 (3)
C5A—C6A1.537 (3)C6B—C61B1.512 (2)
C6A—C61A1.514 (2)C13B—C31B1.503 (3)
C13A—C31A1.510 (2)C21B—C26B1.385 (2)
C21A—C22A1.394 (2)C21B—C22B1.390 (2)
C21A—C26A1.386 (2)C22B—C23B1.387 (3)
C22A—C23A1.386 (3)C23B—C24B1.378 (3)
C23A—C24A1.377 (3)C24B—C25B1.375 (3)
C24A—C25A1.379 (3)C25B—C26B1.387 (3)
C25A—C26A1.386 (3)C31B—C32B1.377 (3)
C31A—C32A1.380 (3)C31B—C36B1.388 (3)
C31A—C36A1.387 (2)C32B—C33B1.381 (3)
C32A—C33A1.382 (3)C33B—C34B1.369 (4)
C33A—C34A1.375 (3)C34B—C35B1.376 (5)
C34A—C35A1.370 (3)C35B—C36B1.376 (4)
C35A—C36A1.384 (3)C61B—C66B1.385 (3)
C61A—C66A1.384 (3)C61B—C62B1.378 (3)
C61A—C62A1.376 (3)C62B—C63B1.385 (3)
C62A—C63A1.383 (3)C63B—C64B1.369 (3)
C63A—C64A1.368 (3)C64B—C65B1.374 (3)
C64A—C65A1.372 (3)C65B—C66B1.381 (3)
C65A—C66A1.384 (3)C2B—H2B1.0000
N1B—C2B1.468 (2)C3B—H3B1.0000
N1B—C6B1.466 (2)C5B—H5C0.9900
C2A—H2A1.0000C5B—H5D0.9900
C3A—H3A1.0000C6B—H6B1.0000
C5A—H5B0.9900C13B—H13C0.9900
C5A—H5A0.9900C13B—H13D0.9900
C6A—H6A1.0000C22B—H22B0.9500
C13A—H13A0.9900C23B—H23B0.9500
C13A—H13B0.9900C24B—H24B0.9500
C22A—H22A0.9500C25B—H25B0.9500
C23A—H23A0.9500C26B—H26B0.9500
C24A—H24A0.9500C32B—H32B0.9500
C25A—H25A0.9500C33B—H33B0.9500
C26A—H26A0.9500C34B—H34B0.9500
C32A—H32A0.9500C35B—H35B0.9500
C33A—H33A0.9500C36B—H36B0.9500
C34A—H34A0.9500C62B—H62B0.9500
C35A—H35A0.9500C63B—H63B0.9500
C36A—H36A0.9500C64B—H64B0.9500
C62A—H62A0.9500C65B—H65B0.9500
C63A—H63A0.9500C66B—H66B0.9500
C2A—N1A—C6A114.30 (13)C65A—C66A—H66A120.00
C2A—N1A—H1A105.9 (12)C2B—N1B—H1B106.4 (14)
C6A—N1A—H1A107.7 (13)C6B—N1B—H1B108.2 (13)
C3A—C2A—C21A111.90 (14)C3B—C2B—C21B112.05 (14)
N1A—C2A—C3A109.14 (13)N1B—C2B—C3B109.53 (13)
N1A—C2A—C21A108.24 (13)N1B—C2B—C21B109.00 (13)
C2A—C3A—C4A107.30 (13)C2B—C3B—C4B107.58 (14)
C2A—C3A—C13A112.08 (13)C2B—C3B—C13B111.16 (13)
C4A—C3A—C13A112.91 (15)C4B—C3B—C13B112.72 (14)
O4A—C4A—C3A122.72 (16)O4B—C4B—C3B122.62 (16)
C3A—C4A—C5A114.66 (15)C3B—C4B—C5B114.85 (15)
O4A—C4A—C5A122.40 (16)O4B—C4B—C5B122.22 (16)
C4A—C5A—C6A108.12 (14)C4B—C5B—C6B107.83 (14)
N1A—C6A—C61A108.91 (14)N1B—C6B—C61B108.48 (14)
C5A—C6A—C61A113.16 (14)C5B—C6B—C61B114.23 (14)
N1A—C6A—C5A107.85 (14)N1B—C6B—C5B107.88 (14)
C3A—C13A—C31A114.52 (14)C3B—C13B—C31B117.21 (15)
C2A—C21A—C26A120.59 (15)C2B—C21B—C26B120.72 (15)
C2A—C21A—C22A120.96 (14)C2B—C21B—C22B120.63 (14)
C22A—C21A—C26A118.45 (16)C22B—C21B—C26B118.64 (16)
C21A—C22A—C23A120.63 (17)C21B—C22B—C23B120.33 (16)
C22A—C23A—C24A120.13 (18)C22B—C23B—C24B120.23 (17)
C23A—C24A—C25A119.87 (18)C23B—C24B—C25B120.01 (18)
C24A—C25A—C26A120.13 (18)C24B—C25B—C26B119.81 (17)
C21A—C26A—C25A120.79 (17)C21B—C26B—C25B120.94 (17)
C13A—C31A—C32A120.87 (16)C13B—C31B—C32B122.60 (17)
C32A—C31A—C36A117.82 (17)C32B—C31B—C36B117.86 (19)
C13A—C31A—C36A121.24 (16)C13B—C31B—C36B119.42 (18)
C31A—C32A—C33A121.30 (18)C31B—C32B—C33B121.1 (2)
C32A—C33A—C34A120.18 (19)C32B—C33B—C34B120.5 (2)
C33A—C34A—C35A119.39 (19)C33B—C34B—C35B119.3 (3)
C34A—C35A—C36A120.45 (18)C34B—C35B—C36B120.3 (3)
C31A—C36A—C35A120.87 (17)C31B—C36B—C35B121.0 (2)
C6A—C61A—C62A120.49 (16)C6B—C61B—C62B120.65 (16)
C62A—C61A—C66A118.35 (16)C62B—C61B—C66B118.05 (16)
C6A—C61A—C66A121.10 (16)C6B—C61B—C66B121.19 (16)
C61A—C62A—C63A120.81 (19)C61B—C62B—C63B121.11 (18)
C62A—C63A—C64A120.4 (2)C62B—C63B—C64B120.2 (2)
C63A—C64A—C65A119.6 (2)C63B—C64B—C65B119.4 (2)
C64A—C65A—C66A120.1 (2)C64B—C65B—C66B120.4 (2)
C61A—C66A—C65A120.76 (19)C61B—C66B—C65B120.77 (19)
C2B—N1B—C6B113.60 (13)N1B—C2B—H2B109.00
C3A—C2A—H2A109.00C3B—C2B—H2B109.00
C21A—C2A—H2A109.00C21B—C2B—H2B109.00
N1A—C2A—H2A109.00C2B—C3B—H3B108.00
C4A—C3A—H3A108.00C4B—C3B—H3B108.00
C13A—C3A—H3A108.00C13B—C3B—H3B108.00
C2A—C3A—H3A108.00C4B—C5B—H5C110.00
C4A—C5A—H5A110.00C4B—C5B—H5D110.00
C4A—C5A—H5B110.00C6B—C5B—H5C110.00
C6A—C5A—H5B110.00C6B—C5B—H5D110.00
H5A—C5A—H5B108.00H5C—C5B—H5D108.00
C6A—C5A—H5A110.00N1B—C6B—H6B109.00
C5A—C6A—H6A109.00C5B—C6B—H6B109.00
C61A—C6A—H6A109.00C61B—C6B—H6B109.00
N1A—C6A—H6A109.00C3B—C13B—H13C108.00
C3A—C13A—H13A109.00C3B—C13B—H13D108.00
C31A—C13A—H13A109.00C31B—C13B—H13C108.00
C31A—C13A—H13B109.00C31B—C13B—H13D108.00
C3A—C13A—H13B109.00H13C—C13B—H13D107.00
H13A—C13A—H13B108.00C21B—C22B—H22B120.00
C23A—C22A—H22A120.00C23B—C22B—H22B120.00
C21A—C22A—H22A120.00C22B—C23B—H23B120.00
C24A—C23A—H23A120.00C24B—C23B—H23B120.00
C22A—C23A—H23A120.00C23B—C24B—H24B120.00
C23A—C24A—H24A120.00C25B—C24B—H24B120.00
C25A—C24A—H24A120.00C24B—C25B—H25B120.00
C24A—C25A—H25A120.00C26B—C25B—H25B120.00
C26A—C25A—H25A120.00C21B—C26B—H26B120.00
C25A—C26A—H26A120.00C25B—C26B—H26B120.00
C21A—C26A—H26A120.00C31B—C32B—H32B119.00
C31A—C32A—H32A119.00C33B—C32B—H32B119.00
C33A—C32A—H32A119.00C32B—C33B—H33B120.00
C34A—C33A—H33A120.00C34B—C33B—H33B120.00
C32A—C33A—H33A120.00C33B—C34B—H34B120.00
C33A—C34A—H34A120.00C35B—C34B—H34B120.00
C35A—C34A—H34A120.00C34B—C35B—H35B120.00
C36A—C35A—H35A120.00C36B—C35B—H35B120.00
C34A—C35A—H35A120.00C31B—C36B—H36B119.00
C31A—C36A—H36A120.00C35B—C36B—H36B120.00
C35A—C36A—H36A120.00C61B—C62B—H62B119.00
C63A—C62A—H62A120.00C63B—C62B—H62B119.00
C61A—C62A—H62A120.00C62B—C63B—H63B120.00
C62A—C63A—H63A120.00C64B—C63B—H63B120.00
C64A—C63A—H63A120.00C63B—C64B—H64B120.00
C65A—C64A—H64A120.00C65B—C64B—H64B120.00
C63A—C64A—H64A120.00C64B—C65B—H65B120.00
C64A—C65A—H65A120.00C66B—C65B—H65B120.00
C66A—C65A—H65A120.00C61B—C66B—H66B120.00
C61A—C66A—H66A120.00C65B—C66B—H66B120.00
C6A—N1A—C2A—C3A61.46 (18)C6B—N1B—C2B—C3B61.29 (18)
C6A—N1A—C2A—C21A176.53 (14)C6B—N1B—C2B—C21B175.80 (14)
C2A—N1A—C6A—C5A62.31 (18)C2B—N1B—C6B—C5B63.35 (18)
C2A—N1A—C6A—C61A174.52 (14)C2B—N1B—C6B—C61B172.43 (14)
C21A—C2A—C3A—C4A173.88 (13)C21B—C2B—C3B—C4B174.28 (13)
N1A—C2A—C3A—C4A54.10 (17)N1B—C2B—C3B—C4B53.20 (17)
N1A—C2A—C3A—C13A178.60 (14)N1B—C2B—C3B—C13B177.05 (14)
N1A—C2A—C21A—C26A133.69 (16)N1B—C2B—C21B—C26B135.23 (16)
C3A—C2A—C21A—C22A74.08 (19)C3B—C2B—C21B—C22B75.98 (19)
C3A—C2A—C21A—C26A106.01 (18)C3B—C2B—C21B—C26B103.38 (18)
C21A—C2A—C3A—C13A61.62 (18)C21B—C2B—C3B—C13B61.87 (18)
N1A—C2A—C21A—C22A46.2 (2)N1B—C2B—C21B—C22B45.4 (2)
C13A—C3A—C4A—O4A5.2 (2)C13B—C3B—C4B—O4B4.0 (2)
C2A—C3A—C4A—O4A118.79 (18)C2B—C3B—C4B—O4B118.88 (18)
C2A—C3A—C4A—C5A55.97 (18)C2B—C3B—C4B—C5B54.85 (18)
C4A—C3A—C13A—C31A75.06 (19)C4B—C3B—C13B—C31B68.0 (2)
C13A—C3A—C4A—C5A179.96 (15)C13B—C3B—C4B—C5B177.74 (15)
C2A—C3A—C13A—C31A163.62 (15)C2B—C3B—C13B—C31B171.14 (15)
O4A—C4A—C5A—C6A116.86 (19)O4B—C4B—C5B—C6B115.95 (19)
C3A—C4A—C5A—C6A57.92 (19)C3B—C4B—C5B—C6B57.81 (19)
C4A—C5A—C6A—C61A177.43 (15)C4B—C5B—C6B—C61B178.78 (15)
C4A—C5A—C6A—N1A56.90 (18)C4B—C5B—C6B—N1B58.09 (18)
N1A—C6A—C61A—C62A129.72 (18)N1B—C6B—C61B—C62B112.54 (19)
N1A—C6A—C61A—C66A47.5 (2)N1B—C6B—C61B—C66B63.5 (2)
C5A—C6A—C61A—C62A110.35 (19)C5B—C6B—C61B—C62B127.11 (18)
C5A—C6A—C61A—C66A72.5 (2)C5B—C6B—C61B—C66B56.8 (2)
C3A—C13A—C31A—C32A51.9 (2)C3B—C13B—C31B—C32B40.2 (3)
C3A—C13A—C31A—C36A131.02 (17)C3B—C13B—C31B—C36B143.99 (18)
C2A—C21A—C22A—C23A179.95 (16)C2B—C21B—C22B—C23B178.94 (16)
C26A—C21A—C22A—C23A0.0 (3)C26B—C21B—C22B—C23B0.4 (3)
C2A—C21A—C26A—C25A179.44 (17)C2B—C21B—C26B—C25B177.54 (17)
C22A—C21A—C26A—C25A0.7 (3)C22B—C21B—C26B—C25B1.8 (3)
C21A—C22A—C23A—C24A0.9 (3)C21B—C22B—C23B—C24B1.4 (3)
C22A—C23A—C24A—C25A1.2 (3)C22B—C23B—C24B—C25B1.9 (3)
C23A—C24A—C25A—C26A0.6 (3)C23B—C24B—C25B—C26B0.5 (3)
C24A—C25A—C26A—C21A0.4 (3)C24B—C25B—C26B—C21B1.4 (3)
C13A—C31A—C32A—C33A177.01 (17)C13B—C31B—C32B—C33B174.7 (2)
C36A—C31A—C32A—C33A0.2 (3)C36B—C31B—C32B—C33B1.2 (3)
C13A—C31A—C36A—C35A176.97 (16)C13B—C31B—C36B—C35B175.8 (2)
C32A—C31A—C36A—C35A0.2 (2)C32B—C31B—C36B—C35B0.2 (3)
C31A—C32A—C33A—C34A0.1 (3)C31B—C32B—C33B—C34B0.8 (4)
C32A—C33A—C34A—C35A0.1 (3)C32B—C33B—C34B—C35B0.7 (4)
C33A—C34A—C35A—C36A0.1 (3)C33B—C34B—C35B—C36B1.7 (4)
C34A—C35A—C36A—C31A0.2 (3)C34B—C35B—C36B—C31B1.3 (4)
C6A—C61A—C62A—C63A176.43 (19)C6B—C61B—C62B—C63B175.47 (17)
C66A—C61A—C62A—C63A0.9 (3)C66B—C61B—C62B—C63B0.7 (3)
C6A—C61A—C66A—C65A176.76 (18)C6B—C61B—C66B—C65B176.13 (17)
C62A—C61A—C66A—C65A0.5 (3)C62B—C61B—C66B—C65B0.1 (3)
C61A—C62A—C63A—C64A0.7 (3)C61B—C62B—C63B—C64B1.0 (3)
C62A—C63A—C64A—C65A0.2 (4)C62B—C63B—C64B—C65B0.6 (3)
C63A—C64A—C65A—C66A0.1 (3)C63B—C64B—C65B—C66B0.1 (3)
C64A—C65A—C66A—C61A0.0 (3)C64B—C65B—C66B—C61B0.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3, Cg6 and Cg7 are the centroids of phenyl rings C21A–C26A, C31A–C36A, C21B–C26B and C31B–C36B, respectively.
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O4Bi0.88 (2)2.41 (2)3.234 (2)158 (2)
N1B—H1B···O4Aii0.90 (2)2.48 (2)3.315 (2)153 (2)
C2A—H2A···Cg6iii1.002.953.9315 (19)167
C2B—H2B···Cg2iv1.003.003.9733 (19)166
C25B—H25B···Cg3v0.952.783.626 (2)150
C64A—H64A···Cg3ii0.952.783.661 (2)155
C64B—H64B···Cg7i0.952.933.796 (2)153
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x+1/2, y+1/2, z1/2; (v) x+1/2, y+1/2, z+3/2.
 

Acknowledgements

We are grateful to the Principal Dr N. Seraman, Chairman Mr R. Sattanathan and Treasurer Mr T. Ramalingam of Thiruvalluvar Arts and Science College for giving permission to carry out research work in the Chemistry Laboratory.

References

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ISSN: 2414-3146
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