1-Benzoyl-c-3,t-3-dimethyl-r-2,c-6-diphenyl­piperidin-4-one

Aravindhan, S.; Ponnuswamy, S.; Umamaheswari, J.; Ramesh, P.; Ponnuswamy, M.N.

doi:10.1107/S1600536809028037

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1975

doi:10.1107/S1600536809028037

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1-Benzoyl-c-3,t-3-dimethyl-r-2,c-6-diphenylpiperidin-4-one

S. Aravindhan,^a S. Ponnuswamy,^b J. Umamaheswari,^b P. Ramesh ^c and M. N. Ponnuswamy ^c ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 30 June 2009; accepted 16 July 2009; online 25 July 2009)

In the title compound, C₂₆H₂₅NO₂, the piperidine ring adopts a distorted boat conformation. The three phenyl rings form dihedral angles of 67.58 (8), 59.82 (8) and 86.41 (8)° with the best plane through the piperidine ring. The crystal packing is governed by intermolecular C—H⋯O interactions.

Related literature

For the biological activity of piperidine derivatives, see: Dimmock et al. (2001 ); Perumal et al. (2001 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₆H₂₅NO₂
M_r = 383.47
Monoclinic, P 2₁ /c
a = 10.8540 (9) Å
b = 17.8050 (17) Å
c = 10.8853 (10) Å
β = 94.987 (3)°
V = 2095.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.977, T_max = 0.985
27356 measured reflections
6189 independent reflections
3897 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.152
S = 0.98
6189 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.98	2.29	2.7346 (17)	106
C2—H2⋯O1ⁱ	0.98	2.56	3.3784 (17)	141
C20—H20A⋯O1ⁱ	0.96	2.47	3.1885 (19)	132
C20—H20B⋯O2ⁱⁱ	0.96	2.52	3.470 (2)	170
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: 10.1107/S1600536809028037/bt2990sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028037/bt2990Isup2.hkl

checkCIF report

Comment top

Piperidones are the important group of heterocyclic compounds in the field of medicinal chemistry due to their biological activities, including cytotoxic and anticancer properties (Dimmock et al., 2001). They were also reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activities (Perumal et al., 2001). In view of these importance and to ascertain the molecular conformation, crystallographic study of the title compound has been carried out.

The ORTEP diagram of the title compound is shown in Fig.1. The piperidine ring adopts distorted boat conformation. The puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) for this ring are q₂ = 0.636 (2) Å, q₃ = 0.104 (2) Å, π = 282.8 (1)° and Δs(C3) =Δs(C6)= 18.6 (1)°. The sum of the angles at N1 (359.7°) is in accrdance with sp² hybridization. The three phenyl rings are twisted away from the best plane of the pyridine ring by 67.58 (8)°, 59.82 (8)° and 86.41 (8)° respectively.

The crystal packing is controlled by C—H···O types of intra and intermolecular interactions in addition to van der Waals forces. Atom C2 at (x, y, z) donates a proton to O1 x, -y + 1/2, z + 1/2, which forms a C(5) (Bernstein, et al., 1995) zigzag chain running along c axis. The combination of C20—H20A···O1 and C20—H20B···O2 intermolecular interactions forms a dimer chain running along c axis shown in Fig. 2.

Related literature top

For the biological activity of piperidine derivatives, see: Dimmock et al. (2001); Perumal et al. (2001). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

A mixture of c-3,t-3-dimethyl-r-2,c-6-diphenylpiperidin-4-one (1.4 g, 5 mmol), benzoyl chloride (1.2 ml, 10 mmol) and triethylamine (2 ml, 14.4 mmol) in anhydrous benzene (20 ml) was stirred at room temperature for 7 h. The precipitated ammonium salt was washed with water (4x10ml). The resulting pasty mass was purified and crystallized from benzene and pet-ether (60–80°C) in the ratio of 95: 5.

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: SHELXL97 (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. Perspective view of the molecule showing displacement ellipsoids at 50% probability level. The H atoms are omitted for clarity.
	Fig. 2. The crystal packing viewed down a axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

1-Benzoyl-c-3,t-3-dimethyl-r-2,c-6- diphenylpiperidin-4-one top

Crystal data top

C₂₆H₂₅NO₂	F(000) = 816
M_r = 383.47	D_x = 1.215 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5746 reflections
a = 10.8540 (9) Å	θ = 1.9–30.4°
b = 17.8050 (17) Å	µ = 0.08 mm⁻¹
c = 10.8853 (10) Å	T = 293 K
β = 94.987 (3)°	Block, colorless
V = 2095.7 (3) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII area-detector diffractometer	6189 independent reflections
Radiation source: fine-focus sealed tube	3897 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω and ϕ scans	θ_max = 30.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→13
T_min = 0.977, T_max = 0.985	k = −25→25
27356 measured reflections	l = −15→15

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.0728P)² + 0.3353P] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.011
6189 reflections	Δρ_max = 0.24 e Å⁻³
265 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0078 (16)

Crystal data top

C₂₆H₂₅NO₂	V = 2095.7 (3) Å³
M_r = 383.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8540 (9) Å	µ = 0.08 mm⁻¹
b = 17.8050 (17) Å	T = 293 K
c = 10.8853 (10) Å	0.30 × 0.25 × 0.20 mm
β = 94.987 (3)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	6189 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3897 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.985	R_int = 0.038
27356 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 0.98	Δρ_max = 0.24 e Å⁻³
6189 reflections	Δρ_min = −0.17 e Å⁻³
265 parameters

Special details top

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 estimating e.s.d.'s 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 > 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.

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

	x	y	z	U_iso*/U_eq
O1	0.14493 (11)	0.19520 (7)	0.50443 (9)	0.0560 (3)
O2	0.41301 (12)	0.16165 (9)	1.02065 (10)	0.0722 (4)
N1	0.17515 (10)	0.16380 (6)	0.70591 (9)	0.0338 (2)
C2	0.12064 (12)	0.15019 (8)	0.82403 (11)	0.0361 (3)
H2	0.0881	0.1980	0.8520	0.043*
C3	0.21997 (14)	0.12271 (9)	0.92293 (12)	0.0466 (4)
H3A	0.1886	0.1294	1.0030	0.056*
H3B	0.2313	0.0692	0.9113	0.056*
C4	0.34508 (15)	0.15986 (10)	0.92630 (13)	0.0493 (4)
C5	0.38114 (14)	0.19299 (9)	0.80660 (13)	0.0446 (3)
C6	0.30890 (12)	0.15316 (7)	0.69712 (11)	0.0362 (3)
H6	0.3282	0.1809	0.6235	0.043*
C7	0.10627 (13)	0.19291 (8)	0.60735 (11)	0.0373 (3)
C8	−0.01836 (13)	0.22524 (8)	0.62390 (11)	0.0376 (3)
C9	−0.12156 (16)	0.19732 (9)	0.55574 (16)	0.0543 (4)
H9	−0.1149	0.1550	0.5067	0.065*
C10	−0.23461 (17)	0.23218 (11)	0.5604 (2)	0.0681 (5)
H10	−0.3040	0.2125	0.5155	0.082*
C11	−0.24602 (16)	0.29517 (10)	0.62980 (18)	0.0600 (4)
H11	−0.3223	0.3187	0.6312	0.072*
C12	−0.14437 (17)	0.32334 (10)	0.69727 (17)	0.0588 (4)
H12	−0.1516	0.3664	0.7445	0.071*
C13	−0.03124 (15)	0.28842 (9)	0.69574 (15)	0.0507 (4)
H13	0.0370	0.3075	0.7433	0.061*
C14	0.01468 (13)	0.09444 (8)	0.80976 (12)	0.0385 (3)
C15	0.01631 (15)	0.03311 (8)	0.73135 (15)	0.0485 (4)
H15	0.0832	0.0259	0.6848	0.058*
C16	−0.08083 (17)	−0.01740 (10)	0.72184 (18)	0.0608 (5)
H16	−0.0791	−0.0582	0.6688	0.073*
C17	−0.18017 (18)	−0.00735 (12)	0.7908 (2)	0.0699 (5)
H17	−0.2455	−0.0413	0.7844	0.084*
C18	−0.18221 (18)	0.05259 (13)	0.8683 (2)	0.0724 (6)
H18	−0.2490	0.0592	0.9152	0.087*
C19	−0.08585 (15)	0.10376 (10)	0.87796 (15)	0.0561 (4)
H19	−0.0888	0.1447	0.9307	0.067*
C20	0.34155 (16)	0.27631 (9)	0.80821 (15)	0.0539 (4)
H20A	0.2550	0.2794	0.8196	0.081*
H20B	0.3569	0.2995	0.7314	0.081*
H20C	0.3882	0.3018	0.8747	0.081*
C21	0.52053 (15)	0.19025 (12)	0.79462 (18)	0.0646 (5)
H21A	0.5634	0.2149	0.8642	0.097*
H21B	0.5386	0.2153	0.7202	0.097*
H21C	0.5470	0.1389	0.7920	0.097*
C22	0.34321 (13)	0.07146 (8)	0.67344 (13)	0.0397 (3)
C23	0.40686 (15)	0.02446 (10)	0.75922 (15)	0.0532 (4)
H23	0.4300	0.0424	0.8381	0.064*
C24	0.43630 (17)	−0.04821 (10)	0.72953 (19)	0.0638 (5)
H24	0.4789	−0.0787	0.7882	0.077*
C25	0.40313 (18)	−0.07557 (10)	0.6143 (2)	0.0700 (5)
H25	0.4234	−0.1246	0.5943	0.084*
C26	0.33977 (17)	−0.03070 (10)	0.52792 (18)	0.0627 (5)
H26	0.3162	−0.0495	0.4497	0.075*
C27	0.31101 (14)	0.04226 (9)	0.55720 (14)	0.0475 (4)
H27	0.2691	0.0724	0.4976	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0589 (7)	0.0747 (8)	0.0352 (5)	0.0155 (6)	0.0096 (5)	0.0121 (5)
O2	0.0575 (8)	0.1115 (11)	0.0444 (6)	−0.0127 (7)	−0.0138 (5)	−0.0013 (6)
N1	0.0348 (6)	0.0364 (6)	0.0304 (5)	−0.0024 (4)	0.0035 (4)	0.0021 (4)
C2	0.0398 (7)	0.0379 (7)	0.0308 (6)	−0.0046 (6)	0.0045 (5)	0.0026 (5)
C3	0.0469 (9)	0.0608 (9)	0.0314 (6)	−0.0062 (7)	−0.0002 (6)	0.0079 (6)
C4	0.0465 (9)	0.0623 (10)	0.0377 (7)	−0.0050 (7)	−0.0046 (6)	−0.0025 (6)
C5	0.0382 (8)	0.0535 (8)	0.0418 (7)	−0.0107 (6)	0.0023 (6)	−0.0053 (6)
C6	0.0346 (7)	0.0400 (7)	0.0342 (6)	−0.0031 (5)	0.0044 (5)	0.0009 (5)
C7	0.0424 (8)	0.0365 (7)	0.0329 (6)	−0.0008 (6)	0.0025 (5)	0.0033 (5)
C8	0.0400 (8)	0.0384 (7)	0.0341 (6)	0.0001 (6)	0.0012 (5)	0.0054 (5)
C9	0.0520 (10)	0.0482 (9)	0.0602 (9)	0.0012 (7)	−0.0090 (7)	−0.0065 (7)
C10	0.0455 (10)	0.0635 (11)	0.0914 (13)	−0.0029 (8)	−0.0171 (9)	−0.0044 (10)
C11	0.0421 (10)	0.0613 (11)	0.0772 (11)	0.0092 (8)	0.0096 (8)	0.0086 (9)
C12	0.0585 (11)	0.0559 (10)	0.0623 (10)	0.0107 (8)	0.0065 (8)	−0.0072 (8)
C13	0.0465 (9)	0.0514 (9)	0.0530 (8)	0.0019 (7)	−0.0029 (7)	−0.0096 (7)
C14	0.0380 (8)	0.0398 (7)	0.0372 (6)	−0.0028 (6)	−0.0002 (5)	0.0102 (5)
C15	0.0461 (9)	0.0402 (8)	0.0588 (9)	−0.0051 (6)	0.0020 (7)	0.0019 (6)
C16	0.0605 (11)	0.0441 (9)	0.0748 (11)	−0.0121 (8)	−0.0106 (9)	0.0065 (8)
C17	0.0543 (11)	0.0667 (12)	0.0860 (13)	−0.0249 (9)	−0.0094 (9)	0.0264 (10)
C18	0.0478 (11)	0.0892 (15)	0.0825 (13)	−0.0161 (10)	0.0185 (9)	0.0165 (11)
C19	0.0482 (10)	0.0659 (11)	0.0556 (9)	−0.0082 (8)	0.0125 (7)	0.0015 (8)
C20	0.0578 (10)	0.0517 (9)	0.0534 (9)	−0.0181 (8)	0.0115 (7)	−0.0115 (7)
C21	0.0408 (10)	0.0849 (13)	0.0679 (11)	−0.0175 (9)	0.0028 (8)	−0.0122 (9)
C22	0.0322 (7)	0.0419 (7)	0.0450 (7)	−0.0006 (6)	0.0034 (5)	0.0021 (6)
C23	0.0476 (9)	0.0557 (9)	0.0546 (9)	0.0042 (7)	−0.0047 (7)	0.0055 (7)
C24	0.0506 (10)	0.0528 (10)	0.0855 (13)	0.0092 (8)	−0.0085 (9)	0.0137 (9)
C25	0.0571 (12)	0.0432 (9)	0.1068 (15)	0.0095 (8)	−0.0094 (10)	−0.0086 (10)
C26	0.0609 (11)	0.0520 (10)	0.0728 (11)	0.0076 (8)	−0.0074 (9)	−0.0174 (8)
C27	0.0454 (9)	0.0468 (8)	0.0493 (8)	0.0055 (7)	−0.0021 (6)	−0.0041 (6)

Geometric parameters (Å, º) top

O1—C7	1.2307 (16)	C14—C19	1.382 (2)
O2—C4	1.2115 (17)	C14—C15	1.387 (2)
N1—C7	1.3561 (16)	C15—C16	1.383 (2)
N1—C6	1.4754 (17)	C15—H15	0.9300
N1—C2	1.4813 (15)	C16—C17	1.378 (3)
C2—C14	1.5170 (19)	C16—H16	0.9300
C2—C3	1.5359 (19)	C17—C18	1.362 (3)
C2—H2	0.9800	C17—H17	0.9300
C3—C4	1.508 (2)	C18—C19	1.384 (3)
C3—H3A	0.9700	C18—H18	0.9300
C3—H3B	0.9700	C19—H19	0.9300
C4—C5	1.513 (2)	C20—H20A	0.9600
C5—C21	1.531 (2)	C20—H20B	0.9600
C5—C6	1.5412 (19)	C20—H20C	0.9600
C5—C20	1.545 (2)	C21—H21A	0.9600
C6—C22	1.529 (2)	C21—H21B	0.9600
C6—H6	0.9800	C21—H21C	0.9600
C7—C8	1.495 (2)	C22—C27	1.384 (2)
C8—C9	1.381 (2)	C22—C23	1.392 (2)
C8—C13	1.384 (2)	C23—C24	1.378 (2)
C9—C10	1.380 (3)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.364 (3)
C10—C11	1.364 (3)	C24—H24	0.9300
C10—H10	0.9300	C25—C26	1.372 (3)
C11—C12	1.367 (3)	C25—H25	0.9300
C11—H11	0.9300	C26—C27	1.380 (2)
C12—C13	1.378 (2)	C26—H26	0.9300
C12—H12	0.9300	C27—H27	0.9300
C13—H13	0.9300

C7—N1—C6	118.40 (10)	C8—C13—H13	119.7
C7—N1—C2	120.99 (11)	C19—C14—C15	118.55 (14)
C6—N1—C2	120.31 (10)	C19—C14—C2	119.56 (13)
N1—C2—C14	112.00 (10)	C15—C14—C2	121.88 (13)
N1—C2—C3	110.59 (11)	C16—C15—C14	120.51 (16)
C14—C2—C3	110.06 (11)	C16—C15—H15	119.7
N1—C2—H2	108.0	C14—C15—H15	119.7
C14—C2—H2	108.0	C17—C16—C15	120.16 (18)
C3—C2—H2	108.0	C17—C16—H16	119.9
C4—C3—C2	116.94 (12)	C15—C16—H16	119.9
C4—C3—H3A	108.1	C18—C17—C16	119.66 (17)
C2—C3—H3A	108.1	C18—C17—H17	120.2
C4—C3—H3B	108.1	C16—C17—H17	120.2
C2—C3—H3B	108.1	C17—C18—C19	120.68 (18)
H3A—C3—H3B	107.3	C17—C18—H18	119.7
O2—C4—C3	120.83 (14)	C19—C18—H18	119.7
O2—C4—C5	122.41 (15)	C14—C19—C18	120.43 (17)
C3—C4—C5	116.74 (12)	C14—C19—H19	119.8
C4—C5—C21	113.12 (14)	C18—C19—H19	119.8
C4—C5—C6	109.53 (12)	C5—C20—H20A	109.5
C21—C5—C6	111.08 (12)	C5—C20—H20B	109.5
C4—C5—C20	105.76 (12)	H20A—C20—H20B	109.5
C21—C5—C20	108.03 (13)	C5—C20—H20C	109.5
C6—C5—C20	109.10 (12)	H20A—C20—H20C	109.5
N1—C6—C22	112.86 (11)	H20B—C20—H20C	109.5
N1—C6—C5	109.16 (10)	C5—C21—H21A	109.5
C22—C6—C5	116.95 (12)	C5—C21—H21B	109.5
N1—C6—H6	105.6	H21A—C21—H21B	109.5
C22—C6—H6	105.6	C5—C21—H21C	109.5
C5—C6—H6	105.6	H21A—C21—H21C	109.5
O1—C7—N1	121.65 (13)	H21B—C21—H21C	109.5
O1—C7—C8	118.71 (12)	C27—C22—C23	117.29 (14)
N1—C7—C8	119.61 (11)	C27—C22—C6	117.74 (12)
C9—C8—C13	118.61 (14)	C23—C22—C6	124.95 (13)
C9—C8—C7	119.78 (13)	C24—C23—C22	121.26 (16)
C13—C8—C7	121.19 (13)	C24—C23—H23	119.4
C10—C9—C8	120.05 (16)	C22—C23—H23	119.4
C10—C9—H9	120.0	C25—C24—C23	120.19 (16)
C8—C9—H9	120.0	C25—C24—H24	119.9
C11—C10—C9	120.93 (17)	C23—C24—H24	119.9
C11—C10—H10	119.5	C24—C25—C26	119.90 (17)
C9—C10—H10	119.5	C24—C25—H25	120.0
C10—C11—C12	119.45 (16)	C26—C25—H25	120.0
C10—C11—H11	120.3	C25—C26—C27	119.99 (17)
C12—C11—H11	120.3	C25—C26—H26	120.0
C11—C12—C13	120.44 (16)	C27—C26—H26	120.0
C11—C12—H12	119.8	C26—C27—C22	121.36 (15)
C13—C12—H12	119.8	C26—C27—H27	119.3
C12—C13—C8	120.50 (15)	C22—C27—H27	119.3
C12—C13—H13	119.7

C7—N1—C2—C14	61.05 (16)	C13—C8—C9—C10	−0.2 (2)
C6—N1—C2—C14	−125.24 (12)	C7—C8—C9—C10	−172.85 (15)
C7—N1—C2—C3	−175.79 (12)	C8—C9—C10—C11	1.3 (3)
C6—N1—C2—C3	−2.08 (16)	C9—C10—C11—C12	−1.1 (3)
N1—C2—C3—C4	40.28 (18)	C10—C11—C12—C13	−0.2 (3)
C14—C2—C3—C4	164.56 (13)	C11—C12—C13—C8	1.3 (3)
C2—C3—C4—O2	154.70 (16)	C9—C8—C13—C12	−1.1 (2)
C2—C3—C4—C5	−26.3 (2)	C7—C8—C13—C12	171.44 (14)
O2—C4—C5—C21	30.2 (2)	N1—C2—C14—C19	−144.35 (13)
C3—C4—C5—C21	−148.72 (15)	C3—C2—C14—C19	92.20 (16)
O2—C4—C5—C6	154.74 (16)	N1—C2—C14—C15	36.78 (18)
C3—C4—C5—C6	−24.22 (19)	C3—C2—C14—C15	−86.67 (15)
O2—C4—C5—C20	−87.8 (2)	C19—C14—C15—C16	0.1 (2)
C3—C4—C5—C20	93.23 (16)	C2—C14—C15—C16	178.96 (13)
C7—N1—C6—C22	−102.18 (13)	C14—C15—C16—C17	−0.3 (2)
C2—N1—C6—C22	83.95 (14)	C15—C16—C17—C18	0.0 (3)
C7—N1—C6—C5	125.98 (13)	C16—C17—C18—C19	0.4 (3)
C2—N1—C6—C5	−47.89 (15)	C15—C14—C19—C18	0.3 (2)
C4—C5—C6—N1	59.99 (15)	C2—C14—C19—C18	−178.58 (16)
C21—C5—C6—N1	−174.33 (13)	C17—C18—C19—C14	−0.6 (3)
C20—C5—C6—N1	−55.34 (14)	N1—C6—C22—C27	72.51 (15)
C4—C5—C6—C22	−69.65 (16)	C5—C6—C22—C27	−159.62 (13)
C21—C5—C6—C22	56.03 (17)	N1—C6—C22—C23	−108.93 (15)
C20—C5—C6—C22	175.02 (11)	C5—C6—C22—C23	18.9 (2)
C6—N1—C7—O1	16.05 (19)	C27—C22—C23—C24	−0.1 (2)
C2—N1—C7—O1	−170.12 (13)	C6—C22—C23—C24	−178.70 (15)
C6—N1—C7—C8	−162.10 (11)	C22—C23—C24—C25	0.0 (3)
C2—N1—C7—C8	11.73 (18)	C23—C24—C25—C26	−0.3 (3)
O1—C7—C8—C9	59.09 (19)	C24—C25—C26—C27	0.8 (3)
N1—C7—C8—C9	−122.69 (15)	C25—C26—C27—C22	−1.0 (3)
O1—C7—C8—C13	−113.39 (16)	C23—C22—C27—C26	0.6 (2)
N1—C7—C8—C13	64.83 (18)	C6—C22—C27—C26	179.29 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.98	2.29	2.7346 (17)	106
C2—H2···O1ⁱ	0.98	2.56	3.3784 (17)	141
C20—H20A···O1ⁱ	0.96	2.47	3.1885 (19)	132
C20—H20B···O2ⁱⁱ	0.96	2.52	3.470 (2)	170

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅NO₂
M_r	383.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.8540 (9), 17.8050 (17), 10.8853 (10)
β (°)	94.987 (3)
V (Å³)	2095.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.977, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	27356, 6189, 3897
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.713

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.152, 0.98
No. of reflections	6189
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.17

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
C6—H6···O1	0.98	2.29	2.7346 (17)	106.4
C2—H2···O1ⁱ	0.98	2.56	3.3784 (17)	140.5
C20—H20A···O1ⁱ	0.96	2.47	3.1885 (19)	131.6
C20—H20B···O2ⁱⁱ	0.96	2.52	3.470 (2)	169.9

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Acknowledgements

SA thanks Dr Babu Varghese, SAIF, IIT–Madras, India, for his help with the data collection.

References

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