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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Dec 15;67(Pt 1):o130. doi: 10.1107/S1600536810051688

2-((Z)-{3-[(Z)-(2-Hy­droxy-5-methyl­benzyl­idene)amino]-2,2-dimethyl­prop­yl}imino­meth­yl)-4-methyl­phenol

Reza Kia a,b,*, Hadi Kargar c, Valiollah Mirkhani d, Fatemeh Ganji c, Muhammad Nawaz Tahir e,*
PMCID: PMC3050403  PMID: 21522641

Abstract

In the title compound, C21H26N2O2, the dihedral angle between the two benzene rings is 73.47 (16)°. Strong intra­molecular O—H⋯N hydrogen bonds generate S(6) ring motifs. The substituted benzene rings are twisted around the central quaternary C atom in opposite directions, making a vault geometry.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Kargar et al. (2009 ▶, 2010 ▶).graphic file with name e-67-0o130-scheme1.jpg

Experimental

Crystal data

  • C21H26N2O2

  • M r = 338.44

  • Orthorhombic, Inline graphic

  • a = 5.8950 (3) Å

  • b = 17.8634 (10) Å

  • c = 18.2140 (11) Å

  • V = 1918.02 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.30 × 0.18 × 0.12 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.978, T max = 0.991

  • 16208 measured reflections

  • 2199 independent reflections

  • 1368 reflections with I > 2σ(I)

  • R int = 0.062

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044

  • wR(F 2) = 0.112

  • S = 1.03

  • 2199 reflections

  • 231 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.12 e Å−3

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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051688/gw2096sup1.cif

e-67-0o130-sup1.cif (21.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051688/gw2096Isup2.hkl

e-67-0o130-Isup2.hkl (108.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯N1 0.82 1.89 2.620 (3) 147
O2—H2A⋯N2 0.82 1.88 2.609 (4) 147
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Acknowledgments

RK thanks the Science and Research Branch, Islamic Azad University. HK and FG thank PNU for financial support. MNT thanks the University of Sargodha, Pakistan, for the research facilities.

supplementary crystallographic information

Comment

Schiff base ligands are one of the most prevalent systems in coordination chemistry. As part of a general study of tetradenate Schiff bases (Kargar et al. 2009; Kargar et al. 2010), we have determined the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a potentially tetradenate Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The dihedral angle between the two phenyl rings is 73.47 (16)°. Strong intramolecular O—H···N hydrogen bonds generate S(6) ring motifs (Bernstein et al., 1995). The title compound has a skew geometry. In the absence of sufficient anomalous scattering the absolute structure could not be determined.

Experimental

The title compound was synthesized by adding 5-methyl-salicylaldehyde (4 mmol) to a solution of 2,2'-dimethylpropylenediamine (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow 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.

Refinement

H atoms of the hydroxy groups were located by a rotating O–H group and constraied to refine with the parent atoms with Uiso(H) = 1.5 Ueq(O), see Table 1. The remaining H atoms were positioned geometrically with C—H = 0.93-0.97 Å and included in a riding model approximation with Uiso (H) = 1.2 or 1.5 Ueq (C). A rotating group model was used for the methyl groups of the benzene rings. In the absence of sufficient anomalous scattering the absolute structure could not be determined and 1580 Friedel pairs were merged.

Figures

Fig. 1.

Fig. 1.

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The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bonds are drawn as dashed lines.

Crystal data

C21H26N2O2 F(000) = 728
Mr = 338.44 Dx = 1.172 Mg m−3
Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 2150 reflections
a = 5.8950 (3) Å θ = 2.5–29.8°
b = 17.8634 (10) Å µ = 0.08 mm−1
c = 18.2140 (11) Å T = 296 K
V = 1918.02 (19) Å3 Plate, yellow
Z = 4 0.30 × 0.18 × 0.12 mm
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Data collection

Bruker SMART APEXII CCD area-detector diffractometer 2199 independent reflections
Radiation source: fine-focus sealed tube 1368 reflections with I > 2σ(I)
graphite Rint = 0.062
φ and ω scans θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005) h = −7→7
Tmin = 0.978, Tmax = 0.991 k = −22→22
16208 measured reflections l = −22→22
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Refinement

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)] = 0.044 H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.082P] where P = (Fo2 + 2Fc2)/3
S = 1.03 (Δ/σ)max < 0.001
2199 reflections Δρmax = 0.15 e Å−3
231 parameters Δρmin = −0.12 e Å−3
0 restraints Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods Extinction coefficient: 0.013 (2)
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Special 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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.4633 (4) 0.71477 (13) 0.18637 (14) 0.0691 (7)
H1A 0.3887 0.6786 0.1999 0.104*
O2 −0.1798 (4) 0.44857 (14) 0.02145 (14) 0.0769 (7)
H2A −0.0936 0.4643 0.0533 0.115*
N1 0.1130 (4) 0.62471 (14) 0.19160 (15) 0.0576 (7)
N2 0.1758 (5) 0.44863 (14) 0.10671 (15) 0.0589 (7)
C1 0.3362 (5) 0.75772 (18) 0.14103 (17) 0.0513 (8)
C2 0.4215 (5) 0.82499 (18) 0.11644 (19) 0.0593 (9)
H2 0.5650 0.8401 0.1316 0.071*
C3 0.2994 (6) 0.87012 (19) 0.07010 (18) 0.0593 (9)
H3 0.3614 0.9153 0.0545 0.071*
C4 0.0828 (5) 0.84926 (18) 0.04596 (18) 0.0558 (9)
C5 −0.0004 (6) 0.78143 (17) 0.07017 (17) 0.0544 (8)
H5 −0.1421 0.7659 0.0537 0.065*
C6 0.1183 (5) 0.73540 (17) 0.11802 (17) 0.0487 (8)
C7 −0.0504 (7) 0.90009 (19) −0.0039 (2) 0.0777 (11)
H7A 0.0048 0.8952 −0.0533 0.117*
H7B −0.0332 0.9510 0.0120 0.117*
H7C −0.2079 0.8865 −0.0023 0.117*
C8 0.0162 (6) 0.66623 (17) 0.14440 (18) 0.0562 (9)
H8 −0.1246 0.6520 0.1261 0.067*
C9 −0.0035 (6) 0.55714 (17) 0.21706 (19) 0.0641 (10)
H9A −0.1067 0.5401 0.1791 0.077*
H9B −0.0929 0.5693 0.2601 0.077*
C10 0.1605 (6) 0.49409 (17) 0.23599 (18) 0.0615 (9)
C11 0.3201 (7) 0.5184 (2) 0.2980 (2) 0.0892 (13)
H11A 0.2336 0.5276 0.3417 0.134*
H11B 0.3982 0.5633 0.2838 0.134*
H11C 0.4286 0.4794 0.3072 0.134*
C12 0.0218 (8) 0.4259 (2) 0.2593 (2) 0.0891 (13)
H12A 0.1216 0.3842 0.2673 0.134*
H12B −0.0850 0.4136 0.2214 0.134*
H12C −0.0582 0.4370 0.3039 0.134*
C13 0.3085 (6) 0.47518 (18) 0.16952 (19) 0.0640 (10)
H13A 0.3929 0.5194 0.1551 0.077*
H13B 0.4171 0.4369 0.1833 0.077*
C14 0.2562 (6) 0.39671 (18) 0.06619 (18) 0.0571 (9)
H14 0.3962 0.3762 0.0784 0.069*
C15 0.1397 (5) 0.36831 (16) 0.00220 (18) 0.0512 (8)
C16 0.2388 (6) 0.31298 (17) −0.04090 (17) 0.0542 (8)
H16 0.3790 0.2940 −0.0267 0.065*
C17 0.1400 (6) 0.28490 (17) −0.10341 (18) 0.0570 (9)
C18 −0.0714 (6) 0.3128 (2) −0.1220 (2) 0.0638 (10)
H18 −0.1438 0.2943 −0.1636 0.077*
C19 −0.1782 (6) 0.3673 (2) −0.08042 (19) 0.0648 (9)
H19 −0.3205 0.3850 −0.0941 0.078*
C20 −0.0727 (5) 0.39531 (18) −0.01880 (19) 0.0542 (9)
C21 0.2588 (7) 0.22644 (19) −0.14975 (19) 0.0775 (12)
H21A 0.3779 0.2497 −0.1775 0.116*
H21B 0.1517 0.2039 −0.1827 0.116*
H21C 0.3222 0.1886 −0.1184 0.116*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0584 (15) 0.0711 (17) 0.0778 (17) 0.0012 (12) −0.0145 (14) 0.0031 (14)
O2 0.0690 (16) 0.0818 (17) 0.0798 (19) 0.0272 (15) 0.0009 (14) −0.0003 (14)
N1 0.0590 (17) 0.0501 (16) 0.0636 (18) 0.0000 (13) 0.0014 (15) −0.0032 (14)
N2 0.0615 (17) 0.0523 (17) 0.0629 (18) 0.0032 (14) −0.0008 (16) 0.0023 (15)
C1 0.0439 (18) 0.0545 (19) 0.056 (2) 0.0055 (16) −0.0042 (16) −0.0062 (16)
C2 0.0503 (19) 0.060 (2) 0.068 (2) −0.0066 (17) −0.0024 (18) −0.0138 (18)
C3 0.057 (2) 0.056 (2) 0.065 (2) −0.0064 (17) 0.0018 (18) −0.0047 (18)
C4 0.056 (2) 0.054 (2) 0.058 (2) 0.0018 (16) 0.0007 (17) −0.0054 (16)
C5 0.0467 (18) 0.055 (2) 0.061 (2) −0.0020 (16) −0.0037 (17) −0.0096 (17)
C6 0.0423 (17) 0.0497 (18) 0.0540 (19) −0.0008 (14) 0.0011 (16) −0.0062 (16)
C7 0.078 (3) 0.070 (2) 0.085 (3) −0.0059 (19) −0.015 (2) 0.014 (2)
C8 0.0485 (19) 0.057 (2) 0.063 (2) −0.0020 (16) 0.0052 (17) −0.0098 (17)
C9 0.067 (2) 0.061 (2) 0.064 (2) −0.0107 (19) 0.0100 (19) −0.0015 (17)
C10 0.072 (2) 0.052 (2) 0.060 (2) −0.0139 (19) −0.0039 (19) 0.0081 (17)
C11 0.109 (3) 0.080 (3) 0.079 (3) −0.012 (2) −0.027 (3) −0.002 (2)
C12 0.116 (3) 0.077 (3) 0.074 (3) −0.032 (3) −0.009 (3) 0.016 (2)
C13 0.060 (2) 0.052 (2) 0.080 (3) −0.0010 (17) −0.006 (2) −0.0061 (18)
C14 0.0495 (19) 0.054 (2) 0.068 (2) 0.0020 (16) −0.0012 (18) 0.0062 (18)
C15 0.0506 (19) 0.0491 (18) 0.0538 (19) 0.0021 (15) 0.0049 (17) 0.0105 (16)
C16 0.0496 (19) 0.0534 (19) 0.059 (2) 0.0028 (15) 0.0031 (17) 0.0083 (17)
C17 0.063 (2) 0.055 (2) 0.053 (2) −0.0015 (17) 0.0069 (18) 0.0096 (17)
C18 0.064 (2) 0.072 (2) 0.055 (2) −0.0100 (19) −0.0029 (19) 0.0109 (18)
C19 0.0495 (19) 0.079 (3) 0.066 (2) 0.0022 (19) −0.002 (2) 0.018 (2)
C20 0.051 (2) 0.0555 (19) 0.057 (2) 0.0067 (16) 0.0082 (17) 0.0106 (17)
C21 0.099 (3) 0.068 (2) 0.065 (2) 0.011 (2) 0.006 (2) −0.0031 (19)
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Geometric parameters (Å, °)

O1—C1 1.354 (3) C10—C12 1.527 (5)
O1—H1A 0.8200 C10—C13 1.530 (4)
O2—C20 1.357 (4) C10—C11 1.533 (5)
O2—H2A 0.8200 C11—H11A 0.9600
N1—C8 1.271 (4) C11—H11B 0.9600
N1—C9 1.464 (4) C11—H11C 0.9600
N2—C14 1.276 (4) C12—H12A 0.9600
N2—C13 1.465 (4) C12—H12B 0.9600
C1—C2 1.377 (4) C12—H12C 0.9600
C1—C6 1.409 (4) C13—H13A 0.9700
C2—C3 1.371 (4) C13—H13B 0.9700
C2—H2 0.9300 C14—C15 1.445 (4)
C3—C4 1.401 (4) C14—H14 0.9300
C3—H3 0.9300 C15—C16 1.391 (4)
C4—C5 1.380 (4) C15—C20 1.395 (4)
C4—C7 1.506 (4) C16—C17 1.374 (4)
C5—C6 1.388 (4) C16—H16 0.9300
C5—H5 0.9300 C17—C18 1.384 (5)
C6—C8 1.456 (4) C17—C21 1.515 (4)
C7—H7A 0.9600 C18—C19 1.386 (5)
C7—H7B 0.9600 C18—H18 0.9300
C7—H7C 0.9600 C19—C20 1.377 (4)
C8—H8 0.9300 C19—H19 0.9300
C9—C10 1.524 (5) C21—H21A 0.9600
C9—H9A 0.9700 C21—H21B 0.9600
C9—H9B 0.9700 C21—H21C 0.9600
C1—O1—H1A 109.5 C10—C11—H11B 109.5
C20—O2—H2A 109.5 H11A—C11—H11B 109.5
C8—N1—C9 119.0 (3) C10—C11—H11C 109.5
C14—N2—C13 119.3 (3) H11A—C11—H11C 109.5
O1—C1—C2 119.4 (3) H11B—C11—H11C 109.5
O1—C1—C6 121.7 (3) C10—C12—H12A 109.5
C2—C1—C6 118.9 (3) C10—C12—H12B 109.5
C3—C2—C1 121.4 (3) H12A—C12—H12B 109.5
C3—C2—H2 119.3 C10—C12—H12C 109.5
C1—C2—H2 119.3 H12A—C12—H12C 109.5
C2—C3—C4 121.0 (3) H12B—C12—H12C 109.5
C2—C3—H3 119.5 N2—C13—C10 112.6 (3)
C4—C3—H3 119.5 N2—C13—H13A 109.1
C5—C4—C3 117.2 (3) C10—C13—H13A 109.1
C5—C4—C7 122.5 (3) N2—C13—H13B 109.1
C3—C4—C7 120.3 (3) C10—C13—H13B 109.1
C4—C5—C6 122.8 (3) H13A—C13—H13B 107.8
C4—C5—H5 118.6 N2—C14—C15 123.0 (3)
C6—C5—H5 118.6 N2—C14—H14 118.5
C5—C6—C1 118.6 (3) C15—C14—H14 118.5
C5—C6—C8 120.1 (3) C16—C15—C20 117.9 (3)
C1—C6—C8 121.3 (3) C16—C15—C14 120.4 (3)
C4—C7—H7A 109.5 C20—C15—C14 121.7 (3)
C4—C7—H7B 109.5 C17—C16—C15 123.3 (3)
H7A—C7—H7B 109.5 C17—C16—H16 118.3
C4—C7—H7C 109.5 C15—C16—H16 118.3
H7A—C7—H7C 109.5 C16—C17—C18 117.0 (3)
H7B—C7—H7C 109.5 C16—C17—C21 121.2 (3)
N1—C8—C6 122.2 (3) C18—C17—C21 121.9 (3)
N1—C8—H8 118.9 C17—C18—C19 121.9 (4)
C6—C8—H8 118.9 C17—C18—H18 119.0
N1—C9—C10 112.6 (3) C19—C18—H18 119.0
N1—C9—H9A 109.1 C20—C19—C18 119.7 (3)
C10—C9—H9A 109.1 C20—C19—H19 120.2
N1—C9—H9B 109.1 C18—C19—H19 120.2
C10—C9—H9B 109.1 O2—C20—C19 119.0 (3)
H9A—C9—H9B 107.8 O2—C20—C15 120.8 (3)
C9—C10—C12 108.2 (3) C19—C20—C15 120.2 (3)
C9—C10—C13 110.2 (3) C17—C21—H21A 109.5
C12—C10—C13 110.4 (3) C17—C21—H21B 109.5
C9—C10—C11 110.3 (3) H21A—C21—H21B 109.5
C12—C10—C11 110.5 (3) C17—C21—H21C 109.5
C13—C10—C11 107.2 (3) H21A—C21—H21C 109.5
C10—C11—H11A 109.5 H21B—C21—H21C 109.5
O1—C1—C2—C3 179.6 (3) C14—N2—C13—C10 −142.8 (3)
C6—C1—C2—C3 −0.3 (5) C9—C10—C13—N2 −61.8 (4)
C1—C2—C3—C4 −0.1 (5) C12—C10—C13—N2 57.8 (4)
C2—C3—C4—C5 −0.6 (5) C11—C10—C13—N2 178.1 (3)
C2—C3—C4—C7 179.0 (3) C13—N2—C14—C15 −178.5 (3)
C3—C4—C5—C6 1.7 (5) N2—C14—C15—C16 178.3 (3)
C7—C4—C5—C6 −177.9 (3) N2—C14—C15—C20 −1.2 (5)
C4—C5—C6—C1 −2.1 (4) C20—C15—C16—C17 1.3 (4)
C4—C5—C6—C8 176.9 (3) C14—C15—C16—C17 −178.3 (3)
O1—C1—C6—C5 −178.6 (3) C15—C16—C17—C18 −1.7 (5)
C2—C1—C6—C5 1.3 (4) C15—C16—C17—C21 177.9 (3)
O1—C1—C6—C8 2.4 (4) C16—C17—C18—C19 1.0 (5)
C2—C1—C6—C8 −177.7 (3) C21—C17—C18—C19 −178.7 (3)
C9—N1—C8—C6 178.2 (3) C17—C18—C19—C20 0.2 (5)
C5—C6—C8—N1 −175.7 (3) C18—C19—C20—O2 −179.8 (3)
C1—C6—C8—N1 3.3 (5) C18—C19—C20—C15 −0.7 (5)
C8—N1—C9—C10 147.8 (3) C16—C15—C20—O2 179.1 (3)
N1—C9—C10—C12 −178.1 (3) C14—C15—C20—O2 −1.3 (5)
N1—C9—C10—C13 −57.2 (4) C16—C15—C20—C19 0.0 (4)
N1—C9—C10—C11 60.9 (4) C14—C15—C20—C19 179.5 (3)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O1—H1A···N1 0.82 1.89 2.620 (3) 147
O2—H2A···N2 0.82 1.88 2.609 (4) 147
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2096).

References

  1. 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.
  2. Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  3. Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Kargar, H., Kia, R., Jamshidvand, A. & Fun, H.-K. (2009). Acta Cryst. E65, o776–o777. [DOI] [PMC free article] [PubMed]
  5. Kargar, H., Kia, R., Ullah Khan, I. & Sahraei, A. (2010). Acta Cryst. E66, o539. [DOI] [PMC free article] [PubMed]
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051688/gw2096sup1.cif

e-67-0o130-sup1.cif (21.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051688/gw2096Isup2.hkl

e-67-0o130-Isup2.hkl (108.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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