6,6′-Diethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethylidyne)]diphenol

Fun, H.-K.; Kargar, H.; Kia, R.; Jamshidvand, A.

doi:10.1107/S1600536809007557

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o707-o708

doi:10.1107/S1600536809007557

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6,6′-Diethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethylidyne)]diphenol

Hoong-Kun Fun,^a ^* Hadi Kargar,^b ‡ Reza Kia ^a and Arezoo Jamshidvand ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 28 February 2009; accepted 2 March 2009; online 6 March 2009)

In the crystal structure, the title Schiff base compound, C₂₃H₃₀N₂O₄, exhibits crystallographic twofold rotation symmetry. The imino group is coplanar with the aromatic ring with an N—C—C—C torsion angle of -179.72 (9)°. An intramolecular O—H⋯N hydrogen bond forms a six-membered ring, producing an S(6) ring motif. The dihedral angle between symmetry related benzene rings is 28.05 (5)°. The ethoxy group makes a C—O—C—C torsion angle of −7.20 (16)° with the benzene ring. The crystal structure is stabilized by intermolecular C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For information on Schiff base ligands, complexes and their applications, see, for example: Calligaris & Randaccio, (1987 ); Casellato & Vigato, (1977 ); Pal et al. (2005 ); Reglinski et al. 2004 ; Hou et al. (2001 ); Ren et al. (2002 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₃H₃₀N₂O₄
M_r = 398.49
Monoclinic, C 2/c
a = 5.6523 (1) Å
b = 12.9591 (2) Å
c = 28.3771 (3) Å
β = 91.282 (1)°
V = 2078.07 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.43 × 0.22 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.880, T_max = 0.997
21349 measured reflections
3560 independent reflections
2743 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.128
S = 1.07
3560 reflections
134 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.5772 (12)	147
C11—H11A⋯Cg1ⁱ	0.96	2.87	3.6007 (12)	133
Symmetry code: (i) x-1, y, z. Cg1 is the centroid of the C1–C6 benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007557/at2735sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007557/at2735Isup2.hkl

checkCIF report

Comment top

The condensation of primary amines with carbonyl compounds yields Schiff base (Casellato & Vigato, 1977) that are still now regarded as one of the most potential group of chelators for facile preparations of metallo-organic hybrid materials. In the past two decades, the synthesis, structure and properties of Schiff base complexes have stimulated much interest for their noteworthy contributions in single molecule-based magnetism, materials science, catalysis of many reactions like carbonylation, hydroformylation, reduction, oxidation, epoxidation and hydrolysis, etc (Pal et al., 2005; Reglinski et al., 2004; Hou et al., 2001; Ren et al., 2002). This is due to the fact that Schiff bases offer opportunities for inducing substrate chirality, tuning the metal-centered electronic factor and enhancing the solubility and stability of either homogeneous or heterogeneous catalysts. Only a relatively small number of free Schiff base ligands have been characterized (Calligaris & Randaccio, 1987). As an extension of our work on the structural characterization of Schiff base compounds, the title compound, is reported here.

The molecule of the title compound, (Fig. 1), has a crystallographic twofold rotation symmetry. The atom C9 lies across a crystallographic twofold rotation symmetry. An intramolecular O—H···N hydrogen bond forms a six-membered ring, producing a S(6) ring motif (Bernstein et al. 1995). The dihedral angle between the symmetry related benzene rings is 28.05 (5)°. The ethoxy group makes a torsion angle (C11—O2—C2—C3) of -7.20 (16)° with the benzene ring. The N atom is in close proximity to the H atom of the methylene group of the diamine segment, with H8B—N1 distance of 2.70 Å. The crystal structure is stabilized by intermolecular C—H···π interactions [Cg1 is the centroid of the C1–C6 benzene ring] (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For information on Schiff base ligands and complexes and their applications, see, for example: Calligaris & Randaccio, (1987); Casellato & Vigato, (1977); Pal et al. (2005); Reglinski et al. 2004; Hou et al. (2001); Ren et al. (2002). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of the C1–C6 benzene ring.

Experimental top

The synthetic method has been described earlier (Reglinski et al., 2004), except that 3-ethoxysalicylaldehyde was used. Single crystals suitable for X-ray diffraction were obtained by evaporation of an methanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms. The suffix A corresponds to symmetry code (-x + 1, y, -z + 1/2).

6,6'-Diethoxy-2,2'-[2,2-dimethylpropane-1,3- diylbis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₃H₃₀N₂O₄	F(000) = 856
M_r = 398.49	D_x = 1.274 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5303 reflections
a = 5.6523 (1) Å	θ = 2.9–31.8°
b = 12.9591 (2) Å	µ = 0.09 mm⁻¹
c = 28.3771 (3) Å	T = 100 K
β = 91.282 (1)°	Plate, yellow
V = 2078.07 (5) Å³	0.43 × 0.22 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3560 independent reflections
Radiation source: fine-focus sealed tube	2743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 31.8°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.880, T_max = 0.997	k = −18→19
21349 measured reflections	l = −42→41

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0621P)² + 0.9557P] where P = (F_o² + 2F_c²)/3
3560 reflections	(Δ/σ)_max = 0.001
134 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₃H₃₀N₂O₄	V = 2078.07 (5) Å³
M_r = 398.49	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 5.6523 (1) Å	µ = 0.09 mm⁻¹
b = 12.9591 (2) Å	T = 100 K
c = 28.3771 (3) Å	0.43 × 0.22 × 0.04 mm
β = 91.282 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3560 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2743 reflections with I > 2σ(I)
T_min = 0.880, T_max = 0.997	R_int = 0.042
21349 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.07	Δρ_max = 0.42 e Å⁻³
3560 reflections	Δρ_min = −0.26 e Å⁻³
134 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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. 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 > 2sigma(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.

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

	x	y	z	U_iso*/U_eq
O2	−0.21577 (13)	0.86647 (6)	0.42709 (3)	0.01900 (18)
O1	0.07879 (14)	0.77817 (6)	0.36945 (3)	0.01951 (18)
H1	0.1800	0.7580	0.3514	0.029*
N1	0.44608 (15)	0.78978 (7)	0.31751 (3)	0.01556 (18)
C1	0.11143 (18)	0.87962 (8)	0.37834 (4)	0.0150 (2)
C2	−0.04483 (18)	0.92916 (8)	0.40916 (4)	0.0157 (2)
C3	−0.01574 (19)	1.03346 (8)	0.41899 (4)	0.0180 (2)
H3A	−0.1215	1.0665	0.4386	0.022*
C4	0.1713 (2)	1.08960 (8)	0.39974 (4)	0.0189 (2)
H4A	0.1897	1.1593	0.4066	0.023*
C5	0.32737 (19)	1.04064 (8)	0.37052 (4)	0.0168 (2)
H5A	0.4531	1.0774	0.3582	0.020*
C6	0.29882 (18)	0.93596 (8)	0.35912 (3)	0.01445 (19)
C7	0.46777 (18)	0.88493 (8)	0.32869 (3)	0.0151 (2)
H7A	0.5941	0.9225	0.3172	0.018*
C8	0.62015 (17)	0.74010 (8)	0.28797 (4)	0.0149 (2)
H8A	0.7249	0.6980	0.3075	0.018*
H8B	0.7150	0.7925	0.2729	0.018*
C9	0.5000	0.67209 (11)	0.2500	0.0132 (3)
C10	0.68697 (18)	0.60294 (9)	0.22779 (4)	0.0175 (2)
H10A	0.7602	0.5606	0.2518	0.026*
H10B	0.8049	0.6451	0.2134	0.026*
H10C	0.6130	0.5597	0.2043	0.026*
C11	−0.36178 (19)	0.90890 (9)	0.46303 (4)	0.0181 (2)
H11A	−0.4504	0.9675	0.4508	0.022*
H11B	−0.2647	0.9318	0.4896	0.022*
C12	−0.5284 (2)	0.82495 (9)	0.47814 (4)	0.0215 (2)
H12A	−0.6358	0.8522	0.5007	0.032*
H12B	−0.4392	0.7694	0.4921	0.032*
H12C	−0.6163	0.7998	0.4512	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0195 (4)	0.0172 (4)	0.0207 (4)	−0.0019 (3)	0.0086 (3)	−0.0030 (3)
O1	0.0212 (4)	0.0142 (4)	0.0235 (4)	−0.0046 (3)	0.0087 (3)	−0.0061 (3)
N1	0.0162 (4)	0.0165 (4)	0.0141 (4)	−0.0009 (3)	0.0029 (3)	−0.0018 (3)
C1	0.0177 (5)	0.0132 (5)	0.0141 (4)	−0.0009 (3)	0.0004 (3)	−0.0010 (3)
C2	0.0165 (4)	0.0159 (5)	0.0147 (4)	−0.0005 (4)	0.0022 (3)	−0.0001 (4)
C3	0.0221 (5)	0.0157 (5)	0.0163 (5)	0.0017 (4)	0.0026 (4)	−0.0015 (4)
C4	0.0249 (5)	0.0128 (5)	0.0190 (5)	0.0002 (4)	0.0010 (4)	−0.0003 (4)
C5	0.0200 (5)	0.0142 (5)	0.0164 (4)	−0.0018 (4)	0.0009 (4)	0.0012 (4)
C6	0.0164 (4)	0.0144 (5)	0.0126 (4)	−0.0006 (3)	0.0008 (3)	0.0004 (3)
C7	0.0155 (4)	0.0166 (5)	0.0134 (4)	−0.0022 (3)	0.0014 (3)	0.0017 (3)
C8	0.0132 (4)	0.0160 (5)	0.0154 (4)	−0.0011 (3)	0.0029 (3)	−0.0002 (3)
C9	0.0132 (6)	0.0131 (6)	0.0134 (6)	0.000	0.0034 (5)	0.000
C10	0.0174 (5)	0.0168 (5)	0.0186 (5)	0.0039 (4)	0.0032 (4)	−0.0005 (4)
C11	0.0194 (5)	0.0196 (5)	0.0157 (4)	0.0015 (4)	0.0051 (4)	−0.0012 (4)
C12	0.0191 (5)	0.0243 (6)	0.0213 (5)	0.0011 (4)	0.0060 (4)	0.0020 (4)

Geometric parameters (Å, º) top

O2—C2	1.3692 (12)	C7—H7A	0.9300
O2—C11	1.4357 (12)	C8—C9	1.5382 (13)
O1—C1	1.3506 (12)	C8—H8A	0.9700
O1—H1	0.8200	C8—H8B	0.9700
N1—C7	1.2784 (13)	C9—C10	1.5319 (13)
N1—C8	1.4568 (13)	C9—C10ⁱ	1.5319 (13)
C1—C6	1.4065 (14)	C9—C8ⁱ	1.5382 (13)
C1—C2	1.4112 (14)	C10—H10A	0.9600
C2—C3	1.3890 (15)	C10—H10B	0.9600
C3—C4	1.4039 (15)	C10—H10C	0.9600
C3—H3A	0.9300	C11—C12	1.5075 (16)
C4—C5	1.3789 (15)	C11—H11A	0.9700
C4—H4A	0.9300	C11—H11B	0.9700
C5—C6	1.4031 (14)	C12—H12A	0.9600
C5—H5A	0.9300	C12—H12B	0.9600
C6—C7	1.4601 (14)	C12—H12C	0.9600

C2—O2—C11	117.29 (8)	N1—C8—H8B	109.4
C1—O1—H1	109.5	C9—C8—H8B	109.4
C7—N1—C8	120.45 (9)	H8A—C8—H8B	108.0
O1—C1—C6	122.26 (9)	C10—C9—C10ⁱ	108.40 (12)
O1—C1—C2	118.29 (9)	C10—C9—C8ⁱ	110.18 (6)
C6—C1—C2	119.43 (9)	C10ⁱ—C9—C8ⁱ	108.99 (6)
O2—C2—C3	125.73 (9)	C10—C9—C8	108.99 (6)
O2—C2—C1	114.65 (9)	C10ⁱ—C9—C8	110.18 (6)
C3—C2—C1	119.62 (9)	C8ⁱ—C9—C8	110.08 (12)
C2—C3—C4	120.85 (10)	C9—C10—H10A	109.5
C2—C3—H3A	119.6	C9—C10—H10B	109.5
C4—C3—H3A	119.6	H10A—C10—H10B	109.5
C5—C4—C3	119.54 (10)	C9—C10—H10C	109.5
C5—C4—H4A	120.2	H10A—C10—H10C	109.5
C3—C4—H4A	120.2	H10B—C10—H10C	109.5
C4—C5—C6	120.77 (10)	O2—C11—C12	107.36 (9)
C4—C5—H5A	119.6	O2—C11—H11A	110.2
C6—C5—H5A	119.6	C12—C11—H11A	110.2
C5—C6—C1	119.75 (9)	O2—C11—H11B	110.2
C5—C6—C7	120.06 (9)	C12—C11—H11B	110.2
C1—C6—C7	120.16 (9)	H11A—C11—H11B	108.5
N1—C7—C6	121.55 (9)	C11—C12—H12A	109.5
N1—C7—H7A	119.2	C11—C12—H12B	109.5
C6—C7—H7A	119.2	H12A—C12—H12B	109.5
N1—C8—C9	111.29 (7)	C11—C12—H12C	109.5
N1—C8—H8A	109.4	H12A—C12—H12C	109.5
C9—C8—H8A	109.4	H12B—C12—H12C	109.5

C11—O2—C2—C3	−7.20 (15)	O1—C1—C6—C5	−178.44 (10)
C11—O2—C2—C1	172.54 (8)	C2—C1—C6—C5	−0.41 (15)
O1—C1—C2—O2	0.25 (14)	O1—C1—C6—C7	−0.50 (15)
C6—C1—C2—O2	−177.86 (9)	C2—C1—C6—C7	177.53 (9)
O1—C1—C2—C3	180.00 (9)	C8—N1—C7—C6	−178.59 (9)
C6—C1—C2—C3	1.89 (15)	C5—C6—C7—N1	−179.73 (10)
O2—C2—C3—C4	177.87 (10)	C1—C6—C7—N1	2.34 (15)
C1—C2—C3—C4	−1.86 (15)	C7—N1—C8—C9	−136.31 (10)
C2—C3—C4—C5	0.31 (16)	N1—C8—C9—C10	−166.89 (8)
C3—C4—C5—C6	1.21 (16)	N1—C8—C9—C10ⁱ	−48.07 (11)
C4—C5—C6—C1	−1.15 (15)	N1—C8—C9—C8ⁱ	72.16 (7)
C4—C5—C6—C7	−179.09 (9)	C2—O2—C11—C12	−178.04 (9)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.5772 (12)	147
C11—H11A···Cg1ⁱⁱ	0.96	2.87	3.6007 (12)	133

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₃₀N₂O₄
M_r	398.49
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	5.6523 (1), 12.9591 (2), 28.3771 (3)
β (°)	91.282 (1)
V (Å³)	2078.07 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.22 × 0.04

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.880, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	21349, 3560, 2743
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.742

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.07
No. of reflections	3560
No. of parameters	134
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.8200	1.8500	2.5772 (12)	147.00
C11—H11A···Cg1ⁱ	0.9600	2.8700	3.6007 (12)	133.00

Symmetry code: (i) x−1, y, z.

Footnotes

‡Additional correspondence author: e-mail: hkargar@pnu.ac.ir.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312). RK thanks Universiti Sains Malaysia for the award of a post-doctoral research fellowship. HK and AJ thank PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o707-o708

doi:10.1107/S1600536809007557

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6,6′-Di­eth­oxy-2,2′-[2,2-di­methylpropane-1,3-diylbis(nitrilo­methyl­idyne)]diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

6,6′-Diethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethylidyne)]diphenol