Literature DB >> 23795078

4-[(E)-(4-Eth-oxy-benzyl-idene)amino]-phenol.

Narissara Kaewmanee¹, Suchada Chantrapromma, Nawong Boonnak, Hoong-Kun Fun.

Abstract

The mol-ecule of the title compound, C15H15NO2, adopts a trans conformation with respect to the methyl-idene C=N bond and is twisted with a dihedral angle of 26.31 (5)° between the two substituted benzene rings. The eth-oxy group is almost coplanar with the bound benzene ring with a C-O-C-C torsion angle of -179.08 (9)°. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds and weak C-H⋯O inter-actions into chains propagating in the [011] and [01-1] directions. C-H⋯π inter-actions are also present.

Entities: Chemical Disease Gene Species

Year: 2013 PMID： 23795078 PMCID： PMC3685059 DOI： 10.1107/S1600536813012580

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For background to and applications of aza-stilbene, see: Cheng et al. (2010 ▶); da Silva et al. (2011 ▶); Kabir et al. (2008 ▶); Lu et al. (2012 ▶); Pavan et al. (2011 ▶). For related structures, see: Sun et al. (2011 ▶); Wang (2009 ▶).

Experimental

Crystal data

C15H15NO2 M = 241.28 Orthorhombic, a = 18.6882 (11) Å b = 10.7420 (6) Å c = 6.3186 (4) Å V = 1268.45 (13) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 100 K 0.59 × 0.27 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.952, T max = 0.979 16922 measured reflections 2382 independent reflections 2319 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.086 S = 1.10 2382 reflections 168 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.35 e Å−3 Δρmin = −0.19 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2009 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012580/rz5061sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012580/rz5061Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813012580/rz5061Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₅NO₂	D_x = 1.263 Mg m⁻³
M_r = 241.28	Melting point = 470–472 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2382 reflections
a = 18.6882 (11) Å	θ = 2.2–32.0°
b = 10.7420 (6) Å	µ = 0.08 mm⁻¹
c = 6.3186 (4) Å	T = 100 K
V = 1268.45 (13) Å³	Block, colourless
Z = 4	0.59 × 0.27 × 0.25 mm
F(000) = 512

Bruker SMART APEXII CCD area-detector diffractometer	2382 independent reflections
Radiation source: fine-focus sealed tube	2319 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 8.33 pixels mm^-1	θ_max = 32.0°, θ_min = 2.2°
ω scans	h = −27→27
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −16→15
T_min = 0.952, T_max = 0.979	l = −9→9
16922 measured reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0562P)² + 0.1397P] where P = (F_o² + 2F_c²)/3
2382 reflections	(Δ/σ)_max = 0.001
168 parameters	Δρ_max = 0.35 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Experimental. The data was collected with the Oxford Cryosystem 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	U_iso*/U_eq
O1	1.07262 (4)	0.90374 (7)	0.65280 (16)	0.02092 (17)
O2	0.68429 (4)	0.01683 (7)	0.72655 (13)	0.01662 (15)
H1O2	0.6732 (11)	0.000 (2)	0.851 (4)	0.038 (5)*
N1	0.85372 (4)	0.43914 (7)	0.61658 (15)	0.01367 (16)
C1	0.93803 (5)	0.59761 (9)	0.72367 (18)	0.01420 (18)
C2	0.97668 (5)	0.64779 (9)	0.89339 (19)	0.01686 (19)
H2A	0.9725	0.6113	1.0298	0.020*
C3	1.02104 (6)	0.75025 (10)	0.86479 (19)	0.0181 (2)
H3A	1.0468	0.7835	0.9813	0.022*
C4	1.02770 (5)	0.80430 (9)	0.66463 (19)	0.01595 (19)
C5	0.98933 (6)	0.75587 (10)	0.49369 (19)	0.01789 (19)
H5A	0.9934	0.7928	0.3576	0.021*
C6	0.94517 (6)	0.65320 (10)	0.52393 (19)	0.01713 (19)
H6A	0.9194	0.6201	0.4072	0.021*
C7	0.89365 (5)	0.48741 (8)	0.76077 (17)	0.01413 (18)
H7A	0.8944	0.4500	0.8970	0.017*
C8	0.81221 (5)	0.33104 (9)	0.65972 (16)	0.01283 (17)
C9	0.78245 (5)	0.30394 (9)	0.85792 (16)	0.01439 (18)
H9A	0.7915	0.3572	0.9750	0.017*
C10	0.73949 (5)	0.19880 (9)	0.88339 (16)	0.01468 (17)
H10A	0.7190	0.1811	1.0176	0.018*
C11	0.72652 (5)	0.11939 (8)	0.71249 (17)	0.01325 (17)
C12	0.75683 (6)	0.14583 (9)	0.51485 (17)	0.01527 (18)
H12A	0.7489	0.0913	0.3988	0.018*
C13	0.79848 (5)	0.25179 (9)	0.48866 (16)	0.01442 (17)
H13A	0.8178	0.2707	0.3534	0.017*
C14	1.08402 (6)	0.95958 (10)	0.4482 (2)	0.0215 (2)
H14A	1.0383	0.9914	0.3904	0.026*
H14B	1.1037	0.8975	0.3482	0.026*
C15	1.13632 (6)	1.06515 (11)	0.4787 (3)	0.0285 (3)
H15A	1.1448	1.1065	0.3427	0.043*
H15B	1.1816	1.0323	0.5335	0.043*
H15C	1.1165	1.1253	0.5795	0.043*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0213 (3)	0.0180 (3)	0.0234 (4)	−0.0072 (3)	−0.0018 (3)	−0.0007 (3)
O2	0.0230 (3)	0.0138 (3)	0.0131 (3)	−0.0056 (2)	0.0018 (3)	−0.0011 (3)
N1	0.0156 (3)	0.0116 (3)	0.0138 (4)	−0.0003 (3)	0.0002 (3)	0.0000 (3)
C1	0.0144 (4)	0.0133 (3)	0.0148 (4)	−0.0003 (3)	−0.0007 (3)	−0.0011 (3)
C2	0.0177 (4)	0.0183 (4)	0.0146 (4)	−0.0008 (3)	−0.0029 (4)	−0.0003 (4)
C3	0.0174 (4)	0.0193 (4)	0.0176 (5)	−0.0023 (3)	−0.0036 (4)	−0.0023 (4)
C4	0.0146 (4)	0.0140 (4)	0.0193 (5)	−0.0013 (3)	−0.0018 (4)	−0.0007 (4)
C5	0.0199 (4)	0.0175 (4)	0.0162 (5)	−0.0045 (3)	−0.0025 (4)	0.0009 (4)
C6	0.0188 (4)	0.0176 (4)	0.0150 (4)	−0.0044 (3)	−0.0017 (4)	−0.0002 (4)
C7	0.0153 (4)	0.0132 (4)	0.0139 (4)	−0.0001 (3)	0.0000 (3)	−0.0002 (3)
C8	0.0144 (3)	0.0114 (3)	0.0126 (4)	0.0002 (3)	−0.0005 (3)	0.0001 (3)
C9	0.0184 (4)	0.0128 (4)	0.0119 (4)	−0.0005 (3)	0.0006 (3)	−0.0015 (3)
C10	0.0192 (4)	0.0137 (4)	0.0111 (4)	−0.0010 (3)	0.0012 (4)	−0.0007 (3)
C11	0.0161 (4)	0.0113 (3)	0.0123 (4)	−0.0001 (3)	0.0005 (3)	−0.0001 (3)
C12	0.0196 (4)	0.0143 (4)	0.0119 (4)	−0.0018 (3)	0.0011 (4)	−0.0015 (3)
C13	0.0181 (4)	0.0146 (4)	0.0106 (4)	−0.0011 (3)	0.0009 (4)	−0.0010 (3)
C14	0.0199 (4)	0.0176 (4)	0.0269 (6)	−0.0038 (3)	−0.0014 (4)	0.0044 (4)
C15	0.0236 (5)	0.0201 (5)	0.0420 (8)	−0.0071 (4)	0.0000 (5)	0.0019 (5)

O1—C4	1.3605 (11)	C7—H7A	0.9500
O1—C14	1.4412 (16)	C8—C13	1.3996 (14)
O2—C11	1.3581 (11)	C8—C9	1.4009 (14)
O2—H1O2	0.83 (3)	C9—C10	1.3951 (13)
N1—C7	1.2867 (13)	C9—H9A	0.9500
N1—C8	1.4228 (12)	C10—C11	1.3973 (14)
C1—C2	1.4008 (15)	C10—H10A	0.9500
C1—C6	1.4026 (16)	C11—C12	1.4004 (15)
C1—C7	1.4643 (13)	C12—C13	1.3887 (13)
C2—C3	1.3898 (14)	C12—H12A	0.9500
C2—H2A	0.9500	C13—H13A	0.9500
C3—C4	1.3972 (16)	C14—C15	1.5094 (15)
C3—H3A	0.9500	C14—H14A	0.9900
C4—C5	1.3970 (15)	C14—H14B	0.9900
C5—C6	1.3906 (14)	C15—H15A	0.9800
C5—H5A	0.9500	C15—H15B	0.9800
C6—H6A	0.9500	C15—H15C	0.9800

C4—O1—C14	117.86 (9)	C10—C9—C8	119.99 (9)
C11—O2—H1O2	112.7 (15)	C10—C9—H9A	120.0
C7—N1—C8	120.62 (9)	C8—C9—H9A	120.0
C2—C1—C6	118.43 (9)	C9—C10—C11	120.33 (9)
C2—C1—C7	118.72 (10)	C9—C10—H10A	119.8
C6—C1—C7	122.83 (9)	C11—C10—H10A	119.8
C3—C2—C1	120.85 (11)	O2—C11—C10	123.06 (9)
C3—C2—H2A	119.6	O2—C11—C12	117.25 (9)
C1—C2—H2A	119.6	C10—C11—C12	119.68 (9)
C2—C3—C4	120.00 (10)	C13—C12—C11	119.95 (9)
C2—C3—H3A	120.0	C13—C12—H12A	120.0
C4—C3—H3A	120.0	C11—C12—H12A	120.0
O1—C4—C5	124.52 (10)	C12—C13—C8	120.62 (9)
O1—C4—C3	115.52 (9)	C12—C13—H13A	119.7
C5—C4—C3	119.96 (9)	C8—C13—H13A	119.7
C6—C5—C4	119.59 (10)	O1—C14—C15	107.10 (11)
C6—C5—H5A	120.2	O1—C14—H14A	110.3
C4—C5—H5A	120.2	C15—C14—H14A	110.3
C5—C6—C1	121.18 (10)	O1—C14—H14B	110.3
C5—C6—H6A	119.4	C15—C14—H14B	110.3
C1—C6—H6A	119.4	H14A—C14—H14B	108.5
N1—C7—C1	122.74 (9)	C14—C15—H15A	109.5
N1—C7—H7A	118.6	C14—C15—H15B	109.5
C1—C7—H7A	118.6	H15A—C15—H15B	109.5
C13—C8—C9	119.41 (9)	C14—C15—H15C	109.5
C13—C8—N1	116.65 (9)	H15A—C15—H15C	109.5
C9—C8—N1	123.87 (9)	H15B—C15—H15C	109.5

C6—C1—C2—C3	0.01 (15)	C6—C1—C7—N1	−5.42 (15)
C7—C1—C2—C3	178.24 (9)	C7—N1—C8—C13	−150.56 (9)
C1—C2—C3—C4	−0.20 (15)	C7—N1—C8—C9	32.46 (13)
C14—O1—C4—C5	−2.99 (14)	C13—C8—C9—C10	−0.07 (14)
C14—O1—C4—C3	177.23 (9)	N1—C8—C9—C10	176.84 (9)
C2—C3—C4—O1	−179.72 (9)	C8—C9—C10—C11	0.67 (14)
C2—C3—C4—C5	0.48 (15)	C9—C10—C11—O2	−178.92 (9)
O1—C4—C5—C6	179.64 (9)	C9—C10—C11—C12	−0.06 (15)
C3—C4—C5—C6	−0.58 (16)	O2—C11—C12—C13	177.76 (9)
C4—C5—C6—C1	0.40 (16)	C10—C11—C12—C13	−1.16 (15)
C2—C1—C6—C5	−0.12 (15)	C11—C12—C13—C8	1.78 (15)
C7—C1—C6—C5	−178.27 (9)	C9—C8—C13—C12	−1.16 (14)
C8—N1—C7—C1	179.23 (8)	N1—C8—C13—C12	−178.29 (9)
C2—C1—C7—N1	176.43 (9)	C4—O1—C14—C15	−179.08 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1ⁱ	0.83 (2)	1.87 (2)	2.6971 (12)	172 (2)
C6—H6A···O2ⁱⁱ	0.95	2.51	3.3956 (14)	156
C9—H9A···O2ⁱⁱⁱ	0.95	2.38	3.3229 (13)	171
C14—H14B···Cg1^iv	0.99	2.90	3.7668 (12)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N1ⁱ	0.83 (2)	1.87 (2)	2.6971 (12)	172 (2)
C6—H6A⋯O2ⁱⁱ	0.95	2.51	3.3956 (14)	156
C9—H9A⋯O2ⁱⁱⁱ	0.95	2.38	3.3229 (13)	171
C14—H14B⋯Cg1^iv	0.99	2.90	3.7668 (12)	147

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

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5. 4-(2,3,4-Trimeth-oxy-6-methyl-benzyl-idene-amino)phenol.

Authors: Cheng-Yun Wang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-03-11

6. 4-[(E)-(4-Fluoro-benzyl-idene)amino]-phenol.

Authors: Li-Xia Sun; Yun-Dan Yu; Guo-Ying Wei
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-06-04

7. Synthesis and Anti-Mycobacterium tuberculosis Evaluation of Aza-Stilbene Derivatives.

Authors: Fernando R Pavan; Gustavo Senra G de Carvalho; Adilson D da Silva; Clarice Q F Leite
Journal: ScientificWorldJournal Date: 2011-05-26

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Authors: Anthony L Spek
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Authors: M Shahjahan Kabir; Kathleen Engelbrecht; Rebecca Polanowski; Sarah M Krueger; Rachel Ignasiak; Marc Rott; William R Schwan; Mary E Stemper; Kurt D Reed; David Sherman; James M Cook; Aaron Monte
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9 in total

2 in total

1. Crystal structure of (E)-2-hy-droxy-4'-meth-oxy-aza-stilbene.

Authors: Suchada Chantrapromma; Narissara Kaewmanee; Nawong Boonnak; Kan Chantrapromma; Hazem A Ghabbour; Hoong-Kun Fun
Journal: Acta Crystallogr E Crystallogr Commun Date: 2015-05-07

2. (E)-2-[(2,4,6-Tri-meth-oxy-benzyl-idene)amino]-phenol.

Authors: Narissara Kaewmanee; Suchada Chantrapromma; Nawong Boonnak; Ching Kheng Quah; Hoong-Kun Fun
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2013-12-14

2 in total