Bis{4-[(2-hy­droxy-5-meth­oxy-3-nitro­benzyl­idene)amino]­phen­yl} ether

Arafath, M.A.; Kwong, H.C.; Adam, F.; Mohiuddin, M.; Sarker, M.S.; Salim, M.; Alam, M.M.

doi:10.1107/S2056989019016852

Bis{4-[(2-hydroxy-5-methoxy-3-nitrobenzylidene)amino]phenyl} ether

M. A. Arafath, H. C. Kwong, F. Adam, M. Mohiuddin, M. S. Sarker, M. Salim and M. M. Alam

The molecule of the title oxybis compound lies on a twofold rotational axis. The conformation of the title compound is discussed and compared to those of related structures. In the crystal, molecules of the title compound are assembled into layers parallel to the ab plane through C—H

O hydrogen bonds.

Keywords: crystal structure; oxybis Schiff base; intermolecular interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019016852/rz5267sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019016852/rz5267Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019016852/rz5267Isup3.cml Supplementary material

CCDC reference: 1445336

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Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C)= 0.007 Å
R factor = 0.100
wR factor = 0.353
Data-to-parameter ratio = 14.7

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Datablock: I

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   1 ALERT level A = Data missing that is essential or data in wrong format
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Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

2-[N-(4-{4-[(2-Hydroxy-5-methoxy-3-nitrobenzylidene)amino]phenoxy}phenyl)carboximidoyl]-4-methoxy-6-nitrophenol top

Crystal data top

C₂₈H₂₂N₄O₉	F(000) = 1160
M_r = 558.49	D_x = 1.501 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.954 (4) Å	Cell parameters from 9905 reflections
b = 5.4599 (12) Å	θ = 3–31°
c = 28.397 (6) Å	µ = 0.11 mm⁻¹
β = 92.299 (5)°	T = 100 K
V = 2471.7 (10) Å³	Block, purple
Z = 4	0.38 × 0.24 × 0.14 mm

Data collection top

Bruker APEX DUO CCD area detector diffractometer	2830 independent reflections
Radiation source: fine-focus sealed tube	2591 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 27.5°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −20→20
T_min = 0.879, T_max = 0.956	k = −7→7
35811 measured reflections	l = −36→36

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.100	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.353	w = 1/[σ²(F_o²) + (0.1539P)² + 17.7934P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
2830 reflections	Δρ_max = 0.31 e Å⁻³
192 parameters	Δρ_min = −0.31 e Å⁻³

Special details top

Experimental. The following wavelength and cell were deduced by SADABS from the direction cosines etc. They are given here for emergency use only: CELL 0.71095 5.463 8.443 28.418 92.106 89.981 108.897

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.000000	−0.2692 (9)	0.250000	0.0444 (13)
O2	0.4044 (2)	0.9524 (8)	0.47761 (16)	0.0525 (11)
O3	0.4346 (3)	0.1480 (8)	0.36154 (14)	0.0475 (10)
O4	0.6359 (2)	0.4545 (9)	0.43220 (19)	0.0664 (14)
O5	0.5853 (3)	0.1292 (9)	0.4007 (2)	0.0710 (15)
N1	0.2747 (2)	0.1732 (8)	0.34224 (14)	0.0371 (9)
N2	0.5771 (3)	0.3336 (9)	0.41607 (16)	0.0417 (10)
C1	0.3380 (3)	0.6629 (9)	0.42249 (18)	0.0364 (10)
H1A	0.284746	0.739136	0.424432	0.044*
C2	0.4061 (3)	0.7544 (9)	0.44839 (17)	0.0355 (10)
C3	0.4833 (3)	0.6438 (9)	0.44506 (17)	0.0365 (10)
H3A	0.530272	0.707394	0.462653	0.044*
C4	0.4934 (3)	0.4407 (9)	0.41635 (16)	0.0337 (10)
C5	0.4255 (3)	0.3424 (9)	0.38929 (16)	0.0332 (10)
C6	0.3471 (3)	0.4586 (9)	0.39343 (16)	0.0337 (10)
C7	0.2723 (3)	0.3645 (9)	0.36861 (17)	0.0366 (10)
H7A	0.220289	0.446315	0.371966	0.044*
C8	0.2016 (3)	0.0754 (9)	0.31932 (16)	0.0335 (10)
C9	0.2115 (3)	−0.1371 (9)	0.29336 (17)	0.0366 (10)
H9A	0.265646	−0.208522	0.291709	0.044*
C10	0.1439 (3)	−0.2462 (9)	0.26992 (16)	0.0369 (10)
H10A	0.151248	−0.392646	0.252498	0.044*
C11	0.0657 (3)	−0.1405 (9)	0.27200 (16)	0.0349 (10)
C12	0.0535 (3)	0.0722 (9)	0.29753 (18)	0.0395 (11)
H12A	−0.000735	0.142841	0.298889	0.047*
C13	0.1217 (3)	0.1799 (9)	0.32098 (17)	0.0386 (11)
H13A	0.114209	0.326303	0.338386	0.046*
C14	0.3252 (3)	1.0498 (11)	0.4876 (2)	0.0477 (13)
H14A	0.332369	1.185096	0.510095	0.072*
H14B	0.290647	0.921682	0.501263	0.072*
H14C	0.297545	1.110264	0.458451	0.072*
H1O3	0.386 (6)	0.117 (15)	0.350 (3)	0.08 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.047 (3)	0.029 (2)	0.055 (3)	0.000	−0.023 (2)	0.000
O2	0.0300 (17)	0.054 (2)	0.073 (3)	0.0037 (16)	−0.0050 (16)	−0.031 (2)
O3	0.0378 (19)	0.054 (2)	0.050 (2)	0.0037 (16)	−0.0020 (15)	−0.0231 (18)
O4	0.0290 (18)	0.074 (3)	0.095 (3)	0.0049 (19)	−0.013 (2)	−0.024 (3)
O5	0.044 (2)	0.069 (3)	0.099 (4)	0.018 (2)	−0.008 (2)	−0.039 (3)
N1	0.0291 (18)	0.043 (2)	0.039 (2)	−0.0034 (16)	−0.0033 (15)	−0.0025 (17)
N2	0.0296 (19)	0.052 (2)	0.044 (2)	0.0046 (18)	0.0000 (16)	−0.0073 (19)
C1	0.027 (2)	0.035 (2)	0.047 (2)	0.0005 (17)	−0.0033 (18)	−0.003 (2)
C2	0.030 (2)	0.037 (2)	0.039 (2)	−0.0011 (18)	0.0016 (17)	−0.0075 (19)
C3	0.027 (2)	0.041 (2)	0.042 (2)	−0.0031 (18)	−0.0018 (17)	−0.006 (2)
C4	0.0241 (19)	0.041 (2)	0.036 (2)	0.0020 (17)	−0.0006 (16)	−0.0026 (18)
C5	0.030 (2)	0.037 (2)	0.033 (2)	−0.0002 (18)	0.0015 (16)	−0.0051 (18)
C6	0.028 (2)	0.040 (2)	0.033 (2)	−0.0040 (18)	−0.0020 (16)	−0.0031 (18)
C7	0.027 (2)	0.043 (3)	0.040 (2)	−0.0021 (18)	−0.0027 (17)	−0.003 (2)
C8	0.031 (2)	0.037 (2)	0.032 (2)	−0.0019 (18)	−0.0028 (16)	0.0004 (18)
C9	0.034 (2)	0.036 (2)	0.039 (2)	0.0035 (18)	−0.0025 (18)	−0.0007 (19)
C10	0.042 (2)	0.033 (2)	0.035 (2)	0.0023 (19)	−0.0030 (18)	−0.0017 (18)
C11	0.039 (2)	0.034 (2)	0.032 (2)	−0.0052 (18)	−0.0086 (17)	0.0028 (18)
C12	0.034 (2)	0.037 (2)	0.046 (3)	0.0053 (19)	−0.0107 (19)	−0.004 (2)
C13	0.037 (2)	0.038 (2)	0.041 (2)	0.0022 (19)	−0.0072 (18)	−0.011 (2)
C14	0.037 (2)	0.046 (3)	0.060 (3)	0.007 (2)	0.003 (2)	−0.017 (3)

Geometric parameters (Å, º) top

O1—C11ⁱ	1.389 (5)	C4—C5	1.409 (6)
O1—C11	1.389 (5)	C5—C6	1.412 (6)
O2—C2	1.364 (6)	C6—C7	1.456 (6)
O2—C14	1.410 (6)	C7—H7A	0.9500
O3—C5	1.333 (6)	C8—C9	1.387 (7)
O3—H1O3	0.85 (9)	C8—C13	1.398 (6)
O4—N2	1.221 (6)	C9—C10	1.380 (7)
O5—N2	1.207 (6)	C9—H9A	0.9500
N1—C7	1.287 (6)	C10—C11	1.379 (7)
N1—C8	1.418 (6)	C10—H10A	0.9500
N2—C4	1.458 (6)	C11—C12	1.387 (7)
C1—C2	1.381 (6)	C12—C13	1.384 (6)
C1—C6	1.398 (7)	C12—H12A	0.9500
C1—H1A	0.9500	C13—H13A	0.9500
C2—C3	1.377 (6)	C14—H14A	0.9800
C3—C4	1.390 (7)	C14—H14B	0.9800
C3—H3A	0.9500	C14—H14C	0.9800

C11ⁱ—O1—C11	119.2 (5)	N1—C7—H7A	119.2
C2—O2—C14	117.5 (4)	C6—C7—H7A	119.2
C5—O3—H1O3	106 (6)	C9—C8—C13	118.9 (4)
C7—N1—C8	121.9 (4)	C9—C8—N1	116.7 (4)
O5—N2—O4	122.8 (5)	C13—C8—N1	124.4 (4)
O5—N2—C4	119.0 (4)	C10—C9—C8	120.9 (4)
O4—N2—C4	118.1 (4)	C10—C9—H9A	119.6
C2—C1—C6	120.3 (4)	C8—C9—H9A	119.6
C2—C1—H1A	119.8	C11—C10—C9	119.4 (4)
C6—C1—H1A	119.8	C11—C10—H10A	120.3
O2—C2—C3	115.4 (4)	C9—C10—H10A	120.3
O2—C2—C1	125.2 (4)	C10—C11—C12	121.2 (4)
C3—C2—C1	119.4 (4)	C10—C11—O1	115.9 (4)
C2—C3—C4	121.0 (4)	C12—C11—O1	122.7 (4)
C2—C3—H3A	119.5	C13—C12—C11	118.9 (4)
C4—C3—H3A	119.5	C13—C12—H12A	120.5
C3—C4—C5	121.3 (4)	C11—C12—H12A	120.5
C3—C4—N2	116.8 (4)	C12—C13—C8	120.7 (4)
C5—C4—N2	121.9 (4)	C12—C13—H13A	119.7
O3—C5—C4	121.8 (4)	C8—C13—H13A	119.7
O3—C5—C6	121.6 (4)	O2—C14—H14A	109.5
C4—C5—C6	116.6 (4)	O2—C14—H14B	109.5
C1—C6—C5	121.4 (4)	H14A—C14—H14B	109.5
C1—C6—C7	117.7 (4)	O2—C14—H14C	109.5
C5—C6—C7	120.9 (4)	H14A—C14—H14C	109.5
N1—C7—C6	121.7 (4)	H14B—C14—H14C	109.5

C14—O2—C2—C3	−170.9 (5)	O3—C5—C6—C7	2.1 (7)
C14—O2—C2—C1	9.8 (8)	C4—C5—C6—C7	−177.2 (4)
C6—C1—C2—O2	179.7 (5)	C8—N1—C7—C6	177.7 (4)
C6—C1—C2—C3	0.5 (8)	C1—C6—C7—N1	−178.0 (5)
O2—C2—C3—C4	−179.8 (5)	C5—C6—C7—N1	0.1 (7)
C1—C2—C3—C4	−0.5 (8)	C7—N1—C8—C9	−177.5 (4)
C2—C3—C4—C5	0.7 (7)	C7—N1—C8—C13	3.2 (8)
C2—C3—C4—N2	−178.6 (5)	C13—C8—C9—C10	−0.7 (7)
O5—N2—C4—C3	163.3 (5)	N1—C8—C9—C10	179.9 (4)
O4—N2—C4—C3	−15.5 (7)	C8—C9—C10—C11	0.7 (7)
O5—N2—C4—C5	−16.1 (8)	C9—C10—C11—C12	−0.5 (7)
O4—N2—C4—C5	165.1 (5)	C9—C10—C11—O1	−176.1 (4)
C3—C4—C5—O3	179.8 (5)	C11ⁱ—O1—C11—C10	−145.5 (5)
N2—C4—C5—O3	−0.9 (7)	C11ⁱ—O1—C11—C12	39.0 (4)
C3—C4—C5—C6	−0.8 (7)	C10—C11—C12—C13	0.4 (8)
N2—C4—C5—C6	178.5 (4)	O1—C11—C12—C13	175.7 (4)
C2—C1—C6—C5	−0.7 (7)	C11—C12—C13—C8	−0.5 (8)
C2—C1—C6—C7	177.4 (5)	C9—C8—C13—C12	0.6 (8)
O3—C5—C6—C1	−179.8 (5)	N1—C8—C13—C12	180.0 (5)
C4—C5—C6—C1	0.8 (7)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N1	0.85 (9)	1.81 (10)	2.591 (6)	153 (7)
C7—H7A···O5ⁱⁱ	0.95	2.54	3.470 (7)	167
C13—H13A···O5ⁱⁱ	0.95	2.48	3.404 (7)	165

Symmetry code: (ii) x−1/2, y+1/2, z.

Selected dihedral and torsion angles (°) top

Dihedral 1 is the dihedral angle between the planes of the central benzene rings. Dihedral 2 is the dihedral angle between the planes of the central and terminal benzene rings.

Compound	R₁	Dihedral 1	Dihedral 2	C6—C7—N1—C8
(I)	4-methoxy-2-nitrophenol	66.0 (2)	4.9 (2), 4.9 (2)	-177.7 (4), -177.7 (4)
DICKUW (Chu & Huang, 2007)	2,4-di-tert-butylphenol	73.8	4.8, 35.5	178.2, 177.2
DICLAD (Chu & Huang, 2007)	2-(tert-butyl)-4-methylphenol	73.8	47.9, 46.3	175.2, -179.9
GIFCEG (Arafath et al., 2018)	2-methylphenol	59.5	36.0, 31.5	178.3, 179.0
HUDJEW (Lee & Lee, 2009)	4-nitrophenyl	75.7	53.0, 18.0	-174.0, 179.2
NATWEM (Khalaji et al., 2012)	2,3,4-trimethoxyphenyl	84.8	57.6, 73.1	-179.2, -175.7
PEHGOA (Kadu et al., 2013)	phenyl	59.8	8.8, 6.0	-179.9, 179.8
PEHHAN (Kadu et al., 2013)	4-methoxyphenyl	60.1	5.3, 5.3	-179.3, -179.3
RIZFEM (Xu et al., 2008)	2-methoxyphenol	69.2	24.3, 24.3	-180.0, -180.0
TOWSOP (Kaabi et al., 2015)	3-(diethylamino)phenol	65.7	41.4, 30.6	-173.1, -176.5
UNUFEP (Shahverdizadeh & Tiekink, 2011)	phenol	54.6	51.6, 51.6	173.5, 173.4
WEFLUQ (Krishna et al., 2012)	naphthalen-2-ol	75.1/70.1	7.7, 9.9/6.1, 19.4	176.5, 177.6/-179.3, -172.9
WIGPOT (Haffar et al., 2013)	naphthalen-2-ol	74.6/69.9	7.7. 9.9/19.6, 5.8	177.2, 176.3/ -172.9, -178.6

Note: there is more than one data set for compounds WEFLUQ and WIGPOT because there is more than one independent molecule in their asymmetric units.

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Bis{4-[(2-hy­droxy-5-meth­oxy-3-nitro­benzyl­idene)amino]­phen­yl} ether

Supporting information

Key indicators

checkCIF/PLATON results

Bis{4-[(2-hydroxy-5-methoxy-3-nitrobenzylidene)amino]phenyl} ether