1-Benzoyl-3-methyl-2,6-diphenyl-4-piperidone

Nithya, P.; Hathwar, V.R.; Kone, S.; Malathi, N.; Khan, F.N.

doi:10.1107/S1600536809023848

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1692-o1693

doi:10.1107/S1600536809023848

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1-Benzoyl-3-methyl-2,6-diphenyl-4-piperidone

P. Nithya,^a Venkatesha R. Hathwar,^b Sriramakrishnaswamy Kone,^a N. Malathi ^a and F. Nawaz Khan ^a ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, and ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
^*Correspondence e-mail: nawaz_f@yahoo.co.in

(Received 18 June 2009; accepted 22 June 2009; online 27 June 2009)

In the title moleclue, C₂₅H₂₃NO₂, the 4-piperidone ring adopts a boat conformation. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond. In the crystal, molecules are connected through weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background, see: Grishina et al. (1994 ); Nalanishi et al. (1974 ); Perumal et al. (2001 ); Ponnuswamy et al. (2002 ). For related structures, see: Gayathri et al. (2008 ); Nithya et al. (2009 ). For details of the synthesis, see: Noller & Baliah (1948 ).

Experimental

Crystal data

C₂₅H₂₃NO₂
M_r = 369.44
Monoclinic, P 2₁ /n
a = 11.7602 (6) Å
b = 9.2404 (3) Å
c = 19.1722 (9) Å
β = 98.797 (4)°
V = 2058.93 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 K
0.36 × 0.24 × 0.18 mm

Data collection

Oxford Xcalibur Eos(Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Tarnton, England.]$ ) T_min = 0.942, T_max = 0.987
22931 measured reflections
3831 independent reflections
2515 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.105
S = 1.00
3831 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.98	2.26	2.7235 (17)	108
C9—H9A⋯O1ⁱ	0.97	2.56	3.4446 (19)	152
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Tarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Tarnton, England.]$ ); 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: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023848/bt2975sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023848/bt2975Isup2.hkl

checkCIF report

Comment top

4-piperidones and their derivatives present potential medical applications (Grishina et al., 1994, Ponnuswamy et al., 2002, Nalanishi et al., 1974). Piperidones are also reported to possess analgesic,anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activity (Perumal et al., 2001). In continouus of our interest in piperidones (Nithya et al., 2009), the crystal structure of title compound is discussed in this paper.

In the title molecule, C₂₅H₂₃NO₂ (Fig. 1), the piperidine ring adopts a boat conformation. In the related crystal structure, the piperidine ring also adopts a chair conformation (Gayathri et al., 2008) but the three substituents on the C atoms of the ring are in axial orientations. In the crystal, the molecules are connected through weak intermolecular C—H···O hydrogen bonds. (Fig. 2).

Related literature top

For general background, see: Grishina et al. (1994); Nalanishi et al. (1974); Perumal et al. (2001); Ponnuswamy et al. (2002). For a related structure, see: Gayathri et al. (2008); (Nithya et al. 2009). For details of the synthesis, see: Noller & Baliah (1948).

Experimental top

To a well stirred solution of 3 methyl-2,6-bis(phenyl)piperidin-4-one (1 equiv.) and triethylamine (1 equiv.) in freshly distilled benzene, benzoyl chloride (1 equiv.) in benzene was added dropwise. Stirring was continued until the completion of reaction. Later, it was poured into water and extracted with DCM, washed well with sodium bicarbonate solution and dried over anhydrous sodium sulfate. This upon evaporation and subsequent recrystallization in distilled ethanol furnished the diffraction-quality crystals of the title compound.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: WinGX (Farrugia, 1997).

Figures top

	Fig. 1. ORTEP diagram of the title compound with 50% probability displacement ellipsoids. Dotted bond indicates the intramolecular C—H···O hydrogen bond.
	Fig. 2. Crystal packing diagram of the title compound. The dotted lines indicate intermolecular C—H···O hydrogen bonds.

1-Benzoyl-3-methyl-2,6-diphenyl-4-piperidone top

Crystal data top

C₂₅H₂₃NO₂	F(000) = 784
M_r = 369.44	D_x = 1.192 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 983 reflections
a = 11.7602 (6) Å	θ = 2.0–21.3°
b = 9.2404 (3) Å	µ = 0.08 mm⁻¹
c = 19.1722 (9) Å	T = 290 K
β = 98.797 (4)°	Block, colorless
V = 2058.93 (16) Å³	0.36 × 0.24 × 0.18 mm
Z = 4

Data collection top

Oxford Xcalibur Eos(Nova) CCD detector diffractometer	3831 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2515 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 25.5°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→14
T_min = 0.942, T_max = 0.987	k = −11→11
22931 measured reflections	l = −23→23

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0536P)²] where P = (F_o² + 2F_c²)/3
3831 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₅H₂₃NO₂	V = 2058.93 (16) Å³
M_r = 369.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.7602 (6) Å	µ = 0.08 mm⁻¹
b = 9.2404 (3) Å	T = 290 K
c = 19.1722 (9) Å	0.36 × 0.24 × 0.18 mm
β = 98.797 (4)°

Data collection top

Oxford Xcalibur Eos(Nova) CCD detector diffractometer	3831 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2515 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.987	R_int = 0.044
22931 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.00	Δρ_max = 0.12 e Å⁻³
3831 reflections	Δρ_min = −0.15 e Å⁻³
254 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
N1	0.84703 (9)	0.33889 (11)	0.02444 (6)	0.0410 (3)
O1	0.85789 (10)	0.57741 (11)	−0.00176 (6)	0.0660 (3)
O2	1.02467 (10)	0.01000 (12)	0.12851 (6)	0.0696 (4)
C1	0.89524 (13)	0.34406 (15)	−0.13261 (8)	0.0502 (4)
H1	0.9616	0.3060	−0.1064	0.060*
C2	0.87411 (16)	0.32413 (18)	−0.20472 (9)	0.0660 (5)
H2	0.9268	0.2739	−0.2271	0.079*
C3	0.77585 (19)	0.3780 (2)	−0.24350 (10)	0.0777 (6)
H3	0.7610	0.3623	−0.2920	0.093*
C4	0.69948 (17)	0.4549 (2)	−0.21091 (11)	0.0813 (6)
H4	0.6327	0.4913	−0.2373	0.098*
C5	0.72094 (15)	0.47875 (17)	−0.13942 (10)	0.0644 (5)
H5	0.6701	0.5342	−0.1179	0.077*
C6	0.81811 (12)	0.42043 (14)	−0.09919 (8)	0.0444 (4)
C7	0.84216 (12)	0.45127 (15)	−0.02206 (8)	0.0458 (4)
C8	0.89332 (12)	0.36834 (15)	0.09936 (7)	0.0446 (4)
H8	0.9286	0.4645	0.1003	0.053*
C9	0.99148 (12)	0.26268 (15)	0.12180 (8)	0.0509 (4)
H9A	1.0553	0.2873	0.0974	0.061*
H9B	1.0175	0.2739	0.1720	0.061*
C10	0.95985 (13)	0.10771 (16)	0.10705 (8)	0.0460 (4)
C11	0.84348 (12)	0.07997 (14)	0.06341 (7)	0.0423 (4)
H11	0.7854	0.0968	0.0941	0.051*
C12	0.81844 (11)	0.18755 (14)	0.00098 (7)	0.0397 (3)
H12	0.8685	0.1616	−0.0335	0.048*
C13	0.69509 (12)	0.17244 (14)	−0.03516 (8)	0.0437 (4)
C14	0.60407 (14)	0.21590 (17)	−0.00264 (9)	0.0575 (4)
H14	0.6182	0.2590	0.0417	0.069*
C15	0.49176 (15)	0.1960 (2)	−0.03526 (11)	0.0741 (5)
H15	0.4312	0.2270	−0.0130	0.089*
C16	0.46924 (17)	0.1311 (2)	−0.09994 (12)	0.0814 (6)
H16	0.3937	0.1163	−0.1213	0.098*
C17	0.55856 (18)	0.0882 (2)	−0.13305 (10)	0.0820 (6)
H17	0.5437	0.0454	−0.1774	0.098*
C18	0.67089 (15)	0.10815 (17)	−0.10088 (9)	0.0627 (5)
H18	0.7310	0.0779	−0.1238	0.075*
C19	0.80010 (13)	0.37833 (15)	0.14586 (8)	0.0467 (4)
C20	0.71183 (14)	0.47793 (16)	0.12868 (9)	0.0580 (4)
H20	0.7110	0.5362	0.0891	0.070*
C21	0.62531 (16)	0.49192 (18)	0.16932 (10)	0.0708 (5)
H21	0.5665	0.5585	0.1568	0.085*
C22	0.62607 (17)	0.4075 (2)	0.22834 (11)	0.0751 (5)
H22	0.5681	0.4172	0.2560	0.090*
C23	0.71230 (17)	0.3091 (2)	0.24616 (10)	0.0790 (6)
H23	0.7127	0.2512	0.2859	0.095*
C24	0.79907 (15)	0.29535 (18)	0.20530 (9)	0.0651 (5)
H24	0.8578	0.2287	0.2183	0.078*
C25	0.83049 (14)	−0.07659 (16)	0.03829 (9)	0.0588 (4)
H25A	0.8866	−0.0972	0.0082	0.088*
H25B	0.7547	−0.0909	0.0126	0.088*
H25C	0.8421	−0.1402	0.0783	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0435 (7)	0.0352 (6)	0.0436 (7)	−0.0058 (5)	0.0047 (6)	−0.0012 (5)
O1	0.0943 (9)	0.0367 (6)	0.0664 (8)	−0.0083 (6)	0.0106 (6)	0.0005 (5)
O2	0.0658 (8)	0.0648 (7)	0.0731 (8)	0.0187 (6)	−0.0059 (6)	0.0089 (6)
C1	0.0486 (10)	0.0461 (8)	0.0549 (10)	0.0004 (7)	0.0054 (8)	0.0059 (7)
C2	0.0783 (13)	0.0635 (11)	0.0584 (12)	−0.0004 (9)	0.0178 (10)	0.0029 (9)
C3	0.0997 (16)	0.0817 (13)	0.0488 (11)	−0.0026 (12)	0.0016 (11)	0.0111 (10)
C4	0.0782 (14)	0.0880 (14)	0.0684 (14)	0.0109 (11)	−0.0188 (11)	0.0197 (11)
C5	0.0589 (11)	0.0628 (10)	0.0694 (13)	0.0128 (8)	0.0032 (9)	0.0124 (9)
C6	0.0434 (9)	0.0375 (7)	0.0514 (10)	−0.0046 (7)	0.0042 (7)	0.0080 (7)
C7	0.0429 (9)	0.0381 (8)	0.0570 (10)	−0.0028 (6)	0.0096 (7)	0.0036 (7)
C8	0.0457 (9)	0.0403 (8)	0.0462 (9)	−0.0068 (6)	0.0025 (7)	−0.0035 (6)
C9	0.0448 (9)	0.0571 (9)	0.0501 (10)	−0.0043 (7)	0.0051 (7)	−0.0005 (7)
C10	0.0459 (9)	0.0530 (9)	0.0412 (9)	0.0058 (7)	0.0132 (7)	0.0062 (7)
C11	0.0409 (8)	0.0381 (7)	0.0499 (9)	−0.0006 (6)	0.0134 (7)	0.0033 (6)
C12	0.0402 (8)	0.0341 (7)	0.0455 (8)	−0.0030 (6)	0.0082 (6)	−0.0006 (6)
C13	0.0448 (9)	0.0357 (7)	0.0495 (9)	−0.0065 (6)	0.0039 (7)	0.0023 (6)
C14	0.0470 (10)	0.0558 (9)	0.0681 (11)	−0.0046 (8)	0.0037 (9)	−0.0043 (8)
C15	0.0456 (11)	0.0762 (12)	0.0989 (15)	−0.0021 (9)	0.0056 (10)	−0.0002 (11)
C16	0.0551 (13)	0.0854 (14)	0.0945 (16)	−0.0163 (10)	−0.0178 (11)	0.0089 (12)
C17	0.0756 (14)	0.0943 (14)	0.0688 (13)	−0.0248 (12)	−0.0122 (11)	−0.0089 (11)
C18	0.0601 (11)	0.0669 (11)	0.0595 (11)	−0.0134 (9)	0.0036 (9)	−0.0088 (9)
C19	0.0495 (9)	0.0436 (8)	0.0463 (9)	−0.0037 (7)	0.0048 (7)	−0.0075 (7)
C20	0.0656 (12)	0.0479 (9)	0.0615 (11)	0.0058 (8)	0.0131 (9)	−0.0020 (8)
C21	0.0699 (13)	0.0615 (11)	0.0843 (14)	0.0134 (9)	0.0221 (11)	−0.0084 (10)
C22	0.0775 (14)	0.0742 (12)	0.0812 (14)	−0.0013 (11)	0.0370 (11)	−0.0141 (11)
C23	0.0956 (15)	0.0831 (13)	0.0641 (12)	0.0116 (12)	0.0309 (11)	0.0071 (10)
C24	0.0705 (12)	0.0706 (11)	0.0567 (11)	0.0142 (9)	0.0179 (9)	0.0043 (9)
C25	0.0631 (11)	0.0419 (9)	0.0715 (12)	−0.0009 (7)	0.0102 (9)	0.0042 (8)

Geometric parameters (Å, º) top

N1—C7	1.3641 (17)	C12—C13	1.5154 (19)
N1—C8	1.4813 (17)	C12—H12	0.9800
N1—C12	1.4916 (16)	C13—C14	1.378 (2)
O1—C7	1.2338 (16)	C13—C18	1.383 (2)
O2—C10	1.2123 (16)	C14—C15	1.385 (2)
C1—C2	1.379 (2)	C14—H14	0.9300
C1—C6	1.3818 (19)	C15—C16	1.366 (3)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.369 (2)	C16—C17	1.367 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.369 (3)	C17—C18	1.382 (2)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.373 (2)	C18—H18	0.9300
C4—H4	0.9300	C19—C24	1.375 (2)
C5—C6	1.386 (2)	C19—C20	1.389 (2)
C5—H5	0.9300	C20—C21	1.379 (2)
C6—C7	1.490 (2)	C20—H20	0.9300
C8—C19	1.5179 (19)	C21—C22	1.374 (2)
C8—C9	1.523 (2)	C21—H21	0.9300
C8—H8	0.9800	C22—C23	1.366 (3)
C9—C10	1.496 (2)	C22—H22	0.9300
C9—H9A	0.9700	C23—C24	1.384 (2)
C9—H9B	0.9700	C23—H23	0.9300
C10—C11	1.513 (2)	C24—H24	0.9300
C11—C25	1.525 (2)	C25—H25A	0.9600
C11—C12	1.5491 (19)	C25—H25B	0.9600
C11—H11	0.9800	C25—H25C	0.9600

C7—N1—C8	117.80 (11)	C13—C12—C11	110.48 (10)
C7—N1—C12	122.12 (11)	N1—C12—H12	107.5
C8—N1—C12	119.80 (10)	C13—C12—H12	107.5
C2—C1—C6	120.18 (15)	C11—C12—H12	107.5
C2—C1—H1	119.9	C14—C13—C18	118.13 (14)
C6—C1—H1	119.9	C14—C13—C12	121.44 (13)
C3—C2—C1	120.25 (17)	C18—C13—C12	120.37 (13)
C3—C2—H2	119.9	C13—C14—C15	120.67 (16)
C1—C2—H2	119.9	C13—C14—H14	119.7
C2—C3—C4	119.96 (18)	C15—C14—H14	119.7
C2—C3—H3	120.0	C16—C15—C14	120.49 (17)
C4—C3—H3	120.0	C16—C15—H15	119.8
C3—C4—C5	120.37 (17)	C14—C15—H15	119.8
C3—C4—H4	119.8	C15—C16—C17	119.53 (17)
C5—C4—H4	119.8	C15—C16—H16	120.2
C4—C5—C6	120.21 (17)	C17—C16—H16	120.2
C4—C5—H5	119.9	C16—C17—C18	120.27 (18)
C6—C5—H5	119.9	C16—C17—H17	119.9
C1—C6—C5	118.97 (15)	C18—C17—H17	119.9
C1—C6—C7	121.30 (13)	C17—C18—C13	120.90 (17)
C5—C6—C7	119.54 (14)	C17—C18—H18	119.6
O1—C7—N1	121.58 (14)	C13—C18—H18	119.6
O1—C7—C6	119.37 (12)	C24—C19—C20	117.71 (14)
N1—C7—C6	119.05 (12)	C24—C19—C8	123.47 (14)
N1—C8—C19	112.91 (11)	C20—C19—C8	118.81 (13)
N1—C8—C9	107.85 (11)	C21—C20—C19	121.17 (16)
C19—C8—C9	117.22 (12)	C21—C20—H20	119.4
N1—C8—H8	106.0	C19—C20—H20	119.4
C19—C8—H8	106.0	C22—C21—C20	119.99 (17)
C9—C8—H8	106.0	C22—C21—H21	120.0
C10—C9—C8	113.86 (12)	C20—C21—H21	120.0
C10—C9—H9A	108.8	C23—C22—C21	119.69 (17)
C8—C9—H9A	108.8	C23—C22—H22	120.2
C10—C9—H9B	108.8	C21—C22—H22	120.2
C8—C9—H9B	108.8	C22—C23—C24	120.21 (17)
H9A—C9—H9B	107.7	C22—C23—H23	119.9
O2—C10—C9	121.58 (14)	C24—C23—H23	119.9
O2—C10—C11	122.02 (13)	C19—C24—C23	121.23 (16)
C9—C10—C11	116.40 (12)	C19—C24—H24	119.4
C10—C11—C25	111.95 (12)	C23—C24—H24	119.4
C10—C11—C12	111.57 (11)	C11—C25—H25A	109.5
C25—C11—C12	111.51 (12)	C11—C25—H25B	109.5
C10—C11—H11	107.2	H25A—C25—H25B	109.5
C25—C11—H11	107.2	C11—C25—H25C	109.5
C12—C11—H11	107.2	H25A—C25—H25C	109.5
N1—C12—C13	112.34 (11)	H25B—C25—H25C	109.5
N1—C12—C11	111.18 (11)

C6—C1—C2—C3	−1.0 (2)	C7—N1—C12—C11	173.99 (12)
C1—C2—C3—C4	1.6 (3)	C8—N1—C12—C11	0.20 (16)
C2—C3—C4—C5	0.1 (3)	C10—C11—C12—N1	−46.08 (15)
C3—C4—C5—C6	−2.4 (3)	C25—C11—C12—N1	−172.09 (11)
C2—C1—C6—C5	−1.3 (2)	C10—C11—C12—C13	−171.51 (11)
C2—C1—C6—C7	−176.24 (13)	C25—C11—C12—C13	62.48 (15)
C4—C5—C6—C1	3.0 (2)	N1—C12—C13—C14	−54.97 (17)
C4—C5—C6—C7	178.01 (15)	C11—C12—C13—C14	69.80 (16)
C8—N1—C7—O1	−11.4 (2)	N1—C12—C13—C18	127.97 (14)
C12—N1—C7—O1	174.69 (12)	C11—C12—C13—C18	−107.26 (15)
C8—N1—C7—C6	168.16 (12)	C18—C13—C14—C15	−0.3 (2)
C12—N1—C7—C6	−5.76 (19)	C12—C13—C14—C15	−177.39 (14)
C1—C6—C7—O1	113.48 (16)	C13—C14—C15—C16	0.9 (3)
C5—C6—C7—O1	−61.43 (19)	C14—C15—C16—C17	−1.2 (3)
C1—C6—C7—N1	−66.08 (18)	C15—C16—C17—C18	1.0 (3)
C5—C6—C7—N1	119.00 (16)	C16—C17—C18—C13	−0.4 (3)
C7—N1—C8—C19	103.78 (14)	C14—C13—C18—C17	0.1 (2)
C12—N1—C8—C19	−82.15 (15)	C12—C13—C18—C17	177.22 (15)
C7—N1—C8—C9	−125.09 (13)	N1—C8—C19—C24	124.75 (15)
C12—N1—C8—C9	48.98 (15)	C9—C8—C19—C24	−1.5 (2)
N1—C8—C9—C10	−52.73 (15)	N1—C8—C19—C20	−56.42 (17)
C19—C8—C9—C10	76.00 (16)	C9—C8—C19—C20	177.30 (13)
C8—C9—C10—O2	−172.09 (13)	C24—C19—C20—C21	−0.8 (2)
C8—C9—C10—C11	8.52 (17)	C8—C19—C20—C21	−179.69 (14)
O2—C10—C11—C25	−11.66 (19)	C19—C20—C21—C22	0.6 (3)
C9—C10—C11—C25	167.74 (12)	C20—C21—C22—C23	−0.5 (3)
O2—C10—C11—C12	−137.43 (14)	C21—C22—C23—C24	0.5 (3)
C9—C10—C11—C12	41.97 (16)	C20—C19—C24—C23	0.8 (2)
C7—N1—C12—C13	−61.62 (16)	C8—C19—C24—C23	179.67 (15)
C8—N1—C12—C13	124.58 (13)	C22—C23—C24—C19	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.98	2.26	2.7235 (17)	108
C9—H9A···O1ⁱ	0.97	2.56	3.4446 (19)	152

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃NO₂
M_r	369.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	290
a, b, c (Å)	11.7602 (6), 9.2404 (3), 19.1722 (9)
β (°)	98.797 (4)
V (Å³)	2058.93 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.36 × 0.24 × 0.18

Data collection
Diffractometer	Oxford Xcalibur Eos(Nova) CCD detector diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.942, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	22931, 3831, 2515
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.105, 1.00
No. of reflections	3831
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1999), WinGX (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.9800	2.2600	2.7235 (17)	108.00
C9—H9A···O1ⁱ	0.9700	2.5600	3.4446 (19)	152.00

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

We thank the Department of Science and Technology, India for the use of the CCD facility setup under the FIST–DST program at SSCU, IISc. We thank Prof T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

References

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