(E)-3-(2-Hy­droxy-5-methyl­phenyl­imino)­indolin-2-one

Zhang, P.-F.; Bi, C.-F.; Wang, Q.; Zuo, J.; Zhang, N.

doi:10.1107/S1600536811034015

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2493

doi:10.1107/S1600536811034015

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(E)-3-(2-Hydroxy-5-methylphenylimino)indolin-2-one

Peng-Fei Zhang,^a Cai-Feng Bi,^a ^* Qiang Wang,^a Jian Zuo ^a and Nan Zhang ^a

^aKey Laboratory of Marine Chemistry, Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao, Shandong 266100, People's Republic of China
^*Correspondence e-mail: bicaifeng301@163.com

(Received 24 June 2011; accepted 19 August 2011; online 27 August 2011)

In the title compound, C₁₅H₁₂N₂O₂, the dihedral angle between the two benzene rings is 83.55 (11)° In the crystal, the molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For general background on Schiff base ligands, see: Guo et al. (2011 ); Drozdzak et al. (2005 ); Weber et al. (2007 ); Liu et al. (2010 ). For standard bond lengths, see: Allen et al. (1987 )

Experimental

Crystal data

C₁₅H₁₂N₂O₂
M_r = 252.27
Monoclinic, P 2₁ /c
a = 12.6211 (11) Å
b = 8.7100 (7) Å
c = 11.2835 (10) Å
β = 90.780 (1)°
V = 1240.28 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.47 × 0.17 mm

Data collection

CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.956, T_max = 0.985
5982 measured reflections
2182 independent reflections
1449 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.114
S = 1.02
2182 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.86	2.6729 (19)	169
N1—H1⋯O2ⁱⁱ	0.86	2.06	2.842 (2)	151
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811034015/ru2008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034015/ru2008Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034015/ru2008Isup3.cml

checkCIF report

Comment top

Being one of the most prevalent sustems in coordination chemistry, Schiff base ligands have received much attention in recent years (Guo et al., 2011), primarily due to their importance in metal complexes with catalytic activities (Drozdzak et al., 2005), special magnetism (Weber et al., 2007) and biological properties, for example, anticancer activities (Liu et al., 2010). In the present paper, the synthesis and structure of a new Schiff base ligand is reported.

The crystal structure of the new ligand is given in Fig.1. The molecular structure of the compound is not coplanar, the dihedral angle between the two benzene rings is 83.55 °, it is almost perpendicular. The bond lengths and angles (Table 1) are within normal values (Allen et al.,1987). In the crystal structure, the adjacent molecules are linked through 0—H···0 and N—H···O hydrogen bonding (Table 2), to generate one-dimensional chain in direction (Fig.2).

Related literature top

For general background on Schiff base ligands, see: Guo et al. (2011); Drozdzak et al. (2005); Weber et al. (2007); Liu et al. (2010). For standard bond lengths, see: Allen et al. (1987)

Experimental top

2,3-indolinedione (5 mmol, 0.736 g) was dissolved in anhydrous ethanol (20 ml), then an anhydrous ethanol solution (10 ml) of 2-amino-4-methylphenol (5 mmol, 0.612 g) was slowly added. The mixture was refluxed for 4 h at 333k,and then cooled down to room temperature. A dark brown solid separated out. The solid was filtered off, washed several times with anhydrous ethanol and dried in vacuum drier. The dark brown single-crystal of the title ligand suitable for X-ray diffraction was trained in anhydrous ethanol at room temperature.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of the crystal structure showing chain to the c linked via O—H···O and N—H···O contacts.

(E)-3-(2-Hydroxy-5-methylphenylimino)indolin-2-one top

Crystal data top

C₁₅H₁₂N₂O₂	F(000) = 528
M_r = 252.27	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 1807 reflections
a = 12.6211 (11) Å	θ = 2.8–25.8°
b = 8.7100 (7) Å	µ = 0.09 mm⁻¹
c = 11.2835 (10) Å	T = 298 K
β = 90.780 (1)°	Block, dark-brown
V = 1240.28 (18) Å³	0.50 × 0.47 × 0.17 mm
Z = 4

Data collection top

CCD area-detector diffractometer	2182 independent reflections
Radiation source: fine-focus sealed tube	1449 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
T_min = 0.956, T_max = 0.985	k = −10→10
5982 measured reflections	l = −10→13

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0486P)² + 0.3363P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2182 reflections	Δρ_max = 0.16 e Å⁻³
173 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (2)

Crystal data top

C₁₅H₁₂N₂O₂	V = 1240.28 (18) Å³
M_r = 252.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6211 (11) Å	µ = 0.09 mm⁻¹
b = 8.7100 (7) Å	T = 298 K
c = 11.2835 (10) Å	0.50 × 0.47 × 0.17 mm
β = 90.780 (1)°

Data collection top

CCD area-detector diffractometer	2182 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1449 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.985	R_int = 0.038
5982 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	Δρ_max = 0.16 e Å⁻³
2182 reflections	Δρ_min = −0.16 e Å⁻³
173 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	0.53216 (12)	0.37862 (19)	0.37637 (13)	0.0391 (4)
H1	0.4865	0.3785	0.3191	0.047*
N2	0.62133 (12)	0.28888 (19)	0.66041 (14)	0.0404 (4)
O1	0.45391 (11)	0.19850 (16)	0.49452 (12)	0.0474 (4)
O2	0.58728 (11)	0.51425 (16)	0.82237 (12)	0.0490 (4)
H2	0.5830	0.5750	0.8776	0.073*
C1	0.52386 (15)	0.2918 (2)	0.47439 (16)	0.0358 (5)
C2	0.61738 (14)	0.3381 (2)	0.55449 (16)	0.0355 (5)
C3	0.67930 (15)	0.4476 (2)	0.48520 (17)	0.0384 (5)
C4	0.62382 (14)	0.4693 (2)	0.37841 (17)	0.0369 (5)
C5	0.65726 (16)	0.5680 (2)	0.29187 (18)	0.0465 (5)
H5	0.6188	0.5816	0.2218	0.056*
C6	0.75054 (18)	0.6460 (3)	0.3136 (2)	0.0564 (6)
H6	0.7756	0.7137	0.2567	0.068*
C7	0.80770 (18)	0.6262 (3)	0.4179 (2)	0.0611 (7)
H7	0.8704	0.6805	0.4299	0.073*
C8	0.77297 (16)	0.5266 (3)	0.5045 (2)	0.0519 (6)
H8	0.8118	0.5131	0.5744	0.062*
C9	0.68333 (15)	0.4423 (2)	0.82729 (17)	0.0400 (5)
C10	0.70454 (15)	0.3352 (2)	0.73941 (16)	0.0398 (5)
C11	0.80213 (16)	0.2627 (3)	0.73843 (19)	0.0496 (6)
H11	0.8161	0.1920	0.6789	0.059*
C12	0.87940 (17)	0.2925 (3)	0.8235 (2)	0.0566 (6)
C13	0.85588 (18)	0.3980 (3)	0.9110 (2)	0.0596 (7)
H13	0.9064	0.4195	0.9695	0.072*
C14	0.75915 (17)	0.4720 (3)	0.91347 (19)	0.0516 (6)
H14	0.7451	0.5421	0.9734	0.062*
C15	0.98450 (19)	0.2096 (4)	0.8213 (3)	0.0907 (10)
H15A	1.0391	0.2757	0.8522	0.136*
H15B	1.0006	0.1817	0.7412	0.136*
H15C	0.9806	0.1186	0.8691	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0391 (9)	0.0482 (10)	0.0300 (9)	0.0008 (8)	−0.0053 (7)	0.0017 (8)
N2	0.0432 (9)	0.0452 (10)	0.0326 (9)	0.0010 (8)	−0.0054 (7)	−0.0002 (8)
O1	0.0487 (8)	0.0530 (9)	0.0403 (8)	−0.0093 (7)	−0.0018 (6)	0.0006 (7)
O2	0.0542 (9)	0.0530 (9)	0.0395 (8)	0.0082 (7)	−0.0098 (7)	−0.0066 (7)
C1	0.0389 (11)	0.0384 (12)	0.0300 (11)	0.0044 (9)	0.0008 (8)	−0.0030 (9)
C2	0.0397 (10)	0.0358 (11)	0.0311 (11)	0.0069 (9)	−0.0014 (8)	−0.0030 (9)
C3	0.0399 (11)	0.0400 (12)	0.0352 (11)	0.0019 (9)	−0.0009 (9)	0.0006 (9)
C4	0.0391 (11)	0.0383 (12)	0.0335 (11)	0.0057 (9)	0.0028 (8)	−0.0010 (9)
C5	0.0520 (13)	0.0494 (13)	0.0380 (12)	0.0034 (11)	0.0011 (10)	0.0066 (10)
C6	0.0611 (14)	0.0521 (15)	0.0562 (15)	−0.0070 (12)	0.0071 (12)	0.0141 (12)
C7	0.0560 (14)	0.0610 (16)	0.0660 (16)	−0.0177 (12)	−0.0049 (12)	0.0104 (13)
C8	0.0507 (13)	0.0544 (15)	0.0502 (13)	−0.0066 (11)	−0.0090 (10)	0.0062 (11)
C9	0.0425 (12)	0.0432 (12)	0.0341 (11)	−0.0041 (9)	−0.0055 (9)	0.0061 (10)
C10	0.0424 (11)	0.0466 (13)	0.0302 (11)	−0.0049 (10)	−0.0037 (8)	0.0053 (9)
C11	0.0457 (12)	0.0609 (15)	0.0421 (13)	0.0020 (11)	0.0026 (10)	0.0035 (11)
C12	0.0414 (12)	0.0746 (17)	0.0537 (14)	−0.0034 (12)	−0.0054 (10)	0.0126 (13)
C13	0.0507 (14)	0.0753 (18)	0.0523 (15)	−0.0169 (13)	−0.0190 (11)	0.0100 (14)
C14	0.0597 (14)	0.0541 (14)	0.0405 (13)	−0.0083 (12)	−0.0115 (10)	0.0005 (11)
C15	0.0469 (14)	0.133 (3)	0.092 (2)	0.0122 (17)	−0.0062 (14)	0.013 (2)

Geometric parameters (Å, º) top

N1—C1	1.345 (2)	C7—C8	1.383 (3)
N1—C4	1.401 (2)	C7—H7	0.9300
N1—H1	0.8600	C8—H8	0.9300
N2—C2	1.270 (2)	C9—C14	1.380 (3)
N2—C10	1.427 (2)	C9—C10	1.390 (3)
O1—C1	1.223 (2)	C10—C11	1.384 (3)
O2—C9	1.365 (2)	C11—C12	1.383 (3)
O2—H2	0.8200	C11—H11	0.9300
C1—C2	1.531 (3)	C12—C13	1.384 (3)
C2—C3	1.466 (3)	C12—C15	1.511 (3)
C3—C8	1.383 (3)	C13—C14	1.381 (3)
C3—C4	1.398 (3)	C13—H13	0.9300
C4—C5	1.372 (3)	C14—H14	0.9300
C5—C6	1.379 (3)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.383 (3)	C15—H15C	0.9600
C6—H6	0.9300

C1—N1—C4	112.15 (16)	C3—C8—H8	120.7
C1—N1—H1	123.9	C7—C8—H8	120.7
C4—N1—H1	123.9	O2—C9—C14	123.33 (19)
C2—N2—C10	120.77 (17)	O2—C9—C10	117.30 (17)
C9—O2—H2	109.5	C14—C9—C10	119.36 (19)
O1—C1—N1	126.19 (18)	C11—C10—C9	119.46 (18)
O1—C1—C2	128.17 (17)	C11—C10—N2	120.89 (19)
N1—C1—C2	105.61 (16)	C9—C10—N2	119.23 (17)
N2—C2—C3	135.01 (18)	C12—C11—C10	121.9 (2)
N2—C2—C1	119.12 (17)	C12—C11—H11	119.1
C3—C2—C1	105.61 (15)	C10—C11—H11	119.1
C8—C3—C4	119.07 (19)	C11—C12—C13	117.6 (2)
C8—C3—C2	134.48 (18)	C11—C12—C15	120.7 (2)
C4—C3—C2	106.45 (16)	C13—C12—C15	121.7 (2)
C5—C4—C3	122.87 (19)	C14—C13—C12	121.5 (2)
C5—C4—N1	127.13 (18)	C14—C13—H13	119.2
C3—C4—N1	109.99 (17)	C12—C13—H13	119.2
C4—C5—C6	116.9 (2)	C9—C14—C13	120.2 (2)
C4—C5—H5	121.5	C9—C14—H14	119.9
C6—C5—H5	121.5	C13—C14—H14	119.9
C5—C6—C7	121.6 (2)	C12—C15—H15A	109.5
C5—C6—H6	119.2	C12—C15—H15B	109.5
C7—C6—H6	119.2	H15A—C15—H15B	109.5
C6—C7—C8	120.9 (2)	C12—C15—H15C	109.5
C6—C7—H7	119.6	H15A—C15—H15C	109.5
C8—C7—H7	119.6	H15B—C15—H15C	109.5
C3—C8—C7	118.6 (2)

C4—N1—C1—O1	−177.50 (18)	C4—C5—C6—C7	−0.2 (3)
C4—N1—C1—C2	4.1 (2)	C5—C6—C7—C8	0.0 (4)
C10—N2—C2—C3	−4.0 (3)	C4—C3—C8—C7	0.9 (3)
C10—N2—C2—C1	−177.06 (16)	C2—C3—C8—C7	−178.5 (2)
O1—C1—C2—N2	−7.8 (3)	C6—C7—C8—C3	−0.4 (4)
N1—C1—C2—N2	170.58 (17)	O2—C9—C10—C11	177.98 (17)
O1—C1—C2—C3	177.25 (18)	C14—C9—C10—C11	−1.3 (3)
N1—C1—C2—C3	−4.36 (19)	O2—C9—C10—N2	−9.3 (3)
N2—C2—C3—C8	8.8 (4)	C14—C9—C10—N2	171.34 (18)
C1—C2—C3—C8	−177.5 (2)	C2—N2—C10—C11	−82.8 (2)
N2—C2—C3—C4	−170.7 (2)	C2—N2—C10—C9	104.6 (2)
C1—C2—C3—C4	3.1 (2)	C9—C10—C11—C12	0.7 (3)
C8—C3—C4—C5	−1.1 (3)	N2—C10—C11—C12	−171.90 (19)
C2—C3—C4—C5	178.45 (18)	C10—C11—C12—C13	0.2 (3)
C8—C3—C4—N1	179.66 (17)	C10—C11—C12—C15	179.0 (2)
C2—C3—C4—N1	−0.8 (2)	C11—C12—C13—C14	−0.4 (3)
C1—N1—C4—C5	178.56 (19)	C15—C12—C13—C14	−179.1 (2)
C1—N1—C4—C3	−2.2 (2)	O2—C9—C14—C13	−178.12 (19)
C3—C4—C5—C6	0.7 (3)	C10—C9—C14—C13	1.2 (3)
N1—C4—C5—C6	179.83 (19)	C12—C13—C14—C9	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.86	2.6729 (19)	169
N1—H1···O2ⁱⁱ	0.86	2.06	2.842 (2)	151

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O₂
M_r	252.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.6211 (11), 8.7100 (7), 11.2835 (10)
β (°)	90.780 (1)
V (Å³)	1240.28 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.47 × 0.17

Data collection
Diffractometer	CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.956, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	5982, 2182, 1449
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.114, 1.02
No. of reflections	2182
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

N2—C2	1.270 (2)	C2—C3	1.466 (3)
N2—C10	1.427 (2)	C9—C10	1.390 (3)
C1—C2	1.531 (3)	C10—C11	1.384 (3)

C2—N2—C10	120.77 (17)	O2—C9—C10	117.30 (17)
N2—C2—C3	135.01 (18)	C11—C10—N2	120.89 (19)
N2—C2—C1	119.12 (17)	C9—C10—N2	119.23 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.86	2.6729 (19)	168.8
N1—H1···O2ⁱⁱ	0.86	2.06	2.842 (2)	150.7

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1.

Acknowledgements

The authors acknowledge the National Science Foundation of China for its financial support of this project (project No. 21071134).

References

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