The asymmetric unit of the title compound, C 30H 28N 2O 2, comprises half of a potential tetra-dentate Schiff base ligand; an inversion centre is situtated at the center of the butane-diamine spacer. The central methylene segment of the diamine spacer is disordered over two positions with a refined siteoccupancy ratio of 0.651 (7):0.349 (7). The phenyl ring and the hydroxysubstituted 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

Kargar, H.

Kia, R.

Tahir, M.

English

MPG.PuRe

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

2-{[(4-{[(2-Hydroxyphenyl)(phenyl)-methylidene]amino}butyl)imino]-(phenyl)methyl}phenolArezoo Jamshidvand,a Reza Kia,b,c* Hadi Kargara andMuhammad Nawaz Tahird*aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I.R. of Iran, bX-ray Crystallography Lab., Plasma Physics Research Center, Science andResearch Branch, Islamic Azad University, Tehran, Iran, cDepartment of Chemistry,Science and Research Branch, Islamic Azad University, Tehran, Iran, anddDepartment of Physics, University of Sargodha, Punjab, PakistanCorrespondence e-mail: zsrkk@yahoo.com, dmntahir_uos@yahoo.comReceived 25 December 2011; accepted 27 December 2011Key indicators: single-crystal X-ray study; T = 291 K; mean (C–C) = 0.002 A˚;disorder in main residue; R factor = 0.045; wR factor = 0.127; data-to-parameterratio = 17.9.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 butane-diamine spacer. The central methylene segment of the diaminespacer is disordered over two positions with a refined site-occupancy ratio of 0.651 (7):0.349 (7). The phenyl ring and thehydroxy-substituted benzene ring are almost perpendicular toeach other, with a dihedral angle of 87.90 (8) A˚. Intra-molecular O—H  N hydrogen bonds make S(6) ring motifs.Related literatureFor standard bond lengths, see: Allen et al. (1987). Forhydrogen bond motifs, see: Bernstein et al. (1995). For back-ground to Schiff bases in coordination chemistry, see: Gran-ovski et al. (1993); Kargar et al. (2009). For a related structure,see: Friscic et al. (1998).ExperimentalCrystal dataC30H28N2O2Mr = 448.54Monoclinic, P21=na = 11.5720 (3) A˚b = 7.7803 (2) A˚c = 13.3914 (4) A˚ = 95.774 (2)V = 1199.56 (6) A˚3Z = 2Mo K radiation = 0.08 mm1T = 291 K0.25  0.16  0.12 mmData collectionBruker SMART APEXII CCDarea-detector diffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2005)Tmin = 0.250, Tmax = 0.45910739 measured reflections2951 independent reflections1706 reflections with I > 2(I)Rint = 0.027RefinementR[F 2 > 2(F 2)] = 0.045wR(F 2) = 0.127S = 1.022951 reflections165 parametersH-atom parameters constrainedmax = 0.16 e A˚3min = 0.13 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AO1—H1  N1 0.82 1.80 2.5328 (16) 148Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT(Bruker, 2005); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:SHELXTL (Sheldrick, 2008); software used to prepare material forpublication: SHELXTL and PLATON (Spek, 2009).HK and AJ thank PNU for financial support, and MNTthanks the GC University of Sargodha, Pakistan for researchfacilities.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: SU2355).ReferencesAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.Int. Ed. Engl. 34, 1555–1573.Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.Friscic, T., Kaitner, B. & Mestrovic, E. (1998). Croat. Chem. Acta, 71, 87–91.Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem.Rev. 126, 1–69.Kargar, H., Kia, R., Jamshidvand, A. & Fun, H.-K. (2009). Acta Cryst. E65,o776–o777.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.organic compoundso292 Jamshidvand et al. doi:10.1107/S1600536811055905 Acta Cryst. (2012). E68, o292Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supporting informationsup-1Acta Cryst. (2012). E68, o292    supporting informationActa Cryst. (2012). E68, o292    [doi:10.1107/S1600536811055905]2-{[(4-{[(2-Hydroxyphenyl)(phenyl)methylidene]amino}butyl)imino](phenyl)-methyl}phenolArezoo Jamshidvand, Reza Kia, Hadi Kargar and Muhammad Nawaz TahirS1. Comment 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).S2. Experimental 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.S3. Refinement The OH and C-bound H-atoms were included in calculated positions and treated as riding atoms: O-H = 0.82 Å, C-H = 0.93 and 0.97 Å for CH and CH2 H-atoms, respectively, with Uiso(H) = k × Ueq(C), where k = 1.5 for OH, and k = 1.2 for all other H-atoms. The methylene segment (C15) of the diamine spacer was disordered over two positions with a refined site occupancy ratio 0.651 (7)/0.349 (7).supporting informationsup-2Acta Cryst. (2012). E68, o292    Figure 1A 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 Crystal data C30H28N2O2Mr = 448.54Monoclinic, P21/nHall symbol: -P 2yna = 11.5720 (3) Åb = 7.7803 (2) Åc = 13.3914 (4) Åβ = 95.774 (2)°V = 1199.56 (6) Å3Z = 2F(000) = 476Dx = 1.242 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 2370 reflectionsθ = 2.5–27.5°µ = 0.08 mm−1T = 291 KBlock, yellow0.25 × 0.16 × 0.12 mmData collection Bruker SMART APEXII CCD area-detector diffractometerRadiation source: fine-focus sealed tubeGraphite monochromatorφ and ω scansAbsorption correction: multi-scan (SADABS; Bruker, 2005)Tmin = 0.250, Tmax = 0.45910739 measured reflections2951 independent reflections1706 reflections with I > 2σ(I)Rint = 0.027θmax = 28.3°, θmin = 2.2°h = −15→11k = −10→9l = −17→17supporting informationsup-3Acta Cryst. (2012). E68, o292    Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.045wR(F2) = 0.127S = 1.022951 reflections165 parameters0 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: inferred from neighbouring sitesH-atom parameters constrainedw = 1/[σ2(Fo2) + (0.0565P)2 + 0.0873P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.16 e Å−3Δρmin = −0.13 e Å−3Special details 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) x y z Uiso*/Ueq 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*supporting informationsup-4Acta Cryst. (2012). E68, o292    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) U11 U22 U33 U12 U13 U23O1 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) O1—C2 1.3373 (17) C10—C11 1.350 (3)O1—H1 0.8200 C10—H10 0.9300N1—C7 1.2867 (17) C11—C12 1.371 (3)N1—C14 1.4631 (18) C11—H11 0.9300C1—C6 1.3994 (19) C12—C13 1.382 (3)C1—C2 1.4087 (19) C12—H12 0.9300C1—C7 1.4703 (19) C13—H13 0.9300C2—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 0.9700C4—C5 1.383 (2) C14—H14B 0.9700C4—H4 0.9300 C14—H14C 0.9599supporting informationsup-5Acta Cryst. (2012). E68, o292    C5—C6 1.374 (2) C14—H14D 0.9600C5—H5 0.9300 C15—C15i 1.512 (7)C6—H6 0.9300 C15—H15A 0.9700C7—C8 1.4984 (19) C15—H15B 0.9700C8—C9 1.377 (2) C15A—C15Ai 1.497 (13)C8—C13 1.378 (2) C15A—H15C 0.9700C9—C10 1.380 (2) C15A—H15D 0.9700C9—H9 0.9300C2—O1—H1 109.5 C8—C13—H13 120.2C7—N1—C14 122.34 (13) C12—C13—H13 120.2C6—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 109.2O1—C2—C1 121.88 (12) C15—C14—H14A 109.2C3—C2—C1 119.51 (13) C15A—C14—H14A 135.7C4—C3—C2 120.74 (14) N1—C14—H14B 109.2C4—C3—H3 119.6 C15—C14—H14B 109.2C2—C3—H3 119.6 C15A—C14—H14B 77.4C3—C4—C5 120.72 (14) H14A—C14—H14B 107.9C3—C4—H4 119.6 N1—C14—H14C 109.9C5—C4—H4 119.6 C15—C14—H14C 76.2C6—C5—C4 119.27 (15) C15A—C14—H14C 109.4C6—C5—H5 120.4 H14A—C14—H14C 36.2C4—C5—H5 120.4 H14B—C14—H14C 134.5C5—C6—C1 121.72 (14) N1—C14—H14D 109.4C5—C6—H6 119.1 C15—C14—H14D 133.6C1—C6—H6 119.1 C15A—C14—H14D 109.7N1—C7—C1 118.45 (12) H14A—C14—H14D 75.0N1—C7—C8 123.60 (12) H14B—C14—H14D 35.3C1—C7—C8 117.95 (12) H14C—C14—H14D 108.3C9—C8—C13 119.12 (15) C14—C15—C15i 114.0 (4)C9—C8—C7 120.37 (14) C14—C15—H14C 36.2C13—C8—C7 120.50 (13) C15i—C15—H14C 148.7C8—C9—C10 120.18 (17) C14—C15—H15A 108.7C8—C9—H9 119.9 C15i—C15—H15A 108.7C10—C9—H9 119.9 H14C—C15—H15A 82.4C11—C10—C9 120.84 (19) C14—C15—H15B 108.7C11—C10—H10 119.6 C15i—C15—H15B 108.7C9—C10—H10 119.6 H14C—C15—H15B 94.6C10—C11—C12 119.46 (18) H15A—C15—H15B 107.6C10—C11—H11 120.3 C15Ai—C15A—C14 113.1 (7)C12—C11—H11 120.3 C15Ai—C15A—H15C 109.0C11—C12—C13 120.74 (19) C14—C15A—H15C 109.0C11—C12—H12 119.6 C15Ai—C15A—H15D 109.0supporting informationsup-6Acta Cryst. (2012). E68, o292    C13—C12—H12 119.6 C14—C15A—H15D 109.0C8—C13—C12 119.62 (18) H15C—C15A—H15D 107.8Symmetry code: (i) −x, −y, −z.Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AO1—H1···N1 0.82 1.80 2.5328 (16) 148

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

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MPG.PuRe

MPG.PuRe