Literature DB >> 21578792

(3E,5E)-3,5-Bis(4-allyl-oxybenzyl-idene)-1-benzyl-piperidin-4-one.

N S Karthikeyan, K Sathiyanarayanan, P G Aravindan, H Ghosh, R S Rathore.

Abstract

In the title compound C(32)H(31)NO(3), the all-yloxy groups on either side of the piperidin-4-one ring are conformationally disordered. The contribution of major and minor components of the allyloxy group at the 3rd position of the ring are 0.576 (4) and 0.424 (4), respectively, and those at the 5th position are 0.885 (3) and 0.115 (3), respectively. The six-membered piperidin-4-one ring adopts a sofa conformation with the benzyl group occupying an equatorial position and the olefinic double bonds possessing an E configuration. Flanking phenyl substituents are stretched out on either side of the six-membered ring. π-π inter-actions with a centroid-centroid distance of 3.885 (1) Å give rise to mol-ecular dimers and short C-H⋯π contacts lead to chains along the c axis.

Entities: CellLine Chemical Disease Species

Year: 2009 PMID： 21578792 PMCID： PMC2971870 DOI： 10.1107/S1600536809046716

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related structures, see: Suresh et al. (2007 ▶); Rathore et al. (2009 ▶); Karthikeyan et al. (2009 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C32H31NO3 M = 477.58 Monoclinic, a = 15.6161 (4) Å b = 9.2654 (2) Å c = 18.9696 (5) Å β = 111.031 (1)° V = 2561.87 (11) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 295 K 0.33 × 0.29 × 0.27 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.896, T max = 0.964 26042 measured reflections 5029 independent reflections 3882 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.114 S = 1.01 5029 reflections 342 parameters 1 restraint H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.19 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046716/bq2170sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046716/bq2170Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₃₂H₃₁NO₃	F(000) = 1016
M_r = 477.58	D_x = 1.238 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 388(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.6161 (4) Å	Cell parameters from 9748 reflections
b = 9.2654 (2) Å	θ = 2.2–28.2°
c = 18.9696 (5) Å	µ = 0.08 mm⁻¹
β = 111.031 (1)°	T = 295 K
V = 2561.87 (11) Å³	Block, yellow
Z = 4	0.33 × 0.29 × 0.27 mm

Bruker APEXII CCD area-detector diffractometer	5029 independent reflections
Radiation source: fine-focus sealed tube	3882 reflections with I > 2σ(I)
graphite	R_int = 0.027
φ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −19→19
T_min = 0.896, T_max = 0.964	k = −11→11
26042 measured reflections	l = −21→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0509P)² + 0.7272P] where P = (F_o² + 2F_c²)/3
5029 reflections	(Δ/σ)_max = 0.001
342 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

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============================================================================Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=dPlane 1 m1 = 0.63145(0.00057) m2 = 0.53630(0.00051) m3 = -0.56005(0.00052) D = 2.64782(0.00814) Atom d s d/s (d/s)**2 C15 * 0.0025 0.0014 1.710 2.924 C16 * 0.0037 0.0016 2.339 5.471 C17 * -0.0099 0.0017 - 5.814 33.804 C18 * 0.0074 0.0016 4.481 20.083 C19 * -0.0002 0.0016 - 0.120 0.014 C20 * -0.0048 0.0016 - 3.021 9.124 O2 0.0675 0.0013 52.104 2714.813 C14 0.1183 0.0014 81.779 6687.801 C28 0.2295 0.0022 106.646 11373.305 ============ Sum((d/s)**2) for starred atoms 71.420 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarityPlane 2 m1 = 0.56481(0.00057) m2 = 0.77772(0.00043) m3 = -0.27594(0.00064) D = 3.26621(0.00176) Atom d s d/s (d/s)**2 C22 * -0.0163 0.0015 - 10.629 112.976 C23 * 0.0112 0.0016 6.834 46.705 C24 * 0.0078 0.0018 4.420 19.537 C25 * -0.0177 0.0017 - 10.604 112.437 C26 * 0.0113 0.0018 6.209 38.547 C27 * 0.0095 0.0017 5.532 30.601 O3 - 0.0627 0.0014 - 46.013 2117.186 C21 - 0.0323 0.0015 - 21.820 476.128 C31' -0.5200 0.0188 - 27.643 764.147 ============ Sum((d/s)**2) for starred atoms 360.801 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarityPlane 3 m1 = 0.32339(0.00075) m2 = 0.92133(0.00036) m3 = -0.21581(0.00070) D = 1.73547(0.00401) Atom d s d/s (d/s)**2 C2 * 0.0298 0.0015 20.137 405.483 C3 * -0.0224 0.0013 - 16.855 284.080 C5 * 0.0224 0.0013 16.863 284.370 C6 * -0.0338 0.0016 - 21.430 459.250 N1 - 0.7279 0.0012 - 601.376 361653.344 C4 - 0.1964 0.0014 - 139.920 19577.652 O1 - 0.4421 0.0012 - 370.110 136981.719 ============ Sum((d/s)**2) for starred atoms 1433.183 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarityPlane 4 m1 = 0.36687(0.00061) m2 = 0.89674(0.00032) m3 = -0.24754(0.00062) D = 1.84491(0.00391) Atom d s d/s (d/s)**2 C2 * 0.0029 0.0015 1.982 3.929 C3 * 0.0394 0.0013 29.495 869.956 C4 * -0.0904 0.0014 - 64.198 4121.393 C5 * 0.0833 0.0013 62.434 3897.966 C6 * -0.0612 0.0016 - 38.795 1505.066 N1 - 0.7792 0.0012 - 642.939 413370.656 O1 - 0.2648 0.0012 - 222.229 49385.770 ============ Sum((d/s)**2) for starred atoms 10398.310 Chi-squared at 95% for 2 degrees of freedom: 5.99 The group of atoms deviates significantly from planarityPlane 5 m1 = -0.85377(0.00041) m2 = -0.38211(0.00073) m3 = -0.35365(0.00075) D = -5.12945(0.00494) Atom d s d/s (d/s)**2 C8 * 0.0012 0.0015 0.816 0.665 C9 * -0.0076 0.0019 - 4.009 16.075 C10 * 0.0086 0.0022 3.946 15.574 C11 * 0.0003 0.0021 0.154 0.024 C12 * -0.0068 0.0020 - 3.356 11.260 C13 * 0.0041 0.0018 2.346 5.506 C7 0.0968 0.0016 59.458 3535.268 N1 - 0.4392 0.0013 - 345.718 119520.734 ============ Sum((d/s)**2) for starred atoms 49.105 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarityDihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 21.83 (0.05) 158.17 (0.05) 1 3 35.00 (0.05) 145.00 (0.05) 1 4 31.66 (0.04) 148.34 (0.04) 1 5 56.91 (0.05) 123.09 (0.05) 2 3 16.52 (0.05) 163.48 (0.05) 2 4 13.36 (0.04) 166.64 (0.04) 2 5 47.02 (0.05) 132.98 (0.05) 3 4 3.39 (0.05) 176.61 (0.05) 3 5 56.51 (0.06) 123.49 (0.06) 4 5 55.37 (0.06) 124.63 (0.06)Ring puckering coordinates following Cremer D. & Pople J.A., JACS (1975).97,1354Ring 1 Atom Internal Cartesian coordinates X Y Z N1 0.0000(0.0000) 1.2939(0.0013) 0.4125(0.0009) C2 1.1736(0.0015) 0.7782(0.0017) -0.2803(0.0009) C3 1.2761(0.0013) -0.6993(0.0017) -0.0383(0.0009) C4 0.0068(0.0016) -1.4276(0.0014) 0.2246(0.0009) C5 - 1.2588(0.0015) -0.7183(0.0019) -0.0924(0.0010) C6 - 1.1977(0.0016) 0.7731(0.0016) -0.2262(0.0010) q2 = 0.5544(0.0013) q3 = 0.2301(0.0014) phi2 = 5.60 (0.14) Total puckering amplitude: QT = 0.6002(0.0013) Spherical polar angles: Theta2 = 67.46 (0.13)Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141N1 C2 C3 C4 C5 C6DS(N1) =0.0379(0.0007) DS(N1 –C6) =0.2957(0.0006) D2(N1) =0.2492(0.0004) D2(N1 –C6) =0.1873(0.0006)DS(C2) =0.3212(0.0007) DS(C2 –N1) =0.3235(0.0006) D2(C2) =0.1726(0.0004) D2(C2 –N1) =0.1338(0.0006)DS(C3) =0.3591(0.0007) DS(C3 –C2) =0.1405(0.0006) D2(C3) =0.1453(0.0005) D2(C3 –C2) =0.3206(0.0006)============================================================================

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.

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.39705 (8)	0.04800 (13)	0.23368 (6)	0.0381 (3)
O1	0.53263 (7)	−0.08595 (13)	0.11005 (6)	0.0554 (3)
O2	0.92659 (8)	0.17546 (14)	0.51308 (7)	0.0697 (4)
O3	0.02843 (8)	0.17577 (15)	−0.19313 (7)	0.0667 (4)
C2	0.49054 (9)	0.10326 (16)	0.26458 (8)	0.0386 (3)
H2A	0.5174	0.0808	0.3180	0.046*
H2B	0.4902	0.2073	0.2588	0.046*
C3	0.54621 (9)	0.03515 (14)	0.22339 (8)	0.0345 (3)
C4	0.49587 (9)	−0.01131 (15)	0.14423 (8)	0.0374 (3)
C5	0.40104 (9)	0.04415 (14)	0.10699 (8)	0.0361 (3)
C6	0.35317 (10)	0.10116 (17)	0.15698 (8)	0.0420 (3)
H6A	0.3548	0.2058	0.1571	0.050*
H6B	0.2894	0.0711	0.1375	0.050*
C7	0.34420 (10)	0.08969 (18)	0.28031 (8)	0.0450 (4)
H7A	0.2797	0.0732	0.2518	0.054*
H7B	0.3524	0.1923	0.2907	0.054*
C8	0.37001 (9)	0.01014 (15)	0.35407 (8)	0.0376 (3)
C9	0.35206 (12)	0.07273 (18)	0.41302 (9)	0.0533 (4)
H9	0.3287	0.1661	0.4079	0.064*
C10	0.36824 (14)	−0.0012 (2)	0.47958 (10)	0.0635 (5)
H10	0.3543	0.0415	0.5185	0.076*
C11	0.40457 (13)	−0.1368 (2)	0.48862 (10)	0.0592 (5)
H11	0.4162	−0.1863	0.5338	0.071*
C12	0.42362 (13)	−0.19922 (18)	0.43080 (10)	0.0572 (4)
H12	0.4488	−0.2914	0.4368	0.069*
C13	0.40589 (11)	−0.12702 (17)	0.36363 (9)	0.0488 (4)
H13	0.4183	−0.1714	0.3244	0.059*
C14	0.63643 (9)	0.01206 (15)	0.25111 (8)	0.0375 (3)
H14	0.6587	−0.0404	0.2196	0.045*
C15	0.70605 (9)	0.05548 (15)	0.32273 (8)	0.0375 (3)
C16	0.78690 (10)	−0.02438 (16)	0.35081 (9)	0.0461 (4)
H16	0.7929	−0.1072	0.3253	0.055*
C17	0.85777 (11)	0.01583 (18)	0.41499 (9)	0.0513 (4)
H17	0.9104	−0.0406	0.4333	0.062*
C18	0.85064 (10)	0.14063 (18)	0.45245 (9)	0.0484 (4)
C19	0.77130 (10)	0.22157 (18)	0.42624 (9)	0.0498 (4)
H19	0.7659	0.3048	0.4517	0.060*
C20	0.70011 (10)	0.17874 (16)	0.36221 (9)	0.0439 (4)
H20	0.6468	0.2338	0.3451	0.053*
C21	0.36595 (10)	0.03912 (15)	0.03158 (8)	0.0398 (3)
H21	0.4053	−0.0002	0.0098	0.048*
C22	0.27741 (10)	0.08384 (16)	−0.02279 (8)	0.0395 (3)
C23	0.25263 (10)	0.02939 (18)	−0.09592 (8)	0.0467 (4)
H23	0.2931	−0.0313	−0.1075	0.056*
C24	0.17044 (11)	0.06261 (19)	−0.15114 (9)	0.0520 (4)
H24	0.1558	0.0242	−0.1993	0.062*
C25	0.10945 (10)	0.15270 (18)	−0.13548 (9)	0.0492 (4)
C26	0.13345 (12)	0.21327 (19)	−0.06456 (9)	0.0552 (4)
H26	0.0938	0.2774	−0.0541	0.066*
C27	0.21633 (11)	0.17866 (18)	−0.00919 (9)	0.0490 (4)
H27	0.2316	0.2199	0.0384	0.059*
C28	0.92820 (13)	0.3094 (2)	0.54962 (12)	0.0745 (6)
H28A	0.8944	0.3026	0.5836	0.089*	0.576 (4)
H28B	0.9007	0.3844	0.5128	0.089*	0.576 (4)
H28C	0.8729	0.3207	0.5612	0.089*	0.424 (4)
H28D	0.9314	0.3883	0.5171	0.089*	0.424 (4)
C29	1.0299 (3)	0.3439 (6)	0.5941 (3)	0.0724 (11)	0.576 (4)
H29	1.0697	0.3548	0.5680	0.087*	0.576 (4)
C30	1.0601 (3)	0.3577 (6)	0.6636 (3)	0.0946 (13)	0.576 (4)
H30A	1.0211	0.3472	0.6905	0.114*	0.576 (4)
H30B	1.1218	0.3786	0.6889	0.114*	0.576 (4)
C29'	1.0091 (5)	0.3105 (9)	0.6193 (4)	0.0724 (11)	0.424 (4)
H29'	1.0120	0.2542	0.6607	0.087*	0.424 (4)
C30'	1.0778 (5)	0.3948 (9)	0.6207 (4)	0.0946 (13)	0.424 (4)
H30C	1.0734	0.4502	0.5787	0.114*	0.424 (4)
H30D	1.1305	0.3990	0.6638	0.114*	0.424 (4)
C31	−0.04398 (14)	0.2435 (3)	−0.17894 (12)	0.0689 (6)	0.885 (3)
H31A	−0.0326	0.3465	−0.1727	0.083*	0.885 (3)
H31B	−0.0485	0.2059	−0.1327	0.083*	0.885 (3)
C32	−0.13050 (19)	0.2170 (4)	−0.24256 (17)	0.0758 (8)	0.885 (3)
H32	−0.1830	0.2596	−0.2395	0.091*	0.885 (3)
C33	−0.1410 (2)	0.1413 (4)	−0.3016 (2)	0.0871 (9)	0.885 (3)
H33A	−0.0908	0.0963	−0.3074	0.105*	0.885 (3)
H33B	−0.1990	0.1314	−0.3386	0.105*	0.885 (3)
C31'	−0.0131 (11)	0.092 (2)	−0.2515 (10)	0.0689 (6)	0.115 (3)
H31C	0.0007	−0.0066	−0.2346	0.083*	0.115 (3)
H31D	0.0156	0.1098	−0.2884	0.083*	0.115 (3)
C32'	−0.1163 (18)	0.102 (3)	−0.2929 (19)	0.0758 (8)	0.115 (3)
H32'	−0.1481	0.0418	−0.3330	0.091*	0.115 (3)
C33'	−0.156 (2)	0.202 (4)	−0.267 (2)	0.0871 (9)	0.115 (3)
H33C	−0.1220	0.2602	−0.2272	0.105*	0.115 (3)
H33D	−0.2195	0.2158	−0.2895	0.105*	0.115 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0340 (6)	0.0505 (7)	0.0313 (6)	0.0005 (5)	0.0134 (5)	0.0023 (5)
O1	0.0495 (6)	0.0671 (7)	0.0453 (6)	0.0114 (5)	0.0118 (5)	−0.0158 (5)
O2	0.0484 (7)	0.0757 (8)	0.0625 (8)	0.0094 (6)	−0.0072 (6)	−0.0245 (6)
O3	0.0483 (7)	0.0974 (10)	0.0458 (7)	0.0175 (6)	0.0066 (5)	0.0048 (6)
C2	0.0375 (7)	0.0442 (8)	0.0335 (8)	−0.0022 (6)	0.0121 (6)	−0.0026 (6)
C3	0.0366 (7)	0.0324 (7)	0.0346 (7)	−0.0029 (5)	0.0128 (6)	0.0007 (5)
C4	0.0396 (7)	0.0360 (7)	0.0370 (8)	−0.0023 (6)	0.0143 (6)	−0.0011 (6)
C5	0.0368 (7)	0.0364 (7)	0.0342 (7)	−0.0038 (6)	0.0118 (6)	0.0004 (6)
C6	0.0385 (7)	0.0521 (9)	0.0344 (8)	0.0038 (6)	0.0118 (6)	0.0034 (6)
C7	0.0397 (8)	0.0576 (9)	0.0411 (8)	0.0087 (7)	0.0185 (7)	0.0065 (7)
C8	0.0347 (7)	0.0433 (8)	0.0372 (8)	−0.0004 (6)	0.0156 (6)	−0.0006 (6)
C9	0.0715 (11)	0.0474 (9)	0.0473 (10)	0.0133 (8)	0.0289 (8)	0.0008 (7)
C10	0.0885 (14)	0.0675 (11)	0.0449 (10)	0.0129 (10)	0.0363 (10)	0.0003 (8)
C11	0.0695 (11)	0.0650 (11)	0.0482 (10)	0.0087 (9)	0.0273 (9)	0.0151 (8)
C12	0.0716 (11)	0.0463 (9)	0.0647 (11)	0.0128 (8)	0.0376 (9)	0.0134 (8)
C13	0.0614 (10)	0.0464 (8)	0.0486 (9)	0.0050 (7)	0.0319 (8)	−0.0013 (7)
C14	0.0398 (7)	0.0359 (7)	0.0376 (8)	0.0004 (6)	0.0151 (6)	−0.0010 (6)
C15	0.0332 (7)	0.0416 (8)	0.0377 (8)	−0.0012 (6)	0.0128 (6)	−0.0003 (6)
C16	0.0428 (8)	0.0417 (8)	0.0509 (9)	0.0035 (6)	0.0132 (7)	−0.0063 (7)
C17	0.0388 (8)	0.0505 (9)	0.0554 (10)	0.0092 (7)	0.0057 (7)	−0.0026 (7)
C18	0.0382 (8)	0.0576 (9)	0.0423 (9)	0.0017 (7)	0.0057 (7)	−0.0063 (7)
C19	0.0429 (8)	0.0525 (9)	0.0495 (9)	0.0033 (7)	0.0112 (7)	−0.0142 (7)
C20	0.0338 (7)	0.0480 (8)	0.0463 (9)	0.0048 (6)	0.0102 (6)	−0.0052 (7)
C21	0.0392 (7)	0.0437 (8)	0.0379 (8)	−0.0025 (6)	0.0153 (6)	−0.0014 (6)
C22	0.0399 (8)	0.0454 (8)	0.0337 (8)	−0.0022 (6)	0.0137 (6)	0.0034 (6)
C23	0.0427 (8)	0.0614 (10)	0.0365 (8)	0.0041 (7)	0.0147 (7)	−0.0028 (7)
C24	0.0485 (9)	0.0724 (11)	0.0324 (8)	0.0028 (8)	0.0111 (7)	−0.0043 (7)
C25	0.0428 (8)	0.0632 (10)	0.0384 (9)	0.0052 (7)	0.0105 (7)	0.0082 (7)
C26	0.0563 (10)	0.0654 (10)	0.0438 (9)	0.0179 (8)	0.0177 (8)	0.0025 (8)
C27	0.0546 (9)	0.0551 (9)	0.0354 (8)	0.0067 (7)	0.0139 (7)	0.0002 (7)
C28	0.0606 (11)	0.0779 (13)	0.0653 (12)	0.0055 (10)	−0.0014 (9)	−0.0281 (10)
C29	0.055 (2)	0.092 (3)	0.065 (3)	−0.0181 (19)	0.0150 (16)	−0.025 (2)
C30	0.064 (2)	0.115 (3)	0.089 (4)	−0.017 (2)	0.007 (2)	−0.022 (3)
C29'	0.055 (2)	0.092 (3)	0.065 (3)	−0.0181 (19)	0.0150 (16)	−0.025 (2)
C30'	0.064 (2)	0.115 (3)	0.089 (4)	−0.017 (2)	0.007 (2)	−0.022 (3)
C31	0.0528 (12)	0.0854 (15)	0.0657 (14)	0.0211 (11)	0.0180 (10)	0.0095 (11)
C32	0.0505 (16)	0.0910 (18)	0.081 (2)	0.0139 (14)	0.0171 (13)	0.0238 (16)
C33	0.0545 (19)	0.106 (3)	0.088 (2)	−0.0036 (16)	0.0107 (18)	0.0102 (19)
C31'	0.0528 (12)	0.0854 (15)	0.0657 (14)	0.0211 (11)	0.0180 (10)	0.0095 (11)
C32'	0.0505 (16)	0.0910 (18)	0.081 (2)	0.0139 (14)	0.0171 (13)	0.0238 (16)
C33'	0.0545 (19)	0.106 (3)	0.088 (2)	−0.0036 (16)	0.0107 (18)	0.0102 (19)

N1—C6	1.4538 (18)	C19—H19	0.9300
N1—C2	1.4570 (17)	C20—H20	0.9300
N1—C7	1.4616 (18)	C21—C22	1.457 (2)
O1—C4	1.2228 (17)	C21—H21	0.9300
O2—C18	1.3618 (18)	C22—C27	1.387 (2)
O2—C28	1.417 (2)	C22—C23	1.394 (2)
O3—C31'	1.314 (19)	C23—C24	1.369 (2)
O3—C25	1.3599 (18)	C23—H23	0.9300
O3—C31	1.401 (2)	C24—C25	1.377 (2)
C2—C3	1.5006 (19)	C24—H24	0.9300
C2—H2A	0.9700	C25—C26	1.380 (2)
C2—H2B	0.9700	C26—C27	1.380 (2)
C3—C14	1.3324 (19)	C26—H26	0.9300
C3—C4	1.4869 (19)	C27—H27	0.9300
C4—C5	1.4851 (19)	C28—C29'	1.465 (8)
C5—C21	1.3365 (19)	C28—C29	1.540 (5)
C5—C6	1.4986 (19)	C28—H28A	0.9700
C6—H6A	0.9700	C28—H28B	0.9700
C6—H6B	0.9700	C28—H28C	0.9700
C7—C8	1.503 (2)	C28—H28D	0.9700
C7—H7A	0.9700	C29—C30	1.237 (8)
C7—H7B	0.9700	C29—H29	0.9300
C8—C13	1.374 (2)	C30—H30A	0.9300
C8—C9	1.375 (2)	C30—H30B	0.9300
C9—C10	1.378 (2)	C29'—C30'	1.319 (11)
C9—H9	0.9300	C29'—H29'	0.9300
C10—C11	1.364 (2)	C30'—H30C	0.9300
C10—H10	0.9300	C30'—H30D	0.9300
C11—C12	1.364 (2)	C31—C32	1.474 (3)
C11—H11	0.9300	C31—H31A	0.9700
C12—C13	1.376 (2)	C31—H31B	0.9700
C12—H12	0.9300	C32—C33	1.280 (4)
C13—H13	0.9300	C32—H32	0.9300
C14—C15	1.4593 (19)	C33—H33A	0.9300
C14—H14	0.9300	C33—H33B	0.9300
C15—C20	1.387 (2)	C31'—C32'	1.52 (3)
C15—C16	1.394 (2)	C31'—H31C	0.9700
C16—C17	1.371 (2)	C31'—H31D	0.9700
C16—H16	0.9300	C32'—C33'	1.307 (10)
C17—C18	1.382 (2)	C32'—H32'	0.9300
C17—H17	0.9300	C33'—H33C	0.9300
C18—C19	1.379 (2)	C33'—H33D	0.9300
C19—C20	1.378 (2)

C6—N1—C2	109.14 (11)	C19—C20—H20	119.2
C6—N1—C7	110.51 (11)	C15—C20—H20	119.2
C2—N1—C7	111.44 (11)	C5—C21—C22	131.92 (14)
C18—O2—C28	118.54 (13)	C5—C21—H21	114.0
C31'—O3—C25	128.3 (7)	C22—C21—H21	114.0
C31'—O3—C31	103.7 (7)	C27—C22—C23	116.76 (14)
C25—O3—C31	119.87 (14)	C27—C22—C21	126.12 (13)
N1—C2—C3	109.08 (11)	C23—C22—C21	117.09 (13)
N1—C2—H2A	109.9	C24—C23—C22	121.95 (15)
C3—C2—H2A	109.9	C24—C23—H23	119.0
N1—C2—H2B	109.9	C22—C23—H23	119.0
C3—C2—H2B	109.9	C23—C24—C25	120.16 (15)
H2A—C2—H2B	108.3	C23—C24—H24	119.9
C14—C3—C4	116.93 (12)	C25—C24—H24	119.9
C14—C3—C2	126.17 (13)	O3—C25—C24	115.97 (14)
C4—C3—C2	116.90 (11)	O3—C25—C26	124.68 (15)
O1—C4—C5	121.41 (13)	C24—C25—C26	119.36 (14)
O1—C4—C3	121.37 (13)	C25—C26—C27	119.99 (15)
C5—C4—C3	117.11 (12)	C25—C26—H26	120.0
C21—C5—C4	116.93 (13)	C27—C26—H26	120.0
C21—C5—C6	125.70 (13)	C26—C27—C22	121.68 (15)
C4—C5—C6	117.37 (12)	C26—C27—H27	119.2
N1—C6—C5	110.54 (12)	C22—C27—H27	119.2
N1—C6—H6A	109.5	O2—C28—C29'	107.8 (3)
C5—C6—H6A	109.5	O2—C28—C29	106.5 (2)
N1—C6—H6B	109.5	O2—C28—H28A	110.4
C5—C6—H6B	109.5	C29—C28—H28A	110.4
H6A—C6—H6B	108.1	O2—C28—H28B	110.4
N1—C7—C8	114.38 (12)	C29—C28—H28B	110.4
N1—C7—H7A	108.7	H28A—C28—H28B	108.6
C8—C7—H7A	108.7	O2—C28—H28C	110.1
N1—C7—H7B	108.7	C29'—C28—H28C	110.1
C8—C7—H7B	108.7	O2—C28—H28D	110.1
H7A—C7—H7B	107.6	C29'—C28—H28D	110.1
C13—C8—C9	118.37 (14)	H28C—C28—H28D	108.5
C13—C8—C7	122.46 (13)	C30—C29—C28	122.0 (5)
C9—C8—C7	119.05 (13)	C30—C29—H29	119.0
C8—C9—C10	120.77 (15)	C28—C29—H29	119.0
C8—C9—H9	119.6	C29—C30—H30A	120.0
C10—C9—H9	119.6	C29—C30—H30B	120.0
C11—C10—C9	120.30 (16)	H30A—C30—H30B	120.0
C11—C10—H10	119.8	C30'—C29'—C28	117.0 (7)
C9—C10—H10	119.8	C30'—C29'—H29'	121.5
C12—C11—C10	119.36 (16)	C28—C29'—H29'	121.5
C12—C11—H11	120.3	C29'—C30'—H30C	120.0
C10—C11—H11	120.3	C29'—C30'—H30D	120.0
C11—C12—C13	120.60 (15)	H30C—C30'—H30D	120.0
C11—C12—H12	119.7	O3—C31—C32	109.5 (2)
C13—C12—H12	119.7	O3—C31—H31A	109.8
C8—C13—C12	120.57 (14)	C32—C31—H31A	109.8
C8—C13—H13	119.7	O3—C31—H31B	109.8
C12—C13—H13	119.7	C32—C31—H31B	109.8
C3—C14—C15	130.70 (13)	H31A—C31—H31B	108.2
C3—C14—H14	114.6	C33—C32—C31	126.9 (3)
C15—C14—H14	114.6	C33—C32—H32	116.6
C20—C15—C16	117.24 (13)	C31—C32—H32	116.6
C20—C15—C14	123.90 (13)	C32—C33—H33A	120.0
C16—C15—C14	118.66 (13)	C32—C33—H33B	120.0
C17—C16—C15	121.81 (14)	H33A—C33—H33B	120.0
C17—C16—H16	119.1	O3—C31'—C32'	120.8 (17)
C15—C16—H16	119.1	O3—C31'—H31C	107.1
C16—C17—C18	119.71 (14)	C32'—C31'—H31C	107.1
C16—C17—H17	120.1	O3—C31'—H31D	107.1
C18—C17—H17	120.1	C32'—C31'—H31D	107.1
O2—C18—C19	124.96 (14)	H31C—C31'—H31D	106.8
O2—C18—C17	115.21 (14)	C33'—C32'—C31'	114 (3)
C19—C18—C17	119.81 (14)	C33'—C32'—H32'	122.9
C20—C19—C18	119.82 (14)	C31'—C32'—H32'	122.9
C20—C19—H19	120.1	C32'—C33'—H33C	120.0
C18—C19—H19	120.1	C32'—C33'—H33D	120.0
C19—C20—C15	121.59 (14)	H33C—C33'—H33D	120.0

C6—N1—C2—C3	−68.12 (14)	C16—C17—C18—O2	−176.47 (16)
C7—N1—C2—C3	169.55 (11)	C16—C17—C18—C19	1.9 (3)
N1—C2—C3—C14	−152.11 (13)	O2—C18—C19—C20	177.17 (16)
N1—C2—C3—C4	27.71 (16)	C17—C18—C19—C20	−1.0 (3)
C14—C3—C4—O1	10.5 (2)	C18—C19—C20—C15	−0.2 (2)
C2—C3—C4—O1	−169.32 (13)	C16—C15—C20—C19	0.5 (2)
C14—C3—C4—C5	−165.87 (12)	C14—C15—C20—C19	−174.31 (15)
C2—C3—C4—C5	14.30 (18)	C4—C5—C21—C22	−179.52 (14)
O1—C4—C5—C21	−15.5 (2)	C6—C5—C21—C22	0.3 (3)
C3—C4—C5—C21	160.86 (12)	C5—C21—C22—C27	18.6 (3)
O1—C4—C5—C6	164.67 (14)	C5—C21—C22—C23	−163.22 (16)
C3—C4—C5—C6	−18.95 (18)	C27—C22—C23—C24	−2.6 (2)
C2—N1—C6—C5	63.70 (15)	C21—C22—C23—C24	178.99 (15)
C7—N1—C6—C5	−173.41 (12)	C22—C23—C24—C25	0.3 (3)
C21—C5—C6—N1	161.14 (13)	C31'—O3—C25—C24	24.9 (11)
C4—C5—C6—N1	−19.07 (18)	C31—O3—C25—C24	168.30 (18)
C6—N1—C7—C8	165.49 (12)	C31'—O3—C25—C26	−155.5 (11)
C2—N1—C7—C8	−72.97 (16)	C31—O3—C25—C26	−12.1 (3)
N1—C7—C8—C13	−28.1 (2)	C23—C24—C25—O3	−177.96 (15)
N1—C7—C8—C9	156.00 (14)	C23—C24—C25—C26	2.4 (3)
C13—C8—C9—C10	−1.1 (3)	O3—C25—C26—C27	177.74 (16)
C7—C8—C9—C10	175.03 (16)	C24—C25—C26—C27	−2.7 (3)
C8—C9—C10—C11	1.6 (3)	C25—C26—C27—C22	0.2 (3)
C9—C10—C11—C12	−0.8 (3)	C23—C22—C27—C26	2.4 (2)
C10—C11—C12—C13	−0.5 (3)	C21—C22—C27—C26	−179.42 (15)
C9—C8—C13—C12	−0.3 (2)	C18—O2—C28—C29'	170.8 (3)
C7—C8—C13—C12	−176.20 (15)	C18—O2—C28—C29	−159.7 (3)
C11—C12—C13—C8	1.0 (3)	O2—C28—C29—C30	−119.0 (5)
C4—C3—C14—C15	173.76 (13)	C29'—C28—C29—C30	−22.0 (7)
C2—C3—C14—C15	−6.4 (2)	O2—C28—C29'—C30'	108.0 (7)
C3—C14—C15—C20	−29.2 (2)	C29—C28—C29'—C30'	16.1 (6)
C3—C14—C15—C16	156.02 (15)	C31'—O3—C31—C32	−11.6 (9)
C20—C15—C16—C17	0.4 (2)	C25—O3—C31—C32	−162.8 (2)
C14—C15—C16—C17	175.49 (14)	O3—C31—C32—C33	1.7 (4)
C15—C16—C17—C18	−1.6 (3)	C25—O3—C31'—C32'	155.8 (16)
C28—O2—C18—C19	−4.7 (3)	C31—O3—C31'—C32'	8(2)
C28—O2—C18—C17	173.51 (17)	O3—C31'—C32'—C33'	3(4)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N1	0.93	2.61	2.912 (2)	100
C14—H14···O1	0.93	2.33	2.7385 (18)	106
C21—H21···O1	0.93	2.34	2.7482 (19)	106
C9—H9···Cg4ⁱ	0.93	2.97	3.8089 (19)	151
C33—H33A···O3	0.93	2.41	2.726 (4)	100
C33—H33B···Cg2ⁱⁱ	0.93	2.86	3.771 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg4ⁱ	0.93	2.97	3.8089 (19)	151
C33—H33B⋯Cg2ⁱⁱ	0.93	2.86	3.771 (4)	165

Symmetry codes: (i) ; (ii) . Cg2 is the centroid of the C8–C13 ring and Cg4 is the centroid of the C22–C27 ring.

4 in total

1. (R)-3,5-Bis[(E)-benzylidene]-1-(1-phenylethyl)piperidin-4-one, 3,5-bis[(E)-4-chlorobenzylidene]-1-[(R)-1-phenylethyl]piperidin-4-one and 3,5-bis[(E)-2-chlorobenzylidene]-1-[(R)-1-phenylethyl]piperidin-4-one.

Authors: J Suresh; R Suresh Kumar; S Perumal; S Natarajan
Journal: Acta Crystallogr C Date: 2007-04-28 Impact factor: 1.172