(E)-4-Meth­oxy-2-(o-tolyl­imino­meth­yl)phenol

Özek, A.; Büyükgüngör, O.; Albayrak, Ç.; Odabaşoğlu, M.

doi:10.1107/S1600536809009192

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o791

doi:10.1107/S1600536809009192

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(E)-4-Methoxy-2-(o-tolyliminomethyl)phenol

Arzu Özek,^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: orhanb@omu.edu.tr

(Received 6 February 2009; accepted 12 March 2009; online 19 March 2009)

In the molecule of the title compound, C₁₅H₁₅NO₂, the aromatic rings are oriented at a dihedral angle of 15.46 (6)°. An intramolecular O—H⋯N hydrogen bond results in the formation of a nearly planar six-membered ring [maximum deviation of 0.035 (5) Å for the N atom] which is almost coplanar with the adjacent ring, making a dihedral angle of 0.8 (3)°. The title organic molecule is a phenol–imine tautomer, as evidenced by the C—O, C—N and C—C bond lengths. Molecules are linked by intermolecular C—H⋯O hydrogen bonds that generate a C(5) chain. C—H⋯π and π–π interactions exist in the structure. The π–π interaction occurs between the phenol ring and its symmetry equivalent at (1 − x, 1 − y, −z), with a centroid–centroid distance of 3.727 (7) Å and a plane-to-plane separation of 3.383 (5) Å, resulting in an offset angle of 24.82 (1)°.

Related literature

For previous work in our structural study of Schiff bases, see: Özek et al. (2007 ); Odabaşoğlu, Arslan et al. (2007 ); Odabaşoğlu, Büyükgüngör et al. (2007 ). For a related compound, see: Albayrak et al. (2005 ).

Experimental

Crystal data

C₁₅H₁₅NO₂
M_r = 241.28
Monoclinic, P 2₁ /c
a = 13.2889 (6) Å
b = 8.5986 (6) Å
c = 11.6714 (6) Å
β = 113.284 (3)°
V = 1225.03 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.59 × 0.47 × 0.30 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.954, T_max = 0.975
6569 measured reflections
2537 independent reflections
2108 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.092
S = 1.02
2537 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.958 (19)	1.68 (2)	2.5794 (13)	154.8 (17)
C8—H8⋯O1ⁱ	0.973 (15)	2.444 (15)	3.4129 (14)	173.5 (12)
C7—H7B⋯Cg2ⁱⁱ	1.01 (2)	2.90 (2)	3.6727 (16)	134 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z.

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/S1600536809009192/bv2115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009192/bv2115Isup2.hkl

checkCIF report

Comment top

The present work is part of a structural study of Schiff bases (Özek et al., 2007; Odabaşoğlu, Büyükgüngör et al., 2007; Odabaşoğlu, Arslan et al., 2007) and we report here the structure of (E)-4-methoxy-2-[(o-tolylimino)methyl]phenol, (I).

In general, o-hydroxy Schiff bases exhibit two possible tautomeric forms, the phenol-imine (or benzenoid) and keto-amine (or quinoid) forms. Depending on the tautomers, two types of intra-molecular hydrogen bonds are possible: O—H···N in benzenoid and N—H···O in quinoid tautomers. The H atom in title compound (I) is located on atom O1, thus the phenol-imine tautomer is favored over the keto-amine form, as indicated by the C2—O1 [1.3579 (2) Å], C8—N1 [1.2865 (2) Å], C1—C8 [1.4519 (2) Å] and C1—C2 [1.4071 (2) Å] bond lengths (Fig. 1). The C2—O1 bond length of 1.357 (2)Å indicates single-bond character, whereas the C8—N1 bond length of 1.286 (2)Å indicates a high degree of double-bond character. Similar results were observed for 2-(3-methoxysalicylideneamino)-1H-benzimidazolemonohydrate [C—O=1.357 (2) Å, C—N= 1.285 (2) Å, Albayrak et al., 2005].

It is known that Schiff bases may exhibit thermochromism or photochromism, depending on the planarity or non-planarity of the molecule, respectively. Therefore, one can expect photochromic properties in (I) caused by non-planarity of the molecules; the dihedral angle between rings A(C1—C6) and B (C9—C14) is 15.46 (6)°. The intramolecular O—H···N hydrogen bond (Table 1) results in the formation of a nearly planar six-membered ring C (O1/H1/N1/C1/C2/C8), oriented with respect to rings A and B at dihedral angles of A/C=0.81 (2)° and B/C= 15.04 (3)°. So, it is coplanar with the adjacent ring A and generates an S(6) ring motif. The O1···N1 distance of 2.579 (2)Å is comparable to those observed for analogous hydrogen bonds in three (E)-2-[(bromophenyl)iminomethyl]-4-methoxyphenols [2.603 (2) Å, 2.638 (7) Å, 2.577 (4) Å; Özek et al., 2007]. In the crystal structure, weak intermolecular C—H···O hydrogen bonds results in the formation of C(5) chains along the c axis (Table 1, Fig. 2). In addition to these intermolecular interactions, C—H···π interactions and π···π interactions play roles in the crystal packing (Table 1, Fig. 3). This slipped π···π interaction occurs between Cg1 (the centroid of the C1—C6 ring) and its symmetry equivalent at (1 - x, 1 - y, -z), with a centroid-to-centroid distance of 3.727 (7)Å and a plane-to-plane separation of 3.383 (5) Å, resulting in an offset angle of 24.82 (1)°.

Related literature top

For related literature, see: Özek et al. (2007); Albayrak et al. (2005); Odabaşoğlu, Arslan et al. (2007); Odabaşoğlu, Büyükgüngör et al. (2007).

Experimental top

The compound (E)-4-methoxy-2-[(o-tolylimino)methyl]phenol was prepared by reflux a mixture of a solution containing 5-methoxysalicylaldehyde (0.5 g 3.3 mmol) in 20 ml ethanol and a solution containing 2-chloraniline (0.420 g 3.3 mmol) in 20 ml ethanol. The reaction mixture was stirred for 1 h under reflux. The crystals of (E)-4-methoxy-2-[(o-tolylimino)methyl]phenol suitable for X-ray analysis were obtained from methanol by slow evaporation (yield % 73; m.p. 343–344 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. A view of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids. Dashed line indicates intramolecular hydrogen bond.
	Fig. 2. A partial packing view of (I), showing the formation of the C(5) chain through C—H···O intermolecular hydrogen bonds. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) x, -y + 3/2, z + 1/2].
	Fig. 3. A partial packing view of (I), showing the intermolecular C—H···π and π···π interactions as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes; (i): 1 - x, -y + 2, 1 - z; (ii): 1 - x, 1 - y, 1 - z].

(E)-4-Methoxy-2-(o-tolyliminomethyl)phenol top

Crystal data top

C₁₅H₁₅NO₂	F(000) = 512
M_r = 241.28	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6569 reflections
a = 13.2889 (6) Å	θ = 1.9–28.0°
b = 8.5986 (6) Å	µ = 0.09 mm⁻¹
c = 11.6714 (6) Å	T = 100 K
β = 113.284 (3)°	Prism, red
V = 1225.03 (12) Å³	0.59 × 0.47 × 0.30 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	2537 independent reflections
Radiation source: fine-focus sealed tube	2108 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.039
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.9°
ω scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→10
T_min = 0.954, T_max = 0.975	l = −14→13
6569 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0457P)² + 0.2485P] where P = (F_o² + 2F_c²)/3
2537 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₅NO₂	V = 1225.03 (12) Å³
M_r = 241.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2889 (6) Å	µ = 0.09 mm⁻¹
b = 8.5986 (6) Å	T = 100 K
c = 11.6714 (6) Å	0.59 × 0.47 × 0.30 mm
β = 113.284 (3)°

Data collection top

Stoe IPDS II diffractometer	2537 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2108 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.975	R_int = 0.039
6569 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.20 e Å⁻³
2537 reflections	Δρ_min = −0.19 e Å⁻³
223 parameters

Special details top

Experimental. 133 frames, detector distance = 80 mm

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	0.50912 (9)	0.80474 (14)	0.44057 (10)	0.0202 (2)
C2	0.50739 (9)	0.87880 (14)	0.33229 (10)	0.0220 (3)
C3	0.41277 (10)	0.95544 (15)	0.25458 (11)	0.0260 (3)
C4	0.32140 (10)	0.95800 (15)	0.28313 (11)	0.0268 (3)
C5	0.32211 (9)	0.88566 (14)	0.39055 (11)	0.0240 (3)
C6	0.41552 (9)	0.80964 (14)	0.46900 (11)	0.0221 (3)
C7	0.22417 (11)	0.82076 (17)	0.51644 (13)	0.0301 (3)
C8	0.60665 (9)	0.72552 (14)	0.52526 (10)	0.0204 (2)
C9	0.78609 (9)	0.62921 (13)	0.57661 (10)	0.0199 (2)
C10	0.88252 (9)	0.65581 (14)	0.55698 (10)	0.0220 (3)
C11	0.97626 (10)	0.57301 (15)	0.62954 (11)	0.0253 (3)
C12	0.97591 (10)	0.46596 (15)	0.71788 (11)	0.0273 (3)
C13	0.87983 (10)	0.43903 (15)	0.73477 (11)	0.0267 (3)
C14	0.78528 (10)	0.52031 (15)	0.66497 (11)	0.0238 (3)
C15	0.88540 (10)	0.77174 (16)	0.46210 (13)	0.0271 (3)
N1	0.69160 (8)	0.71244 (11)	0.49897 (9)	0.0201 (2)
O1	0.59622 (7)	0.88000 (11)	0.30225 (8)	0.0259 (2)
O2	0.22688 (7)	0.89755 (11)	0.40973 (9)	0.0299 (2)
H1	0.6488 (15)	0.821 (2)	0.3689 (18)	0.052 (5)*
H3	0.4132 (12)	1.0039 (19)	0.1796 (14)	0.034 (4)*
H4	0.2560 (12)	1.0104 (19)	0.2304 (14)	0.034 (4)*
H6	0.4193 (11)	0.7593 (18)	0.5449 (14)	0.027 (3)*
H7A	0.2795 (12)	0.8655 (18)	0.5964 (14)	0.030 (4)*
H7B	0.2372 (13)	0.705 (2)	0.5150 (15)	0.038 (4)*
H8	0.6040 (11)	0.6867 (17)	0.6023 (14)	0.026 (3)*
H11	1.0416 (12)	0.5929 (17)	0.6150 (13)	0.030 (4)*
H12	1.0432 (12)	0.4111 (18)	0.7671 (14)	0.032 (4)*
H13	0.8786 (12)	0.3638 (19)	0.7957 (14)	0.033 (4)*
H14	0.7188 (12)	0.4974 (18)	0.6756 (13)	0.028 (4)*
H15A	0.9547 (15)	0.772 (2)	0.4543 (16)	0.046 (5)*
H15B	0.8291 (13)	0.7525 (19)	0.3784 (15)	0.036 (4)*
H7C	0.1484 (13)	0.838 (2)	0.5114 (15)	0.039 (4)*
H15C	0.8706 (14)	0.879 (2)	0.4830 (16)	0.048 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0214 (5)	0.0197 (6)	0.0185 (5)	−0.0007 (4)	0.0068 (4)	−0.0023 (4)
C2	0.0249 (5)	0.0209 (6)	0.0206 (5)	−0.0010 (5)	0.0093 (4)	−0.0025 (4)
C3	0.0313 (6)	0.0239 (6)	0.0201 (5)	0.0010 (5)	0.0072 (5)	0.0020 (5)
C4	0.0238 (6)	0.0249 (6)	0.0256 (6)	0.0033 (5)	0.0033 (5)	0.0004 (5)
C5	0.0205 (5)	0.0221 (6)	0.0287 (6)	−0.0003 (5)	0.0088 (5)	−0.0041 (5)
C6	0.0242 (6)	0.0211 (6)	0.0212 (5)	0.0006 (5)	0.0091 (4)	−0.0002 (4)
C7	0.0252 (6)	0.0313 (7)	0.0381 (7)	−0.0007 (5)	0.0172 (5)	−0.0039 (6)
C8	0.0234 (5)	0.0203 (6)	0.0179 (5)	−0.0002 (4)	0.0083 (4)	−0.0015 (4)
C9	0.0211 (5)	0.0196 (6)	0.0177 (5)	0.0012 (4)	0.0063 (4)	−0.0034 (4)
C10	0.0235 (5)	0.0193 (6)	0.0223 (5)	−0.0004 (4)	0.0083 (4)	−0.0038 (5)
C11	0.0200 (5)	0.0250 (6)	0.0297 (6)	−0.0005 (5)	0.0086 (5)	−0.0034 (5)
C12	0.0239 (6)	0.0277 (7)	0.0255 (6)	0.0053 (5)	0.0047 (5)	−0.0011 (5)
C13	0.0325 (6)	0.0258 (6)	0.0221 (6)	0.0053 (5)	0.0112 (5)	0.0036 (5)
C14	0.0248 (6)	0.0248 (6)	0.0231 (5)	0.0020 (5)	0.0110 (4)	−0.0002 (5)
C15	0.0240 (6)	0.0274 (7)	0.0326 (7)	0.0012 (5)	0.0139 (5)	0.0033 (5)
N1	0.0209 (5)	0.0197 (5)	0.0194 (4)	0.0007 (4)	0.0076 (4)	−0.0012 (4)
O1	0.0280 (4)	0.0300 (5)	0.0229 (4)	0.0028 (4)	0.0135 (3)	0.0043 (4)
O2	0.0206 (4)	0.0305 (5)	0.0391 (5)	0.0038 (4)	0.0122 (4)	0.0027 (4)

Geometric parameters (Å, º) top

C1—C2	1.4071 (16)	C8—H8	0.973 (15)
C1—C6	1.4091 (16)	C9—C14	1.3961 (17)
C1—C8	1.4519 (16)	C9—C10	1.4068 (16)
C2—O1	1.3579 (14)	C9—N1	1.4179 (14)
C2—C3	1.3916 (17)	C10—C11	1.3934 (16)
C3—C4	1.3805 (18)	C10—C15	1.5017 (17)
C3—H3	0.971 (16)	C11—C12	1.3836 (18)
C4—C5	1.3962 (18)	C11—H11	0.963 (16)
C4—H4	0.956 (16)	C12—C13	1.3862 (18)
C5—O2	1.3734 (15)	C12—H12	0.973 (15)
C5—C6	1.3812 (17)	C13—C14	1.3862 (17)
C6—H6	0.969 (15)	C13—H13	0.966 (16)
C7—O2	1.4226 (17)	C14—H14	0.959 (15)
C7—H7A	1.008 (15)	C15—H15A	0.960 (18)
C7—H7B	1.008 (18)	C15—H15B	0.981 (16)
C7—H7C	0.996 (17)	C15—H15C	0.99 (2)
C8—N1	1.2865 (15)	O1—H1	0.958 (19)

C2—C1—C6	119.70 (10)	C14—C9—C10	120.19 (10)
C2—C1—C8	121.13 (10)	C14—C9—N1	123.17 (10)
C6—C1—C8	119.16 (10)	C10—C9—N1	116.58 (10)
O1—C2—C3	118.81 (11)	C11—C10—C9	118.10 (11)
O1—C2—C1	121.88 (10)	C11—C10—C15	120.67 (11)
C3—C2—C1	119.30 (11)	C9—C10—C15	121.22 (10)
C4—C3—C2	120.30 (11)	C12—C11—C10	121.82 (11)
C4—C3—H3	122.0 (9)	C12—C11—H11	121.2 (9)
C2—C3—H3	117.7 (9)	C10—C11—H11	117.0 (9)
C3—C4—C5	121.02 (11)	C11—C12—C13	119.45 (11)
C3—C4—H4	120.9 (9)	C11—C12—H12	119.3 (9)
C5—C4—H4	118.0 (9)	C13—C12—H12	121.2 (9)
O2—C5—C6	124.87 (11)	C12—C13—C14	120.27 (12)
O2—C5—C4	115.69 (11)	C12—C13—H13	120.1 (9)
C6—C5—C4	119.43 (11)	C14—C13—H13	119.6 (9)
C5—C6—C1	120.25 (11)	C13—C14—C9	120.16 (11)
C5—C6—H6	121.7 (8)	C13—C14—H14	119.2 (9)
C1—C6—H6	118.1 (8)	C9—C14—H14	120.6 (9)
O2—C7—H7A	111.8 (9)	C10—C15—H15A	112.1 (11)
O2—C7—H7B	112.2 (9)	C10—C15—H15B	112.9 (10)
H7A—C7—H7B	108.9 (13)	H15A—C15—H15B	106.8 (14)
O2—C7—H7C	104.7 (9)	C10—C15—H15C	111.7 (10)
H7A—C7—H7C	110.4 (13)	H15A—C15—H15C	108.2 (15)
H7B—C7—H7C	108.8 (13)	H15B—C15—H15C	104.7 (14)
N1—C8—C1	120.66 (10)	C8—N1—C9	122.05 (10)
N1—C8—H8	123.1 (8)	C2—O1—H1	102.5 (11)
C1—C8—H8	116.2 (8)	C5—O2—C7	116.87 (9)

C6—C1—C2—O1	178.64 (11)	N1—C9—C10—C11	−178.42 (10)
C8—C1—C2—O1	−0.16 (17)	C14—C9—C10—C15	179.71 (11)
C6—C1—C2—C3	−0.23 (17)	N1—C9—C10—C15	2.50 (16)
C8—C1—C2—C3	−179.03 (11)	C9—C10—C11—C12	0.70 (18)
O1—C2—C3—C4	−179.26 (11)	C15—C10—C11—C12	179.77 (12)
C1—C2—C3—C4	−0.36 (18)	C10—C11—C12—C13	0.37 (19)
C2—C3—C4—C5	0.67 (19)	C11—C12—C13—C14	−0.92 (19)
C3—C4—C5—O2	179.29 (11)	C12—C13—C14—C9	0.40 (18)
C3—C4—C5—C6	−0.38 (19)	C10—C9—C14—C13	0.69 (17)
O2—C5—C6—C1	−179.85 (11)	N1—C9—C14—C13	177.71 (11)
C4—C5—C6—C1	−0.21 (18)	C1—C8—N1—C9	−176.83 (10)
C2—C1—C6—C5	0.51 (17)	C14—C9—N1—C8	18.82 (17)
C8—C1—C6—C5	179.34 (11)	C10—C9—N1—C8	−164.07 (11)
C2—C1—C8—N1	−4.59 (17)	C6—C5—O2—C7	−2.26 (17)
C6—C1—C8—N1	176.60 (11)	C4—C5—O2—C7	178.09 (11)
C14—C9—C10—C11	−1.22 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.958 (19)	1.68 (2)	2.5794 (13)	154.8 (17)
C8—H8···O1ⁱ	0.973 (15)	2.444 (15)	3.4129 (14)	173.5 (12)
C7—H7B···Cg2ⁱⁱ	1.008 (18)	2.903 (17)	3.6727 (16)	134.1 (16)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₂
M_r	241.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.2889 (6), 8.5986 (6), 11.6714 (6)
β (°)	113.284 (3)
V (Å³)	1225.03 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.59 × 0.47 × 0.30

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.954, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	6569, 2537, 2108
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.092, 1.02
No. of reflections	2537
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

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
O1—H1···N1	0.958 (19)	1.68 (2)	2.5794 (13)	154.8 (17)
C8—H8···O1ⁱ	0.973 (15)	2.444 (15)	3.4129 (14)	173.5 (12)
C7—H7B···Cg2ⁱⁱ	1.008 (18)	2.903 (17)	3.6727 (16)	134.1 (16)

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F.279 of the University Research Fund).

References

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