1-Allyl-3,3-di-p-tolyl­indolin-2-one

Nirmala, S.; Theboral Sugi Kamala, E.; Sudha, L.; Naresh Raj, A.R.; Huq, C.A.M.A.

doi:10.1107/S1600536808010088

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o879

doi:10.1107/S1600536808010088

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1-Allyl-3,3-di-p-tolylindolin-2-one

S. Nirmala,^a E. Theboral Sugi Kamala,^a L. Sudha,^b ^* A. R. Naresh Raj ^c and C. A. M. A. Huq ^c

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and ^cPost Graduate Research, Department of Chemistry, The New College, Chennai 600 014, India
^*Correspondence e-mail: sudharose18@gmail.com

(Received 6 December 2007; accepted 13 April 2008; online 23 April 2008)

In the title compound, C₂₅H₂₃NO, the indoline system is essentially planar. The molecular structure is stabilized by weak intramolecular C—H⋯N interactions and the crystal packing is determined by intermolecular C—H⋯π interactions.

Related literature

For related literature, see: Harris & Uhle (1960 ); Ho et al. (1986 ); Rajeswaran et al. (1999 ); Stevenson et al. (2000 ); Sethusankar et al. (2002 ).

Experimental

Crystal data

C₂₅H₂₃NO
M_r = 353.44
Triclinic, $[P \overline 1]$
a = 9.3311 (2) Å
b = 9.5793 (2) Å
c = 11.5736 (2) Å
α = 92.163 (1)°
β = 103.192 (1)°
γ = 101.520 (1)°
V = 983.15 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 (2) K
0.26 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.982, T_max = 0.986
25969 measured reflections
6260 independent reflections
4310 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.156
S = 0.99
6260 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cgⁱ	0.93	2.94	3.740 (2)	145
C12—H12A⋯N1	0.93	2.54	2.858 (2)	100
Symmetry code: (i) -x+1, -y, -z+1. Cg denotes the centroid of the C20–C25 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010088/gw2036sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010088/gw2036Isup2.hkl

checkCIF report

Comment top

Indole compounds can be used as bioactive drugs (Stevenson et al., 2000). Indole derivatives exhibit anti-allergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). Indoles have also been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). In view of this biological importance, an X-ray study of the title compound, (I), was carried out.

An ORTEP (Farrugia,1997) plot of the molecular is shown in Fig.1. The indole moiety is planar [maximum deviation of 0.038 (1) from the least square plane defined by all non hydrogen atoms in the molecule] and is nearly orthogonal to methylphenyl rings A and B, and makes a dihedral angle of 72.3 (4)° with the ring A, 76.7 (3)° with the ring B. Both the p-tolyl rings A and B are oriented at an angle of 72.6 (4)° with respect to each other. The sum of angles around N1 [360.0]° is in accordance with sp² hybridization. The endocyclic angles around C4 is narrowed while those at C9 is widened from 120°. This may be caused by fusion of the smaller pyrrole ring to the six membered benzene ring of oxindole. A similar effect has also been observed by Sethu Sankar et al. (2002). The bond lengths in the oxindole ring systems indicate electron delocalization. The torsion angles C19—C16—C15—C14 [–179.5 (2)°], C19—C16—C17—C18 [179.7 (2)°] and C26—C23—C24—C25 [–179.6 (2)°], C26—C23—C22—C21 [179.8 (2)°] indicates that the methyl groups are coplanar with the plane of the attached benzene rings A and B. The allyl group deviates significantly from the plane of the indole moiety [C12—C11—C10—N1 = – 4.5 (3)°].

Weak intramolecular C—H···N and intermolecular C—H··· Cg interactions, with C5···Cg = 3.740 (2) Å, [Cg denotes centroid of C20—C25 ring] are observed in the molecular structure. In addition the packing is stabilized by van der Waals forces.

Related literature top

For related literature, see: Harris & Uhle (1960); Ho et al. (1986); Rajeswaran et al. (1999); Stevenson et al. (2000); Sethu Sankar et al. (2002).

Experimental top

To a solution of p-methyl phenyl magnesium bromide in dry THF, at 0°C under N₂ atm.,1-N-allyl isatin (0.0125 mol, 2.34 g), in dry THF, was added dropwise. After the complete addition, the mixture was stirred at 0°C for 1 hr and then it was stirred at room temperature for 5 hrs. On completion of the reaction, a saturated solution of NH₄Cl was added slowly at 0°C. The aqueous layer was extracted with ether, and the combined organic layer was extracted with ether. The crude mass was obtained., which was purified over a column of silica gel using hexane/ethyl acetate as eluent. Compound was recrystallized from methanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids
	Fig. 2. The packing of the molecules viewed down b axis.

1-Allyl-3,3-di-p-tolylindolin-2-one top

Crystal data top

C₂₅H₂₃NO	Z = 2
M_r = 353.44	F(000) = 376
Triclinic, P1	D_x = 1.194 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3311 (2) Å	Cell parameters from 9112 reflections
b = 9.5793 (2) Å	θ = 2.3–30.1°
c = 11.5736 (2) Å	µ = 0.07 mm⁻¹
α = 92.163 (1)°	T = 293 K
β = 103.192 (1)°	Prism, colourless
γ = 101.520 (1)°	0.26 × 0.20 × 0.20 mm
V = 983.15 (3) Å³

Data collection top

Bruker Kappa APEXII diffractometer	6260 independent reflections
Radiation source: fine-focus sealed tube	4310 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and ϕ scan	θ_max = 31.0°, θ_min = 2.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −13→13
T_min = 0.982, T_max = 0.986	k = −13→13
25969 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0731P)² + 0.1889P] where P = (F_o² + 2F_c²)/3
6260 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₅H₂₃NO	γ = 101.520 (1)°
M_r = 353.44	V = 983.15 (3) Å³
Triclinic, P1	Z = 2
a = 9.3311 (2) Å	Mo Kα radiation
b = 9.5793 (2) Å	µ = 0.07 mm⁻¹
c = 11.5736 (2) Å	T = 293 K
α = 92.163 (1)°	0.26 × 0.20 × 0.20 mm
β = 103.192 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	6260 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	4310 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.986	R_int = 0.023
25969 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.00	Δρ_max = 0.25 e Å⁻³
6260 reflections	Δρ_min = −0.21 e Å⁻³
244 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
C2	0.21981 (13)	0.10769 (13)	0.14416 (10)	0.0403 (2)
C3	0.29661 (11)	0.03653 (12)	0.25302 (9)	0.0361 (2)
C4	0.45434 (12)	0.05217 (12)	0.23447 (10)	0.0391 (2)
C5	0.57669 (13)	0.00390 (15)	0.29710 (12)	0.0497 (3)
H5	0.5699	−0.0478	0.3628	0.060*
C6	0.71037 (15)	0.03411 (17)	0.26019 (15)	0.0602 (4)
H6	0.7938	0.0024	0.3018	0.072*
C7	0.72086 (16)	0.10999 (18)	0.16332 (16)	0.0629 (4)
H7	0.8116	0.1295	0.1405	0.075*
C8	0.59809 (17)	0.15830 (17)	0.09859 (14)	0.0587 (4)
H8	0.6049	0.2096	0.0327	0.070*
C9	0.46580 (14)	0.12724 (13)	0.13582 (11)	0.0443 (3)
C10	0.29599 (19)	0.24323 (18)	−0.01709 (12)	0.0614 (4)
H10A	0.1917	0.2102	−0.0604	0.074*
H10B	0.3589	0.2267	−0.0701	0.074*
C11	0.32409 (19)	0.39967 (19)	0.01642 (16)	0.0658 (4)
H11	0.3133	0.4583	−0.0458	0.079*
C12	0.3620 (2)	0.4623 (2)	0.12318 (19)	0.0749 (5)
H12A	0.3742	0.4084	0.1885	0.090*
H12B	0.3770	0.5612	0.1347	0.090*
C13	0.22090 (12)	−0.12027 (12)	0.25034 (10)	0.0391 (2)
C14	0.24490 (16)	−0.19198 (15)	0.35239 (13)	0.0541 (3)
H14	0.3029	−0.1423	0.4237	0.065*
C15	0.18392 (18)	−0.33608 (16)	0.34970 (16)	0.0626 (4)
H15	0.2020	−0.3818	0.4194	0.075*
C16	0.09700 (17)	−0.41371 (15)	0.24620 (16)	0.0592 (4)
C17	0.07309 (17)	−0.34194 (16)	0.14492 (15)	0.0603 (4)
H17	0.0145	−0.3920	0.0739	0.072*
C18	0.13362 (15)	−0.19778 (14)	0.14583 (12)	0.0490 (3)
H18	0.1156	−0.1526	0.0759	0.059*
C19	0.0294 (3)	−0.57073 (17)	0.2435 (2)	0.0907 (6)
H19A	−0.0262	−0.6064	0.1639	0.136*
H19B	−0.0372	−0.5842	0.2963	0.136*
H19C	0.1083	−0.6216	0.2686	0.136*
C20	0.28928 (12)	0.12652 (12)	0.36267 (10)	0.0372 (2)
C21	0.40937 (13)	0.23204 (14)	0.42458 (11)	0.0445 (3)
H21	0.5003	0.2467	0.4020	0.053*
C22	0.39541 (16)	0.31600 (15)	0.51984 (12)	0.0530 (3)
H22	0.4778	0.3858	0.5605	0.064*
C23	0.26275 (17)	0.29871 (17)	0.55575 (12)	0.0553 (3)
C24	0.14184 (16)	0.19372 (17)	0.49283 (13)	0.0561 (3)
H24	0.0506	0.1801	0.5150	0.067*
C25	0.15471 (14)	0.10923 (15)	0.39803 (12)	0.0483 (3)
H25	0.0721	0.0398	0.3573	0.058*
C26	0.2485 (3)	0.3901 (3)	0.65992 (18)	0.0932 (7)
H26A	0.1485	0.3626	0.6718	0.140*
H26B	0.2675	0.4889	0.6439	0.140*
H26C	0.3204	0.3771	0.7304	0.140*
N1	0.32609 (13)	0.15965 (12)	0.08421 (9)	0.0484 (3)
O1	0.08971 (10)	0.11949 (10)	0.11825 (8)	0.0515 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0417 (5)	0.0399 (6)	0.0385 (5)	0.0124 (4)	0.0053 (4)	0.0024 (4)
C3	0.0306 (5)	0.0386 (6)	0.0381 (5)	0.0075 (4)	0.0059 (4)	0.0061 (4)
C4	0.0342 (5)	0.0399 (6)	0.0429 (6)	0.0077 (4)	0.0094 (4)	0.0027 (4)
C5	0.0372 (6)	0.0554 (8)	0.0569 (7)	0.0132 (5)	0.0086 (5)	0.0103 (6)
C6	0.0364 (6)	0.0650 (9)	0.0805 (10)	0.0145 (6)	0.0135 (6)	0.0057 (8)
C7	0.0444 (7)	0.0637 (9)	0.0859 (11)	0.0079 (6)	0.0305 (7)	0.0025 (8)
C8	0.0586 (8)	0.0602 (9)	0.0656 (9)	0.0114 (7)	0.0317 (7)	0.0128 (7)
C9	0.0444 (6)	0.0442 (6)	0.0468 (6)	0.0109 (5)	0.0148 (5)	0.0051 (5)
C10	0.0757 (10)	0.0732 (10)	0.0455 (7)	0.0298 (8)	0.0202 (7)	0.0229 (7)
C11	0.0697 (9)	0.0666 (10)	0.0719 (10)	0.0222 (8)	0.0280 (8)	0.0323 (8)
C12	0.0729 (11)	0.0612 (10)	0.0954 (13)	0.0132 (8)	0.0299 (10)	0.0153 (9)
C13	0.0318 (5)	0.0389 (6)	0.0461 (6)	0.0085 (4)	0.0074 (4)	0.0048 (5)
C14	0.0522 (7)	0.0470 (7)	0.0556 (7)	0.0060 (6)	0.0005 (6)	0.0122 (6)
C15	0.0626 (9)	0.0476 (8)	0.0785 (10)	0.0132 (6)	0.0152 (7)	0.0224 (7)
C16	0.0542 (7)	0.0368 (7)	0.0920 (11)	0.0108 (6)	0.0280 (7)	0.0023 (7)
C17	0.0582 (8)	0.0462 (8)	0.0716 (9)	0.0058 (6)	0.0133 (7)	−0.0137 (7)
C18	0.0499 (7)	0.0470 (7)	0.0480 (6)	0.0096 (5)	0.0092 (5)	−0.0022 (5)
C19	0.0989 (14)	0.0380 (8)	0.1420 (19)	0.0073 (8)	0.0500 (14)	0.0009 (10)
C20	0.0339 (5)	0.0404 (6)	0.0373 (5)	0.0077 (4)	0.0078 (4)	0.0079 (4)
C21	0.0372 (5)	0.0475 (7)	0.0461 (6)	0.0038 (5)	0.0097 (5)	0.0032 (5)
C22	0.0521 (7)	0.0519 (8)	0.0491 (7)	0.0055 (6)	0.0063 (6)	−0.0046 (6)
C23	0.0607 (8)	0.0625 (9)	0.0456 (7)	0.0186 (7)	0.0145 (6)	0.0007 (6)
C24	0.0486 (7)	0.0701 (9)	0.0558 (7)	0.0148 (6)	0.0229 (6)	0.0056 (7)
C25	0.0361 (5)	0.0550 (7)	0.0522 (7)	0.0046 (5)	0.0121 (5)	0.0027 (6)
C26	0.0965 (14)	0.1150 (17)	0.0707 (11)	0.0262 (12)	0.0279 (10)	−0.0268 (11)
N1	0.0520 (6)	0.0551 (6)	0.0434 (5)	0.0188 (5)	0.0140 (5)	0.0154 (5)
O1	0.0433 (4)	0.0595 (6)	0.0515 (5)	0.0207 (4)	0.0023 (4)	0.0074 (4)

Geometric parameters (Å, º) top

C2—O1	1.2114 (14)	C14—C15	1.380 (2)
C2—N1	1.3621 (16)	C14—H14	0.9300
C2—C3	1.5535 (15)	C15—C16	1.376 (2)
C3—C4	1.5143 (15)	C15—H15	0.9300
C3—C13	1.5228 (16)	C16—C17	1.378 (2)
C3—C20	1.5294 (16)	C16—C19	1.507 (2)
C4—C5	1.3788 (16)	C17—C18	1.382 (2)
C4—C9	1.3853 (17)	C17—H17	0.9300
C5—C6	1.3895 (19)	C18—H18	0.9300
C5—H5	0.9300	C19—H19A	0.9600
C6—C7	1.371 (2)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C8	1.391 (2)	C20—C21	1.3847 (16)
C7—H7	0.9300	C20—C25	1.3885 (16)
C8—C9	1.3798 (19)	C21—C22	1.3857 (19)
C8—H8	0.9300	C21—H21	0.9300
C9—N1	1.4046 (16)	C22—C23	1.375 (2)
C10—N1	1.4508 (16)	C22—H22	0.9300
C10—C11	1.489 (2)	C23—C24	1.390 (2)
C10—H10A	0.9700	C23—C26	1.509 (2)
C10—H10B	0.9700	C24—C25	1.380 (2)
C11—C12	1.293 (3)	C24—H24	0.9300
C11—H11	0.9300	C25—H25	0.9300
C12—H12A	0.9300	C26—H26A	0.9600
C12—H12B	0.9300	C26—H26B	0.9600
C13—C18	1.3852 (17)	C26—H26C	0.9600
C13—C14	1.3853 (17)

O1—C2—N1	125.45 (11)	C16—C15—C14	121.51 (14)
O1—C2—C3	126.57 (11)	C16—C15—H15	119.2
N1—C2—C3	107.95 (9)	C14—C15—H15	119.2
C4—C3—C13	111.14 (9)	C15—C16—C17	117.38 (13)
C4—C3—C20	113.55 (9)	C15—C16—C19	121.49 (17)
C13—C3—C20	112.94 (9)	C17—C16—C19	121.13 (17)
C4—C3—C2	101.28 (9)	C16—C17—C18	121.93 (14)
C13—C3—C2	111.74 (9)	C16—C17—H17	119.0
C20—C3—C2	105.46 (9)	C18—C17—H17	119.0
C5—C4—C9	119.89 (11)	C17—C18—C13	120.39 (13)
C5—C4—C3	130.70 (11)	C17—C18—H18	119.8
C9—C4—C3	109.40 (9)	C13—C18—H18	119.8
C4—C5—C6	118.68 (13)	C16—C19—H19A	109.5
C4—C5—H5	120.7	C16—C19—H19B	109.5
C6—C5—H5	120.7	H19A—C19—H19B	109.5
C7—C6—C5	120.88 (13)	C16—C19—H19C	109.5
C7—C6—H6	119.6	H19A—C19—H19C	109.5
C5—C6—H6	119.6	H19B—C19—H19C	109.5
C6—C7—C8	121.13 (13)	C21—C20—C25	117.95 (11)
C6—C7—H7	119.4	C21—C20—C3	122.56 (10)
C8—C7—H7	119.4	C25—C20—C3	119.36 (10)
C9—C8—C7	117.48 (14)	C20—C21—C22	120.67 (12)
C9—C8—H8	121.3	C20—C21—H21	119.7
C7—C8—H8	121.3	C22—C21—H21	119.7
C8—C9—C4	121.93 (12)	C23—C22—C21	121.62 (13)
C8—C9—N1	128.51 (12)	C23—C22—H22	119.2
C4—C9—N1	109.54 (10)	C21—C22—H22	119.2
N1—C10—C11	113.55 (13)	C22—C23—C24	117.66 (13)
N1—C10—H10A	108.9	C22—C23—C26	121.35 (15)
C11—C10—H10A	108.9	C24—C23—C26	120.99 (15)
N1—C10—H10B	108.9	C25—C24—C23	121.17 (13)
C11—C10—H10B	108.9	C25—C24—H24	119.4
H10A—C10—H10B	107.7	C23—C24—H24	119.4
C12—C11—C10	126.66 (15)	C24—C25—C20	120.91 (12)
C12—C11—H11	116.7	C24—C25—H25	119.5
C10—C11—H11	116.7	C20—C25—H25	119.5
C11—C12—H12A	120.0	C23—C26—H26A	109.5
C11—C12—H12B	120.0	C23—C26—H26B	109.5
H12A—C12—H12B	120.0	H26A—C26—H26B	109.5
C18—C13—C14	117.85 (12)	C23—C26—H26C	109.5
C18—C13—C3	121.72 (11)	H26A—C26—H26C	109.5
C14—C13—C3	120.33 (10)	H26B—C26—H26C	109.5
C15—C14—C13	120.95 (13)	C2—N1—C9	111.71 (10)
C15—C14—H14	119.5	C2—N1—C10	122.67 (11)
C13—C14—H14	119.5	C9—N1—C10	125.57 (12)

O1—C2—C3—C4	178.68 (12)	C14—C15—C16—C17	0.0 (2)
N1—C2—C3—C4	−3.41 (12)	C14—C15—C16—C19	−179.48 (16)
O1—C2—C3—C13	60.29 (16)	C15—C16—C17—C18	0.2 (2)
N1—C2—C3—C13	−121.80 (11)	C19—C16—C17—C18	179.68 (15)
O1—C2—C3—C20	−62.78 (15)	C16—C17—C18—C13	−0.2 (2)
N1—C2—C3—C20	115.14 (10)	C14—C13—C18—C17	0.1 (2)
C13—C3—C4—C5	−57.30 (16)	C3—C13—C18—C17	176.45 (12)
C20—C3—C4—C5	71.33 (16)	C4—C3—C20—C21	11.87 (15)
C2—C3—C4—C5	−176.12 (13)	C13—C3—C20—C21	139.58 (11)
C13—C3—C4—C9	121.92 (11)	C2—C3—C20—C21	−98.13 (12)
C20—C3—C4—C9	−109.45 (11)	C4—C3—C20—C25	−172.36 (10)
C2—C3—C4—C9	3.10 (12)	C13—C3—C20—C25	−44.66 (14)
C9—C4—C5—C6	1.0 (2)	C2—C3—C20—C25	77.64 (13)
C3—C4—C5—C6	−179.88 (12)	C25—C20—C21—C22	0.88 (18)
C4—C5—C6—C7	−0.2 (2)	C3—C20—C21—C22	176.71 (11)
C5—C6—C7—C8	−0.4 (2)	C20—C21—C22—C23	−0.5 (2)
C6—C7—C8—C9	0.2 (2)	C21—C22—C23—C24	−0.2 (2)
C7—C8—C9—C4	0.7 (2)	C21—C22—C23—C26	179.75 (16)
C7—C8—C9—N1	−177.86 (14)	C22—C23—C24—C25	0.4 (2)
C5—C4—C9—C8	−1.2 (2)	C26—C23—C24—C25	−179.55 (16)
C3—C4—C9—C8	179.45 (12)	C23—C24—C25—C20	0.1 (2)
C5—C4—C9—N1	177.52 (12)	C21—C20—C25—C24	−0.69 (19)
C3—C4—C9—N1	−1.79 (14)	C3—C20—C25—C24	−176.65 (12)
N1—C10—C11—C12	−4.5 (3)	O1—C2—N1—C9	−179.43 (12)
C4—C3—C13—C18	−91.47 (13)	C3—C2—N1—C9	2.63 (14)
C20—C3—C13—C18	139.57 (11)	O1—C2—N1—C10	3.1 (2)
C2—C3—C13—C18	20.86 (15)	C3—C2—N1—C10	−174.88 (12)
C4—C3—C13—C14	84.82 (14)	C8—C9—N1—C2	178.07 (13)
C20—C3—C13—C14	−44.14 (14)	C4—C9—N1—C2	−0.58 (15)
C2—C3—C13—C14	−162.84 (11)	C8—C9—N1—C10	−4.5 (2)
C18—C13—C14—C15	0.1 (2)	C4—C9—N1—C10	176.83 (13)
C3—C13—C14—C15	−176.30 (13)	C11—C10—N1—C2	88.62 (17)
C13—C14—C15—C16	−0.2 (2)	C11—C10—N1—C9	−88.53 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cgⁱ	0.93	2.94	3.740 (2)	145
C12—H12A···N1	0.93	2.54	2.858 (2)	100

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃NO
M_r	353.44
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.3311 (2), 9.5793 (2), 11.5736 (2)
α, β, γ (°)	92.163 (1), 103.192 (1), 101.520 (1)
V (Å³)	983.15 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.26 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.982, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	25969, 6260, 4310
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.725

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.156, 1.00
No. of reflections	6260
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

C2—O1	1.2114 (14)	C9—N1	1.4046 (16)
C2—N1	1.3621 (16)	C10—N1	1.4508 (16)

O1—C2—N1	125.45 (11)	C4—C9—N1	109.54 (10)
O1—C2—C3	126.57 (11)	N1—C10—C11	113.55 (13)
N1—C2—C3	107.95 (9)	C2—N1—C9	111.71 (10)
C5—C4—C9	119.89 (11)	C2—N1—C10	122.67 (11)
C8—C9—C4	121.93 (12)	C9—N1—C10	125.57 (12)
C8—C9—N1	128.51 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cgⁱ	0.93	2.94	3.740 (2)	145
C12—H12A···N1	0.93	2.54	2.858 (2)	100

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions. SN thanks SRM management for their support.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harris, L. S. & Uhle, F. C. (1960). J. Pharmacol. Exp. Ther. 128, 353–363. Google Scholar
Ho, C. Y., Haegman, W. E. & Perisco, F. (1986). J. Med. Chem. 29, 118–121. Google Scholar
Rajeswaran, W. G., Labroo, R. B., Cohen, L. A. & King, M. M. (1999). J. Org. Chem. 64, 1369–1371. Web of Science CrossRef CAS Google Scholar
Sethu Sankar, K., Kannadasan, S., Velmurugan, D., Srinivasan, P. C., Shanmuga Sundara Raj, S. & Fun, H.-K. (2002). Acta Cryst. C58, o277–o279. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stevenson, G. I., Smith, A. L., Lewis, S., Michie, S. G., Neduvelil, J. G., Patel, S., Marwood, R., Patel, S. & Castro, J. L. (2000). Bioorg. Med. Chem. Lett. 10, 2697–2704. Web of Science CrossRef PubMed CAS Google Scholar