4-[(E)-(4-Eth-oxy-phen-yl)imino-meth-yl]phenol.

In the title compound, C(15)H(15)NO(2), the dihedral angle between the benzene rings is 52.04 (5)° and the mol-ecule has an E conformation about the central C=N bond. In the crystal, mol-ecules are connected by O-H⋯N hydrogen bonds, forming zigzag chains along the b axis. The crystal packing also features weak C-H⋯O inter-actions.

Related literature

For Schiff base derivatives and related structures, see: Fejfarová et al. (2010 ▶); Özek et al. (2010 ▶); Akkurt et al. (2008 ▶); Khalaji et al. (2008 ▶, 2009 ▶) For applications and properties of Schiff bases, see: Dalapati et al. (2011 ▶); Keypour et al. (2010 ▶); Khalil et al. (2009 ▶); Khanmohammadi et al. (2009 ▶); Sun et al. (2012 ▶); Da Silva et al. (2011 ▶).

Experimental

Crystal data

C15H15NO2

M = 241.3

Orthorhombic,

a = 10.9155 (2) Å

b = 9.4056 (2) Å

c = 25.0422 (5) Å

V = 2571.00 (9) Å3

Z = 8

Cu Kα radiation

μ = 0.67 mm−1

T = 120 K

0.54 × 0.20 × 0.03 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.795, T max = 1

22644 measured reflections

1978 independent reflections

1780 reflections with I > 3σ(I)

R int = 0.028

θmax = 61.1°

Refinement

R[F 2 > 3σ(F 2)] = 0.031

wR(F 2) = 0.103

S = 1.71

1978 reflections

166 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.11 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034253/bt5991sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034253/bt5991Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034253/bt5991Isup3.cml

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

C15H15NO2	F(000) = 1024
Mr = 241.3	Dx = 1.246 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14821 reflections
a = 10.9155 (2) Å	θ = 3.5–61.1°
b = 9.4056 (2) Å	µ = 0.67 mm−1
c = 25.0422 (5) Å	T = 120 K
V = 2571.00 (9) Å3	Plate, light yellow
Z = 8	0.54 × 0.20 × 0.03 mm

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1978 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1780 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.028
Detector resolution: 10.3784 pixels mm-1	θmax = 61.1°, θmin = 3.5°
Rotation method data acquisition using ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→10
Tmin = 0.795, Tmax = 1	l = −28→27
22644 measured reflections

Refinement on F2	57 constraints
R[F2 > 2σ(F2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0025000002I2)
S = 1.71	(Δ/σ)max = 0.006
1978 reflections	Δρmax = 0.11 e Å−3
166 parameters	Δρmin = −0.11 e Å−3
0 restraints

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2011). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
O1	−0.08099 (8)	0.58106 (10)	0.55939 (4)	0.0344 (3)
O2	0.50129 (8)	−0.13939 (9)	0.85269 (3)	0.0251 (3)
N1	0.26997 (8)	0.30259 (10)	0.68326 (4)	0.0196 (3)
C1	0.18053 (10)	0.37189 (12)	0.65100 (4)	0.0200 (3)
C2	0.06035 (11)	0.32217 (13)	0.64660 (4)	0.0234 (4)
C3	−0.02398 (11)	0.39425 (13)	0.61577 (5)	0.0260 (4)
C4	0.00974 (12)	0.51683 (14)	0.58837 (4)	0.0259 (4)
C5	0.12999 (11)	0.56466 (13)	0.59109 (5)	0.0251 (4)
C6	0.21487 (11)	0.49095 (12)	0.62174 (5)	0.0228 (4)
C7	−0.04877 (15)	0.70560 (14)	0.52934 (5)	0.0357 (4)
C8	−0.16378 (16)	0.75963 (18)	0.50327 (7)	0.0509 (5)
C9	0.23493 (11)	0.24457 (11)	0.72715 (5)	0.0208 (4)
C10	0.42099 (10)	0.09397 (12)	0.74119 (5)	0.0198 (4)
C11	0.48630 (10)	−0.00196 (12)	0.77159 (4)	0.0199 (4)
C12	0.44379 (10)	−0.04176 (12)	0.82220 (4)	0.0205 (4)
C13	0.33635 (10)	0.01912 (12)	0.84201 (5)	0.0230 (4)
C14	0.27084 (11)	0.11386 (12)	0.81106 (4)	0.0228 (4)
C15	0.31179 (10)	0.15335 (12)	0.76005 (4)	0.0202 (4)
H2	0.036296	0.23732	0.665154	0.028*
H3	−0.106486	0.35958	0.613196	0.0313*
H5	0.154298	0.648332	0.571861	0.0301*
H6	0.298437	0.52267	0.622731	0.0273*
H7a	0.009871	0.680691	0.502344	0.0429*
H7b	−0.017107	0.776855	0.553066	0.0429*
H8a	−0.144624	0.840538	0.481436	0.0764*
H8b	−0.198521	0.686045	0.48144	0.0764*
H8c	−0.221636	0.786824	0.530273	0.0764*
H9	0.152732	0.262562	0.738996	0.0249*
H10	0.450945	0.120386	0.706538	0.0237*
H11	0.561133	−0.041581	0.758022	0.0239*
H13	0.308026	−0.0049	0.877165	0.0276*
H14	0.196003	0.153391	0.82466	0.0273*
H2o	0.5725 (16)	−0.1625 (16)	0.8374 (6)	0.0377*

	U11	U22	U33	U12	U13	U23
O1	0.0303 (5)	0.0399 (6)	0.0330 (5)	0.0097 (4)	−0.0083 (4)	0.0063 (4)
O2	0.0188 (5)	0.0286 (5)	0.0279 (5)	0.0040 (3)	0.0011 (3)	0.0074 (3)
N1	0.0168 (5)	0.0182 (5)	0.0238 (5)	−0.0005 (4)	−0.0022 (4)	−0.0012 (4)
C1	0.0181 (6)	0.0208 (6)	0.0210 (6)	0.0025 (4)	0.0003 (4)	−0.0033 (5)
C2	0.0218 (6)	0.0235 (7)	0.0248 (6)	−0.0005 (5)	−0.0009 (5)	−0.0002 (5)
C3	0.0180 (6)	0.0325 (7)	0.0277 (7)	0.0002 (5)	−0.0020 (5)	−0.0016 (5)
C4	0.0263 (7)	0.0303 (7)	0.0212 (6)	0.0081 (5)	−0.0028 (5)	−0.0019 (5)
C5	0.0281 (7)	0.0243 (6)	0.0229 (6)	0.0017 (5)	0.0022 (5)	0.0005 (5)
C6	0.0204 (6)	0.0238 (6)	0.0241 (6)	−0.0003 (5)	0.0014 (5)	−0.0020 (5)
C7	0.0496 (9)	0.0313 (7)	0.0262 (7)	0.0121 (6)	−0.0067 (6)	0.0008 (5)
C8	0.0644 (11)	0.0465 (9)	0.0418 (9)	0.0231 (8)	−0.0190 (8)	−0.0003 (7)
C9	0.0166 (6)	0.0199 (6)	0.0259 (7)	−0.0002 (4)	−0.0001 (5)	−0.0030 (5)
C10	0.0176 (6)	0.0207 (6)	0.0209 (6)	−0.0030 (4)	−0.0007 (4)	−0.0011 (4)
C11	0.0154 (6)	0.0205 (6)	0.0239 (6)	−0.0006 (4)	−0.0010 (4)	−0.0023 (5)
C12	0.0169 (6)	0.0196 (6)	0.0249 (6)	−0.0035 (4)	−0.0041 (4)	−0.0005 (5)
C13	0.0190 (6)	0.0271 (7)	0.0228 (6)	−0.0026 (5)	0.0014 (5)	0.0015 (5)
C14	0.0167 (6)	0.0248 (6)	0.0267 (6)	0.0005 (5)	0.0007 (5)	−0.0014 (5)
C15	0.0171 (6)	0.0193 (6)	0.0243 (6)	−0.0030 (4)	−0.0026 (5)	−0.0025 (5)

O1—C4	1.3684 (15)	C7—H7a	0.96
O1—C7	1.4360 (16)	C7—H7b	0.96
O2—C12	1.3492 (14)	C8—H8a	0.96
O2—H2o	0.894 (17)	C8—H8b	0.96
N1—C1	1.4250 (14)	C8—H8c	0.96
N1—C9	1.2853 (14)	C9—C15	1.4557 (16)
C1—C2	1.3971 (16)	C9—H9	0.96
C1—C6	1.3897 (16)	C10—C11	1.3791 (16)
C2—C3	1.3795 (17)	C10—C15	1.3985 (15)
C2—H2	0.96	C10—H10	0.96
C3—C4	1.3913 (17)	C11—C12	1.4006 (15)
C3—H3	0.96	C11—H11	0.96
C4—C5	1.3892 (17)	C12—C13	1.3961 (16)
C5—C6	1.3887 (16)	C13—C14	1.3807 (16)
C5—H5	0.96	C13—H13	0.96
C6—H6	0.96	C14—C15	1.4033 (16)
C7—C8	1.504 (2)	C14—H14	0.96
C4—O1—C7	117.43 (10)	C7—C8—H8a	109.47
C12—O2—H2o	109.1 (9)	C7—C8—H8b	109.47
C1—N1—C9	118.37 (9)	C7—C8—H8c	109.47
N1—C1—C2	122.33 (10)	H8a—C8—H8b	109.47
N1—C1—C6	118.86 (10)	H8a—C8—H8c	109.47
C2—C1—C6	118.78 (10)	H8b—C8—H8c	109.47
C1—C2—C3	120.40 (11)	N1—C9—C15	124.24 (10)
C1—C2—H2	119.8	N1—C9—H9	117.88
C3—C2—H2	119.8	C15—C9—H9	117.88
C2—C3—C4	120.45 (11)	C11—C10—C15	121.02 (10)
C2—C3—H3	119.77	C11—C10—H10	119.49
C4—C3—H3	119.77	C15—C10—H10	119.49
O1—C4—C3	115.84 (11)	C10—C11—C12	120.21 (10)
O1—C4—C5	124.54 (11)	C10—C11—H11	119.89
C3—C4—C5	119.61 (11)	C12—C11—H11	119.9
C4—C5—C6	119.73 (11)	O2—C12—C11	122.68 (10)
C4—C5—H5	120.14	O2—C12—C13	117.95 (10)
C6—C5—H5	120.14	C11—C12—C13	119.35 (10)
C1—C6—C5	120.91 (11)	C12—C13—C14	120.02 (11)
C1—C6—H6	119.54	C12—C13—H13	119.99
C5—C6—H6	119.54	C14—C13—H13	119.99
O1—C7—C8	107.38 (12)	C13—C14—C15	121.12 (10)
O1—C7—H7a	109.47	C13—C14—H14	119.44
O1—C7—H7b	109.47	C15—C14—H14	119.44
C8—C7—H7a	109.47	C9—C15—C10	122.37 (10)
C8—C7—H7b	109.47	C9—C15—C14	119.18 (10)
H7a—C7—H7b	111.48	C10—C15—C14	118.24 (10)
C4—O1—C7—C8	−177.51 (11)	N1—C9—C15—C10	−15.04 (18)
C9—N1—C1—C2	−35.10 (15)	N1—C9—C15—C14	170.16 (11)
C9—N1—C1—C6	146.67 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7b···O2i	0.96	2.50	3.3393 (15)	147
O2—H2o···N1ii	0.894 (17)	1.825 (17)	2.7098 (12)	170.0 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7b⋯O2i	0.96	2.50	3.3393 (15)	147
O2—H2o⋯N1ii	0.894 (17)	1.825 (17)	2.7098 (12)	170.0 (14)

Symmetry codes: (i) ; (ii) .