2-Amino-N-(2-hydr-oxy-3-methoxy-benzyl-idene)aniline.

In the title compound, C(14)H(14)N(2)O(2), the dihedral angle between the two benzene rings is 9.67 (10)°. Two intra-molecular O-H⋯N and N-H⋯N hydrogen bonds involving the hydr-oxy and amino groups generate S(6) and S(5) ring motifs, respectively. In the crystal structure, N-H⋯O hydrogen bonds link neighboring mol-ecules. Mol-ecules are also stacked in a head-to-tail fashion along the c axis through π-π inter-actions [centroid-centroid separation of 3.7357 (12) Å] and are further linked by weak inter-molecular C-H⋯π inter-actions, giving a zigzag arrangement along the b axis.

Related literature

For related literature on hydrogen bond motifs, see: Bernstein et al. (1995 ▶). For values of bond lengths, see: Allen et al. (1987 ▶). For the biological activity of imines, see, for example: Singh & Dash (1988 ▶); More et al. (2001 ▶); Baseer et al. (2000 ▶); El-Masry et al. (2000 ▶); Kabeer et al. (2001 ▶); Kuz’min et al. (2000 ▶); Desai et al. (2001 ▶). For related structures, see, for example: Corden et al. (1996 ▶); Govindasamy et al. (1999 ▶). For synthesis, see: Al-Douh et al. (2006 ▶, 2007 ▶). For related literature, see: Berger (2001 ▶); Elerman & Kabak (1997 ▶); Latif et al. (1983 ▶); Liu et al. (2006 ▶); Shah et al. (2008 ▶).

Experimental

Crystal data

C14H14N2O2

M = 242.27

Monoclinic,

a = 13.2790 (6) Å

b = 14.4810 (6) Å

c = 6.1928 (3) Å

β = 103.116 (3)°

V = 1159.77 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100.0 (1) K

0.45 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.959, T max = 0.996

19968 measured reflections

3402 independent reflections

2532 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.206

S = 1.06

3402 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016292/sj2510sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016292/sj2510Isup2.hkl

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

C14H14N2O2	F000 = 512
Mr = 242.27	Dx = 1.388 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4220 reflections
a = 13.2790 (6) Å	θ = 2.8–29.4º
b = 14.4810 (6) Å	µ = 0.09 mm−1
c = 6.1928 (3) Å	T = 100.0 (1) K
β = 103.116 (3)º	Needle, yellow
V = 1159.77 (9) Å3	0.45 × 0.15 × 0.05 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3402 independent reflections
Radiation source: fine-focus sealed tube	2532 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.052
T = 100.0(1) K	θmax = 30.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −18→18
Tmin = 0.959, Tmax = 0.996	k = −20→20
19968 measured reflections	l = −8→8

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)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.206	w = 1/[σ2(Fo2) + (0.099P)2 + 1.0519P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3402 reflections	Δρmax = 0.66 e Å−3
194 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O1	0.12067 (11)	1.03082 (11)	0.3256 (2)	0.0223 (4)
H1O1	0.1550	1.0024	0.2388	0.027*
O2	0.07156 (12)	1.12650 (11)	0.6488 (3)	0.0227 (4)
N1	0.26011 (14)	0.97668 (12)	0.1182 (3)	0.0184 (4)
N2	0.10257 (15)	0.90586 (15)	−0.2092 (3)	0.0251 (4)
H1N2	0.058 (2)	0.909 (2)	−0.349 (5)	0.030*
H2N2	0.110 (2)	0.954 (2)	−0.124 (5)	0.030*
C1	0.20451 (16)	0.89186 (15)	−0.2205 (3)	0.0192 (4)
C2	0.22641 (18)	0.83919 (16)	−0.3939 (4)	0.0225 (4)
H2	0.165 (2)	0.8218 (19)	−0.497 (5)	0.027*
C3	0.32708 (19)	0.82255 (14)	−0.4076 (4)	0.0219 (5)
H3	0.339 (2)	0.7874 (19)	−0.528 (5)	0.026*
C4	0.40918 (18)	0.85597 (15)	−0.2452 (4)	0.0216 (4)
H4	0.477 (2)	0.8429 (19)	−0.253 (4)	0.026*
C5	0.38917 (17)	0.90701 (14)	−0.0713 (4)	0.0196 (4)
H5	0.447 (2)	0.9297 (18)	0.037 (5)	0.024*
C6	0.28785 (16)	0.92618 (14)	−0.0560 (3)	0.0168 (4)
C7	0.32762 (16)	1.02164 (14)	0.2604 (3)	0.0192 (4)
H7	0.403 (2)	1.0240 (18)	0.247 (4)	0.023*
C8	0.30011 (16)	1.07288 (14)	0.4405 (3)	0.0174 (4)
C9	0.37772 (17)	1.11996 (14)	0.5926 (4)	0.0195 (4)
H9	0.449 (2)	1.1215 (18)	0.569 (4)	0.023*
C10	0.35346 (17)	1.16977 (14)	0.7632 (4)	0.0196 (4)
H10	0.407 (2)	1.2018 (18)	0.862 (5)	0.024*
C11	0.25165 (17)	1.17414 (14)	0.7875 (3)	0.0189 (4)
H11	0.238 (2)	1.2072 (18)	0.902 (5)	0.023*
C12	0.17424 (16)	1.12778 (14)	0.6423 (3)	0.0177 (4)
C13	0.19759 (15)	1.07615 (14)	0.4659 (3)	0.0170 (4)
C14	0.04456 (18)	1.17522 (17)	0.8283 (4)	0.0263 (5)
H14A	0.0835	1.1510	0.9665	0.039*
H14B	−0.0280	1.1678	0.8209	0.039*
H14C	0.0600	1.2396	0.8181	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0173 (7)	0.0307 (8)	0.0180 (7)	−0.0022 (6)	0.0024 (6)	−0.0069 (6)
O2	0.0202 (8)	0.0294 (8)	0.0203 (7)	−0.0001 (6)	0.0081 (6)	−0.0067 (6)
N1	0.0189 (8)	0.0220 (9)	0.0144 (8)	0.0017 (7)	0.0042 (7)	0.0003 (6)
N2	0.0188 (9)	0.0345 (11)	0.0220 (10)	0.0020 (8)	0.0045 (8)	−0.0037 (8)
C1	0.0186 (10)	0.0229 (10)	0.0166 (9)	0.0026 (7)	0.0052 (8)	0.0020 (8)
C2	0.0253 (11)	0.0247 (10)	0.0156 (10)	−0.0014 (8)	0.0009 (8)	−0.0010 (8)
C3	0.0354 (12)	0.0175 (10)	0.0149 (9)	0.0024 (8)	0.0103 (9)	−0.0014 (7)
C4	0.0214 (10)	0.0217 (10)	0.0245 (11)	0.0023 (8)	0.0110 (9)	0.0031 (8)
C5	0.0182 (10)	0.0201 (9)	0.0196 (10)	−0.0015 (8)	0.0026 (8)	0.0005 (8)
C6	0.0219 (10)	0.0163 (9)	0.0126 (9)	0.0008 (7)	0.0045 (7)	0.0003 (7)
C7	0.0203 (10)	0.0207 (10)	0.0174 (10)	0.0007 (8)	0.0056 (8)	0.0022 (7)
C8	0.0200 (10)	0.0176 (9)	0.0154 (9)	0.0026 (7)	0.0054 (7)	0.0014 (7)
C9	0.0171 (10)	0.0220 (10)	0.0195 (10)	0.0003 (8)	0.0042 (8)	0.0032 (8)
C10	0.0205 (10)	0.0195 (9)	0.0168 (10)	−0.0020 (8)	0.0000 (8)	0.0002 (8)
C11	0.0258 (11)	0.0175 (9)	0.0139 (9)	0.0013 (8)	0.0055 (8)	−0.0014 (7)
C12	0.0165 (9)	0.0211 (9)	0.0161 (9)	0.0027 (7)	0.0049 (7)	0.0019 (7)
C13	0.0178 (10)	0.0188 (9)	0.0130 (9)	−0.0004 (7)	0.0003 (7)	0.0006 (7)
C14	0.0252 (11)	0.0362 (13)	0.0194 (11)	0.0023 (9)	0.0095 (9)	−0.0055 (9)

O1—C13	1.351 (2)	C5—C6	1.398 (3)
O1—H1O1	0.8812	C5—H5	0.95 (3)
O2—C12	1.373 (2)	C7—C8	1.454 (3)
O2—C14	1.429 (3)	C7—H7	1.03 (3)
N1—C7	1.282 (3)	C8—C9	1.405 (3)
N1—C6	1.419 (3)	C8—C13	1.406 (3)
N2—C1	1.386 (3)	C9—C10	1.376 (3)
N2—H1N2	0.93 (3)	C9—H9	1.00 (3)
N2—H2N2	0.86 (3)	C10—C11	1.395 (3)
C1—C2	1.400 (3)	C10—H10	0.95 (3)
C1—C6	1.413 (3)	C11—C12	1.377 (3)
C2—C3	1.380 (3)	C11—H11	0.91 (3)
C2—H2	0.94 (3)	C12—C13	1.415 (3)
C3—C4	1.392 (3)	C14—H14A	0.9600
C3—H3	0.95 (3)	C14—H14B	0.9600
C4—C5	1.381 (3)	C14—H14C	0.9600
C4—H4	0.94 (3)
C13—O1—H1O1	101.4	C8—C7—H7	117.8 (15)
C12—O2—C14	116.25 (17)	C9—C8—C13	119.34 (18)
C7—N1—C6	121.47 (18)	C9—C8—C7	119.24 (19)
C1—N2—H1N2	112.5 (18)	C13—C8—C7	121.42 (19)
C1—N2—H2N2	100 (2)	C10—C9—C8	120.3 (2)
H1N2—N2—H2N2	119 (3)	C10—C9—H9	119.9 (15)
N2—C1—C2	119.6 (2)	C8—C9—H9	119.5 (15)
N2—C1—C6	121.74 (19)	C9—C10—C11	120.5 (2)
C2—C1—C6	118.64 (19)	C9—C10—H10	118.3 (16)
C3—C2—C1	121.0 (2)	C11—C10—H10	121.2 (16)
C3—C2—H2	127.5 (17)	C12—C11—C10	120.37 (19)
C1—C2—H2	111.4 (17)	C12—C11—H11	121.2 (17)
C2—C3—C4	120.38 (19)	C10—C11—H11	118.4 (17)
C2—C3—H3	118.6 (16)	O2—C12—C11	125.89 (18)
C4—C3—H3	121.0 (17)	O2—C12—C13	114.12 (18)
C5—C4—C3	119.5 (2)	C11—C12—C13	119.99 (19)
C5—C4—H4	120.7 (17)	O1—C13—C8	121.42 (18)
C3—C4—H4	119.9 (17)	O1—C13—C12	119.14 (18)
C4—C5—C6	121.2 (2)	C8—C13—C12	119.44 (18)
C4—C5—H5	117.7 (17)	O2—C14—H14A	109.5
C6—C5—H5	121.1 (16)	O2—C14—H14B	109.5
C5—C6—C1	119.32 (18)	H14A—C14—H14B	109.5
C5—C6—N1	124.99 (19)	O2—C14—H14C	109.5
C1—C6—N1	115.67 (18)	H14A—C14—H14C	109.5
N1—C7—C8	121.86 (19)	H14B—C14—H14C	109.5
N1—C7—H7	120.3 (15)
N2—C1—C2—C3	−178.8 (2)	C13—C8—C9—C10	−0.8 (3)
C6—C1—C2—C3	−1.4 (3)	C7—C8—C9—C10	179.32 (19)
C1—C2—C3—C4	1.7 (3)	C8—C9—C10—C11	0.0 (3)
C2—C3—C4—C5	−0.8 (3)	C9—C10—C11—C12	0.7 (3)
C3—C4—C5—C6	−0.4 (3)	C14—O2—C12—C11	−2.4 (3)
C4—C5—C6—C1	0.6 (3)	C14—O2—C12—C13	178.04 (18)
C4—C5—C6—N1	178.96 (19)	C10—C11—C12—O2	179.84 (19)
N2—C1—C6—C5	177.56 (19)	C10—C11—C12—C13	−0.7 (3)
C2—C1—C6—C5	0.2 (3)	C9—C8—C13—O1	−179.00 (18)
N2—C1—C6—N1	−0.9 (3)	C7—C8—C13—O1	0.9 (3)
C2—C1—C6—N1	−178.23 (19)	C9—C8—C13—C12	0.9 (3)
C7—N1—C6—C5	11.1 (3)	C7—C8—C13—C12	−179.28 (18)
C7—N1—C6—C1	−170.51 (19)	O2—C12—C13—O1	−0.7 (3)
C6—N1—C7—C8	−179.44 (18)	C11—C12—C13—O1	179.74 (18)
N1—C7—C8—C9	179.29 (19)	O2—C12—C13—C8	179.42 (17)
N1—C7—C8—C13	−0.6 (3)	C11—C12—C13—C8	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.88	1.77	2.602 (2)	158
N2—H1N2···O1i	0.93 (3)	2.56 (3)	3.030 (3)	111 (2)
N2—H1N2···O2i	0.93 (3)	2.29 (3)	3.181 (3)	161 (3)
N2—H2N2···N1	0.87 (3)	2.23 (3)	2.759 (3)	119 (2)
C3—H3···Cg1ii	0.94 (3)	2.64 (3)	3.458 (2)	145 (2)
C11—H11···Cg2iii	0.91 (3)	2.87 (3)	3.538 (2)	142 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.88	1.77	2.602 (2)	158
N2—H1N2⋯O1i	0.93 (3)	2.56 (3)	3.030 (3)	111 (2)
N2—H1N2⋯O2i	0.93 (3)	2.29 (3)	3.181 (3)	161 (3)
N2—H2N2⋯N1	0.87 (3)	2.23 (3)	2.759 (3)	119 (2)
C3—H3⋯Cg1ii	0.94 (3)	2.64 (3)	3.458 (2)	145 (2)
C11—H11⋯Cg2iii	0.91 (3)	2.87 (3)	3.538 (2)	142 (2)

Symmetry codes: (i) ; (ii) ; (iii) .