1-Allyl-3,3-diphenyl­indolin-2-one

Nirmala, S.; Kamala, E.T.S.; Sudha, L.; Raj, A.R.N.; Huq, C.A.M.A.

doi:10.1107/S1600536808009446

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o834

doi:10.1107/S1600536808009446

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1-Allyl-3,3-diphenylindolin-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 ^cPostgraduate Research, Department of Chemistry, New College, Chennai 600014, India
^*Correspondence e-mail: sudharose18@gmail.com

(Received 22 December 2007; accepted 7 April 2008; online 16 April 2008)

In the title compound, C₂₃H₁₉NO, the oxindole residue is essentially planar and is almost perpendicular to the phenyl rings [dihedral angles = 72.1 (6) and 77.6 (6)°]. The molecular packing is stabilized by C—H⋯O hydrogen bonds and C—H⋯N interactions.

Related literature

For related literature, see: Bandini et al. (2005 ); Florin et al. (1980 ); Govind et al. (2003 ); Rajeswaran et al. (1999 ); Ramirez & Garcia-Rubio (2003 ).

Experimental

Crystal data

C₂₃H₁₉NO
M_r = 325.39
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.8449 (3) Å
b = 12.3879 (4) Å
c = 16.0377 (4) Å
V = 1757.25 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 (2) K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEX2 diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.978, T_max = 0.985
14793 measured reflections
3559 independent reflections
2611 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.141
S = 1.09
3559 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.31 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
C12—H12A⋯N1	0.93	2.59	2.905 (4)	100
C10—H10A⋯O1ⁱ	0.97	2.49	3.446 (3)	170
C23—H23⋯O1ⁱⁱ	0.93	2.55	3.356 (3)	146
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536808009446/gw2038sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009446/gw2038Isup2.hkl

checkCIF report

Comment top

Indole and its derivatives form a class of toxic recalcitrant N – heterocyclic compounds that are considered as pollutants (Florin et al., 1980). Derivatives of indole have received much attention because of their widespread applications in materials science, agrichemicals, and pharmaceuticals (Ramirez & Garcia-Rubio, 2003).Their preparation and functionalization continues to be a fascinating subject in organic synthesis due to the frequent appearance of indoles in biologically interesting compounds (Bandini et al., 2005). Compounds containing the indole moiety have been proven to display high activity of aldose reductase inhibition (Rajeswaran et al., 1999). In view of this importance, an X-ray study of the title compound, (I), was carried out.

An ORTEP (Farrugia,1997) plot of the molecule is shown in Fig.1. The indole moiety (N1/C2 – C9) is planar with the maximum deviation of 0.040 (8) for C2 atom. The oxindole ring is nearly orthogonal to phenyl rings A (C13 – C18) and B (C19 – C24), and makes a dihedral angle of 72.1 (6)° with the ring A, 77.6 (6)° with the ring B. Both the phenyl rings A and B are oriented at an angle of 70.4 (7)° with respect to each other. The sum of angles at N1 [360.0]° indicate sp²hybridization. In the oxindole ring systems, the variation in endocyclic angles are due to fusion of five and six membered rings (Govind et al., 2003). The N1— C2 and C2— O1 bond lengths indicate electron delocalization over atoms N1, C2 and O1. The torsion angle C12—C11—C10—N1 = – 0.3 (4)° indicate that the allyl group deviates significantly from the plane of the attached indole moiety.

Weak intramolecular C—H···N and C—H··· π interactions stabilize the molecule. The crystal packing also involves inter molecular C—H···O interactions and van der Waals forces.

Related literature top

For related literature, see: Bandini et al. (2005); Florin et al. (1980); Govind et al. (2003); Rajeswaran et al. (1999); Ramirez & Garcia-Rubio (2003).

Experimental top

To a solution of phenyl magnesium bromide in dry THF, at 0°C under N₂ atm.,1-N-allyl isatin (0.005 mol, 0.935 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. The progress of the reaction was followed by TLC. On completion of the reaction, a saturated solution of NH₄Cl was added slowly at 0°C. The aqueous layer was washed with brine (50 ml) and dried. On removal of the solvent under reduced pressure, a crude mass was obtained., which was purified over a column of silica gel (100–200 mesh) 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 a axis.

1-Allyl-3,3-diphenylindolin-2-one top

Crystal data top

C₂₃H₁₉NO	F(000) = 688
M_r = 325.39	D_x = 1.230 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2ac 2ab	Cell parameters from 4984 reflections
a = 8.8449 (3) Å	θ = 2.5–30.3°
b = 12.3879 (4) Å	µ = 0.08 mm⁻¹
c = 16.0377 (4) Å	T = 293 K
V = 1757.25 (9) Å³	Prism, yellow
Z = 4	0.30 × 0.24 × 0.20 mm

Data collection top

Bruker Kappa APEX2 diffractometer	3559 independent reflections
Radiation source: fine-focus sealed tube	2611 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scans	θ_max = 32.6°, θ_min = 2.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −13→11
T_min = 0.978, T_max = 0.985	k = −18→14
14793 measured reflections	l = −20→24

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0653P)² + 0.2107P] where P = (F_o² + 2F_c²)/3
3559 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₃H₁₉NO	V = 1757.25 (9) Å³
M_r = 325.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.8449 (3) Å	µ = 0.08 mm⁻¹
b = 12.3879 (4) Å	T = 293 K
c = 16.0377 (4) Å	0.30 × 0.24 × 0.20 mm

Data collection top

Bruker Kappa APEX2 diffractometer	3559 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	2611 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.985	R_int = 0.026
14793 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.09	Δρ_max = 0.31 e Å⁻³
3559 reflections	Δρ_min = −0.21 e Å⁻³
226 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	0.7623 (2)	0.14099 (15)	0.09508 (12)	0.0367 (4)
C3	0.7846 (2)	0.02597 (14)	0.13122 (10)	0.0331 (3)
C4	0.8751 (2)	−0.02725 (15)	0.06249 (11)	0.0349 (4)
C5	0.9240 (3)	−0.13195 (17)	0.05340 (13)	0.0454 (5)
H5	0.9017	−0.1836	0.0937	0.055*
C6	1.0075 (3)	−0.1595 (2)	−0.01711 (14)	0.0523 (5)
H6	1.0420	−0.2299	−0.0239	0.063*
C7	1.0390 (3)	−0.0829 (2)	−0.07656 (14)	0.0570 (6)
H7	1.0952	−0.1025	−0.1231	0.068*
C8	0.9897 (3)	0.0220 (2)	−0.06920 (13)	0.0517 (5)
H8	1.0119	0.0733	−0.1097	0.062*
C9	0.9059 (2)	0.04807 (16)	0.00085 (11)	0.0387 (4)
C10	0.8516 (3)	0.24727 (19)	−0.02570 (15)	0.0543 (6)
H10A	0.9527	0.2513	−0.0490	0.065*
H10B	0.8404	0.3073	0.0126	0.065*
C11	0.7411 (3)	0.2612 (2)	−0.09456 (17)	0.0675 (7)
H11	0.7486	0.3252	−0.1246	0.081*
C12	0.6406 (4)	0.1988 (3)	−0.1170 (2)	0.0792 (9)
H12A	0.6272	0.1334	−0.0894	0.095*
H12B	0.5781	0.2170	−0.1614	0.095*
C13	0.8731 (2)	0.03991 (15)	0.21273 (11)	0.0363 (4)
C14	0.8029 (3)	0.08647 (16)	0.28170 (13)	0.0439 (4)
H14	0.7018	0.1067	0.2784	0.053*
C15	0.8814 (3)	0.10282 (19)	0.35467 (14)	0.0534 (6)
H15	0.8327	0.1333	0.4004	0.064*
C16	1.0312 (3)	0.0745 (2)	0.36051 (15)	0.0643 (7)
H16	1.0845	0.0863	0.4097	0.077*
C17	1.1015 (3)	0.0285 (3)	0.29290 (17)	0.0782 (9)
H17	1.2028	0.0090	0.2964	0.094*
C18	1.0225 (3)	0.0110 (3)	0.21964 (15)	0.0597 (6)
H18	1.0713	−0.0208	0.1745	0.072*
C19	0.6328 (2)	−0.03049 (15)	0.14321 (11)	0.0347 (4)
C20	0.5121 (2)	−0.00927 (18)	0.09117 (14)	0.0446 (5)
H20	0.5221	0.0426	0.0496	0.054*
C21	0.3761 (3)	−0.0640 (2)	0.09980 (17)	0.0548 (6)
H21	0.2957	−0.0484	0.0645	0.066*
C22	0.3604 (3)	−0.1413 (2)	0.16061 (17)	0.0572 (6)
H22	0.2690	−0.1775	0.1669	0.069*
C23	0.4792 (3)	−0.1650 (2)	0.21185 (15)	0.0596 (6)
H23	0.4688	−0.2178	0.2526	0.072*
C24	0.6155 (3)	−0.11038 (18)	0.20325 (13)	0.0500 (5)
H24	0.6961	−0.1275	0.2381	0.060*
N1	0.8393 (2)	0.14731 (13)	0.02162 (10)	0.0414 (4)
O1	0.69142 (19)	0.21379 (12)	0.12636 (10)	0.0505 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0361 (9)	0.0371 (9)	0.0367 (8)	−0.0015 (7)	0.0006 (7)	0.0024 (7)
C3	0.0331 (8)	0.0371 (8)	0.0290 (7)	0.0005 (7)	0.0027 (6)	0.0012 (7)
C4	0.0326 (8)	0.0408 (9)	0.0313 (8)	−0.0012 (7)	0.0004 (7)	−0.0026 (7)
C5	0.0469 (11)	0.0442 (10)	0.0452 (10)	0.0025 (9)	0.0027 (9)	−0.0034 (9)
C6	0.0480 (12)	0.0570 (12)	0.0518 (12)	0.0076 (10)	0.0008 (10)	−0.0170 (10)
C7	0.0455 (12)	0.0809 (17)	0.0446 (11)	−0.0002 (11)	0.0090 (10)	−0.0169 (11)
C8	0.0486 (12)	0.0700 (14)	0.0363 (10)	−0.0056 (11)	0.0102 (9)	0.0001 (10)
C9	0.0349 (9)	0.0463 (9)	0.0351 (8)	−0.0051 (8)	0.0027 (7)	0.0006 (8)
C10	0.0559 (13)	0.0514 (11)	0.0557 (13)	−0.0076 (10)	0.0055 (11)	0.0204 (11)
C11	0.0746 (17)	0.0706 (17)	0.0574 (15)	0.0029 (15)	−0.0022 (14)	0.0130 (13)
C12	0.088 (2)	0.084 (2)	0.0650 (17)	0.0092 (19)	0.0007 (16)	−0.0026 (15)
C13	0.0369 (9)	0.0391 (9)	0.0329 (8)	−0.0001 (7)	0.0011 (7)	0.0000 (7)
C14	0.0458 (11)	0.0473 (10)	0.0386 (10)	0.0052 (9)	0.0013 (8)	−0.0040 (8)
C15	0.0651 (15)	0.0582 (13)	0.0369 (10)	0.0023 (12)	0.0004 (10)	−0.0089 (9)
C16	0.0631 (16)	0.0861 (18)	0.0437 (12)	−0.0075 (14)	−0.0126 (11)	−0.0102 (12)
C17	0.0463 (13)	0.126 (3)	0.0618 (15)	0.0108 (17)	−0.0163 (12)	−0.0218 (18)
C18	0.0395 (11)	0.0917 (18)	0.0479 (11)	0.0075 (12)	−0.0028 (9)	−0.0165 (12)
C19	0.0354 (9)	0.0368 (8)	0.0319 (8)	−0.0017 (7)	0.0050 (6)	0.0008 (7)
C20	0.0394 (10)	0.0457 (10)	0.0489 (11)	0.0001 (8)	0.0001 (8)	0.0063 (9)
C21	0.0343 (10)	0.0569 (13)	0.0730 (15)	−0.0010 (9)	−0.0001 (10)	−0.0082 (12)
C22	0.0471 (12)	0.0530 (12)	0.0713 (15)	−0.0151 (10)	0.0185 (11)	−0.0132 (12)
C23	0.0773 (17)	0.0548 (13)	0.0468 (11)	−0.0253 (12)	0.0135 (12)	0.0028 (10)
C24	0.0602 (14)	0.0513 (12)	0.0387 (10)	−0.0141 (11)	−0.0024 (9)	0.0105 (9)
N1	0.0439 (9)	0.0401 (8)	0.0401 (8)	−0.0042 (7)	0.0052 (7)	0.0081 (7)
O1	0.0565 (9)	0.0411 (7)	0.0539 (9)	0.0091 (7)	0.0066 (7)	0.0007 (6)

Geometric parameters (Å, º) top

C2—O1	1.207 (2)	C12—H12B	0.9300
C2—N1	1.363 (2)	C13—C18	1.374 (3)
C2—C3	1.551 (3)	C13—C14	1.393 (3)
C3—C4	1.513 (2)	C14—C15	1.376 (3)
C3—C19	1.526 (3)	C14—H14	0.9300
C3—C13	1.533 (2)	C15—C16	1.374 (4)
C4—C5	1.375 (3)	C15—H15	0.9300
C4—C9	1.387 (3)	C16—C17	1.373 (4)
C5—C6	1.393 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.384 (3)
C6—C7	1.374 (3)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.375 (4)	C19—C20	1.380 (3)
C7—H7	0.9300	C19—C24	1.389 (3)
C8—C9	1.384 (3)	C20—C21	1.388 (3)
C8—H8	0.9300	C20—H20	0.9300
C9—N1	1.404 (3)	C21—C22	1.374 (4)
C10—N1	1.456 (3)	C21—H21	0.9300
C10—C11	1.485 (4)	C22—C23	1.366 (4)
C10—H10A	0.9700	C22—H22	0.9300
C10—H10B	0.9700	C23—C24	1.390 (3)
C11—C12	1.232 (4)	C23—H23	0.9300
C11—H11	0.9300	C24—H24	0.9300
C12—H12A	0.9300

O1—C2—N1	125.14 (18)	C18—C13—C14	118.21 (19)
O1—C2—C3	126.65 (17)	C18—C13—C3	122.03 (18)
N1—C2—C3	108.20 (15)	C14—C13—C3	119.73 (17)
C4—C3—C19	110.95 (15)	C15—C14—C13	120.7 (2)
C4—C3—C13	113.58 (15)	C15—C14—H14	119.6
C19—C3—C13	113.16 (14)	C13—C14—H14	119.6
C4—C3—C2	101.25 (14)	C16—C15—C14	120.5 (2)
C19—C3—C2	110.88 (15)	C16—C15—H15	119.8
C13—C3—C2	106.26 (14)	C14—C15—H15	119.8
C5—C4—C9	119.81 (17)	C17—C16—C15	119.2 (2)
C5—C4—C3	130.89 (17)	C17—C16—H16	120.4
C9—C4—C3	109.29 (16)	C15—C16—H16	120.4
C4—C5—C6	118.9 (2)	C16—C17—C18	120.5 (2)
C4—C5—H5	120.5	C16—C17—H17	119.8
C6—C5—H5	120.5	C18—C17—H17	119.8
C7—C6—C5	120.1 (2)	C13—C18—C17	120.8 (2)
C7—C6—H6	119.9	C13—C18—H18	119.6
C5—C6—H6	119.9	C17—C18—H18	119.6
C6—C7—C8	121.9 (2)	C20—C19—C24	118.03 (18)
C6—C7—H7	119.0	C20—C19—C3	121.12 (16)
C8—C7—H7	119.0	C24—C19—C3	120.69 (18)
C7—C8—C9	117.4 (2)	C19—C20—C21	121.1 (2)
C7—C8—H8	121.3	C19—C20—H20	119.4
C9—C8—H8	121.3	C21—C20—H20	119.4
C8—C9—C4	121.79 (19)	C22—C21—C20	119.9 (2)
C8—C9—N1	128.49 (18)	C22—C21—H21	120.0
C4—C9—N1	109.72 (16)	C20—C21—H21	120.0
N1—C10—C11	115.9 (2)	C23—C22—C21	119.9 (2)
N1—C10—H10A	108.3	C23—C22—H22	120.0
C11—C10—H10A	108.3	C21—C22—H22	120.0
N1—C10—H10B	108.3	C22—C23—C24	120.2 (2)
C11—C10—H10B	108.3	C22—C23—H23	119.9
H10A—C10—H10B	107.4	C24—C23—H23	119.9
C12—C11—C10	128.2 (3)	C19—C24—C23	120.7 (2)
C12—C11—H11	115.9	C19—C24—H24	119.6
C10—C11—H11	115.9	C23—C24—H24	119.6
C11—C12—H12A	120.0	C2—N1—C9	111.39 (15)
C11—C12—H12B	120.0	C2—N1—C10	122.46 (18)
H12A—C12—H12B	120.0	C9—N1—C10	126.12 (17)

O1—C2—C3—C4	177.4 (2)	C3—C13—C14—C15	−177.99 (18)
N1—C2—C3—C4	−3.70 (18)	C13—C14—C15—C16	0.7 (4)
O1—C2—C3—C19	59.6 (2)	C14—C15—C16—C17	−0.7 (4)
N1—C2—C3—C19	−121.48 (16)	C15—C16—C17—C18	0.1 (5)
O1—C2—C3—C13	−63.8 (2)	C14—C13—C18—C17	−0.6 (4)
N1—C2—C3—C13	115.17 (16)	C3—C13—C18—C17	177.3 (3)
C19—C3—C4—C5	−57.8 (3)	C16—C17—C18—C13	0.6 (5)
C13—C3—C4—C5	71.0 (3)	C4—C3—C19—C20	−80.4 (2)
C2—C3—C4—C5	−175.6 (2)	C13—C3—C19—C20	150.58 (17)
C19—C3—C4—C9	120.96 (17)	C2—C3—C19—C20	31.3 (2)
C13—C3—C4—C9	−110.24 (17)	C4—C3—C19—C24	95.0 (2)
C2—C3—C4—C9	3.23 (18)	C13—C3—C19—C24	−34.0 (2)
C9—C4—C5—C6	1.6 (3)	C2—C3—C19—C24	−153.30 (18)
C3—C4—C5—C6	−179.68 (19)	C24—C19—C20—C21	1.6 (3)
C4—C5—C6—C7	−0.5 (3)	C3—C19—C20—C21	177.17 (19)
C5—C6—C7—C8	−0.3 (4)	C19—C20—C21—C22	−0.5 (4)
C6—C7—C8—C9	−0.2 (4)	C20—C21—C22—C23	−0.7 (4)
C7—C8—C9—C4	1.4 (3)	C21—C22—C23—C24	0.6 (4)
C7—C8—C9—N1	−177.8 (2)	C20—C19—C24—C23	−1.7 (3)
C5—C4—C9—C8	−2.2 (3)	C3—C19—C24—C23	−177.3 (2)
C3—C4—C9—C8	178.88 (19)	C22—C23—C24—C19	0.6 (4)
C5—C4—C9—N1	177.21 (18)	O1—C2—N1—C9	−178.1 (2)
C3—C4—C9—N1	−1.7 (2)	C3—C2—N1—C9	3.0 (2)
N1—C10—C11—C12	−0.3 (4)	O1—C2—N1—C10	3.8 (3)
C4—C3—C13—C18	3.0 (3)	C3—C2—N1—C10	−175.20 (18)
C19—C3—C13—C18	130.7 (2)	C8—C9—N1—C2	178.5 (2)
C2—C3—C13—C18	−107.4 (2)	C4—C9—N1—C2	−0.8 (2)
C4—C3—C13—C14	−179.13 (17)	C8—C9—N1—C10	−3.4 (4)
C19—C3—C13—C14	−51.5 (2)	C4—C9—N1—C10	177.25 (19)
C2—C3—C13—C14	70.4 (2)	C11—C10—N1—C2	−96.5 (3)
C18—C13—C14—C15	−0.1 (3)	C11—C10—N1—C9	85.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···N1	0.93	2.59	2.905 (4)	100
C10—H10A···O1ⁱ	0.97	2.49	3.446 (3)	170
C23—H23···O1ⁱⁱ	0.93	2.55	3.356 (3)	146

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉NO
M_r	325.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.8449 (3), 12.3879 (4), 16.0377 (4)
V (Å³)	1757.25 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEX2 diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.978, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	14793, 3559, 2611
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.142, 1.09
No. of reflections	3559
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −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	1.207 (2)	C9—N1	1.404 (3)
C2—N1	1.363 (2)	C10—N1	1.456 (3)

O1—C2—N1	125.14 (18)	C4—C9—N1	109.72 (16)
O1—C2—C3	126.65 (17)	N1—C10—C11	115.9 (2)
N1—C2—C3	108.20 (15)	C2—N1—C9	111.39 (15)
C5—C4—C9	119.81 (17)	C2—N1—C10	122.46 (18)
C8—C9—C4	121.79 (19)	C9—N1—C10	126.12 (17)
C8—C9—N1	128.49 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···N1	0.93	2.59	2.905 (4)	100
C10—H10A···O1ⁱ	0.97	2.49	3.446 (3)	170
C23—H23···O1ⁱⁱ	0.93	2.55	3.356 (3)	146

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

Acknowledgements

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

References

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