2-{[(4-{[(2-Hy­droxy­phen­yl)(phen­yl)methyl­idene]amino}­but­yl)imino](phen­yl)meth­yl}phenol

Jamshidvand, A.; Kia, R.; Kargar, H.; Tahir, M.N.

doi:10.1107/S1600536811055905

organic compounds

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Volume 68| Part 2| February 2012| Page o292

doi:10.1107/S1600536811055905

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2-{[(4-{[(2-Hydroxyphenyl)(phenyl)methylidene]amino}butyl)imino](phenyl)methyl}phenol

Arezoo Jamshidvand,^a Reza Kia,^b,^c ^* Hadi Kargar ^a and Muhammad Nawaz Tahir ^d ^*

^aDepartment of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, I. R. of Iran, ^bX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^dDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: zsrkk@yahoo.com, dmntahir_uos@yahoo.com

(Received 25 December 2011; accepted 27 December 2011; online 7 January 2012)

The asymmetric unit of the title compound, C₃₀H₂₈N₂O₂, comprises half of a potential tetradentate Schiff base ligand; an inversion centre is situtated at the center of the butanediamine spacer. The central methylene segment of the diamine spacer is disordered over two positions with a refined site-occupancy ratio of 0.651 (7):0.349 (7). The phenyl ring and the hydroxy-substituted benzene ring are almost perpendicular to each other, with a dihedral angle of 87.90 (8) Å. Intramolecular O—H⋯N hydrogen bonds make S(6) ring motifs.

Related literature

For standard bond lengths, see: Allen et al. (1987 ). For hydrogen bond motifs, see: Bernstein et al. (1995 ). For background to Schiff bases in coordination chemistry, see: Granovski et al. (1993 ); Kargar et al. (2009 ). For a related structure, see: Friscic et al. (1998 ).

Experimental

Crystal data

C₃₀H₂₈N₂O₂
M_r = 448.54
Monoclinic, P 2₁ /n
a = 11.5720 (3) Å
b = 7.7803 (2) Å
c = 13.3914 (4) Å
β = 95.774 (2)°
V = 1199.56 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 K
0.25 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.250, T_max = 0.459
10739 measured reflections
2951 independent reflections
1706 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.127
S = 1.02
2951 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 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	1.80	2.5328 (16)	148

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055905/su2355sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055905/su2355Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055905/su2355Isup3.cml

checkCIF report

Comment top

Schiff base ligands are one of the most prevalent systems in coordination chemistry (Granovski et al., 1993; Kargar et al., 2009). As part of a general study of potential tetradenate Schiff bases (Kargar et al., 2009), we have synthesized the title compound and report herein on its crystal structure.

The asymmetric unit of the title compound, Fig. 1, comprises half of a potential tetradentate Schiff base ligand. The inversion centre is situtated at the center of the butanediamine spacer. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those reported for a related structure (Friscic et al., 1998).

There are intramolecular O—H···N hydrogen bonds (Table 1) making S(6) ring motifs (Bernstein et al., 1995). The phenyl ring and the hydroxy-substituted benzene ring are almost perpendicular to each other with a dihedral angle of 87.90 (8)Å. The central methylene segment (C15) of the diamine spacer was disordered over two positions with a refined site occupancy ratio of 0.651 (7)/0.349 (7).

Related literature top

For standard bond lengths, see: Allen et al. (1987). For hydrogen bond motifs, see: Bernstein et al. (1995). For background to Schiff bases in coordination chemistry, see: Granovski et al. (1993); Kargar et al. (2009). For a related structure, see: Friscic et al. (1998).

Experimental top

The title compound was synthesized by adding 2-hydroxybenzophenone (2 mmol) to a solution of 1,4-butylenediamine (1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 30 min. The resultant solution was filtered. Yellow single crystals of the title compound, suitable for X-ray structure determination, were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days. The sample was hygroscopic and for the data collection it was sealed in fine glass cappilary under an inert atmosphere.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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. A view of the molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The dashed lines show the intramolecular O-H···N hydrogen bonds [symmetry code: (A) -x, -y, -z].

2-{[(4-{[(2- Hydroxyphenyl)(phenyl)methylidene]amino}butyl)imino](phenyl)methyl}phenol top

Crystal data top

C₃₀H₂₈N₂O₂	F(000) = 476
M_r = 448.54	D_x = 1.242 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2370 reflections
a = 11.5720 (3) Å	θ = 2.5–27.5°
b = 7.7803 (2) Å	µ = 0.08 mm⁻¹
c = 13.3914 (4) Å	T = 291 K
β = 95.774 (2)°	Block, yellow
V = 1199.56 (6) Å³	0.25 × 0.16 × 0.12 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2951 independent reflections
Radiation source: fine-focus sealed tube	1706 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→11
T_min = 0.250, T_max = 0.459	k = −10→9
10739 measured reflections	l = −17→17

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) = 0.127	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0565P)² + 0.0873P] where P = (F_o² + 2F_c²)/3
2951 reflections	(Δ/σ)_max < 0.001
165 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₃₀H₂₈N₂O₂	V = 1199.56 (6) Å³
M_r = 448.54	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.5720 (3) Å	µ = 0.08 mm⁻¹
b = 7.7803 (2) Å	T = 291 K
c = 13.3914 (4) Å	0.25 × 0.16 × 0.12 mm
β = 95.774 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2951 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1706 reflections with I > 2σ(I)
T_min = 0.250, T_max = 0.459	R_int = 0.027
10739 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	Δρ_max = 0.16 e Å⁻³
2951 reflections	Δρ_min = −0.13 e Å⁻³
165 parameters

Special details top

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	Occ. (<1)
O1	0.08671 (10)	−0.51502 (14)	0.09514 (8)	0.0613 (3)
H1	0.0426	−0.4348	0.0797	0.092*
N1	−0.04017 (10)	−0.25674 (14)	0.12091 (9)	0.0500 (3)
C1	0.04494 (11)	−0.42065 (16)	0.25836 (10)	0.0428 (3)
C2	0.10105 (12)	−0.53074 (17)	0.19507 (11)	0.0469 (4)
C3	0.17362 (13)	−0.6602 (2)	0.23703 (13)	0.0595 (4)
H3	0.2106	−0.7332	0.1954	0.071*
C4	0.19106 (14)	−0.6812 (2)	0.33870 (13)	0.0654 (5)
H4	0.2400	−0.7681	0.3655	0.078*
C5	0.13674 (14)	−0.5747 (2)	0.40225 (12)	0.0631 (4)
H5	0.1488	−0.5897	0.4714	0.076*
C6	0.06477 (13)	−0.44660 (19)	0.36208 (11)	0.0535 (4)
H6	0.0283	−0.3752	0.4049	0.064*
C7	−0.03030 (11)	−0.28060 (16)	0.21646 (10)	0.0436 (3)
C8	−0.09188 (12)	−0.17392 (18)	0.28775 (10)	0.0481 (4)
C9	−0.19981 (14)	−0.2220 (2)	0.31276 (13)	0.0633 (4)
H9	−0.2363	−0.3183	0.2830	0.076*
C10	−0.25395 (17)	−0.1277 (3)	0.38186 (15)	0.0814 (6)
H10	−0.3269	−0.1610	0.3982	0.098*
C11	−0.2023 (2)	0.0122 (3)	0.42610 (15)	0.0852 (6)
H11	−0.2384	0.0731	0.4741	0.102*
C12	−0.0963 (2)	0.0639 (3)	0.39977 (16)	0.0891 (6)
H12	−0.0615	0.1621	0.4288	0.107*
C13	−0.04048 (15)	−0.0282 (2)	0.33051 (13)	0.0701 (5)
H13	0.0313	0.0080	0.3129	0.084*
C14	−0.11235 (13)	−0.1200 (2)	0.07252 (12)	0.0592 (4)
H14A	−0.1640	−0.0764	0.1194	0.071*	0.651 (7)
H14B	−0.1598	−0.1670	0.0152	0.071*	0.651 (7)
H14C	−0.1226	−0.0301	0.1200	0.071*	0.349 (7)
H14D	−0.1874	−0.1654	0.0494	0.071*	0.349 (7)
C15	−0.0405 (3)	0.0257 (4)	0.0383 (3)	0.0529 (10)	0.651 (7)
H15A	0.0050	0.0741	0.0963	0.063*	0.651 (7)
H15B	−0.0923	0.1148	0.0096	0.063*	0.651 (7)
C15A	−0.0554 (5)	−0.0468 (8)	−0.0156 (5)	0.0503 (19)	0.349 (7)
H15C	−0.0394	−0.1399	−0.0604	0.060*	0.349 (7)
H15D	−0.1092	0.0314	−0.0525	0.060*	0.349 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0729 (8)	0.0651 (7)	0.0466 (7)	0.0139 (5)	0.0090 (5)	−0.0025 (5)
N1	0.0544 (8)	0.0472 (7)	0.0489 (8)	0.0007 (5)	0.0084 (6)	0.0125 (5)
C1	0.0432 (8)	0.0421 (7)	0.0436 (8)	−0.0038 (6)	0.0061 (6)	0.0031 (6)
C2	0.0466 (8)	0.0459 (8)	0.0481 (9)	−0.0032 (6)	0.0045 (6)	−0.0001 (6)
C3	0.0580 (10)	0.0555 (9)	0.0646 (11)	0.0104 (7)	0.0036 (8)	−0.0051 (8)
C4	0.0620 (11)	0.0620 (10)	0.0700 (12)	0.0148 (8)	−0.0038 (8)	0.0092 (9)
C5	0.0661 (11)	0.0728 (11)	0.0488 (9)	0.0081 (8)	−0.0019 (8)	0.0126 (8)
C6	0.0565 (10)	0.0591 (9)	0.0455 (9)	0.0037 (7)	0.0084 (7)	0.0026 (7)
C7	0.0418 (8)	0.0423 (8)	0.0473 (9)	−0.0051 (6)	0.0080 (6)	0.0048 (6)
C8	0.0497 (9)	0.0467 (8)	0.0483 (8)	0.0060 (6)	0.0074 (7)	0.0050 (6)
C9	0.0580 (10)	0.0638 (10)	0.0709 (11)	0.0014 (8)	0.0199 (8)	0.0080 (8)
C10	0.0747 (13)	0.0904 (15)	0.0849 (14)	0.0239 (11)	0.0370 (11)	0.0235 (12)
C11	0.1070 (17)	0.0843 (15)	0.0679 (13)	0.0450 (13)	0.0262 (12)	0.0066 (11)
C12	0.1096 (17)	0.0709 (12)	0.0858 (15)	0.0154 (11)	0.0050 (12)	−0.0255 (10)
C13	0.0653 (11)	0.0635 (10)	0.0822 (13)	−0.0011 (8)	0.0106 (9)	−0.0142 (9)
C14	0.0587 (10)	0.0596 (10)	0.0599 (10)	0.0060 (7)	0.0080 (7)	0.0204 (8)
C15	0.063 (2)	0.0466 (16)	0.0497 (19)	0.0073 (13)	0.0104 (14)	0.0057 (15)
C15A	0.057 (4)	0.048 (3)	0.044 (4)	0.008 (2)	−0.003 (2)	0.009 (3)

Geometric parameters (Å, º) top

O1—C2	1.3373 (17)	C10—C11	1.350 (3)
O1—H1	0.8200	C10—H10	0.9300
N1—C7	1.2867 (17)	C11—C12	1.371 (3)
N1—C14	1.4631 (18)	C11—H11	0.9300
C1—C6	1.3994 (19)	C12—C13	1.382 (3)
C1—C2	1.4087 (19)	C12—H12	0.9300
C1—C7	1.4703 (19)	C13—H13	0.9300
C2—C3	1.393 (2)	C14—C15	1.504 (3)
C3—C4	1.366 (2)	C14—C15A	1.519 (6)
C3—H3	0.9300	C14—H14A	0.9700
C4—C5	1.383 (2)	C14—H14B	0.9700
C4—H4	0.9300	C14—H14C	0.9599
C5—C6	1.374 (2)	C14—H14D	0.9600
C5—H5	0.9300	C15—C15ⁱ	1.512 (7)
C6—H6	0.9300	C15—H15A	0.9700
C7—C8	1.4984 (19)	C15—H15B	0.9700
C8—C9	1.377 (2)	C15A—C15Aⁱ	1.497 (13)
C8—C13	1.378 (2)	C15A—H15C	0.9700
C9—C10	1.380 (2)	C15A—H15D	0.9700
C9—H9	0.9300

C2—O1—H1	109.5	C8—C13—H13	120.2
C7—N1—C14	122.34 (13)	C12—C13—H13	120.2
C6—C1—C2	118.03 (12)	N1—C14—C15	112.01 (15)
C6—C1—C7	121.16 (13)	N1—C14—C15A	110.1 (2)
C2—C1—C7	120.80 (12)	C15—C14—C15A	35.4 (2)
O1—C2—C3	118.61 (13)	N1—C14—H14A	109.2
O1—C2—C1	121.88 (12)	C15—C14—H14A	109.2
C3—C2—C1	119.51 (13)	C15A—C14—H14A	135.7
C4—C3—C2	120.74 (14)	N1—C14—H14B	109.2
C4—C3—H3	119.6	C15—C14—H14B	109.2
C2—C3—H3	119.6	C15A—C14—H14B	77.4
C3—C4—C5	120.72 (14)	H14A—C14—H14B	107.9
C3—C4—H4	119.6	N1—C14—H14C	109.9
C5—C4—H4	119.6	C15—C14—H14C	76.2
C6—C5—C4	119.27 (15)	C15A—C14—H14C	109.4
C6—C5—H5	120.4	H14A—C14—H14C	36.2
C4—C5—H5	120.4	H14B—C14—H14C	134.5
C5—C6—C1	121.72 (14)	N1—C14—H14D	109.4
C5—C6—H6	119.1	C15—C14—H14D	133.6
C1—C6—H6	119.1	C15A—C14—H14D	109.7
N1—C7—C1	118.45 (12)	H14A—C14—H14D	75.0
N1—C7—C8	123.60 (12)	H14B—C14—H14D	35.3
C1—C7—C8	117.95 (12)	H14C—C14—H14D	108.3
C9—C8—C13	119.12 (15)	C14—C15—C15ⁱ	114.0 (4)
C9—C8—C7	120.37 (14)	C14—C15—H14C	36.2
C13—C8—C7	120.50 (13)	C15ⁱ—C15—H14C	148.7
C8—C9—C10	120.18 (17)	C14—C15—H15A	108.7
C8—C9—H9	119.9	C15ⁱ—C15—H15A	108.7
C10—C9—H9	119.9	H14C—C15—H15A	82.4
C11—C10—C9	120.84 (19)	C14—C15—H15B	108.7
C11—C10—H10	119.6	C15ⁱ—C15—H15B	108.7
C9—C10—H10	119.6	H14C—C15—H15B	94.6
C10—C11—C12	119.46 (18)	H15A—C15—H15B	107.6
C10—C11—H11	120.3	C15Aⁱ—C15A—C14	113.1 (7)
C12—C11—H11	120.3	C15Aⁱ—C15A—H15C	109.0
C11—C12—C13	120.74 (19)	C14—C15A—H15C	109.0
C11—C12—H12	119.6	C15Aⁱ—C15A—H15D	109.0
C13—C12—H12	119.6	C14—C15A—H15D	109.0
C8—C13—C12	119.62 (18)	H15C—C15A—H15D	107.8

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.80	2.5328 (16)	148

Experimental details

Crystal data
Chemical formula	C₃₀H₂₈N₂O₂
M_r	448.54
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	11.5720 (3), 7.7803 (2), 13.3914 (4)
β (°)	95.774 (2)
V (Å³)	1199.56 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.250, 0.459
No. of measured, independent and observed [I > 2σ(I)] reflections	10739, 2951, 1706
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.127, 1.02
No. of reflections	2951
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.13

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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	0.82	1.80	2.5328 (16)	148

Acknowledgements

HK and AJ thank PNU for financial support, and MNT thanks the GC University of Sargodha, Pakistan for research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Friscic, T., Kaitner, B. & Mestrovic, E. (1998). Croat. Chem. Acta, 71, 87–91. CAS Google Scholar
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. Google Scholar
Kargar, H., Kia, R., Jamshidvand, A. & Fun, H.-K. (2009). Acta Cryst. E65, o776–o777. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

2-{[(4-{[(2-Hy­dr­oxy­phen­yl)(phen­yl)methyl­­idene]amino}­but­yl)imino](phen­yl)meth­yl}phenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{[(4-{[(2-Hydroxyphenyl)(phenyl)methylidene]amino}butyl)imino](phenyl)methyl}phenol