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

Aravindhan, S.; Ponnuswamy, S.; Jamesh, M.; Ramesh, P.; Ponnuswamy, M.N.

doi:10.1107/S1600536809028049

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1974

doi:10.1107/S1600536809028049

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

S. Aravindhan,^a S. Ponnuswamy,^b M. Jamesh,^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, C₂₁H₂₃NO₂, the piperidine ring adopts a distorted boat conformation. The two phenyl rings form dihedral angles of 64.6 (1) and 87.8 (1)° 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: Ponnuswamy et al. (2002 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₁H₂₃NO₂
M_r = 321.40
Monoclinic, P 2₁
a = 7.5622 (4) Å
b = 10.6369 (5) Å
c = 11.1497 (7) Å
β = 100.373 (3)°
V = 882.21 (8) Å³
Z = 2
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
12819 measured reflections
3457 independent reflections
2400 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.145
S = 1.02
3457 reflections
220 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 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
C8—H8A⋯O2ⁱ	0.96	2.53	3.442 (3)	159
C14—H14⋯O1ⁱⁱ	0.93	2.39	3.124 (3)	135
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (ii) x-1, y, 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: 10.1107/S1600536809028049/bt2989sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028049/bt2989Isup2.hkl

checkCIF report

Comment top

The design and synthesis of conformationally anchored molecules are important due its potency and selectivity for designing drugs. The piperidin-4-ones are one such class of compounds to be investigated to understand the stereodynamics and other structural features (Ponnuswamy et al., 2002). 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 a distorted boat conformation. The puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) for this ring are q₂ = 0.592 (2) Å, q₃ = 0.116 (2) Å, π = 284.8 (2)° and Δs(C3) =Δs(C6)= 15.2 (2)°. The sum of the angles at N1 (359.03°) is in accrdance with sp² hybridization. The two phenyl rings are twisted away from the best plane of the pyridine ring by 64.6 (1)° and 87.8 (1)°, respectively.

The crystal packing is controlled by C—H···O types of intra and intermolecular interactions in addition to van der Waals forces. Atom C8 at (x, y, z) donates a proton to O2 (1 - x,1/2 + y,-z), which forms a C(8) (Bernstein, et al., 1995) zigzag chain running along b axis shown in Fig. 2.

Related literature top

For the biological activity of piperidine derivatives, see: Ponnuswamy et al. (2002). 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), acetyl chloride (0.7 ml, 10 mmol) and triethylamine (2 ml, 14.4 mmol) in anhydrous benzene (50 ml) was stirred at room temparature for 7 h. The precipitated ammonium salt was filtered off and the filtrate 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 with displacement ellipsoids at the 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-Acetyl-c-3,t-3-dimethyl-r-2,c-6- diphenylpiperidin-4-one top

Crystal data top

C₂₁H₂₃NO₂	F(000) = 344
M_r = 321.40	D_x = 1.210 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3546 reflections
a = 7.5622 (4) Å	θ = 1.9–34.8°
b = 10.6369 (5) Å	µ = 0.08 mm⁻¹
c = 11.1497 (7) Å	T = 293 K
β = 100.373 (3)°	Block, colorless
V = 882.21 (8) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Bruker Kappa APEXII area-detector diffractometer	3457 independent reflections
Radiation source: fine-focus sealed tube	2400 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω and ϕ scans	θ_max = 34.8°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
T_min = 0.977, T_max = 0.985	k = −17→11
12819 measured reflections	l = −16→16

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0853P)²] where P = (F_o² + 2F_c²)/3
3457 reflections	(Δ/σ)_max = 0.012
220 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₁H₂₃NO₂	V = 882.21 (8) Å³
M_r = 321.40	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.5622 (4) Å	µ = 0.08 mm⁻¹
b = 10.6369 (5) Å	T = 293 K
c = 11.1497 (7) Å	0.30 × 0.25 × 0.20 mm
β = 100.373 (3)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	3457 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2400 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.985	R_int = 0.042
12819 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.145	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
3457 reflections	Δρ_min = −0.17 e Å⁻³
220 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	1.0626 (2)	0.57532 (19)	0.23859 (18)	0.0680 (5)
O2	0.4399 (3)	0.3113 (2)	−0.07440 (15)	0.0763 (5)
N1	0.7953 (2)	0.47573 (14)	0.20329 (14)	0.0393 (3)
C2	0.6053 (2)	0.47297 (17)	0.21592 (15)	0.0392 (3)
H2	0.5538	0.5559	0.1928	0.047*
C3	0.4980 (3)	0.3754 (2)	0.13125 (18)	0.0493 (4)
H3A	0.5087	0.2952	0.1735	0.059*
H3B	0.3722	0.3993	0.1187	0.059*
C4	0.5484 (3)	0.3556 (2)	0.00799 (18)	0.0507 (5)
C5	0.7355 (3)	0.3903 (2)	−0.00532 (17)	0.0492 (4)
C6	0.8617 (3)	0.38858 (19)	0.11952 (16)	0.0414 (4)
H6	0.9759	0.4240	0.1055	0.050*
C7	0.9060 (3)	0.57188 (19)	0.25158 (18)	0.0464 (4)
C8	0.8306 (4)	0.6735 (2)	0.3207 (2)	0.0600 (5)
H8A	0.7347	0.7155	0.2675	0.090*
H8B	0.9234	0.7330	0.3509	0.090*
H8C	0.7852	0.6371	0.3879	0.090*
C9	0.5778 (2)	0.44554 (17)	0.34515 (16)	0.0406 (4)
C10	0.6819 (3)	0.3583 (2)	0.41885 (18)	0.0508 (4)
H10	0.7759	0.3178	0.3912	0.061*
C11	0.6462 (4)	0.3315 (2)	0.5329 (2)	0.0606 (6)
H11	0.7158	0.2726	0.5819	0.073*
C12	0.5085 (4)	0.3913 (3)	0.5744 (2)	0.0670 (7)
H12	0.4851	0.3732	0.6517	0.080*
C13	0.4058 (4)	0.4773 (3)	0.5026 (3)	0.0726 (7)
H13	0.3123	0.5175	0.5310	0.087*
C14	0.4399 (3)	0.5051 (2)	0.3878 (2)	0.0571 (5)
H14	0.3696	0.5641	0.3393	0.069*
C15	0.7232 (4)	0.5268 (2)	−0.0542 (2)	0.0616 (6)
H15A	0.6699	0.5795	−0.0005	0.092*
H15B	0.6505	0.5286	−0.1341	0.092*
H15C	0.8416	0.5571	−0.0581	0.092*
C16	0.8096 (4)	0.3069 (3)	−0.0963 (2)	0.0699 (7)
H16A	0.7373	0.3168	−0.1758	0.105*
H16B	0.8067	0.2206	−0.0714	0.105*
H16C	0.9313	0.3308	−0.0988	0.105*
C17	0.9083 (2)	0.26144 (18)	0.17969 (16)	0.0417 (4)
C18	0.8065 (3)	0.1533 (2)	0.1580 (2)	0.0525 (5)
H18	0.7036	0.1538	0.0981	0.063*
C19	0.8543 (4)	0.0441 (2)	0.2235 (2)	0.0634 (6)
H19	0.7835	−0.0276	0.2077	0.076*
C20	1.0062 (4)	0.0418 (2)	0.3117 (2)	0.0654 (6)
H20	1.0375	−0.0309	0.3570	0.079*
C21	1.1104 (3)	0.1459 (3)	0.3327 (2)	0.0600 (6)
H21	1.2149	0.1434	0.3912	0.072*
C22	1.0634 (3)	0.2562 (2)	0.26817 (18)	0.0500 (4)
H22	1.1360	0.3270	0.2842	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0472 (8)	0.0620 (10)	0.0923 (12)	−0.0134 (8)	0.0056 (8)	0.0097 (9)
O2	0.0845 (12)	0.0894 (13)	0.0451 (9)	−0.0115 (11)	−0.0149 (8)	−0.0095 (9)
N1	0.0402 (7)	0.0397 (7)	0.0373 (7)	−0.0037 (6)	0.0051 (6)	0.0018 (6)
C2	0.0390 (8)	0.0421 (8)	0.0349 (8)	−0.0003 (7)	0.0023 (6)	0.0005 (6)
C3	0.0429 (9)	0.0589 (12)	0.0433 (10)	−0.0061 (8)	−0.0001 (7)	−0.0048 (8)
C4	0.0613 (12)	0.0512 (10)	0.0343 (9)	0.0020 (9)	−0.0058 (8)	0.0008 (7)
C5	0.0658 (12)	0.0487 (10)	0.0327 (8)	0.0094 (9)	0.0081 (8)	0.0039 (7)
C6	0.0429 (8)	0.0453 (9)	0.0368 (8)	0.0025 (7)	0.0093 (7)	0.0054 (7)
C7	0.0499 (10)	0.0398 (9)	0.0456 (9)	−0.0071 (8)	−0.0018 (8)	0.0104 (7)
C8	0.0766 (14)	0.0449 (11)	0.0548 (12)	−0.0111 (10)	0.0022 (10)	−0.0039 (9)
C9	0.0403 (8)	0.0428 (9)	0.0387 (8)	−0.0052 (7)	0.0069 (7)	−0.0029 (7)
C10	0.0585 (11)	0.0520 (10)	0.0434 (10)	0.0020 (9)	0.0134 (8)	0.0051 (8)
C11	0.0724 (14)	0.0623 (13)	0.0475 (11)	−0.0077 (11)	0.0120 (10)	0.0099 (10)
C12	0.0712 (14)	0.0869 (17)	0.0465 (11)	−0.0237 (13)	0.0207 (11)	−0.0022 (11)
C13	0.0619 (13)	0.0986 (19)	0.0638 (15)	−0.0010 (15)	0.0287 (12)	−0.0103 (14)
C14	0.0493 (10)	0.0683 (14)	0.0547 (12)	0.0055 (10)	0.0118 (9)	−0.0031 (10)
C15	0.0848 (16)	0.0563 (12)	0.0443 (11)	0.0116 (11)	0.0129 (11)	0.0159 (9)
C16	0.0966 (19)	0.0713 (14)	0.0444 (12)	0.0180 (14)	0.0198 (12)	−0.0011 (11)
C17	0.0436 (9)	0.0458 (9)	0.0364 (8)	0.0071 (8)	0.0093 (7)	0.0044 (7)
C18	0.0543 (11)	0.0496 (10)	0.0504 (11)	0.0035 (9)	0.0011 (9)	0.0042 (8)
C19	0.0725 (14)	0.0477 (12)	0.0696 (15)	0.0031 (11)	0.0117 (12)	0.0106 (10)
C20	0.0843 (16)	0.0561 (13)	0.0573 (13)	0.0203 (12)	0.0163 (12)	0.0162 (10)
C21	0.0579 (12)	0.0752 (15)	0.0446 (11)	0.0216 (11)	0.0027 (9)	0.0064 (10)
C22	0.0463 (10)	0.0573 (11)	0.0460 (10)	0.0080 (9)	0.0068 (8)	0.0006 (9)

Geometric parameters (Å, º) top

O1—C7	1.219 (3)	C11—C12	1.370 (4)
O2—C4	1.211 (3)	C11—H11	0.9300
N1—C7	1.369 (2)	C12—C13	1.362 (4)
N1—C6	1.467 (2)	C12—H12	0.9300
N1—C2	1.469 (2)	C13—C14	1.383 (4)
C2—C9	1.521 (2)	C13—H13	0.9300
C2—C3	1.534 (3)	C14—H14	0.9300
C2—H2	0.9800	C15—H15A	0.9600
C3—C4	1.506 (3)	C15—H15B	0.9600
C3—H3A	0.9700	C15—H15C	0.9600
C3—H3B	0.9700	C16—H16A	0.9600
C4—C5	1.495 (3)	C16—H16B	0.9600
C5—C16	1.528 (3)	C16—H16C	0.9600
C5—C6	1.540 (3)	C17—C18	1.381 (3)
C5—C15	1.548 (3)	C17—C22	1.391 (3)
C6—C17	1.523 (3)	C18—C19	1.385 (3)
C6—H6	0.9800	C18—H18	0.9300
C7—C8	1.499 (3)	C19—C20	1.371 (4)
C8—H8A	0.9600	C19—H19	0.9300
C8—H8B	0.9600	C20—C21	1.355 (4)
C8—H8C	0.9600	C20—H20	0.9300
C9—C14	1.376 (3)	C21—C22	1.389 (3)
C9—C10	1.387 (3)	C21—H21	0.9300
C10—C11	1.376 (3)	C22—H22	0.9300
C10—H10	0.9300

C7—N1—C6	117.82 (15)	C9—C10—H10	120.0
C7—N1—C2	121.12 (15)	C12—C11—C10	120.3 (2)
C6—N1—C2	120.09 (15)	C12—C11—H11	119.9
N1—C2—C9	113.43 (14)	C10—C11—H11	119.9
N1—C2—C3	111.90 (14)	C13—C12—C11	120.0 (2)
C9—C2—C3	107.80 (15)	C13—C12—H12	120.0
N1—C2—H2	107.8	C11—C12—H12	120.0
C9—C2—H2	107.8	C12—C13—C14	120.4 (2)
C3—C2—H2	107.8	C12—C13—H13	119.8
C4—C3—C2	117.60 (17)	C14—C13—H13	119.8
C4—C3—H3A	107.9	C9—C14—C13	120.0 (2)
C2—C3—H3A	107.9	C9—C14—H14	120.0
C4—C3—H3B	107.9	C13—C14—H14	120.0
C2—C3—H3B	107.9	C5—C15—H15A	109.5
H3A—C3—H3B	107.2	C5—C15—H15B	109.5
O2—C4—C5	123.0 (2)	H15A—C15—H15B	109.5
O2—C4—C3	119.9 (2)	C5—C15—H15C	109.5
C5—C4—C3	117.11 (17)	H15A—C15—H15C	109.5
C4—C5—C16	112.9 (2)	H15B—C15—H15C	109.5
C4—C5—C6	110.54 (15)	C5—C16—H16A	109.5
C16—C5—C6	110.58 (18)	C5—C16—H16B	109.5
C4—C5—C15	105.60 (19)	H16A—C16—H16B	109.5
C16—C5—C15	108.50 (18)	C5—C16—H16C	109.5
C6—C5—C15	108.51 (18)	H16A—C16—H16C	109.5
N1—C6—C17	111.05 (14)	H16B—C16—H16C	109.5
N1—C6—C5	109.90 (15)	C18—C17—C22	117.57 (18)
C17—C6—C5	117.75 (17)	C18—C17—C6	125.84 (17)
N1—C6—H6	105.7	C22—C17—C6	116.52 (18)
C17—C6—H6	105.7	C17—C18—C19	121.5 (2)
C5—C6—H6	105.7	C17—C18—H18	119.3
O1—C7—N1	120.9 (2)	C19—C18—H18	119.3
O1—C7—C8	120.5 (2)	C20—C19—C18	119.9 (2)
N1—C7—C8	118.58 (18)	C20—C19—H19	120.1
C7—C8—H8A	109.5	C18—C19—H19	120.1
C7—C8—H8B	109.5	C21—C20—C19	119.7 (2)
H8A—C8—H8B	109.5	C21—C20—H20	120.1
C7—C8—H8C	109.5	C19—C20—H20	120.1
H8A—C8—H8C	109.5	C20—C21—C22	121.0 (2)
H8B—C8—H8C	109.5	C20—C21—H21	119.5
C14—C9—C10	119.22 (17)	C22—C21—H21	119.5
C14—C9—C2	118.71 (18)	C21—C22—C17	120.4 (2)
C10—C9—C2	122.00 (16)	C21—C22—H22	119.8
C11—C10—C9	120.1 (2)	C17—C22—H22	119.8
C11—C10—H10	120.0

C7—N1—C2—C9	−70.9 (2)	C6—N1—C7—C8	170.20 (17)
C6—N1—C2—C9	120.55 (17)	C2—N1—C7—C8	1.4 (3)
C7—N1—C2—C3	166.82 (16)	N1—C2—C9—C14	143.64 (19)
C6—N1—C2—C3	−1.7 (2)	C3—C2—C9—C14	−91.9 (2)
N1—C2—C3—C4	−35.4 (2)	N1—C2—C9—C10	−39.4 (2)
C9—C2—C3—C4	−160.78 (17)	C3—C2—C9—C10	85.1 (2)
C2—C3—C4—O2	−157.6 (2)	C14—C9—C10—C11	0.4 (3)
C2—C3—C4—C5	23.6 (3)	C2—C9—C10—C11	−176.5 (2)
O2—C4—C5—C16	−31.1 (3)	C9—C10—C11—C12	−0.4 (4)
C3—C4—C5—C16	147.7 (2)	C10—C11—C12—C13	0.3 (4)
O2—C4—C5—C6	−155.5 (2)	C11—C12—C13—C14	−0.2 (4)
C3—C4—C5—C6	23.3 (3)	C10—C9—C14—C13	−0.3 (3)
O2—C4—C5—C15	87.3 (3)	C2—C9—C14—C13	176.7 (2)
C3—C4—C5—C15	−93.9 (2)	C12—C13—C14—C9	0.2 (4)
C7—N1—C6—C17	107.34 (18)	N1—C6—C17—C18	104.0 (2)
C2—N1—C6—C17	−83.8 (2)	C5—C6—C17—C18	−23.9 (3)
C7—N1—C6—C5	−120.60 (18)	N1—C6—C17—C22	−73.0 (2)
C2—N1—C6—C5	48.3 (2)	C5—C6—C17—C22	159.13 (16)
C4—C5—C6—N1	−58.1 (2)	C22—C17—C18—C19	1.4 (3)
C16—C5—C6—N1	176.13 (18)	C6—C17—C18—C19	−175.6 (2)
C15—C5—C6—N1	57.2 (2)	C17—C18—C19—C20	−0.3 (4)
C4—C5—C6—C17	70.3 (2)	C18—C19—C20—C21	−1.2 (4)
C16—C5—C6—C17	−55.4 (2)	C19—C20—C21—C22	1.6 (4)
C15—C5—C6—C17	−174.30 (17)	C20—C21—C22—C17	−0.5 (3)
C6—N1—C7—O1	−9.6 (3)	C18—C17—C22—C21	−1.0 (3)
C2—N1—C7—O1	−178.35 (18)	C6—C17—C22—C21	176.26 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.98	2.21	2.700 (3)	110
C8—H8A···O2ⁱ	0.96	2.53	3.442 (3)	159
C14—H14···O1ⁱⁱ	0.93	2.39	3.124 (3)	135

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃NO₂
M_r	321.40
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	7.5622 (4), 10.6369 (5), 11.1497 (7)
β (°)	100.373 (3)
V (Å³)	882.21 (8)
Z	2
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	12819, 3457, 2400
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.803

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.145, 1.02
No. of reflections	3457
No. of parameters	220
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −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	2.21	2.700 (3)	109.7
C8—H8A···O2ⁱ	0.96	2.53	3.442 (3)	159.0
C14—H14···O1ⁱⁱ	0.93	2.39	3.124 (3)	135.3

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

Acknowledgements

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

References

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