(E)-3-[(4-Butyl­phen­yl)imino­meth­yl]benzene-1,2-diol

Keleşoğlu, Z.; Büyükgüngör, O.; Albayrak, Ç.; Odabaşoğlu, M.

doi:10.1107/S1600536809029316

organic compounds

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Volume 65| Part 8| August 2009| Page o2022

doi:10.1107/S1600536809029316

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(E)-3-[(4-Butylphenyl)iminomethyl]benzene-1,2-diol

Zeynep Keleşoğlu,^a Orhan Büyükgüngör,^a ^* Çiğdem Albayrak ^b and Mustafa Odabaşoğlu ^c

^aDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, ^bSinop University, Sinop Faculty of Education, Sinop, Turkey, and ^cPamukkale University, Denizli Technical Vocational School, Denizli, Turkey
^*Correspondence e-mail: zeynep.kelesoglu@omu.edu.tr

(Received 21 July 2009; accepted 23 July 2009; online 29 July 2009)

The title compound, C₁₇H₁₉NO₂, exists as an enol–imine tautomer. The dihedral angle between the two benzene rings is 4.6 (2)°. The molecular structure is stabilized by intramolecular O—H⋯O and O—H⋯N hydrogen bonds which generate S(5) and S(6) ring motifs, respectively. In the crystal, molecules are linked into centrosymmetric dimers by pairs of O—H⋯O hydrogen bonds. In addition, C—H⋯π interactions involving both benzene rings are observed.

Related literature

For general background to Schiff bases, see: Lozier et al. (1975 ); Calligaris et al. (1972 ); Maslen & Waters (1975 ); Steward & Lingafelter (1959 ). For the photochromic and thermochromic characteristics of Schiff base compounds, see: Hadjoudis et al. (1987 ); Moustakali-Mavridis et al. (1980 ). For graph-set motifs, see: Bernstein et al. (1995 ). For related structures, see: Temel et al. (2007 ); Koşar et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₉NO₂
M_r = 269.33
Monoclinic, P 2₁ /c
a = 16.2774 (13) Å
b = 6.0148 (6) Å
c = 17.6166 (14) Å
β = 121.476 (5)°
V = 1471.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.50 × 0.45 × 0.03 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.954, T_max = 0.998
8711 measured reflections
3061 independent reflections
1643 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.163
S = 1.07
3061 reflections
189 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.86 (2)	2.21 (3)	2.728 (2)	118 (3)
O2—H2⋯O1ⁱ	0.86 (2)	2.08 (3)	2.802 (3)	141 (3)
O1—H1⋯N1	0.88 (2)	1.74 (2)	2.555 (2)	155 (3)
C6—H6⋯Cg2ⁱⁱ	0.93	2.85	3.645 (3)	144
C10—H10⋯Cg1ⁱⁱ	0.93	2.80	3.491 (3)	132
Symmetry codes: (i) -x+1, -y+3, -z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029316/ci2863sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029316/ci2863Isup2.hkl

checkCIF report

Comment top

Schiff bases are widely used as ligands in the field of coordination chemistry and they play an important role in various field of chemistry due to their biological activities (Lozier et al., 1975). o-Hydroxy Schiff bases derived from the reaction of o-hydroxy aldehydes with aniline have been examined extensively (Steward & Lingafelter, 1959; Calligaris et al., 1972; Maslen & Waters, 1975). Some Schiff bases derived from salicylaldehyde have attracted the interest of chemists and physicists because they show thermochromism and photochromism in the solid state by H-atom transfer from the hydroxy O atom to the N atom (Hadjoudis, et al., 1987). It has been proposed that molecules showing thermochromism are planar while those showing photochromism are non-planar (Moustakali-Mavridis et al., 1980). There are two types of intramolecular hydrogen bonds in Schiff bases arising from the keto-amine (N—H···O) and enol-imine (N···H—O) tautomeric forms.

X-ray analysis shows that compound (I) prefers the enol-imine tautomeric form with a strong intramolecular O—H···N hydrogen bond. A H atom is located on atom O1, thus the enol-imine tautomer is favoured over the keto-amine form, as indicated by the C2—O1 [1.333 (2) Å], C7—N1 [1.297 (2) Å], C1—C7 [1.433 (2) Å] and C1—C2 [1.406 (2) Å] bond lengths (Fig. 1). The C2—O1 bond length of 1.333 (2) Å indicates a single-bond character, whereas the C7—N1 bond length of 1.297 (2) Å indicates a high degree of double-bond character. Similar results were observed for (E)-3-[(2-fluorophenylimino)methyl]benzene-1,2-diol [C—O = 1.354 (19) Å, C—N = 1.285 (2) Å; Temel et al., 2007].

The molecule of (I) is nearly planar, with a dihedral angle between the benzene rings A(C1-C6) and B(C8-C13) of 4.6 (2) Å. Intramolecular O—H···O and O—H···N hydrogen bonds generate S(5) and S(6) ring motifs, respectively (Bernstein et al., 1995) (Fig. 1). The nearly planar S(6) ring forms dihedral angles of 2.3 (4)° and 2.5 (5)° with the rings A and B, respectively.

In the crystal, molecules of (I) are linked by intermolecular O—H···O hydrogen bonds forming centrosymmetric dimers (Fig.2). In addition, C6—H6···Cg2 and C10—H10···Cg1 interactions (Cg1 and Cg2 are the centroids of the C1—C6 and C8—C13 rings, respectively) are observed (Table 1).

Related literature top

For general background to Schiff bases, see: Lozier et al. (1975); Calligaris et al. (1972); Maslen & Waters (1975); Steward & Lingafelter (1959). For the photochromic and thermochromic characteristics of Schiff base compounds, see: Hadjoudis et al. (1987); Moustakali-Mavridis et al. (1980). For graph-set motifs, see: Bernstein et al. (1995). For related structures, see: Temel et al. (2007); Koşar et al. (2005). Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

Experimental top

Compound (I) was prepared by refluxing a mixture of 2,3-dihydroxy benzaldehyde (0.5 g, 0.0036 mol) in ethanol (20 ml) and 4-butilanilyne (0.54 g 0.0036 mol) in ethanol (20 ml). The reaction mixture was stirred for 1 h under reflux. The crystals of (I) suitable for X-ray analysis were obtained from a methanol solution by slow evaporation (yield 85%; m.p. 363–364 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. An ORTEP view of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids. Dashed lines indicate H-bonds.
	Fig. 2. A packing diagram for (I), showing the formation of dimers through O—H···O hydrogen bonds. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity [symmetry code (i): 1-x, 3-y, -z].

(E)-3-[(4-Butylphenyl)iminomethyl]benzene-1,2-diol top

Crystal data top

C₁₇H₁₉NO₂	F(000) = 576
M_r = 269.33	D_x = 1.216 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8711 reflections
a = 16.2774 (13) Å	θ = 1.4–27.4°
b = 6.0148 (6) Å	µ = 0.08 mm⁻¹
c = 17.6166 (14) Å	T = 296 K
β = 121.476 (5)°	Thin plate, red
V = 1471.0 (2) Å³	0.50 × 0.45 × 0.03 mm
Z = 4

Data collection top

Stoe IPDSII diffractometer	3061 independent reflections
Radiation source: fine-focus sealed tube	1643 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.5°
rotation method scans	h = −20→20
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
T_min = 0.954, T_max = 0.998	l = −22→22
8711 measured reflections

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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.0648P)² + 0.0507P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.044
3061 reflections	Δρ_max = 0.15 e Å⁻³
189 parameters	Δρ_min = −0.15 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0060 (18)

Crystal data top

C₁₇H₁₉NO₂	V = 1471.0 (2) Å³
M_r = 269.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.2774 (13) Å	µ = 0.08 mm⁻¹
b = 6.0148 (6) Å	T = 296 K
c = 17.6166 (14) Å	0.50 × 0.45 × 0.03 mm
β = 121.476 (5)°

Data collection top

Stoe IPDSII diffractometer	3061 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1643 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.998	R_int = 0.062
8711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	2 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.15 e Å⁻³
3061 reflections	Δρ_min = −0.15 e Å⁻³
189 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
C1	0.57490 (18)	0.9538 (4)	0.13401 (17)	0.0578 (6)
C2	0.57322 (18)	1.1547 (4)	0.09238 (17)	0.0572 (6)
C3	0.64541 (18)	1.1943 (4)	0.07262 (18)	0.0613 (7)
C4	0.71906 (19)	1.0448 (5)	0.0989 (2)	0.0690 (8)
H4	0.7677	1.0749	0.0876	0.083*
C5	0.7222 (2)	0.8493 (5)	0.1423 (2)	0.0733 (8)
H5	0.7726	0.7496	0.1597	0.088*
C6	0.65099 (19)	0.8032 (4)	0.15939 (18)	0.0666 (7)
H6	0.6530	0.6715	0.1880	0.080*
C7	0.49848 (19)	0.9019 (4)	0.14886 (18)	0.0621 (7)
H7	0.4991	0.7663	0.1746	0.074*
C8	0.34786 (18)	0.9936 (4)	0.13574 (17)	0.0586 (6)
C9	0.3369 (2)	0.8029 (5)	0.1736 (2)	0.0760 (8)
H9	0.3838	0.6926	0.1947	0.091*
C10	0.2569 (2)	0.7761 (5)	0.1801 (2)	0.0787 (9)
H10	0.2511	0.6477	0.2064	0.094*
C11	0.1851 (2)	0.9339 (5)	0.1489 (2)	0.0697 (8)
C12	0.1964 (2)	1.1213 (5)	0.1113 (2)	0.0789 (9)
H12	0.1490	1.2305	0.0898	0.095*
C13	0.2768 (2)	1.1527 (4)	0.1044 (2)	0.0732 (8)
H13	0.2826	1.2819	0.0785	0.088*
C14	0.0994 (2)	0.9044 (5)	0.1604 (3)	0.0939 (10)
H14A	0.1223	0.9125	0.2234	0.113*
H14B	0.0555	1.0278	0.1314	0.113*
C15	0.0450 (2)	0.6941 (6)	0.1246 (2)	0.0910 (10)
H15A	0.0880	0.5706	0.1557	0.109*
H15B	0.0247	0.6822	0.0623	0.109*
C16	−0.0432 (2)	0.6723 (6)	0.1326 (3)	0.0975 (11)
H16A	−0.0230	0.6826	0.1949	0.117*
H16B	−0.0862	0.7959	0.1018	0.117*
C17	−0.0972 (3)	0.4600 (6)	0.0956 (3)	0.1137 (13)
H17A	−0.1126	0.4420	0.0354	0.171*
H17B	−0.1555	0.4640	0.0967	0.171*
H17C	−0.0581	0.3375	0.1310	0.171*
N1	0.42843 (15)	1.0402 (3)	0.12717 (14)	0.0599 (6)
O1	0.50446 (13)	1.3071 (3)	0.06822 (13)	0.0666 (5)
O2	0.64235 (14)	1.3817 (3)	0.02744 (15)	0.0767 (6)
H1	0.466 (2)	1.247 (5)	0.083 (2)	0.115*
H2	0.5901 (17)	1.449 (5)	0.016 (2)	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0654 (15)	0.0468 (13)	0.0619 (17)	−0.0011 (12)	0.0337 (14)	0.0022 (12)
C2	0.0608 (15)	0.0481 (13)	0.0663 (17)	−0.0007 (12)	0.0355 (14)	−0.0042 (12)
C3	0.0708 (16)	0.0471 (13)	0.0725 (19)	−0.0035 (12)	0.0421 (15)	−0.0018 (13)
C4	0.0678 (16)	0.0638 (16)	0.083 (2)	−0.0022 (14)	0.0445 (16)	−0.0101 (16)
C5	0.0736 (18)	0.0612 (17)	0.088 (2)	0.0099 (14)	0.0442 (17)	−0.0008 (16)
C6	0.0732 (17)	0.0527 (14)	0.0730 (19)	0.0058 (13)	0.0375 (15)	0.0042 (14)
C7	0.0723 (17)	0.0512 (14)	0.0642 (18)	−0.0018 (13)	0.0367 (14)	0.0041 (13)
C8	0.0630 (15)	0.0535 (14)	0.0608 (17)	−0.0019 (12)	0.0335 (13)	−0.0001 (13)
C9	0.0702 (17)	0.0635 (16)	0.097 (2)	0.0085 (14)	0.0454 (17)	0.0242 (17)
C10	0.0731 (17)	0.0723 (18)	0.096 (2)	0.0003 (15)	0.0476 (17)	0.0199 (17)
C11	0.0681 (17)	0.0650 (17)	0.081 (2)	0.0001 (14)	0.0426 (16)	−0.0011 (16)
C12	0.0754 (19)	0.0657 (17)	0.103 (2)	0.0118 (15)	0.0521 (19)	0.0094 (17)
C13	0.0798 (18)	0.0568 (15)	0.091 (2)	0.0072 (14)	0.0504 (17)	0.0138 (16)
C14	0.087 (2)	0.084 (2)	0.129 (3)	−0.0094 (18)	0.069 (2)	−0.016 (2)
C15	0.0775 (19)	0.091 (2)	0.117 (3)	−0.0056 (18)	0.059 (2)	−0.007 (2)
C16	0.084 (2)	0.107 (3)	0.121 (3)	−0.0090 (19)	0.066 (2)	−0.008 (2)
C17	0.106 (3)	0.095 (3)	0.161 (4)	−0.010 (2)	0.085 (3)	−0.002 (3)
N1	0.0647 (12)	0.0532 (12)	0.0649 (15)	−0.0010 (11)	0.0361 (11)	0.0026 (11)
O1	0.0737 (12)	0.0515 (10)	0.0877 (14)	0.0050 (9)	0.0512 (11)	0.0095 (10)
O2	0.0887 (14)	0.0557 (11)	0.1117 (17)	0.0022 (10)	0.0704 (14)	0.0086 (11)

Geometric parameters (Å, º) top

C1—C6	1.406 (3)	C10—H10	0.93
C1—C2	1.406 (3)	C11—C12	1.367 (4)
C1—C7	1.433 (3)	C11—C14	1.520 (4)
C2—O1	1.333 (3)	C12—C13	1.389 (4)
C2—C3	1.409 (3)	C12—H12	0.93
C3—O2	1.365 (3)	C13—H13	0.93
C3—C4	1.371 (4)	C14—C15	1.483 (4)
C4—C5	1.389 (4)	C14—H14A	0.97
C4—H4	0.93	C14—H14B	0.97
C5—C6	1.370 (4)	C15—C16	1.519 (4)
C5—H5	0.93	C15—H15A	0.97
C6—H6	0.93	C15—H15B	0.97
C7—N1	1.297 (3)	C16—C17	1.493 (5)
C7—H7	0.93	C16—H16A	0.97
C8—C13	1.375 (3)	C16—H16B	0.97
C8—C9	1.384 (3)	C17—H17A	0.96
C8—N1	1.424 (3)	C17—H17B	0.96
C9—C10	1.375 (4)	C17—H17C	0.96
C9—H9	0.93	O1—H1	0.88 (2)
C10—C11	1.379 (4)	O2—H2	0.86 (2)

C6—C1—C2	119.6 (2)	C11—C12—C13	121.7 (3)
C6—C1—C7	120.4 (2)	C11—C12—H12	119.1
C2—C1—C7	120.0 (2)	C13—C12—H12	119.1
O1—C2—C1	122.8 (2)	C8—C13—C12	120.2 (3)
O1—C2—C3	118.3 (2)	C8—C13—H13	119.9
C1—C2—C3	118.9 (2)	C12—C13—H13	119.9
O2—C3—C4	119.8 (2)	C15—C14—C11	115.4 (3)
O2—C3—C2	120.2 (2)	C15—C14—H14A	108.4
C4—C3—C2	120.0 (2)	C11—C14—H14A	108.4
C3—C4—C5	121.1 (2)	C15—C14—H14B	108.4
C3—C4—H4	119.5	C11—C14—H14B	108.4
C5—C4—H4	119.5	H14A—C14—H14B	107.5
C6—C5—C4	120.0 (3)	C14—C15—C16	114.7 (3)
C6—C5—H5	120.0	C14—C15—H15A	108.6
C4—C5—H5	120.0	C16—C15—H15A	108.6
C5—C6—C1	120.4 (3)	C14—C15—H15B	108.6
C5—C6—H6	119.8	C16—C15—H15B	108.6
C1—C6—H6	119.8	H15A—C15—H15B	107.6
N1—C7—C1	121.3 (2)	C17—C16—C15	113.8 (3)
N1—C7—H7	119.3	C17—C16—H16A	108.8
C1—C7—H7	119.3	C15—C16—H16A	108.8
C13—C8—C9	118.5 (2)	C17—C16—H16B	108.8
C13—C8—N1	116.7 (2)	C15—C16—H16B	108.8
C9—C8—N1	124.8 (2)	H16A—C16—H16B	107.7
C10—C9—C8	120.2 (3)	C16—C17—H17A	109.5
C10—C9—H9	119.9	C16—C17—H17B	109.5
C8—C9—H9	119.9	H17A—C17—H17B	109.5
C9—C10—C11	121.9 (3)	C16—C17—H17C	109.5
C9—C10—H10	119.0	H17A—C17—H17C	109.5
C11—C10—H10	119.0	H17B—C17—H17C	109.5
C12—C11—C10	117.4 (2)	C7—N1—C8	124.0 (2)
C12—C11—C14	121.7 (3)	C2—O1—H1	104 (2)
C10—C11—C14	120.8 (3)	C3—O2—H2	105 (2)

C6—C1—C2—O1	−178.6 (2)	N1—C8—C9—C10	178.8 (3)
C7—C1—C2—O1	2.6 (4)	C8—C9—C10—C11	0.8 (5)
C6—C1—C2—C3	3.5 (4)	C9—C10—C11—C12	−0.5 (5)
C7—C1—C2—C3	−175.4 (2)	C9—C10—C11—C14	−177.4 (3)
O1—C2—C3—O2	−2.0 (4)	C10—C11—C12—C13	0.1 (5)
C1—C2—C3—O2	176.0 (2)	C14—C11—C12—C13	177.0 (3)
O1—C2—C3—C4	177.9 (2)	C9—C8—C13—C12	0.3 (4)
C1—C2—C3—C4	−4.1 (4)	N1—C8—C13—C12	−179.2 (2)
O2—C3—C4—C5	−177.8 (3)	C11—C12—C13—C8	0.0 (5)
C2—C3—C4—C5	2.4 (4)	C12—C11—C14—C15	128.0 (4)
C3—C4—C5—C6	0.0 (4)	C10—C11—C14—C15	−55.2 (4)
C4—C5—C6—C1	−0.6 (4)	C11—C14—C15—C16	−177.2 (3)
C2—C1—C6—C5	−1.2 (4)	C14—C15—C16—C17	179.6 (3)
C7—C1—C6—C5	177.6 (3)	C1—C7—N1—C8	176.5 (2)
C6—C1—C7—N1	178.9 (3)	C13—C8—N1—C7	−176.0 (3)
C2—C1—C7—N1	−2.2 (4)	C9—C8—N1—C7	4.6 (4)
C13—C8—C9—C10	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.86 (2)	2.21 (3)	2.728 (2)	118 (3)
O2—H2···O1ⁱ	0.86 (2)	2.08 (3)	2.802 (3)	141 (3)
O1—H1···N1	0.88 (2)	1.74 (2)	2.555 (2)	155 (3)
C6—H6···Cg2ⁱⁱ	0.93	2.85	3.645 (3)	144
C10—H10···Cg1ⁱⁱ	0.93	2.80	3.491 (3)	132

Symmetry codes: (i) −x+1, −y+3, −z; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₂
M_r	269.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.2774 (13), 6.0148 (6), 17.6166 (14)
β (°)	121.476 (5)
V (Å³)	1471.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.45 × 0.03

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.954, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	8711, 3061, 1643
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.163, 1.07
No. of reflections	3061
No. of parameters	189
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.86 (2)	2.21 (3)	2.728 (2)	118 (3)
O2—H2···O1ⁱ	0.86 (2)	2.08 (3)	2.802 (3)	141 (3)
O1—H1···N1	0.88 (2)	1.74 (2)	2.555 (2)	155 (3)
C6—H6···Cg2ⁱⁱ	0.93	2.85	3.645 (3)	144
C10—H10···Cg1ⁱⁱ	0.93	2.80	3.491 (3)	132

Symmetry codes: (i) −x+1, −y+3, −z; (ii) −x+1, y−1/2, −z+1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

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