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

Kia, R.; Kargar, H.; Mirkhani, V.; Ganji, F.; Tahir, M.N.

doi:10.1107/S1600536810051688

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o130

https://doi.org/10.1107/S1600536810051688

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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 and Muhammad Nawaz Tahir ^e ^*

^aDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^bX-ray Crystallography Laboratory, Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^cDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, ^dDepartment of Chemistry, University of Isfahan, Isfahan, 81746-73441, Iran, and ^eDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: rkia@srbiau.ac.ir, zsrkk@yahoo.com, dmntahir_uos@yahoo.com

(Received 4 December 2010; accepted 9 December 2010; online 15 December 2010)

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 ).

Experimental

Crystal data

C₂₁H₂₆N₂O₂
M_r = 338.44
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.112
S = 1.03
2199 reflections
231 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.12 e Å⁻³

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

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: https://doi.org/10.1107/S1600536810051688/gw2096sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051688/gw2096Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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).

Experimental top

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.

Structure description top

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).

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

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

Crystal data top

C₂₁H₂₆N₂O₂	F(000) = 728
M_r = 338.44	D_x = 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

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2199 independent reflections
Radiation source: fine-focus sealed tube	1368 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
φ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
T_min = 0.978, T_max = 0.991	k = −22→22
16208 measured reflections	l = −22→22

Refinement top

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(F_o²) + (0.0485P)² + 0.082P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2199 reflections	Δρ_max = 0.15 e Å⁻³
231 parameters	Δρ_min = −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)

Crystal data top

C₂₁H₂₆N₂O₂	V = 1918.02 (19) Å³
M_r = 338.44	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.8950 (3) Å	µ = 0.08 mm⁻¹
b = 17.8634 (10) Å	T = 296 K
c = 18.2140 (11) Å	0.30 × 0.18 × 0.12 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2199 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1368 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.991	R_int = 0.062
16208 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
2199 reflections	Δρ_min = −0.12 e Å⁻³
231 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₆N₂O₂
M_r	338.44
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.8950 (3), 17.8634 (10), 18.2140 (11)
V (Å³)	1918.02 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.18 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.978, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	16208, 2199, 1368
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.112, 1.03
No. of reflections	2199
No. of parameters	231
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.12

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—H1A···N1	0.82	1.89	2.620 (3)	147
O2—H2A···N2	0.82	1.88	2.609 (4)	147

Acknowledgements

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.

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. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Kargar, H., Kia, R., Ullah Khan, I. & Sahraei, A. (2010). Acta Cryst. E66, o539. Web of Science CSD CrossRef 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-((Z)-{3-[(Z)-(2-Hy­dr­oxy-5-methyl­benzyl­­idene)amino]-2,2-di­methyl­prop­yl}imino­meth­yl)-4-methyl­phenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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