Literature DB >> 21754087

2-[N-(4-{4-[(E)-(2-Hydroxybenzyl-idene)amino]phenoxy}phenyl)carbox-imidoyl]phenol.

Gholam Hossein Shahverdizadeh, Edward R T Tiekink.

Abstract

The mol-ecular structure of the title Schiff base compound, C(26)H(20)N(2)O(3), shows that respective methyl-idene residues are almost coplanar with the adjacent terminal benzene ring owing to the presence of intra-molecular O-H⋯N hydrogen bonds [the N-C-C-C torsion angles are -6.6 (7) and -6.7 (7)°]. However, twists are exhibited about each methyl-idene and respective benzene ring connected to the central O atom; the dihedral angles formed between the two inner and two outer benzene rings are 54.6 (2) and 45.6 (3)°, respectively. The conformation about each of the C=N bonds [1.285 (5) and 1.295 (5) Å] is E. In the crystal, extensive C-H⋯π contacts involving all benzene rings results in the formation of layers in the ac plane.

Entities: Chemical Disease Gene

Year: 2011 PMID： 21754087 PMCID： PMC3100046 DOI： 10.1107/S1600536811007847

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

Related literature

For related structures of Schiff base ligands, see: Chu & Huang (2007 ▶); Xu et al. (2008 ▶); Prasath et al. (2010 ▶). For details of crystallization from a U-tube under non-ambient conditions, see: Harrowfield et al. (1996 ▶).

Experimental

Crystal data

C26H20N2O3 M = 408.44 Monoclinic, a = 6.0234 (9) Å b = 46.225 (7) Å c = 9.4371 (11) Å β = 129.636 (7)° V = 2023.5 (5) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 K 0.35 × 0.24 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.856, T max = 1.000 10647 measured reflections 3567 independent reflections 1468 reflections with I > 2σ(I) R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.069 wR(F 2) = 0.242 S = 1.05 3567 reflections 283 parameters H-atom parameters constrained Δρmax = 0.33 e Å−3 Δρmin = −0.31 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007847/hg5006sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007847/hg5006Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₆H₂₀N₂O₃	F(000) = 856
M_r = 408.44	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 806 reflections
a = 6.0234 (9) Å	θ = 2.6–20.9°
b = 46.225 (7) Å	µ = 0.09 mm⁻¹
c = 9.4371 (11) Å	T = 293 K
β = 129.636 (7)°	Prism, yellow
V = 2023.5 (5) Å³	0.35 × 0.24 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	3567 independent reflections
Radiation source: fine-focus sealed tube	1468 reflections with I > 2σ(I)
graphite	R_int = 0.089
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.856, T_max = 1.000	k = −54→31
10647 measured reflections	l = −11→11

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)] = 0.069	H-atom parameters constrained
wR(F²) = 0.242	w = 1/[σ²(F_o²) + (0.0859P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3567 reflections	Δρ_max = 0.33 e Å⁻³
283 parameters	Δρ_min = −0.31 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: 0.012 (2)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.9581 (7)	0.39134 (8)	0.7320 (5)	0.0577 (11)
H1o	0.8694	0.3762	0.7075	0.087*
O2	0.1380 (6)	0.24995 (7)	0.6475 (4)	0.0383 (9)
O3	0.7882 (8)	0.10965 (8)	0.5591 (5)	0.0560 (11)
H3o	0.7480	0.1245	0.5856	0.084*
N1	0.5304 (8)	0.35847 (8)	0.6345 (5)	0.0365 (10)
N2	0.5548 (8)	0.14148 (9)	0.6585 (5)	0.0384 (10)
C1	0.7827 (10)	0.41395 (11)	0.6882 (6)	0.0405 (13)
C2	0.4989 (10)	0.40991 (10)	0.6172 (6)	0.0339 (11)
C3	0.3264 (11)	0.43421 (11)	0.5699 (6)	0.0428 (13)
H3	0.1367	0.4318	0.5221	0.051*
C4	0.4323 (12)	0.46186 (11)	0.5928 (7)	0.0525 (15)
H4	0.3142	0.4779	0.5581	0.063*
C5	0.7160 (13)	0.46527 (12)	0.6678 (7)	0.0545 (15)
H5	0.7903	0.4838	0.6866	0.065*
C6	0.8909 (12)	0.44174 (12)	0.7155 (7)	0.0509 (15)
H6	1.0818	0.4444	0.7661	0.061*
C7	0.3857 (10)	0.38160 (10)	0.6009 (6)	0.0372 (12)
H7	0.2021	0.3800	0.5649	0.045*
C8	0.4255 (9)	0.33115 (10)	0.6359 (6)	0.0315 (11)
C9	0.4603 (9)	0.30768 (10)	0.5600 (6)	0.0339 (11)
H9	0.5465	0.3104	0.5071	0.041*
C10	0.3696 (10)	0.28052 (10)	0.5618 (6)	0.0366 (12)
H10	0.3878	0.2651	0.5067	0.044*
C11	0.2507 (9)	0.27635 (9)	0.6465 (6)	0.0322 (12)
C12	0.2179 (9)	0.29916 (10)	0.7254 (6)	0.0338 (12)
H12	0.1379	0.2962	0.7820	0.041*
C13	0.3047 (9)	0.32640 (10)	0.7197 (6)	0.0349 (12)
H13	0.2823	0.3419	0.7726	0.042*
C14	0.2517 (10)	0.22375 (10)	0.6487 (6)	0.0313 (12)
C15	0.5385 (10)	0.21951 (10)	0.7314 (6)	0.0377 (13)
H15	0.6668	0.2350	0.7849	0.045*
C16	0.6329 (10)	0.19221 (10)	0.7340 (6)	0.0352 (12)
H16	0.8251	0.1895	0.7878	0.042*
C17	0.4477 (9)	0.16882 (10)	0.6583 (6)	0.0339 (12)
C18	0.1595 (9)	0.17341 (10)	0.5739 (6)	0.0357 (12)
H18	0.0316	0.1579	0.5211	0.043*
C19	0.0608 (9)	0.20082 (10)	0.5677 (6)	0.0349 (12)
H19	−0.1331	0.2038	0.5092	0.042*
C20	0.4768 (10)	0.11806 (10)	0.6915 (6)	0.0389 (13)
H20	0.3650	0.1194	0.7276	0.047*
C21	0.5609 (9)	0.08991 (10)	0.6732 (6)	0.0348 (12)
C22	0.7033 (10)	0.08644 (11)	0.6017 (6)	0.0386 (12)
C23	0.7609 (11)	0.05915 (12)	0.5731 (7)	0.0485 (14)
H23	0.8522	0.0570	0.5231	0.058*
C24	0.6833 (11)	0.03516 (12)	0.6185 (7)	0.0555 (16)
H24	0.7213	0.0168	0.5983	0.067*
C25	0.5489 (12)	0.03808 (12)	0.6941 (7)	0.0549 (15)
H25	0.5031	0.0218	0.7284	0.066*
C26	0.4831 (11)	0.06532 (11)	0.7186 (6)	0.0443 (13)
H26	0.3868	0.0673	0.7652	0.053*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.046 (2)	0.053 (3)	0.078 (3)	0.0038 (19)	0.041 (2)	−0.001 (2)
O2	0.0476 (19)	0.0225 (19)	0.051 (2)	0.0009 (16)	0.0340 (18)	0.0014 (14)
O3	0.072 (3)	0.046 (3)	0.075 (3)	−0.003 (2)	0.059 (2)	−0.002 (2)
N1	0.043 (2)	0.031 (2)	0.036 (2)	−0.003 (2)	0.026 (2)	−0.0042 (18)
N2	0.036 (2)	0.034 (3)	0.038 (2)	−0.0007 (19)	0.020 (2)	−0.0003 (18)
C1	0.046 (3)	0.038 (3)	0.040 (3)	−0.002 (3)	0.029 (3)	−0.003 (2)
C2	0.036 (3)	0.029 (3)	0.036 (3)	−0.002 (2)	0.023 (2)	−0.001 (2)
C3	0.047 (3)	0.034 (3)	0.046 (3)	0.000 (3)	0.029 (3)	−0.001 (2)
C4	0.070 (4)	0.030 (3)	0.053 (4)	0.003 (3)	0.037 (3)	−0.002 (3)
C5	0.071 (4)	0.039 (4)	0.053 (4)	−0.021 (3)	0.039 (3)	−0.007 (3)
C6	0.054 (3)	0.051 (4)	0.053 (4)	−0.008 (3)	0.036 (3)	−0.001 (3)
C7	0.035 (3)	0.035 (3)	0.042 (3)	0.002 (2)	0.025 (2)	−0.002 (2)
C8	0.032 (3)	0.028 (3)	0.031 (3)	0.001 (2)	0.019 (2)	0.000 (2)
C9	0.040 (3)	0.033 (3)	0.036 (3)	0.000 (2)	0.027 (2)	−0.002 (2)
C10	0.048 (3)	0.029 (3)	0.039 (3)	0.006 (2)	0.031 (3)	0.000 (2)
C11	0.036 (3)	0.028 (3)	0.028 (3)	0.002 (2)	0.019 (2)	0.001 (2)
C12	0.037 (3)	0.034 (3)	0.034 (3)	0.003 (2)	0.025 (2)	−0.002 (2)
C13	0.044 (3)	0.028 (3)	0.036 (3)	0.002 (2)	0.027 (3)	−0.006 (2)
C14	0.038 (3)	0.027 (3)	0.032 (3)	0.002 (2)	0.024 (3)	0.001 (2)
C15	0.040 (3)	0.032 (3)	0.033 (3)	−0.005 (2)	0.019 (3)	−0.001 (2)
C16	0.032 (3)	0.029 (3)	0.037 (3)	−0.002 (2)	0.019 (2)	−0.002 (2)
C17	0.036 (3)	0.037 (3)	0.030 (3)	0.001 (2)	0.022 (2)	−0.001 (2)
C18	0.039 (3)	0.026 (3)	0.039 (3)	−0.006 (2)	0.023 (2)	−0.005 (2)
C19	0.032 (3)	0.036 (3)	0.034 (3)	−0.003 (2)	0.020 (2)	0.000 (2)
C20	0.044 (3)	0.036 (3)	0.039 (3)	−0.003 (3)	0.028 (3)	−0.001 (2)
C21	0.033 (3)	0.031 (3)	0.037 (3)	−0.001 (2)	0.020 (2)	−0.001 (2)
C22	0.039 (3)	0.032 (3)	0.041 (3)	0.002 (2)	0.024 (3)	0.000 (2)
C23	0.045 (3)	0.046 (4)	0.052 (4)	0.006 (3)	0.030 (3)	−0.003 (3)
C24	0.049 (3)	0.037 (4)	0.059 (4)	0.006 (3)	0.025 (3)	−0.005 (3)
C25	0.061 (4)	0.032 (3)	0.056 (4)	−0.002 (3)	0.030 (3)	0.008 (3)
C26	0.052 (3)	0.033 (3)	0.048 (3)	−0.003 (3)	0.032 (3)	0.005 (2)

O1—C1	1.350 (5)	C10—H10	0.9300
O1—H1o	0.8200	C11—C12	1.376 (6)
O2—C14	1.388 (5)	C12—C13	1.378 (6)
O2—C11	1.399 (5)	C12—H12	0.9300
O3—C22	1.356 (5)	C13—H13	0.9300
O3—H3o	0.8200	C14—C19	1.381 (6)
N1—C7	1.285 (5)	C14—C15	1.382 (6)
N1—C8	1.416 (6)	C15—C16	1.378 (6)
N2—C20	1.295 (5)	C15—H15	0.9300
N2—C17	1.418 (6)	C16—C17	1.381 (6)
C1—C6	1.388 (7)	C16—H16	0.9300
C1—C2	1.395 (6)	C17—C18	1.389 (6)
C2—C3	1.396 (6)	C18—C19	1.385 (6)
C2—C7	1.438 (6)	C18—H18	0.9300
C3—C4	1.383 (6)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.447 (6)
C4—C5	1.379 (7)	C20—H20	0.9300
C4—H4	0.9300	C21—C26	1.397 (6)
C5—C6	1.375 (7)	C21—C22	1.398 (7)
C5—H5	0.9300	C22—C23	1.380 (6)
C6—H6	0.9300	C23—C24	1.374 (7)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.387 (6)	C24—C25	1.386 (8)
C8—C13	1.392 (6)	C24—H24	0.9300
C9—C10	1.374 (6)	C25—C26	1.383 (7)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.385 (6)	C26—H26	0.9300

C1—O1—H1o	109.5	C12—C13—H13	119.5
C14—O2—C11	121.5 (4)	C8—C13—H13	119.5
C22—O3—H3o	109.5	C19—C14—C15	120.2 (4)
C7—N1—C8	120.5 (4)	C19—C14—O2	115.6 (4)
C20—N2—C17	120.7 (4)	C15—C14—O2	124.1 (4)
O1—C1—C6	118.5 (5)	C16—C15—C14	119.5 (5)
O1—C1—C2	121.6 (4)	C16—C15—H15	120.2
C6—C1—C2	120.0 (5)	C14—C15—H15	120.2
C1—C2—C3	118.7 (5)	C15—C16—C17	121.3 (4)
C1—C2—C7	121.7 (4)	C15—C16—H16	119.3
C3—C2—C7	119.5 (4)	C17—C16—H16	119.3
C4—C3—C2	121.3 (5)	C16—C17—C18	118.6 (5)
C4—C3—H3	119.4	C16—C17—N2	118.7 (4)
C2—C3—H3	119.4	C18—C17—N2	122.5 (4)
C5—C4—C3	118.9 (5)	C19—C18—C17	120.6 (4)
C5—C4—H4	120.6	C19—C18—H18	119.7
C3—C4—H4	120.6	C17—C18—H18	119.7
C6—C5—C4	121.1 (5)	C14—C19—C18	119.7 (4)
C6—C5—H5	119.4	C14—C19—H19	120.2
C4—C5—H5	119.4	C18—C19—H19	120.2
C5—C6—C1	120.0 (5)	N2—C20—C21	121.0 (5)
C5—C6—H6	120.0	N2—C20—H20	119.5
C1—C6—H6	120.0	C21—C20—H20	119.5
N1—C7—C2	122.0 (4)	C26—C21—C22	118.9 (5)
N1—C7—H7	119.0	C26—C21—C20	118.9 (5)
C2—C7—H7	119.0	C22—C21—C20	122.0 (4)
C9—C8—C13	118.4 (4)	O3—C22—C23	118.4 (5)
C9—C8—N1	118.5 (4)	O3—C22—C21	121.1 (4)
C13—C8—N1	122.9 (4)	C23—C22—C21	120.5 (5)
C10—C9—C8	121.1 (4)	C24—C23—C22	119.9 (5)
C10—C9—H9	119.5	C24—C23—H23	120.0
C8—C9—H9	119.5	C22—C23—H23	120.0
C9—C10—C11	119.4 (4)	C23—C24—C25	120.6 (5)
C9—C10—H10	120.3	C23—C24—H24	119.7
C11—C10—H10	120.3	C25—C24—H24	119.7
C12—C11—C10	120.7 (4)	C26—C25—C24	119.9 (5)
C12—C11—O2	115.3 (4)	C26—C25—H25	120.1
C10—C11—O2	123.8 (4)	C24—C25—H25	120.1
C11—C12—C13	119.4 (4)	C25—C26—C21	120.1 (5)
C11—C12—H12	120.3	C25—C26—H26	119.9
C13—C12—H12	120.3	C21—C26—H26	119.9
C12—C13—C8	121.0 (4)

O1—C1—C2—C3	−178.2 (4)	C11—O2—C14—C19	−151.5 (4)
C6—C1—C2—C3	1.9 (7)	C11—O2—C14—C15	31.5 (6)
O1—C1—C2—C7	5.1 (7)	C19—C14—C15—C16	−0.7 (7)
C6—C1—C2—C7	−174.8 (5)	O2—C14—C15—C16	176.3 (4)
C1—C2—C3—C4	−0.2 (7)	C14—C15—C16—C17	−1.1 (7)
C7—C2—C3—C4	176.6 (4)	C15—C16—C17—C18	1.8 (7)
C2—C3—C4—C5	−1.5 (8)	C15—C16—C17—N2	177.5 (4)
C3—C4—C5—C6	1.6 (8)	C20—N2—C17—C16	140.5 (4)
C4—C5—C6—C1	0.1 (8)	C20—N2—C17—C18	−44.0 (6)
O1—C1—C6—C5	178.3 (5)	C16—C17—C18—C19	−0.7 (7)
C2—C1—C6—C5	−1.8 (7)	N2—C17—C18—C19	−176.2 (4)
C8—N1—C7—C2	173.4 (4)	C15—C14—C19—C18	1.7 (7)
C1—C2—C7—N1	−6.6 (7)	O2—C14—C19—C18	−175.5 (4)
C3—C2—C7—N1	176.7 (4)	C17—C18—C19—C14	−1.0 (7)
C7—N1—C8—C9	140.4 (4)	C17—N2—C20—C21	173.5 (4)
C7—N1—C8—C13	−43.6 (6)	N2—C20—C21—C26	177.0 (4)
C13—C8—C9—C10	2.1 (6)	N2—C20—C21—C22	−6.7 (7)
N1—C8—C9—C10	178.3 (4)	C26—C21—C22—O3	−178.7 (4)
C8—C9—C10—C11	−2.3 (7)	C20—C21—C22—O3	5.0 (7)
C9—C10—C11—C12	1.2 (7)	C26—C21—C22—C23	1.3 (7)
C9—C10—C11—O2	176.5 (4)	C20—C21—C22—C23	−175.1 (4)
C14—O2—C11—C12	−152.1 (4)	O3—C22—C23—C24	178.6 (4)
C14—O2—C11—C10	32.4 (6)	C21—C22—C23—C24	−1.3 (8)
C10—C11—C12—C13	0.0 (7)	C22—C23—C24—C25	−0.4 (8)
O2—C11—C12—C13	−175.7 (4)	C23—C24—C25—C26	2.2 (8)
C11—C12—C13—C8	−0.2 (7)	C24—C25—C26—C21	−2.3 (8)
C9—C8—C13—C12	−0.9 (6)	C22—C21—C26—C25	0.6 (7)
N1—C8—C13—C12	−176.9 (4)	C20—C21—C26—C25	177.0 (4)

Cg1–Cg4 are the centroids of the C1—C6, C8–C13, C14–C19 and C21–C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.82	1.88	2.602 (5)	147
O3—H3o···N2	0.82	1.86	2.589 (5)	147
C23—H23···Cg1ⁱ	0.93	2.90	3.556 (6)	129
C26—H26···Cg1ⁱⁱ	0.93	2.90	3.566 (6)	129
C16—H16···Cg2ⁱⁱⁱ	0.93	2.76	3.469 (6)	133
C19—H19···Cg2^iv	0.93	2.86	3.582 (5)	135
C9—H9···Cg3ⁱ	0.93	2.76	3.462 (5)	133
C12—H12···Cg3ⁱⁱ	0.93	2.88	3.584 (5)	134
C3—H3···Cg4^iv	0.93	2.87	3.512 (6)	128
C6—H6···Cg4ⁱⁱⁱ	0.93	2.95	3.626 (7)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1–Cg4 are the centroids of the C1—C6, C8–C13, C14–C19 and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.82	1.88	2.602 (5)	147
O3—H3o⋯N2	0.82	1.86	2.589 (5)	147
C23—H23⋯Cg1ⁱ	0.93	2.90	3.556 (6)	129
C26—H26⋯Cg1ⁱⁱ	0.93	2.90	3.566 (6)	129
C16—H16⋯Cg2ⁱⁱⁱ	0.93	2.76	3.469 (6)	133
C19—H19⋯Cg2^iv	0.93	2.86	3.582 (5)	135
C9—H9⋯Cg3ⁱ	0.93	2.76	3.462 (5)	133
C12—H12⋯Cg3ⁱⁱ	0.93	2.88	3.584 (5)	134
C3—H3⋯Cg4^iv	0.93	2.87	3.512 (6)	128
C6—H6⋯Cg4ⁱⁱⁱ	0.93	2.95	3.626 (7)	131

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

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