Synthesis of N-substituted 3-(2-aryl-2-oxoeth­yl)-3-hy­droxy­indolin-2-ones and their conversion to N-substituted (E)-3-(2-aryl-2-oxo­ethyl­idene)indolin-2-ones: synthetic sequence, spectroscopic characterization and structures of four 3-hy­droxy com­pounds and five oxo­ethyl­idene products

. 2020 Apr 20;76(Pt 5):433–445. doi: 10.1107/S2053229620004143

	(IIe)	(IIg)	(IIh)
Crystal data
Chemical formula	C₂₂H₁₆N₂O₂	C₂₁H₁₅NO₂S	C₂₃H₁₅Cl₂NO₂
M _r	340.37	345.40	408.26
Crystal system, space group	Monoclinic, P2₁/n	Orthorhombic, P b c a	Triclinic, P
a, b, c (Å)	7.3457 (6), 18.0675 (16), 13.1813 (13)	17.5058 (14), 8.8163 (6), 21.2092 (16)	8.2010 (6), 9.7629 (7), 12.1740 (9)
α, β, γ (°)	90, 105.994 (3), 90	90, 90, 90	76.755 (3), 87.675 (3), 76.211 (3)
V (Å³)	1681.7 (3)	3273.4 (4)	921.34 (12)
Z	4	8	2
μ (mm⁻¹)	0.09	0.21	0.37
Crystal size (mm)	0.16 × 0.15 × 0.12	0.15 × 0.07 × 0.05	0.40 × 0.16 × 0.07

Data collection
T _min, T _max	0.878, 0.990	0.942, 0.989	0.924, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	4167, 4167, 3281	32005, 4154, 3280	51788, 4558, 3867
R _int	N/A	0.065	0.053
(sin θ/λ)_max (Å⁻¹)	0.668	0.672	0.667

Refinement
R[F ² > 2σ(F ²)], wR(F ²), S	0.044, 0.121, 1.09	0.038, 0.092, 1.04	0.032, 0.082, 1.11
No. of reflections	4167	4154	4558
No. of parameters	237	239	253
No. of restraints	0	10	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.19	0.29, −0.31	0.44, −0.34

Computer programs: APEX3 (Bruker, 2018 ▸), SAINT (Bruker, 2017 ▸), SHELXT2014 (Sheldrick, 2015a ▸), SHELXL2014 (Sheldrick, 2015b ▸) and PLATON (Spek, 2020 ▸).