organic compounds
t-3-Benzyl-r-2,c-6-diphenylpiperidin-4-one
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
The 24H23NO, 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 –A–B–A–B– chains along [100]. In addition, five C—H⋯π interactions are also present, linking the chains to form a three-dimensional structure.
of the title compound, CCCDC reference: 1451096
Structure description
The and Fig. 2), 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.
of the title compound, (Fig. 1An AutoMolFit of molecule A on molecule B gives the best fit (Fig. 3; Spek, 2009). 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°.
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). In addition, there are a number of C—H⋯π interactions present, linking the chains to form a three-dimensional structure (Table 1).
Jayabharathi et al., (2008) have reported the 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) have reported the 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 .
details are summarized in Table 2
|
Structural data
CCDC reference: 1451096
https://doi.org/10.1107/S2414314616001887/su4012sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616001887/su4012Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616001887/su4012Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314616001887/su4012Isup4.cml
Data collection: APEX3 (Bruker, 2015); cell
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).C24H23NO | F(000) = 1456 |
Mr = 341.43 | Dx = 1.211 Mg m−3 |
Monoclinic, P21/n | Melting point: 471 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8918 (5) Å | Cell parameters from 7035 reflections |
b = 30.6042 (12) Å | θ = 2.6–22.8° |
c = 12.3878 (6) Å | µ = 0.07 mm−1 |
β = 92.426 (2)° | T = 178 K |
V = 3746.8 (3) Å3 | Plate, colourless |
Z = 8 | 0.40 × 0.36 × 0.16 mm |
Bruker Kappa APEXIII CCD area-detector diffractometer | 10617 independent reflections |
Radiation source: fine-focus sealed tube | 6350 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.078 |
φ and ω scans | θmax = 29.7°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −13→13 |
Tmin = 0.81, Tmax = 0.99 | k = −42→42 |
58653 measured reflections | l = −14→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: mixed |
wR(F2) = 0.150 | H 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 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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 |
x | y | z | Uiso*/Ueq | ||
O4A | 0.66207 (13) | 0.14287 (4) | 0.97486 (11) | 0.0395 (5) | |
N1A | 0.29441 (15) | 0.17242 (5) | 0.87397 (13) | 0.0294 (5) | |
C2A | 0.33073 (17) | 0.12682 (5) | 0.89839 (14) | 0.0255 (5) | |
C3A | 0.42875 (17) | 0.12561 (5) | 0.99936 (14) | 0.0258 (5) | |
C4A | 0.54612 (18) | 0.15567 (6) | 0.97724 (14) | 0.0287 (5) | |
O4B | 0.64521 (13) | 0.35463 (4) | 0.14639 (11) | 0.0398 (4) | |
C5A | 0.50630 (18) | 0.20176 (6) | 0.94862 (15) | 0.0310 (6) | |
C6A | 0.40932 (18) | 0.20027 (5) | 0.84847 (14) | 0.0281 (5) | |
C13A | 0.4738 (2) | 0.07909 (6) | 1.02805 (14) | 0.0316 (6) | |
C21A | 0.20186 (17) | 0.10166 (5) | 0.91607 (13) | 0.0256 (5) | |
C22A | 0.10267 (19) | 0.11842 (6) | 0.98114 (15) | 0.0327 (6) | |
C23A | −0.0152 (2) | 0.09519 (7) | 0.99688 (16) | 0.0376 (6) | |
C24A | −0.0346 (2) | 0.05489 (7) | 0.94932 (16) | 0.0385 (7) | |
C25A | 0.0624 (2) | 0.03799 (6) | 0.88431 (16) | 0.0371 (6) | |
C26A | 0.17976 (19) | 0.06132 (6) | 0.86759 (15) | 0.0314 (6) | |
C31A | 0.53595 (17) | 0.07396 (5) | 1.14082 (14) | 0.0260 (5) | |
C32A | 0.4699 (2) | 0.08900 (6) | 1.22942 (16) | 0.0368 (6) | |
C33A | 0.5230 (2) | 0.08269 (7) | 1.33323 (17) | 0.0462 (7) | |
C34A | 0.6440 (2) | 0.06114 (7) | 1.35011 (17) | 0.0440 (7) | |
C35A | 0.7111 (2) | 0.04598 (6) | 1.26319 (17) | 0.0393 (6) | |
C36A | 0.65797 (18) | 0.05231 (5) | 1.15920 (15) | 0.0315 (6) | |
C61A | 0.35679 (18) | 0.24486 (5) | 0.81445 (15) | 0.0292 (6) | |
C62A | 0.3975 (2) | 0.26388 (6) | 0.72053 (17) | 0.0437 (7) | |
C63A | 0.3443 (3) | 0.30352 (7) | 0.68587 (19) | 0.0560 (9) | |
C64A | 0.2511 (2) | 0.32475 (7) | 0.74529 (19) | 0.0490 (8) | |
C65A | 0.2101 (2) | 0.30642 (7) | 0.83958 (19) | 0.0484 (8) | |
C66A | 0.2627 (2) | 0.26665 (6) | 0.87408 (18) | 0.0425 (7) | |
N1B | 0.28747 (15) | 0.32434 (5) | 0.24447 (13) | 0.0290 (5) | |
C2B | 0.31937 (17) | 0.36986 (5) | 0.21806 (14) | 0.0260 (5) | |
C3B | 0.40928 (17) | 0.37099 (5) | 0.11867 (14) | 0.0254 (5) | |
C4B | 0.52943 (18) | 0.34139 (6) | 0.14279 (14) | 0.0282 (5) | |
C5B | 0.49399 (19) | 0.29549 (6) | 0.17362 (15) | 0.0323 (6) | |
C6B | 0.40709 (17) | 0.29780 (5) | 0.27294 (14) | 0.0280 (5) | |
C13B | 0.45080 (19) | 0.41762 (6) | 0.09216 (15) | 0.0311 (6) | |
C21B | 0.18873 (17) | 0.39485 (5) | 0.19832 (13) | 0.0258 (5) | |
C22B | 0.08347 (18) | 0.37718 (6) | 0.13450 (14) | 0.0308 (6) | |
C23B | −0.03523 (19) | 0.40058 (6) | 0.11528 (15) | 0.0347 (6) | |
C24B | −0.0486 (2) | 0.44195 (6) | 0.15741 (16) | 0.0370 (6) | |
C25B | 0.0544 (2) | 0.45969 (6) | 0.22133 (16) | 0.0378 (6) | |
C26B | 0.17202 (19) | 0.43595 (6) | 0.24253 (15) | 0.0323 (6) | |
C31B | 0.52074 (18) | 0.42469 (6) | −0.01175 (15) | 0.0306 (6) | |
C32B | 0.4822 (2) | 0.40348 (7) | −0.10618 (16) | 0.0419 (7) | |
C33B | 0.5413 (3) | 0.41335 (9) | −0.20217 (18) | 0.0574 (9) | |
C34B | 0.6411 (3) | 0.44425 (10) | −0.2052 (3) | 0.0717 (11) | |
C35B | 0.6830 (3) | 0.46507 (9) | −0.1112 (3) | 0.0744 (13) | |
C36B | 0.6227 (2) | 0.45573 (7) | −0.0158 (2) | 0.0507 (8) | |
C61B | 0.36041 (18) | 0.25385 (5) | 0.31273 (15) | 0.0291 (5) | |
C62B | 0.3830 (2) | 0.24185 (6) | 0.41921 (16) | 0.0392 (7) | |
C63B | 0.3325 (2) | 0.20300 (7) | 0.45824 (18) | 0.0478 (7) | |
C64B | 0.2605 (2) | 0.17535 (7) | 0.39071 (18) | 0.0444 (7) | |
C65B | 0.2378 (2) | 0.18668 (7) | 0.28414 (19) | 0.0486 (8) | |
C66B | 0.2869 (2) | 0.22564 (6) | 0.24535 (17) | 0.0424 (7) | |
H1A | 0.2395 (19) | 0.1715 (6) | 0.8167 (16) | 0.032 (5)* | |
H2A | 0.37692 | 0.11399 | 0.83550 | 0.0306* | |
H3A | 0.38018 | 0.13776 | 1.06185 | 0.0310* | |
H5A | 0.58761 | 0.21914 | 0.93306 | 0.0372* | |
H5B | 0.46113 | 0.21559 | 1.00971 | 0.0372* | |
H6A | 0.45740 | 0.18695 | 0.78715 | 0.0338* | |
H13A | 0.39449 | 0.05946 | 1.02003 | 0.0379* | |
H13B | 0.54056 | 0.06950 | 0.97562 | 0.0379* | |
H22A | 0.11594 | 0.14603 | 1.01501 | 0.0392* | |
H23A | −0.08264 | 0.10710 | 1.04059 | 0.0451* | |
H24A | −0.11467 | 0.03876 | 0.96126 | 0.0461* | |
H25A | 0.04871 | 0.01030 | 0.85092 | 0.0445* | |
H26A | 0.24584 | 0.04953 | 0.82236 | 0.0376* | |
H32A | 0.38624 | 0.10399 | 1.21885 | 0.0441* | |
H33A | 0.47574 | 0.09327 | 1.39309 | 0.0554* | |
H34A | 0.68070 | 0.05681 | 1.42141 | 0.0528* | |
H35A | 0.79466 | 0.03102 | 1.27435 | 0.0471* | |
H36A | 0.70571 | 0.04169 | 1.09964 | 0.0378* | |
H62A | 0.46288 | 0.24961 | 0.67898 | 0.0523* | |
H63A | 0.37263 | 0.31607 | 0.62044 | 0.0672* | |
H64A | 0.21491 | 0.35202 | 0.72143 | 0.0588* | |
H65A | 0.14561 | 0.32105 | 0.88125 | 0.0580* | |
H66A | 0.23387 | 0.25417 | 0.93945 | 0.0510* | |
H1B | 0.235 (2) | 0.3253 (7) | 0.3023 (18) | 0.050 (7)* | |
H2B | 0.37069 | 0.38323 | 0.28103 | 0.0312* | |
H3B | 0.35600 | 0.35885 | 0.05514 | 0.0305* | |
H5C | 0.44317 | 0.28096 | 0.11314 | 0.0387* | |
H5D | 0.57736 | 0.27849 | 0.19060 | 0.0387* | |
H6B | 0.46029 | 0.31264 | 0.33280 | 0.0336* | |
H13C | 0.51134 | 0.42836 | 0.15210 | 0.0373* | |
H13D | 0.36851 | 0.43606 | 0.09058 | 0.0373* | |
H22B | 0.09285 | 0.34893 | 0.10390 | 0.0369* | |
H23B | −0.10755 | 0.38805 | 0.07293 | 0.0417* | |
H24B | −0.12897 | 0.45821 | 0.14230 | 0.0444* | |
H25B | 0.04501 | 0.48812 | 0.25088 | 0.0453* | |
H26B | 0.24209 | 0.44807 | 0.28802 | 0.0387* | |
H32B | 0.41384 | 0.38169 | −0.10523 | 0.0503* | |
H33B | 0.51247 | 0.39860 | −0.26658 | 0.0688* | |
H34B | 0.68106 | 0.45124 | −0.27144 | 0.0860* | |
H35B | 0.75387 | 0.48600 | −0.11212 | 0.0891* | |
H36B | 0.65135 | 0.47074 | 0.04831 | 0.0608* | |
H62B | 0.43397 | 0.26056 | 0.46664 | 0.0470* | |
H63B | 0.34799 | 0.19550 | 0.53215 | 0.0573* | |
H64B | 0.22648 | 0.14857 | 0.41727 | 0.0533* | |
H65B | 0.18806 | 0.16759 | 0.23683 | 0.0583* | |
H66B | 0.27005 | 0.23318 | 0.17162 | 0.0509* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4A | 0.0305 (7) | 0.0438 (8) | 0.0443 (9) | 0.0043 (6) | 0.0016 (6) | 0.0055 (6) |
N1A | 0.0308 (8) | 0.0251 (7) | 0.0316 (9) | −0.0028 (6) | −0.0066 (7) | 0.0049 (6) |
C2A | 0.0304 (9) | 0.0229 (8) | 0.0231 (9) | −0.0009 (7) | 0.0001 (7) | −0.0003 (7) |
C3A | 0.0297 (9) | 0.0248 (8) | 0.0229 (9) | 0.0011 (7) | 0.0003 (7) | −0.0011 (7) |
C4A | 0.0313 (10) | 0.0341 (9) | 0.0204 (9) | −0.0003 (8) | −0.0031 (7) | −0.0024 (7) |
O4B | 0.0283 (7) | 0.0468 (8) | 0.0442 (8) | −0.0015 (6) | 0.0012 (6) | 0.0078 (6) |
C5A | 0.0312 (10) | 0.0277 (9) | 0.0337 (10) | −0.0050 (7) | −0.0020 (8) | −0.0011 (8) |
C6A | 0.0315 (10) | 0.0244 (8) | 0.0286 (10) | −0.0020 (7) | 0.0021 (8) | 0.0002 (7) |
C13A | 0.0411 (11) | 0.0263 (9) | 0.0272 (10) | 0.0031 (8) | −0.0014 (8) | −0.0001 (7) |
C21A | 0.0304 (9) | 0.0258 (8) | 0.0202 (9) | 0.0003 (7) | −0.0018 (7) | 0.0053 (7) |
C22A | 0.0362 (10) | 0.0321 (10) | 0.0297 (10) | 0.0016 (8) | 0.0008 (8) | −0.0009 (8) |
C23A | 0.0330 (10) | 0.0501 (12) | 0.0300 (10) | 0.0028 (9) | 0.0052 (8) | 0.0054 (9) |
C24A | 0.0346 (11) | 0.0454 (12) | 0.0351 (11) | −0.0084 (9) | −0.0013 (9) | 0.0143 (9) |
C25A | 0.0449 (12) | 0.0290 (9) | 0.0371 (11) | −0.0091 (9) | −0.0010 (9) | 0.0027 (8) |
C26A | 0.0367 (10) | 0.0264 (9) | 0.0312 (10) | −0.0031 (8) | 0.0036 (8) | 0.0009 (7) |
C31A | 0.0293 (9) | 0.0212 (8) | 0.0276 (10) | −0.0026 (7) | 0.0016 (8) | 0.0032 (7) |
C32A | 0.0347 (10) | 0.0420 (11) | 0.0338 (11) | 0.0067 (9) | 0.0043 (9) | 0.0042 (9) |
C33A | 0.0590 (14) | 0.0516 (13) | 0.0283 (11) | 0.0007 (11) | 0.0068 (10) | 0.0012 (9) |
C34A | 0.0560 (14) | 0.0418 (11) | 0.0329 (12) | −0.0073 (10) | −0.0124 (10) | 0.0072 (9) |
C35A | 0.0340 (10) | 0.0316 (10) | 0.0511 (13) | −0.0010 (8) | −0.0117 (10) | 0.0077 (9) |
C36A | 0.0315 (10) | 0.0249 (9) | 0.0383 (11) | −0.0001 (7) | 0.0041 (8) | 0.0017 (8) |
C61A | 0.0331 (10) | 0.0243 (9) | 0.0299 (10) | −0.0047 (7) | −0.0023 (8) | −0.0008 (7) |
C62A | 0.0594 (14) | 0.0316 (10) | 0.0407 (12) | 0.0011 (10) | 0.0106 (10) | 0.0053 (9) |
C63A | 0.0872 (19) | 0.0361 (12) | 0.0454 (14) | 0.0026 (12) | 0.0110 (13) | 0.0135 (10) |
C64A | 0.0661 (15) | 0.0275 (10) | 0.0525 (14) | 0.0041 (10) | −0.0089 (12) | 0.0060 (10) |
C65A | 0.0529 (14) | 0.0333 (11) | 0.0591 (15) | 0.0089 (10) | 0.0041 (11) | −0.0025 (10) |
C66A | 0.0503 (13) | 0.0331 (10) | 0.0447 (12) | 0.0049 (9) | 0.0094 (10) | 0.0048 (9) |
N1B | 0.0293 (8) | 0.0259 (7) | 0.0324 (9) | 0.0046 (6) | 0.0077 (7) | 0.0047 (6) |
C2B | 0.0285 (9) | 0.0254 (8) | 0.0239 (9) | 0.0026 (7) | 0.0004 (7) | −0.0011 (7) |
C3B | 0.0274 (9) | 0.0259 (8) | 0.0230 (9) | 0.0000 (7) | 0.0007 (7) | −0.0019 (7) |
C4B | 0.0290 (10) | 0.0335 (9) | 0.0223 (9) | 0.0015 (8) | 0.0030 (7) | −0.0020 (7) |
C5B | 0.0307 (10) | 0.0295 (9) | 0.0370 (11) | 0.0068 (8) | 0.0053 (8) | −0.0002 (8) |
C6B | 0.0305 (10) | 0.0246 (8) | 0.0289 (10) | 0.0023 (7) | 0.0000 (8) | 0.0001 (7) |
C13B | 0.0345 (10) | 0.0280 (9) | 0.0308 (10) | −0.0021 (8) | 0.0028 (8) | 0.0009 (7) |
C21B | 0.0291 (9) | 0.0259 (8) | 0.0229 (9) | 0.0020 (7) | 0.0059 (7) | 0.0038 (7) |
C22B | 0.0356 (10) | 0.0308 (9) | 0.0260 (10) | 0.0006 (8) | 0.0030 (8) | −0.0003 (7) |
C23B | 0.0299 (10) | 0.0477 (11) | 0.0264 (10) | 0.0000 (9) | −0.0003 (8) | 0.0048 (8) |
C24B | 0.0338 (10) | 0.0422 (11) | 0.0356 (11) | 0.0100 (9) | 0.0078 (9) | 0.0101 (9) |
C25B | 0.0423 (11) | 0.0288 (9) | 0.0430 (12) | 0.0092 (8) | 0.0111 (9) | 0.0008 (8) |
C26B | 0.0338 (10) | 0.0298 (9) | 0.0334 (10) | 0.0019 (8) | 0.0041 (8) | −0.0026 (8) |
C31B | 0.0260 (9) | 0.0305 (9) | 0.0354 (11) | 0.0068 (7) | 0.0043 (8) | 0.0092 (8) |
C32B | 0.0374 (11) | 0.0545 (13) | 0.0340 (11) | 0.0056 (10) | 0.0033 (9) | 0.0087 (10) |
C33B | 0.0589 (15) | 0.0794 (17) | 0.0346 (13) | 0.0313 (14) | 0.0113 (11) | 0.0167 (12) |
C34B | 0.0725 (19) | 0.0713 (18) | 0.075 (2) | 0.0380 (15) | 0.0477 (16) | 0.0439 (16) |
C35B | 0.0626 (17) | 0.0534 (15) | 0.111 (3) | 0.0014 (13) | 0.0478 (18) | 0.0283 (17) |
C36B | 0.0422 (12) | 0.0402 (12) | 0.0706 (16) | −0.0054 (10) | 0.0148 (12) | 0.0075 (11) |
C61B | 0.0297 (9) | 0.0252 (9) | 0.0324 (10) | 0.0059 (7) | 0.0024 (8) | 0.0036 (7) |
C62B | 0.0477 (12) | 0.0332 (10) | 0.0364 (12) | −0.0031 (9) | −0.0022 (9) | 0.0042 (8) |
C63B | 0.0610 (14) | 0.0415 (12) | 0.0405 (12) | −0.0029 (10) | −0.0008 (11) | 0.0137 (10) |
C64B | 0.0461 (12) | 0.0313 (10) | 0.0559 (14) | −0.0024 (9) | 0.0022 (10) | 0.0115 (10) |
C65B | 0.0564 (14) | 0.0355 (11) | 0.0533 (14) | −0.0110 (10) | −0.0057 (11) | 0.0017 (10) |
C66B | 0.0524 (13) | 0.0366 (11) | 0.0375 (12) | −0.0057 (10) | −0.0055 (10) | 0.0045 (9) |
O4A—C4A | 1.214 (2) | C64A—H64A | 0.9500 |
N1A—C2A | 1.469 (2) | C65A—H65A | 0.9500 |
N1A—C6A | 1.466 (2) | C66A—H66A | 0.9500 |
N1A—H1A | 0.876 (19) | N1B—H1B | 0.90 (2) |
C2A—C3A | 1.550 (2) | C2B—C3B | 1.549 (2) |
C2A—C21A | 1.513 (2) | C2B—C21B | 1.513 (2) |
C3A—C4A | 1.515 (2) | C3B—C4B | 1.514 (2) |
C3A—C13A | 1.529 (2) | C3B—C13B | 1.525 (2) |
C4A—C5A | 1.503 (3) | C4B—C5B | 1.501 (3) |
O4B—C4B | 1.214 (2) | C5B—C6B | 1.532 (3) |
C5A—C6A | 1.537 (3) | C6B—C61B | 1.512 (2) |
C6A—C61A | 1.514 (2) | C13B—C31B | 1.503 (3) |
C13A—C31A | 1.510 (2) | C21B—C26B | 1.385 (2) |
C21A—C22A | 1.394 (2) | C21B—C22B | 1.390 (2) |
C21A—C26A | 1.386 (2) | C22B—C23B | 1.387 (3) |
C22A—C23A | 1.386 (3) | C23B—C24B | 1.378 (3) |
C23A—C24A | 1.377 (3) | C24B—C25B | 1.375 (3) |
C24A—C25A | 1.379 (3) | C25B—C26B | 1.387 (3) |
C25A—C26A | 1.386 (3) | C31B—C32B | 1.377 (3) |
C31A—C32A | 1.380 (3) | C31B—C36B | 1.388 (3) |
C31A—C36A | 1.387 (2) | C32B—C33B | 1.381 (3) |
C32A—C33A | 1.382 (3) | C33B—C34B | 1.369 (4) |
C33A—C34A | 1.375 (3) | C34B—C35B | 1.376 (5) |
C34A—C35A | 1.370 (3) | C35B—C36B | 1.376 (4) |
C35A—C36A | 1.384 (3) | C61B—C66B | 1.385 (3) |
C61A—C66A | 1.384 (3) | C61B—C62B | 1.378 (3) |
C61A—C62A | 1.376 (3) | C62B—C63B | 1.385 (3) |
C62A—C63A | 1.383 (3) | C63B—C64B | 1.369 (3) |
C63A—C64A | 1.368 (3) | C64B—C65B | 1.374 (3) |
C64A—C65A | 1.372 (3) | C65B—C66B | 1.381 (3) |
C65A—C66A | 1.384 (3) | C2B—H2B | 1.0000 |
N1B—C2B | 1.468 (2) | C3B—H3B | 1.0000 |
N1B—C6B | 1.466 (2) | C5B—H5C | 0.9900 |
C2A—H2A | 1.0000 | C5B—H5D | 0.9900 |
C3A—H3A | 1.0000 | C6B—H6B | 1.0000 |
C5A—H5B | 0.9900 | C13B—H13C | 0.9900 |
C5A—H5A | 0.9900 | C13B—H13D | 0.9900 |
C6A—H6A | 1.0000 | C22B—H22B | 0.9500 |
C13A—H13A | 0.9900 | C23B—H23B | 0.9500 |
C13A—H13B | 0.9900 | C24B—H24B | 0.9500 |
C22A—H22A | 0.9500 | C25B—H25B | 0.9500 |
C23A—H23A | 0.9500 | C26B—H26B | 0.9500 |
C24A—H24A | 0.9500 | C32B—H32B | 0.9500 |
C25A—H25A | 0.9500 | C33B—H33B | 0.9500 |
C26A—H26A | 0.9500 | C34B—H34B | 0.9500 |
C32A—H32A | 0.9500 | C35B—H35B | 0.9500 |
C33A—H33A | 0.9500 | C36B—H36B | 0.9500 |
C34A—H34A | 0.9500 | C62B—H62B | 0.9500 |
C35A—H35A | 0.9500 | C63B—H63B | 0.9500 |
C36A—H36A | 0.9500 | C64B—H64B | 0.9500 |
C62A—H62A | 0.9500 | C65B—H65B | 0.9500 |
C63A—H63A | 0.9500 | C66B—H66B | 0.9500 |
C2A—N1A—C6A | 114.30 (13) | C65A—C66A—H66A | 120.00 |
C2A—N1A—H1A | 105.9 (12) | C2B—N1B—H1B | 106.4 (14) |
C6A—N1A—H1A | 107.7 (13) | C6B—N1B—H1B | 108.2 (13) |
C3A—C2A—C21A | 111.90 (14) | C3B—C2B—C21B | 112.05 (14) |
N1A—C2A—C3A | 109.14 (13) | N1B—C2B—C3B | 109.53 (13) |
N1A—C2A—C21A | 108.24 (13) | N1B—C2B—C21B | 109.00 (13) |
C2A—C3A—C4A | 107.30 (13) | C2B—C3B—C4B | 107.58 (14) |
C2A—C3A—C13A | 112.08 (13) | C2B—C3B—C13B | 111.16 (13) |
C4A—C3A—C13A | 112.91 (15) | C4B—C3B—C13B | 112.72 (14) |
O4A—C4A—C3A | 122.72 (16) | O4B—C4B—C3B | 122.62 (16) |
C3A—C4A—C5A | 114.66 (15) | C3B—C4B—C5B | 114.85 (15) |
O4A—C4A—C5A | 122.40 (16) | O4B—C4B—C5B | 122.22 (16) |
C4A—C5A—C6A | 108.12 (14) | C4B—C5B—C6B | 107.83 (14) |
N1A—C6A—C61A | 108.91 (14) | N1B—C6B—C61B | 108.48 (14) |
C5A—C6A—C61A | 113.16 (14) | C5B—C6B—C61B | 114.23 (14) |
N1A—C6A—C5A | 107.85 (14) | N1B—C6B—C5B | 107.88 (14) |
C3A—C13A—C31A | 114.52 (14) | C3B—C13B—C31B | 117.21 (15) |
C2A—C21A—C26A | 120.59 (15) | C2B—C21B—C26B | 120.72 (15) |
C2A—C21A—C22A | 120.96 (14) | C2B—C21B—C22B | 120.63 (14) |
C22A—C21A—C26A | 118.45 (16) | C22B—C21B—C26B | 118.64 (16) |
C21A—C22A—C23A | 120.63 (17) | C21B—C22B—C23B | 120.33 (16) |
C22A—C23A—C24A | 120.13 (18) | C22B—C23B—C24B | 120.23 (17) |
C23A—C24A—C25A | 119.87 (18) | C23B—C24B—C25B | 120.01 (18) |
C24A—C25A—C26A | 120.13 (18) | C24B—C25B—C26B | 119.81 (17) |
C21A—C26A—C25A | 120.79 (17) | C21B—C26B—C25B | 120.94 (17) |
C13A—C31A—C32A | 120.87 (16) | C13B—C31B—C32B | 122.60 (17) |
C32A—C31A—C36A | 117.82 (17) | C32B—C31B—C36B | 117.86 (19) |
C13A—C31A—C36A | 121.24 (16) | C13B—C31B—C36B | 119.42 (18) |
C31A—C32A—C33A | 121.30 (18) | C31B—C32B—C33B | 121.1 (2) |
C32A—C33A—C34A | 120.18 (19) | C32B—C33B—C34B | 120.5 (2) |
C33A—C34A—C35A | 119.39 (19) | C33B—C34B—C35B | 119.3 (3) |
C34A—C35A—C36A | 120.45 (18) | C34B—C35B—C36B | 120.3 (3) |
C31A—C36A—C35A | 120.87 (17) | C31B—C36B—C35B | 121.0 (2) |
C6A—C61A—C62A | 120.49 (16) | C6B—C61B—C62B | 120.65 (16) |
C62A—C61A—C66A | 118.35 (16) | C62B—C61B—C66B | 118.05 (16) |
C6A—C61A—C66A | 121.10 (16) | C6B—C61B—C66B | 121.19 (16) |
C61A—C62A—C63A | 120.81 (19) | C61B—C62B—C63B | 121.11 (18) |
C62A—C63A—C64A | 120.4 (2) | C62B—C63B—C64B | 120.2 (2) |
C63A—C64A—C65A | 119.6 (2) | C63B—C64B—C65B | 119.4 (2) |
C64A—C65A—C66A | 120.1 (2) | C64B—C65B—C66B | 120.4 (2) |
C61A—C66A—C65A | 120.76 (19) | C61B—C66B—C65B | 120.77 (19) |
C2B—N1B—C6B | 113.60 (13) | N1B—C2B—H2B | 109.00 |
C3A—C2A—H2A | 109.00 | C3B—C2B—H2B | 109.00 |
C21A—C2A—H2A | 109.00 | C21B—C2B—H2B | 109.00 |
N1A—C2A—H2A | 109.00 | C2B—C3B—H3B | 108.00 |
C4A—C3A—H3A | 108.00 | C4B—C3B—H3B | 108.00 |
C13A—C3A—H3A | 108.00 | C13B—C3B—H3B | 108.00 |
C2A—C3A—H3A | 108.00 | C4B—C5B—H5C | 110.00 |
C4A—C5A—H5A | 110.00 | C4B—C5B—H5D | 110.00 |
C4A—C5A—H5B | 110.00 | C6B—C5B—H5C | 110.00 |
C6A—C5A—H5B | 110.00 | C6B—C5B—H5D | 110.00 |
H5A—C5A—H5B | 108.00 | H5C—C5B—H5D | 108.00 |
C6A—C5A—H5A | 110.00 | N1B—C6B—H6B | 109.00 |
C5A—C6A—H6A | 109.00 | C5B—C6B—H6B | 109.00 |
C61A—C6A—H6A | 109.00 | C61B—C6B—H6B | 109.00 |
N1A—C6A—H6A | 109.00 | C3B—C13B—H13C | 108.00 |
C3A—C13A—H13A | 109.00 | C3B—C13B—H13D | 108.00 |
C31A—C13A—H13A | 109.00 | C31B—C13B—H13C | 108.00 |
C31A—C13A—H13B | 109.00 | C31B—C13B—H13D | 108.00 |
C3A—C13A—H13B | 109.00 | H13C—C13B—H13D | 107.00 |
H13A—C13A—H13B | 108.00 | C21B—C22B—H22B | 120.00 |
C23A—C22A—H22A | 120.00 | C23B—C22B—H22B | 120.00 |
C21A—C22A—H22A | 120.00 | C22B—C23B—H23B | 120.00 |
C24A—C23A—H23A | 120.00 | C24B—C23B—H23B | 120.00 |
C22A—C23A—H23A | 120.00 | C23B—C24B—H24B | 120.00 |
C23A—C24A—H24A | 120.00 | C25B—C24B—H24B | 120.00 |
C25A—C24A—H24A | 120.00 | C24B—C25B—H25B | 120.00 |
C24A—C25A—H25A | 120.00 | C26B—C25B—H25B | 120.00 |
C26A—C25A—H25A | 120.00 | C21B—C26B—H26B | 120.00 |
C25A—C26A—H26A | 120.00 | C25B—C26B—H26B | 120.00 |
C21A—C26A—H26A | 120.00 | C31B—C32B—H32B | 119.00 |
C31A—C32A—H32A | 119.00 | C33B—C32B—H32B | 119.00 |
C33A—C32A—H32A | 119.00 | C32B—C33B—H33B | 120.00 |
C34A—C33A—H33A | 120.00 | C34B—C33B—H33B | 120.00 |
C32A—C33A—H33A | 120.00 | C33B—C34B—H34B | 120.00 |
C33A—C34A—H34A | 120.00 | C35B—C34B—H34B | 120.00 |
C35A—C34A—H34A | 120.00 | C34B—C35B—H35B | 120.00 |
C36A—C35A—H35A | 120.00 | C36B—C35B—H35B | 120.00 |
C34A—C35A—H35A | 120.00 | C31B—C36B—H36B | 119.00 |
C31A—C36A—H36A | 120.00 | C35B—C36B—H36B | 120.00 |
C35A—C36A—H36A | 120.00 | C61B—C62B—H62B | 119.00 |
C63A—C62A—H62A | 120.00 | C63B—C62B—H62B | 119.00 |
C61A—C62A—H62A | 120.00 | C62B—C63B—H63B | 120.00 |
C62A—C63A—H63A | 120.00 | C64B—C63B—H63B | 120.00 |
C64A—C63A—H63A | 120.00 | C63B—C64B—H64B | 120.00 |
C65A—C64A—H64A | 120.00 | C65B—C64B—H64B | 120.00 |
C63A—C64A—H64A | 120.00 | C64B—C65B—H65B | 120.00 |
C64A—C65A—H65A | 120.00 | C66B—C65B—H65B | 120.00 |
C66A—C65A—H65A | 120.00 | C61B—C66B—H66B | 120.00 |
C61A—C66A—H66A | 120.00 | C65B—C66B—H66B | 120.00 |
C6A—N1A—C2A—C3A | 61.46 (18) | C6B—N1B—C2B—C3B | 61.29 (18) |
C6A—N1A—C2A—C21A | −176.53 (14) | C6B—N1B—C2B—C21B | −175.80 (14) |
C2A—N1A—C6A—C5A | −62.31 (18) | C2B—N1B—C6B—C5B | −63.35 (18) |
C2A—N1A—C6A—C61A | 174.52 (14) | C2B—N1B—C6B—C61B | 172.43 (14) |
C21A—C2A—C3A—C4A | −173.88 (13) | C21B—C2B—C3B—C4B | −174.28 (13) |
N1A—C2A—C3A—C4A | −54.10 (17) | N1B—C2B—C3B—C4B | −53.20 (17) |
N1A—C2A—C3A—C13A | −178.60 (14) | N1B—C2B—C3B—C13B | −177.05 (14) |
N1A—C2A—C21A—C26A | 133.69 (16) | N1B—C2B—C21B—C26B | 135.23 (16) |
C3A—C2A—C21A—C22A | 74.08 (19) | C3B—C2B—C21B—C22B | 75.98 (19) |
C3A—C2A—C21A—C26A | −106.01 (18) | C3B—C2B—C21B—C26B | −103.38 (18) |
C21A—C2A—C3A—C13A | 61.62 (18) | C21B—C2B—C3B—C13B | 61.87 (18) |
N1A—C2A—C21A—C22A | −46.2 (2) | N1B—C2B—C21B—C22B | −45.4 (2) |
C13A—C3A—C4A—O4A | 5.2 (2) | C13B—C3B—C4B—O4B | 4.0 (2) |
C2A—C3A—C4A—O4A | −118.79 (18) | C2B—C3B—C4B—O4B | −118.88 (18) |
C2A—C3A—C4A—C5A | 55.97 (18) | C2B—C3B—C4B—C5B | 54.85 (18) |
C4A—C3A—C13A—C31A | 75.06 (19) | C4B—C3B—C13B—C31B | 68.0 (2) |
C13A—C3A—C4A—C5A | 179.96 (15) | C13B—C3B—C4B—C5B | 177.74 (15) |
C2A—C3A—C13A—C31A | −163.62 (15) | C2B—C3B—C13B—C31B | −171.14 (15) |
O4A—C4A—C5A—C6A | 116.86 (19) | O4B—C4B—C5B—C6B | 115.95 (19) |
C3A—C4A—C5A—C6A | −57.92 (19) | C3B—C4B—C5B—C6B | −57.81 (19) |
C4A—C5A—C6A—C61A | 177.43 (15) | C4B—C5B—C6B—C61B | 178.78 (15) |
C4A—C5A—C6A—N1A | 56.90 (18) | C4B—C5B—C6B—N1B | 58.09 (18) |
N1A—C6A—C61A—C62A | −129.72 (18) | N1B—C6B—C61B—C62B | −112.54 (19) |
N1A—C6A—C61A—C66A | 47.5 (2) | N1B—C6B—C61B—C66B | 63.5 (2) |
C5A—C6A—C61A—C62A | 110.35 (19) | C5B—C6B—C61B—C62B | 127.11 (18) |
C5A—C6A—C61A—C66A | −72.5 (2) | C5B—C6B—C61B—C66B | −56.8 (2) |
C3A—C13A—C31A—C32A | 51.9 (2) | C3B—C13B—C31B—C32B | 40.2 (3) |
C3A—C13A—C31A—C36A | −131.02 (17) | C3B—C13B—C31B—C36B | −143.99 (18) |
C2A—C21A—C22A—C23A | 179.95 (16) | C2B—C21B—C22B—C23B | −178.94 (16) |
C26A—C21A—C22A—C23A | 0.0 (3) | C26B—C21B—C22B—C23B | 0.4 (3) |
C2A—C21A—C26A—C25A | 179.44 (17) | C2B—C21B—C26B—C25B | 177.54 (17) |
C22A—C21A—C26A—C25A | −0.7 (3) | C22B—C21B—C26B—C25B | −1.8 (3) |
C21A—C22A—C23A—C24A | 0.9 (3) | C21B—C22B—C23B—C24B | 1.4 (3) |
C22A—C23A—C24A—C25A | −1.2 (3) | C22B—C23B—C24B—C25B | −1.9 (3) |
C23A—C24A—C25A—C26A | 0.6 (3) | C23B—C24B—C25B—C26B | 0.5 (3) |
C24A—C25A—C26A—C21A | 0.4 (3) | C24B—C25B—C26B—C21B | 1.4 (3) |
C13A—C31A—C32A—C33A | 177.01 (17) | C13B—C31B—C32B—C33B | 174.7 (2) |
C36A—C31A—C32A—C33A | −0.2 (3) | C36B—C31B—C32B—C33B | −1.2 (3) |
C13A—C31A—C36A—C35A | −176.97 (16) | C13B—C31B—C36B—C35B | −175.8 (2) |
C32A—C31A—C36A—C35A | 0.2 (2) | C32B—C31B—C36B—C35B | 0.2 (3) |
C31A—C32A—C33A—C34A | 0.1 (3) | C31B—C32B—C33B—C34B | 0.8 (4) |
C32A—C33A—C34A—C35A | −0.1 (3) | C32B—C33B—C34B—C35B | 0.7 (4) |
C33A—C34A—C35A—C36A | 0.1 (3) | C33B—C34B—C35B—C36B | −1.7 (4) |
C34A—C35A—C36A—C31A | −0.2 (3) | C34B—C35B—C36B—C31B | 1.3 (4) |
C6A—C61A—C62A—C63A | 176.43 (19) | C6B—C61B—C62B—C63B | 175.47 (17) |
C66A—C61A—C62A—C63A | −0.9 (3) | C66B—C61B—C62B—C63B | −0.7 (3) |
C6A—C61A—C66A—C65A | −176.76 (18) | C6B—C61B—C66B—C65B | −176.13 (17) |
C62A—C61A—C66A—C65A | 0.5 (3) | C62B—C61B—C66B—C65B | 0.1 (3) |
C61A—C62A—C63A—C64A | 0.7 (3) | C61B—C62B—C63B—C64B | 1.0 (3) |
C62A—C63A—C64A—C65A | −0.2 (4) | C62B—C63B—C64B—C65B | −0.6 (3) |
C63A—C64A—C65A—C66A | −0.1 (3) | C63B—C64B—C65B—C66B | −0.1 (3) |
C64A—C65A—C66A—C61A | 0.0 (3) | C64B—C65B—C66B—C61B | 0.4 (3) |
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 | D···A | 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—H2A···Cg6iii | 1.00 | 2.95 | 3.9315 (19) | 167 |
C2B—H2B···Cg2iv | 1.00 | 3.00 | 3.9733 (19) | 166 |
C25B—H25B···Cg3v | 0.95 | 2.78 | 3.626 (2) | 150 |
C64A—H64A···Cg3ii | 0.95 | 2.78 | 3.661 (2) | 155 |
C64B—H64B···Cg7i | 0.95 | 2.93 | 3.796 (2) | 153 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x+1/2, −y+1/2, z−1/2; (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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