(E)-3-(2-Hy-droxy-5-methyl-phenyl-imino)-indolin-2-one.

In the title compound, C(15)H(12)N(2)O(2), 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 = 252.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.114

S = 1.02

2182 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034015/ru2008sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811034015/ru2008Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12N2O2	F(000) = 528
Mr = 252.27	Dx = 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

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

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(Fo2) + (0.0486P)2 + 0.3363P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2182 reflections	Δρmax = 0.16 e Å−3
173 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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.

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) ; (ii) .