3,3,5,5-Tetra­methyl-r-2,c-6-diphenyl­piperidin-4-one

Govindaraju, C.; Valliappan, R.; Sundari, V.

doi:10.1107/S1600536812018983

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2097

https://doi.org/10.1107/S1600536812018983

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3,3,5,5-Tetramethyl-r-2,c-6-diphenylpiperidin-4-one

C. Govindaraju,^a ^* R. Valliappan ^a and V. Sundari ^a

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India
^*Correspondence e-mail: chitragovi12@gmail.com

(Received 28 March 2012; accepted 27 April 2012; online 13 June 2012)

The piperidone ring of the title compound, C₂₁H₂₅NO, adopts a chair conformation with the two phenyl groups equatorially oriented and cis to each other. In the crystal, molecules are linked by weak N—H⋯O hydrogen bonds, forming chains parallel to [100].

Related literature

For some bioactive properties of piperidones, see: Mobio et al. (1989 ). For piperidone ring conformations in related compounds, see: Parthiban et al. (2008 ); Lakshminarayana et al. (2009 ); Ravichandran et al. (2010 ). For the synthesis, see: Noller & Baliah (1948 ). For ring puckering parameters, see: Nardelli (1983 ); Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₁H₂₅NO
M_r = 307.42
Triclinic, $[P \overline 1]$
a = 6.9227 (11) Å
b = 11.540 (2) Å
c = 12.472 (2) Å
α = 64.771 (4)°
β = 80.755 (5)°
γ = 72.675 (4)°
V = 859.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.919, T_max = 0.986
12752 measured reflections
2659 independent reflections
2123 reflections with I > 2σ(I)
R_int = 0.032
θ_max = 24.0°

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.152
S = 1.15
2659 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.94 (3)	2.39 (3)	3.258 (3)	153 (2)
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812018983/lr2058sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812018983/lr2058Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812018983/lr2058Isup3.cml

checkCIF report

Comment top

Aryl substituted piperidine-4-ones are important heterocyclic entities present in natural products like alkaloids.The piperidones exhibit diverse bioactivities such as bactericidal, fungicidal and herbicidal activities (Mobio et al., 1989).The six-membered ring of piperidones adopts, predominantly, a chair conformation (Parthiban et al., 2008) but many often the conformation depends on the substitution in the piperidone ring (Lakshminarayana et al., 2009; Ravichandran et al., 2010). The determination of the crystal structure of the title compound was mainly undertaken to evaluate the impact of four methyl groups at C2 and C4 carbon atoms. The ORTEP diagram of the title compound is shown in Fig. 1. In the title compound C₂₁H₂₅NO, the piperidone ring adopts a chair conformation with ring puckering parameters (Nardelli, 1983; Cremer & Pople, 1975) of Q=0.543 (2)°, θ = 155.55 (3)° and φ=136.72 (2)°. The two phenyl groups are equatorial oriented and cis to each other. The crystal packing is stabilized by a week N—H···O hydrogen bond [d(N—O)=3.257 (4) Å and angle N—H···O= 151.11 (2)°]. The N—H···O hydrogen bond connects the adjacent molecule into a head to tail fashion to generate a one dimensional chain extending parallel to the [1 0 0] direction.

Related literature top

For some bioactive properties of piperidones, see: Mobio et al. (1989). For piperidone ring conformations in related compounds, see: Parthiban et al. (2008); Lakshminarayana et al. (2009); Ravichandran et al. (2010). For the synthesis, see: Noller & Baliah (1948). For ring puckering parameters, see: Nardelli (1983); Cremer & Pople (1975).

Experimental top

The title compound was prepared by one pot synthesis from 3,4-dimethy-3-pentanone, benzaldehyde and ammonium acetate at 1:2:1 proportion in ethanol as solvent by adopting the literature procedure reported by (Noller & Baliah, 1948). Crystals suitable for single-crystal X-raydiffraction were grown by slow evaporation of a solution in benzene (m.p. 467–469 K).

Structure description top

For some bioactive properties of piperidones, see: Mobio et al. (1989). For piperidone ring conformations in related compounds, see: Parthiban et al. (2008); Lakshminarayana et al. (2009); Ravichandran et al. (2010). For the synthesis, see: Noller & Baliah (1948). For ring puckering parameters, see: Nardelli (1983); Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. Part of crystal structure showing the packing of the molecules in the unit cell and formation of N1—H1A···O1 hydrogen bond.

3,3,5,5-Tetramethyl-r-2,c-6-diphenylpiperidin-4-one top

Crystal data top

C₂₁H₂₅NO	Z = 2
M_r = 307.42	F(000) = 332
Triclinic, P1	D_x = 1.187 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9227 (11) Å	Cell parameters from 4779 reflections
b = 11.540 (2) Å	θ = 2.1–23.8°
c = 12.472 (2) Å	µ = 0.07 mm⁻¹
α = 64.771 (4)°	T = 295 K
β = 80.755 (5)°	Block, colourless
γ = 72.675 (4)°	0.30 × 0.25 × 0.20 mm
V = 859.8 (3) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2659 independent reflections
Radiation source: fine-focus sealed tube	2123 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and φ scan	θ_max = 24.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
T_min = 0.919, T_max = 0.986	k = −13→13
12752 measured reflections	l = −14→14

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.0562P)² + 0.4957P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
2659 reflections	Δρ_max = 0.23 e Å⁻³
217 parameters	Δρ_min = −0.18 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: 0.020 (4)

Crystal data top

C₂₁H₂₅NO	γ = 72.675 (4)°
M_r = 307.42	V = 859.8 (3) Å³
Triclinic, P1	Z = 2
a = 6.9227 (11) Å	Mo Kα radiation
b = 11.540 (2) Å	µ = 0.07 mm⁻¹
c = 12.472 (2) Å	T = 295 K
α = 64.771 (4)°	0.30 × 0.25 × 0.20 mm
β = 80.755 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2659 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2123 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.986	R_int = 0.032
12752 measured reflections	θ_max = 24.0°

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	Δρ_max = 0.23 e Å⁻³
2659 reflections	Δρ_min = −0.18 e Å⁻³
217 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
C1	0.7201 (4)	0.4000 (2)	0.1945 (2)	0.0372 (6)
H1	0.7165	0.4280	0.1087	0.045*
C2	0.9321 (4)	0.3963 (2)	0.2220 (2)	0.0407 (6)
C3	1.0898 (4)	0.2903 (2)	0.1901 (2)	0.0435 (6)
C4	1.0442 (4)	0.1603 (2)	0.2102 (2)	0.0446 (6)
C5	0.8169 (4)	0.1810 (2)	0.1951 (2)	0.0386 (6)
H5	0.7920	0.2263	0.1100	0.046*
C6	0.5498 (4)	0.4960 (2)	0.2302 (2)	0.0394 (6)
C7	0.4653 (4)	0.4602 (3)	0.3438 (2)	0.0496 (7)
H7	0.5133	0.3750	0.4003	0.059*
C8	0.3102 (5)	0.5492 (3)	0.3749 (3)	0.0633 (8)
H8	0.2544	0.5234	0.4518	0.076*
C9	0.2383 (5)	0.6751 (3)	0.2932 (3)	0.0657 (9)
H9	0.1351	0.7354	0.3144	0.079*
C10	0.3196 (5)	0.7116 (3)	0.1799 (3)	0.0641 (9)
H10	0.2705	0.7970	0.1239	0.077*
C11	0.4734 (4)	0.6232 (2)	0.1478 (3)	0.0514 (7)
H11	0.5265	0.6493	0.0703	0.062*
C12	0.7552 (4)	0.0522 (2)	0.2417 (2)	0.0408 (6)
C13	0.7551 (4)	−0.0084 (3)	0.1664 (3)	0.0533 (7)
H13	0.7920	0.0311	0.0866	0.064*
C14	0.7008 (5)	−0.1267 (3)	0.2086 (3)	0.0647 (9)
H14	0.7004	−0.1655	0.1568	0.078*
C15	0.6482 (5)	−0.1867 (3)	0.3250 (3)	0.0655 (9)
H15	0.6137	−0.2669	0.3532	0.079*
C16	0.6461 (4)	−0.1284 (3)	0.4009 (3)	0.0597 (8)
H16	0.6098	−0.1689	0.4807	0.072*
C17	0.6982 (4)	−0.0093 (2)	0.3588 (2)	0.0483 (7)
H17	0.6945	0.0300	0.4108	0.058*
C18	0.9507 (5)	0.3605 (3)	0.3540 (3)	0.0632 (8)
H18A	0.9024	0.2832	0.4010	0.095*
H18B	0.8713	0.4332	0.3736	0.095*
H18C	1.0900	0.3429	0.3700	0.095*
C19	0.9807 (4)	0.5297 (3)	0.1504 (3)	0.0569 (8)
H19A	1.1159	0.5236	0.1653	0.085*
H19B	0.8867	0.5960	0.1733	0.085*
H19C	0.9702	0.5535	0.0675	0.085*
C20	1.1125 (5)	0.0629 (3)	0.3352 (3)	0.0691 (9)
H20A	1.2464	0.0646	0.3447	0.104*
H20B	1.1131	−0.0249	0.3467	0.104*
H20C	1.0207	0.0879	0.3927	0.104*
C21	1.1721 (5)	0.1079 (3)	0.1211 (3)	0.0707 (10)
H21A	1.1335	0.1695	0.0422	0.106*
H21B	1.1507	0.0238	0.1359	0.106*
H21C	1.3126	0.0973	0.1293	0.106*
N1	0.6901 (3)	0.26610 (18)	0.25244 (18)	0.0388 (5)
O1	1.2574 (3)	0.30563 (19)	0.1531 (2)	0.0641 (6)
H1A	0.554 (4)	0.268 (2)	0.251 (2)	0.042 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0395 (14)	0.0324 (12)	0.0436 (14)	−0.0100 (10)	−0.0031 (10)	−0.0179 (11)
C2	0.0389 (14)	0.0400 (14)	0.0502 (15)	−0.0132 (11)	−0.0018 (11)	−0.0225 (12)
C3	0.0344 (15)	0.0428 (14)	0.0531 (15)	−0.0111 (11)	−0.0032 (11)	−0.0179 (12)
C4	0.0370 (15)	0.0330 (13)	0.0583 (16)	−0.0050 (10)	0.0008 (11)	−0.0169 (12)
C5	0.0393 (14)	0.0320 (12)	0.0441 (14)	−0.0047 (10)	−0.0036 (10)	−0.0171 (11)
C6	0.0391 (14)	0.0319 (13)	0.0546 (16)	−0.0104 (10)	−0.0028 (11)	−0.0230 (12)
C7	0.0482 (16)	0.0434 (15)	0.0598 (17)	−0.0111 (12)	0.0030 (13)	−0.0254 (13)
C8	0.0566 (19)	0.073 (2)	0.078 (2)	−0.0182 (16)	0.0122 (15)	−0.0510 (18)
C9	0.0520 (19)	0.0570 (19)	0.105 (3)	−0.0006 (14)	−0.0078 (17)	−0.055 (2)
C10	0.063 (2)	0.0361 (15)	0.094 (2)	0.0003 (13)	−0.0180 (18)	−0.0303 (16)
C11	0.0548 (17)	0.0365 (14)	0.0644 (18)	−0.0099 (12)	−0.0086 (13)	−0.0207 (13)
C12	0.0366 (14)	0.0295 (12)	0.0541 (16)	−0.0022 (10)	−0.0059 (11)	−0.0176 (11)
C13	0.0601 (19)	0.0417 (15)	0.0627 (18)	−0.0091 (13)	−0.0059 (14)	−0.0266 (14)
C14	0.070 (2)	0.0442 (17)	0.093 (2)	−0.0083 (14)	−0.0144 (18)	−0.0399 (17)
C15	0.0576 (19)	0.0381 (16)	0.102 (3)	−0.0130 (13)	−0.0099 (17)	−0.0264 (17)
C16	0.0537 (19)	0.0442 (16)	0.073 (2)	−0.0170 (13)	−0.0043 (14)	−0.0122 (15)
C17	0.0473 (16)	0.0415 (14)	0.0591 (17)	−0.0146 (12)	−0.0013 (12)	−0.0211 (13)
C18	0.0543 (19)	0.086 (2)	0.0630 (19)	−0.0170 (16)	−0.0097 (14)	−0.0406 (17)
C19	0.0506 (18)	0.0462 (16)	0.085 (2)	−0.0197 (13)	0.0024 (14)	−0.0335 (15)
C20	0.0489 (18)	0.0526 (18)	0.084 (2)	−0.0073 (14)	−0.0257 (16)	−0.0032 (16)
C21	0.0541 (19)	0.0559 (18)	0.108 (3)	−0.0136 (14)	0.0245 (17)	−0.0487 (18)
N1	0.0331 (12)	0.0320 (11)	0.0558 (13)	−0.0103 (8)	0.0015 (9)	−0.0217 (9)
O1	0.0380 (12)	0.0621 (13)	0.0986 (16)	−0.0187 (9)	0.0098 (10)	−0.0387 (12)

Geometric parameters (Å, º) top

C1—N1	1.464 (3)	C11—H11	0.9300
C1—C6	1.513 (3)	C12—C17	1.375 (4)
C1—C2	1.545 (3)	C12—C13	1.390 (4)
C1—H1	0.9800	C13—C14	1.383 (4)
C2—C19	1.523 (3)	C13—H13	0.9300
C2—C3	1.525 (3)	C14—C15	1.359 (5)
C2—C18	1.534 (4)	C14—H14	0.9300
C3—O1	1.213 (3)	C15—C16	1.372 (4)
C3—C4	1.532 (3)	C15—H15	0.9300
C4—C21	1.523 (4)	C16—C17	1.383 (4)
C4—C20	1.531 (4)	C16—H16	0.9300
C4—C5	1.550 (3)	C17—H17	0.9300
C5—N1	1.460 (3)	C18—H18A	0.9600
C5—C12	1.514 (3)	C18—H18B	0.9600
C5—H5	0.9800	C18—H18C	0.9600
C6—C7	1.378 (4)	C19—H19A	0.9600
C6—C11	1.385 (3)	C19—H19B	0.9600
C7—C8	1.381 (4)	C19—H19C	0.9600
C7—H7	0.9300	C20—H20A	0.9600
C8—C9	1.367 (4)	C20—H20B	0.9600
C8—H8	0.9300	C20—H20C	0.9600
C9—C10	1.367 (5)	C21—H21A	0.9600
C9—H9	0.9300	C21—H21B	0.9600
C10—C11	1.378 (4)	C21—H21C	0.9600
C10—H10	0.9300	N1—H1A	0.94 (3)

N1—C1—C6	110.46 (19)	C17—C12—C13	117.6 (2)
N1—C1—C2	109.22 (19)	C17—C12—C5	121.9 (2)
C6—C1—C2	113.51 (18)	C13—C12—C5	120.5 (2)
N1—C1—H1	107.8	C14—C13—C12	120.9 (3)
C6—C1—H1	107.8	C14—C13—H13	119.6
C2—C1—H1	107.8	C12—C13—H13	119.6
C19—C2—C3	109.0 (2)	C15—C14—C13	120.5 (3)
C19—C2—C18	108.4 (2)	C15—C14—H14	119.8
C3—C2—C18	107.4 (2)	C13—C14—H14	119.8
C19—C2—C1	110.9 (2)	C14—C15—C16	119.7 (3)
C3—C2—C1	108.89 (19)	C14—C15—H15	120.2
C18—C2—C1	112.2 (2)	C16—C15—H15	120.2
O1—C3—C2	119.9 (2)	C15—C16—C17	120.0 (3)
O1—C3—C4	118.9 (2)	C15—C16—H16	120.0
C2—C3—C4	121.1 (2)	C17—C16—H16	120.0
C21—C4—C20	108.7 (2)	C12—C17—C16	121.4 (3)
C21—C4—C3	108.7 (2)	C12—C17—H17	119.3
C20—C4—C3	106.0 (2)	C16—C17—H17	119.3
C21—C4—C5	109.6 (2)	C2—C18—H18A	109.5
C20—C4—C5	112.4 (2)	C2—C18—H18B	109.5
C3—C4—C5	111.33 (19)	H18A—C18—H18B	109.5
N1—C5—C12	109.7 (2)	C2—C18—H18C	109.5
N1—C5—C4	110.6 (2)	H18A—C18—H18C	109.5
C12—C5—C4	113.06 (19)	H18B—C18—H18C	109.5
N1—C5—H5	107.7	C2—C19—H19A	109.5
C12—C5—H5	107.7	C2—C19—H19B	109.5
C4—C5—H5	107.7	H19A—C19—H19B	109.5
C7—C6—C11	118.1 (2)	C2—C19—H19C	109.5
C7—C6—C1	121.7 (2)	H19A—C19—H19C	109.5
C11—C6—C1	120.2 (2)	H19B—C19—H19C	109.5
C6—C7—C8	120.9 (3)	C4—C20—H20A	109.5
C6—C7—H7	119.5	C4—C20—H20B	109.5
C8—C7—H7	119.5	H20A—C20—H20B	109.5
C9—C8—C7	120.3 (3)	C4—C20—H20C	109.5
C9—C8—H8	119.8	H20A—C20—H20C	109.5
C7—C8—H8	119.8	H20B—C20—H20C	109.5
C8—C9—C10	119.4 (3)	C4—C21—H21A	109.5
C8—C9—H9	120.3	C4—C21—H21B	109.5
C10—C9—H9	120.3	H21A—C21—H21B	109.5
C9—C10—C11	120.7 (3)	C4—C21—H21C	109.5
C9—C10—H10	119.6	H21A—C21—H21C	109.5
C11—C10—H10	119.6	H21B—C21—H21C	109.5
C10—C11—C6	120.5 (3)	C5—N1—C1	111.10 (19)
C10—C11—H11	119.7	C5—N1—H1A	109.0 (15)
C6—C11—H11	119.7	C1—N1—H1A	111.2 (15)

N1—C1—C2—C19	172.5 (2)	N1—C1—C6—C11	−141.9 (2)
C6—C1—C2—C19	−63.7 (3)	C2—C1—C6—C11	95.1 (3)
N1—C1—C2—C3	52.6 (3)	C11—C6—C7—C8	−0.6 (4)
C6—C1—C2—C3	176.3 (2)	C1—C6—C7—C8	179.8 (2)
N1—C1—C2—C18	−66.1 (3)	C6—C7—C8—C9	−0.3 (4)
C6—C1—C2—C18	57.6 (3)	C7—C8—C9—C10	0.8 (5)
C19—C2—C3—O1	25.8 (3)	C8—C9—C10—C11	−0.4 (5)
C18—C2—C3—O1	−91.4 (3)	C9—C10—C11—C6	−0.5 (4)
C1—C2—C3—O1	146.9 (2)	C7—C6—C11—C10	1.0 (4)
C19—C2—C3—C4	−157.6 (2)	C1—C6—C11—C10	−179.4 (2)
C18—C2—C3—C4	85.2 (3)	N1—C5—C12—C17	−37.9 (3)
C1—C2—C3—C4	−36.5 (3)	C4—C5—C12—C17	86.1 (3)
O1—C3—C4—C21	−30.6 (3)	N1—C5—C12—C13	142.3 (2)
C2—C3—C4—C21	152.7 (2)	C4—C5—C12—C13	−93.7 (3)
O1—C3—C4—C20	86.0 (3)	C17—C12—C13—C14	−0.4 (4)
C2—C3—C4—C20	−90.6 (3)	C5—C12—C13—C14	179.4 (2)
O1—C3—C4—C5	−151.4 (2)	C12—C13—C14—C15	−0.6 (4)
C2—C3—C4—C5	31.9 (3)	C13—C14—C15—C16	0.9 (5)
C21—C4—C5—N1	−163.2 (2)	C14—C15—C16—C17	−0.2 (4)
C20—C4—C5—N1	75.8 (3)	C13—C12—C17—C16	1.2 (4)
C3—C4—C5—N1	−42.9 (3)	C5—C12—C17—C16	−178.6 (2)
C21—C4—C5—C12	73.3 (3)	C15—C16—C17—C12	−0.9 (4)
C20—C4—C5—C12	−47.7 (3)	C12—C5—N1—C1	−169.68 (19)
C3—C4—C5—C12	−166.4 (2)	C4—C5—N1—C1	64.9 (2)
N1—C1—C6—C7	37.7 (3)	C6—C1—N1—C5	163.89 (19)
C2—C1—C6—C7	−85.3 (3)	C2—C1—N1—C5	−70.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.94 (3)	2.39 (3)	3.258 (3)	153 (2)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₅NO
M_r	307.42
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.9227 (11), 11.540 (2), 12.472 (2)
α, β, γ (°)	64.771 (4), 80.755 (5), 72.675 (4)
V (Å³)	859.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.919, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	12752, 2659, 2123
R_int	0.032
θ_max (°)	24.0
(sin θ/λ)_max (Å⁻¹)	0.572

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.152, 1.15
No. of reflections	2659
No. of parameters	217
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.94 (3)	2.39 (3)	3.258 (3)	153 (2)

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors thank the SAIF, IIT Madras, for the X- ray data collection.

References

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