c-3,t-3-Dimethyl-4-oxo-r-2,c-6-diphenyl­piperidine-1-carboxamide

Thenmozhi, M.; Kavitha, T.; Ponnuswamy, S.; Jamesh, M.; Ponnuswamy, M.N.

doi:10.1107/S1600536809041579

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2808

https://doi.org/10.1107/S1600536809041579

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c-3,t-3-Dimethyl-4-oxo-r-2,c-6-diphenylpiperidine-1-carboxamide

M. Thenmozhi,^a T. Kavitha,^a S. Ponnuswamy,^b M. Jamesh ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 12 September 2009; accepted 12 October 2009; online 23 October 2009)

In the title compound, C₂₆H₂₆N₂O₂, the piperidinone ring adopts a distorted boat conformation. The two phenyl rings substituted at positions 2 and 6 of the piperidinone ring occupy axial and equatorial orientations, which are approximately perpendicular to each other [89.14 (8)°]. The phenylcarbamoyl group adopts an extended conformation. The crystal structure is stabilized by intermolecular C—H⋯O interactions.

Related literature

For general background to the pharmaceutical activity of piperidine derivatives, see: Mobio et al. (1989 ); Palani et al. (2002 ). For hybridization, see: Beddoes et al. (1986 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₆H₂₆N₂O₂
M_r = 398.49
Triclinic, $[P \overline 1]$
a = 9.6648 (2) Å
b = 10.7938 (3) Å
c = 11.4233 (3) Å
α = 101.303 (2)°
β = 90.158 (1)°
γ = 113.191 (1)°
V = 1069.91 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.12 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.991, T_max = 0.992
26776 measured reflections
6362 independent reflections
4483 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.129
S = 1.03
6362 reflections
278 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.93	2.56	3.4488 (17)	161
C20—H20B⋯O1ⁱⁱ	0.96	2.52	3.4520 (17)	162
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809041579/bt5059sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041579/bt5059Isup2.hkl

checkCIF report

Comment top

Several 2,6-disubstituted piperidine derivatives have fungicidal, herbicidal and bactericidal properties. Both the natural and synthetic piperidine derivatives exhibit high pharmaceutical values (Mobio et al., 1989). Piperidines have a favourable pharmacokinetic profile in rodents and primates, excellent oral bioavailability, and potent antiviral activity against a wide range of primary HIV-1 isolates and considered as promising new candidate for the treatment of HIV-1 infection (Palani et al., 2002).

The ORTEP plot of the molecule is shown in Fig. 1. The piperidine ring adopts distorted boat conformation, with the puckering amplitudes q2 = 0.5877 (13)°, q3 =-0.1100 (13)°, φ = 258.06 (12)° (Cremer & Pople, 1975) and asymmetry parameters Δ_s(C2)=Δ_s(C5) = 18.55 (12)° (Nardelli, 1983). The planar phenyl rings substituted at positions 2 and 6 occupy axial [70.71 (13)°] and equatorial [-162.73 (11)°] orientations and are approximately perpendicular to each other [89.14 (8)°]. One of the methyl groups attached at position 3 of the piperidine ring occupy equatorial [N1-C2-C3-C20 = 177.95 (10)°] orientation and other one is in axial [N1-C2-C3-C21 = 58.31 (12)°] orientation. The sum of the bond angles around N1[358.2 (3)°] indicates sp² hybridization (Beddoes et al., 1986).

The phenylcarbamoyl group attached to the N1 atom adopts an extended conformation which is evidenced from the torsion angle [N1-C7-N2-C8=]169.19 (11)°. The crystal structure is stabilized by C-H···O type of intermolecular interactions in addition to van der Waals forces. The C20-H20B···O1 interaction between the molecules lead to the dimer arrangement along the bc plane. These dimers are interconnected by C18-H18···O2 hydrogen bonds, which form a one dimensional chain running along a - axis (Fig. 2).

Related literature top

For general background to the pharmaceutical activity of piperidine derivatives, see: Mobio et al. (1989); Palani et al. (2002). For hybridization, see: Beddoes et al. (1986). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

A mixture of c-3,t-3-dimethyl-r-2,c-6-diphenylpiperidin-4-one (1.4g), phenylisocyanate (1.1ml) and triethylamine (2ml) in anhydrous benzene (20ml) was stirred at room temperature for 7 hours. The precipitated ammonium salt was washed with water (40ml). The resulting pasty mass was purified by crystallization from benzene and pet-ether (60-80°C) in the ratio of 95 : 5.

Structure description top

For general background to the pharmaceutical activity of piperidine derivatives, see: Mobio et al. (1989); Palani et al. (2002). For hybridization, see: Beddoes et al. (1986). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The ORTEP plot of the molecule with 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the molecules viewed along a - axis.

c-3,t-3-Dimethyl-4-oxo-r-2,c-6- diphenylpiperidine-1-carboxamide top

Crystal data top

C₂₆H₂₆N₂O₂	Z = 2
M_r = 398.49	F(000) = 424
Triclinic, P1	D_x = 1.237 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6648 (2) Å	Cell parameters from 6362 reflections
b = 10.7938 (3) Å	θ = 2.1–30.3°
c = 11.4233 (3) Å	µ = 0.08 mm⁻¹
α = 101.303 (2)°	T = 293 K
β = 90.158 (1)°	Block, colourless
γ = 113.191 (1)°	0.12 × 0.12 × 0.10 mm
V = 1069.91 (5) Å³

Data collection top

Bruker Kappa APEXII area-detector diffractometer	6362 independent reflections
Radiation source: fine-focus sealed tube	4483 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and φ scans	θ_max = 30.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −13→13
T_min = 0.991, T_max = 0.992	k = −15→15
26776 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0562P)² + 0.1478P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.010
6362 reflections	Δρ_max = 0.23 e Å⁻³
278 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (3)

Crystal data top

C₂₆H₂₆N₂O₂	γ = 113.191 (1)°
M_r = 398.49	V = 1069.91 (5) Å³
Triclinic, P1	Z = 2
a = 9.6648 (2) Å	Mo Kα radiation
b = 10.7938 (3) Å	µ = 0.08 mm⁻¹
c = 11.4233 (3) Å	T = 293 K
α = 101.303 (2)°	0.12 × 0.12 × 0.10 mm
β = 90.158 (1)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	6362 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	4483 reflections with I > 2σ(I)
T_min = 0.991, T_max = 0.992	R_int = 0.027
26776 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.23 e Å⁻³
6362 reflections	Δρ_min = −0.16 e Å⁻³
278 parameters

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.

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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C2	0.44729 (12)	0.65312 (11)	0.17958 (10)	0.0397 (2)
H2	0.4661	0.5889	0.1148	0.048*
C3	0.27465 (12)	0.60768 (12)	0.17189 (11)	0.0464 (3)
C4	0.23264 (13)	0.71273 (13)	0.25470 (11)	0.0482 (3)
C5	0.34974 (13)	0.85807 (13)	0.28686 (12)	0.0486 (3)
H5A	0.3981	0.8718	0.3656	0.058*
H5B	0.2979	0.9197	0.2936	0.058*
C6	0.47423 (12)	0.90306 (11)	0.20204 (10)	0.0414 (2)
H6	0.4324	0.9268	0.1356	0.050*
C7	0.60634 (12)	0.79834 (11)	0.05299 (10)	0.0397 (2)
C8	0.78032 (12)	0.96713 (11)	−0.05439 (10)	0.0404 (2)
C9	0.77964 (15)	0.88317 (13)	−0.16236 (11)	0.0503 (3)
H9	0.7057	0.7938	−0.1843	0.060*
C10	0.89077 (17)	0.93379 (15)	−0.23770 (13)	0.0628 (4)
H10	0.8916	0.8770	−0.3101	0.075*
C11	0.99929 (16)	1.06556 (15)	−0.20790 (14)	0.0628 (4)
H11	1.0729	1.0980	−0.2596	0.075*
C12	0.99842 (15)	1.14898 (14)	−0.10158 (14)	0.0582 (3)
H12	1.0711	1.2390	−0.0812	0.070*
C13	0.89053 (14)	1.10043 (12)	−0.02441 (11)	0.0485 (3)
H13	0.8916	1.1575	0.0484	0.058*
C14	0.52831 (12)	0.64977 (11)	0.29232 (10)	0.0419 (2)
C15	0.48157 (15)	0.66344 (14)	0.40654 (12)	0.0550 (3)
H15	0.3888	0.6690	0.4183	0.066*
C16	0.5715 (2)	0.66892 (17)	0.50407 (14)	0.0684 (4)
H16	0.5387	0.6785	0.5805	0.082*
C17	0.70797 (18)	0.66035 (16)	0.48857 (15)	0.0683 (4)
H17	0.7680	0.6646	0.5543	0.082*
C18	0.75602 (15)	0.64543 (15)	0.37601 (15)	0.0630 (4)
H18	0.8486	0.6392	0.3651	0.076*
C19	0.66678 (13)	0.63960 (13)	0.27891 (13)	0.0510 (3)
H19	0.6999	0.6286	0.2027	0.061*
C20	0.19496 (16)	0.46380 (14)	0.19745 (15)	0.0632 (4)
H20A	0.2215	0.4659	0.2791	0.095*
H20B	0.2257	0.4003	0.1447	0.095*
H20C	0.0876	0.4347	0.1847	0.095*
C21	0.22210 (16)	0.60584 (16)	0.04407 (13)	0.0628 (4)
H21A	0.1147	0.5793	0.0374	0.094*
H21B	0.2470	0.5409	−0.0124	0.094*
H21C	0.2718	0.6962	0.0275	0.094*
C22	0.60341 (13)	1.03354 (12)	0.26859 (11)	0.0474 (3)
C23	0.70016 (15)	1.02965 (15)	0.35611 (12)	0.0587 (3)
H23	0.6878	0.9455	0.3737	0.070*
C24	0.81482 (18)	1.1497 (2)	0.41752 (16)	0.0796 (5)
H24	0.8786	1.1460	0.4766	0.095*
C25	0.8349 (2)	1.27372 (19)	0.3918 (2)	0.0935 (6)
H25	0.9122	1.3543	0.4334	0.112*
C26	0.7412 (2)	1.27938 (16)	0.3048 (2)	0.0903 (6)
H26	0.7558	1.3639	0.2870	0.108*
C27	0.62430 (18)	1.15950 (14)	0.24296 (15)	0.0664 (4)
H27	0.5603	1.1640	0.1845	0.080*
N1	0.52148 (10)	0.79071 (9)	0.15014 (8)	0.0386 (2)
N2	0.67000 (12)	0.92692 (11)	0.02715 (9)	0.0469 (2)
O1	0.62406 (11)	0.69939 (9)	−0.00520 (8)	0.0565 (2)
O2	0.11166 (10)	0.68212 (11)	0.29595 (10)	0.0686 (3)
H2A	0.6752 (17)	0.9942 (16)	0.0847 (14)	0.061 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0345 (5)	0.0362 (5)	0.0476 (6)	0.0130 (4)	0.0116 (4)	0.0097 (4)
C3	0.0332 (5)	0.0434 (6)	0.0576 (7)	0.0109 (4)	0.0071 (5)	0.0091 (5)
C4	0.0336 (5)	0.0558 (7)	0.0562 (7)	0.0185 (5)	0.0092 (5)	0.0132 (5)
C5	0.0407 (6)	0.0486 (6)	0.0588 (7)	0.0219 (5)	0.0163 (5)	0.0078 (5)
C6	0.0381 (5)	0.0406 (5)	0.0475 (6)	0.0186 (4)	0.0088 (4)	0.0081 (4)
C7	0.0360 (5)	0.0403 (5)	0.0425 (5)	0.0149 (4)	0.0079 (4)	0.0090 (4)
C8	0.0395 (5)	0.0421 (6)	0.0443 (6)	0.0190 (5)	0.0088 (4)	0.0145 (4)
C9	0.0519 (7)	0.0447 (6)	0.0498 (6)	0.0154 (5)	0.0129 (5)	0.0084 (5)
C10	0.0709 (9)	0.0624 (8)	0.0555 (8)	0.0271 (7)	0.0264 (7)	0.0123 (6)
C11	0.0537 (8)	0.0642 (9)	0.0750 (9)	0.0229 (7)	0.0297 (7)	0.0265 (7)
C12	0.0436 (7)	0.0491 (7)	0.0772 (9)	0.0112 (5)	0.0121 (6)	0.0187 (6)
C13	0.0466 (6)	0.0443 (6)	0.0531 (7)	0.0171 (5)	0.0063 (5)	0.0099 (5)
C14	0.0374 (5)	0.0363 (5)	0.0525 (6)	0.0135 (4)	0.0101 (5)	0.0134 (4)
C15	0.0532 (7)	0.0634 (8)	0.0559 (7)	0.0281 (6)	0.0154 (6)	0.0192 (6)
C16	0.0810 (10)	0.0730 (10)	0.0530 (8)	0.0312 (8)	0.0074 (7)	0.0168 (7)
C17	0.0655 (9)	0.0618 (9)	0.0740 (10)	0.0196 (7)	−0.0122 (7)	0.0197 (7)
C18	0.0425 (7)	0.0569 (8)	0.0917 (11)	0.0185 (6)	0.0011 (7)	0.0237 (7)
C19	0.0410 (6)	0.0506 (7)	0.0660 (8)	0.0195 (5)	0.0136 (5)	0.0199 (6)
C20	0.0460 (7)	0.0478 (7)	0.0863 (10)	0.0084 (6)	0.0184 (7)	0.0154 (7)
C21	0.0466 (7)	0.0664 (9)	0.0634 (8)	0.0150 (6)	−0.0062 (6)	0.0037 (7)
C22	0.0423 (6)	0.0429 (6)	0.0523 (6)	0.0161 (5)	0.0160 (5)	0.0012 (5)
C23	0.0482 (7)	0.0603 (8)	0.0567 (7)	0.0163 (6)	0.0078 (6)	0.0002 (6)
C24	0.0541 (8)	0.0866 (10)	0.0687 (10)	0.0134 (8)	0.0045 (7)	−0.0170 (8)
C25	0.0692 (11)	0.0643 (9)	0.1014 (14)	0.0008 (8)	0.0184 (10)	−0.0282 (8)
C26	0.0941 (13)	0.0401 (8)	0.1177 (16)	0.0155 (8)	0.0353 (12)	−0.0011 (8)
C27	0.0710 (9)	0.0430 (7)	0.0821 (10)	0.0227 (6)	0.0206 (8)	0.0062 (6)
N1	0.0362 (4)	0.0361 (4)	0.0446 (5)	0.0151 (4)	0.0113 (4)	0.0094 (4)
N2	0.0549 (6)	0.0398 (5)	0.0472 (5)	0.0194 (4)	0.0190 (4)	0.0108 (4)
O1	0.0640 (6)	0.0426 (5)	0.0640 (5)	0.0224 (4)	0.0311 (4)	0.0117 (4)
O2	0.0388 (5)	0.0738 (7)	0.0890 (7)	0.0197 (4)	0.0237 (5)	0.0137 (5)

Geometric parameters (Å, º) top

C2—N1	1.4802 (13)	C14—C15	1.3816 (17)
C2—C14	1.5193 (16)	C14—C19	1.3917 (16)
C2—C3	1.5395 (15)	C15—C16	1.389 (2)
C2—H2	0.9800	C15—H15	0.9300
C3—C4	1.5132 (17)	C16—C17	1.368 (2)
C3—C20	1.5256 (18)	C16—H16	0.9300
C3—C21	1.5384 (19)	C17—C18	1.370 (2)
C4—O2	1.2075 (14)	C17—H17	0.9300
C4—C5	1.5001 (17)	C18—C19	1.379 (2)
C5—C6	1.5339 (15)	C18—H18	0.9300
C5—H5A	0.9700	C19—H19	0.9300
C5—H5B	0.9700	C20—H20A	0.9600
C6—N1	1.4786 (13)	C20—H20B	0.9600
C6—C22	1.5201 (16)	C20—H20C	0.9600
C6—H6	0.9800	C21—H21A	0.9600
C7—O1	1.2159 (13)	C21—H21B	0.9600
C7—N2	1.3715 (15)	C21—H21C	0.9600
C7—N1	1.3779 (13)	C22—C27	1.3839 (19)
C8—C9	1.3783 (16)	C22—C23	1.385 (2)
C8—C13	1.3856 (16)	C23—C24	1.381 (2)
C8—N2	1.4115 (14)	C23—H23	0.9300
C9—C10	1.3856 (17)	C24—C25	1.366 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.368 (2)	C25—C26	1.369 (3)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.365 (2)	C26—C27	1.392 (2)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.3765 (18)	C27—H27	0.9300
C12—H12	0.9300	N2—H2A	0.864 (16)
C13—H13	0.9300

N1—C2—C14	109.54 (9)	C14—C15—C16	120.74 (13)
N1—C2—C3	110.26 (9)	C14—C15—H15	119.6
C14—C2—C3	119.32 (9)	C16—C15—H15	119.6
N1—C2—H2	105.6	C17—C16—C15	120.48 (14)
C14—C2—H2	105.6	C17—C16—H16	119.8
C3—C2—H2	105.6	C15—C16—H16	119.8
C4—C3—C20	111.63 (10)	C16—C17—C18	119.82 (14)
C4—C3—C21	106.12 (11)	C16—C17—H17	120.1
C20—C3—C21	109.08 (11)	C18—C17—H17	120.1
C4—C3—C2	110.60 (9)	C17—C18—C19	119.84 (13)
C20—C3—C2	111.34 (10)	C17—C18—H18	120.1
C21—C3—C2	107.87 (10)	C19—C18—H18	120.1
O2—C4—C5	120.53 (11)	C18—C19—C14	121.52 (13)
O2—C4—C3	122.26 (11)	C18—C19—H19	119.2
C5—C4—C3	117.19 (9)	C14—C19—H19	119.2
C4—C5—C6	117.78 (10)	C3—C20—H20A	109.5
C4—C5—H5A	107.9	C3—C20—H20B	109.5
C6—C5—H5A	107.9	H20A—C20—H20B	109.5
C4—C5—H5B	107.9	C3—C20—H20C	109.5
C6—C5—H5B	107.9	H20A—C20—H20C	109.5
H5A—C5—H5B	107.2	H20B—C20—H20C	109.5
N1—C6—C22	113.61 (9)	C3—C21—H21A	109.5
N1—C6—C5	112.05 (9)	C3—C21—H21B	109.5
C22—C6—C5	108.49 (9)	H21A—C21—H21B	109.5
N1—C6—H6	107.5	C3—C21—H21C	109.5
C22—C6—H6	107.5	H21A—C21—H21C	109.5
C5—C6—H6	107.5	H21B—C21—H21C	109.5
O1—C7—N2	122.47 (10)	C27—C22—C23	118.93 (13)
O1—C7—N1	122.90 (10)	C27—C22—C6	119.72 (13)
N2—C7—N1	114.63 (9)	C23—C22—C6	121.35 (12)
C9—C8—C13	119.39 (10)	C24—C23—C22	120.53 (16)
C9—C8—N2	123.48 (10)	C24—C23—H23	119.7
C13—C8—N2	117.08 (10)	C22—C23—H23	119.7
C8—C9—C10	119.03 (12)	C25—C24—C23	120.28 (19)
C8—C9—H9	120.5	C25—C24—H24	119.9
C10—C9—H9	120.5	C23—C24—H24	119.9
C11—C10—C9	121.42 (13)	C24—C25—C26	119.99 (16)
C11—C10—H10	119.3	C24—C25—H25	120.0
C9—C10—H10	119.3	C26—C25—H25	120.0
C12—C11—C10	119.36 (12)	C25—C26—C27	120.40 (18)
C12—C11—H11	120.3	C25—C26—H26	119.8
C10—C11—H11	120.3	C27—C26—H26	119.8
C11—C12—C13	120.31 (12)	C22—C27—C26	119.87 (18)
C11—C12—H12	119.8	C22—C27—H27	120.1
C13—C12—H12	119.8	C26—C27—H27	120.1
C12—C13—C8	120.47 (12)	C7—N1—C6	121.29 (9)
C12—C13—H13	119.8	C7—N1—C2	116.56 (8)
C8—C13—H13	119.8	C6—N1—C2	120.31 (8)
C15—C14—C19	117.59 (12)	C7—N2—C8	125.58 (9)
C15—C14—C2	126.22 (10)	C7—N2—H2A	115.1 (10)
C19—C14—C2	116.09 (10)	C8—N2—H2A	113.3 (10)

N1—C2—C3—C4	−57.33 (13)	C16—C17—C18—C19	0.2 (2)
C14—C2—C3—C4	70.71 (13)	C17—C18—C19—C14	0.6 (2)
N1—C2—C3—C20	177.95 (10)	C15—C14—C19—C18	−1.17 (18)
C14—C2—C3—C20	−54.01 (14)	C2—C14—C19—C18	175.36 (11)
N1—C2—C3—C21	58.31 (12)	N1—C6—C22—C27	129.49 (12)
C14—C2—C3—C21	−173.65 (10)	C5—C6—C22—C27	−105.18 (13)
C20—C3—C4—O2	−29.31 (18)	N1—C6—C22—C23	−51.43 (14)
C21—C3—C4—O2	89.41 (15)	C5—C6—C22—C23	73.89 (13)
C2—C3—C4—O2	−153.86 (13)	C27—C22—C23—C24	0.55 (19)
C20—C3—C4—C5	149.20 (12)	C6—C22—C23—C24	−178.53 (12)
C21—C3—C4—C5	−92.08 (13)	C22—C23—C24—C25	−0.6 (2)
C2—C3—C4—C5	24.65 (15)	C23—C24—C25—C26	0.0 (3)
O2—C4—C5—C6	−158.95 (12)	C24—C25—C26—C27	0.7 (3)
C3—C4—C5—C6	22.51 (17)	C23—C22—C27—C26	0.1 (2)
C4—C5—C6—N1	−36.49 (15)	C6—C22—C27—C26	179.15 (13)
C4—C5—C6—C22	−162.73 (11)	C25—C26—C27—C22	−0.7 (2)
C13—C8—C9—C10	0.85 (19)	O1—C7—N1—C6	−166.29 (11)
N2—C8—C9—C10	178.19 (12)	N2—C7—N1—C6	13.92 (15)
C8—C9—C10—C11	−1.0 (2)	O1—C7—N1—C2	−1.72 (16)
C9—C10—C11—C12	0.1 (2)	N2—C7—N1—C2	178.49 (10)
C10—C11—C12—C13	0.8 (2)	C22—C6—N1—C7	−71.04 (14)
C11—C12—C13—C8	−0.9 (2)	C5—C6—N1—C7	165.56 (10)
C9—C8—C13—C12	0.09 (19)	C22—C6—N1—C2	124.96 (11)
N2—C8—C13—C12	−177.42 (12)	C5—C6—N1—C2	1.56 (14)
N1—C2—C14—C15	100.75 (13)	C14—C2—N1—C7	107.12 (10)
C3—C2—C14—C15	−27.62 (17)	C3—C2—N1—C7	−119.65 (10)
N1—C2—C14—C19	−75.44 (12)	C14—C2—N1—C6	−88.14 (11)
C3—C2—C14—C19	156.19 (10)	C3—C2—N1—C6	45.08 (13)
C19—C14—C15—C16	1.00 (19)	O1—C7—N2—C8	−10.60 (19)
C2—C14—C15—C16	−175.14 (12)	N1—C7—N2—C8	169.19 (11)
C14—C15—C16—C17	−0.2 (2)	C9—C8—N2—C7	39.03 (18)
C15—C16—C17—C18	−0.4 (2)	C13—C8—N2—C7	−143.58 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.56	3.4488 (17)	161
C20—H20B···O1ⁱⁱ	0.96	2.52	3.4520 (17)	162

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆N₂O₂
M_r	398.49
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.6648 (2), 10.7938 (3), 11.4233 (3)
α, β, γ (°)	101.303 (2), 90.158 (1), 113.191 (1)
V (Å³)	1069.91 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.12 × 0.12 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.991, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	26776, 6362, 4483
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.709

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.129, 1.03
No. of reflections	6362
No. of parameters	278
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.56	3.4488 (17)	161.2
C20—H20B···O1ⁱⁱ	0.96	2.52	3.4520 (17)	162.4

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z.

Acknowledgements

MT thanks Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection. SP thanks the UGC, India, for financial support.

References

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