2-[(E)-(2,4-Dimethyl­phen­yl)imino­meth­yl]phenol

Fun, H.-K.; Quah, C.K.; Viveka, S.; Madhukumar, D.J.; Nagaraja, G.K.

doi:10.1107/S1600536811026110

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1933

doi:10.1107/S1600536811026110

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2-[(E)-(2,4-Dimethylphenyl)iminomethyl]phenol

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § S. Viveka,^b D. J. Madhukumar ^b and G. K. Nagaraja ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 28 June 2011; accepted 1 July 2011; online 6 July 2011)

The asymmetric unit of the title compound, C₁₅H₁₅NO, contains two independent molecules, both of which exist in trans configurations with respect to the C=N bonds [1.278 (2) and 1.279 (2) Å]. In each molecule, intramolecular O—H⋯N hydrogen bonds generate S(6) ring motifs. In one molecule, the benzene rings form a dihedral angle of 13.38 (9)°, while in the other molecule the dihedral angle is 30.60 (10)°. In the crystal, the two independent molecules are linked via weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background to and the pharmacological activity of Schiff base compounds, see: Gallant et al. (2004 ); Kulkarni (1975 ); Zhao et al. (1988 ); Ma & Zhao (1988 ). For a related structure, see: Fun et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₅NO
M_r = 225.28
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3161 (4) Å
b = 12.0287 (7) Å
c = 28.1634 (15) Å
V = 2478.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.51 × 0.35 × 0.32 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.963, T_max = 0.976
39373 measured reflections
4117 independent reflections
3381 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.122
S = 1.02
4117 reflections
319 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯N1A	0.88 (2)	1.80 (2)	2.5854 (19)	147 (2)
O1B—H1OB⋯N1B	0.90 (2)	1.82 (2)	2.604 (2)	145 (2)
C5A—H5AA⋯O1Bⁱ	0.93	2.56	3.455 (2)	162
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: 10.1107/S1600536811026110/lh5275sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026110/lh5275Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026110/lh5275Isup3.cml

checkCIF report

Comment top

During the last 50 years, a vast number of structural studies on Schiff bases derived from hydroxyaryl aldehydes have been studied. Schiff bases can be synthesized from an aromatic amine and a carbonyl compound in a nucleophilic addition to a hemiaminal followed by elimination of water to the imine (Gallant et al., 2004). These Schiff bases have shown varied redox and electrical behaviors, depending on the involvement of active coordination sites (Kulkarni, 1975; Zhao et al., 1988; Ma & Zhao, 1988). Among the organic reagents actually used, Schiff bases possess excellent characteristics, structural similarities with natural biological substances, relatively simple preparation procedures and the synthetic flexibility that enables the design of suitable structural properties.

The asymmetric unit contains two independent molecules (Fig. 1), A and B. Both molecules exist in trans configurations with respect to the C7═N1 bonds [C7A═N1A = 1.278 (2) Å, C7B═N1B = 1.279 (2) Å]. The molecular structure is stabilized by intramolecular O1A–H1OA···N1A and O1B–H1OB···N1B hydrogen bonds (Table 1) which generate S(6) ring motifs (Fig. 1, Bernstein et al., 1995). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Fun et al., 2011). In molecule A, the benzene rings (C1A-C6A and C8A-C13A) form a dihedral angle of 13.38 (9)°. The corresponding dihedral angle for molecule B is 30.60 (10)°.

In the crystal structure, Fig. 2, molecules A are linked to molecules B via weak intermolecular C5A–H5AA···O1Bⁱ hydrogen bonds (Table 1) into pairs.

Related literature top

For general background to and the pharmacological activity of Schiff base compounds, see: Gallant et al. (2004); Kulkarni (1975); Zhao et al. (1988); Ma & Zhao (1988). For a related structure, see: Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For standard bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of salicylaldehyde (0.01 mol) and 2,4 dimethyl aniline (0.01 mol) in presence of glacial acetic acid (0.5 mL) in ethanol (25 mL) was refluxed gently for 4-5 h. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into a beaker containing crushed ice. The precipitate thus obtained was filtered, dried and recrystallized from ethanol. Yield: 80%, m.p. 425-428 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. Part of the crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

2-[(E)-(2,4-Dimethylphenyl)iminomethyl]phenol top

Crystal data top

C₁₅H₁₅NO	F(000) = 960
M_r = 225.28	D_x = 1.207 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9995 reflections
a = 7.3161 (4) Å	θ = 2.8–29.8°
b = 12.0287 (7) Å	µ = 0.08 mm⁻¹
c = 28.1634 (15) Å	T = 296 K
V = 2478.5 (2) Å³	Block, yellow
Z = 8	0.51 × 0.35 × 0.32 mm

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4117 independent reflections
Radiation source: fine-focus sealed tube	3381 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.963, T_max = 0.976	k = −16→16
39373 measured reflections	l = −39→39

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0711P)² + 0.1832P] where P = (F_o² + 2F_c²)/3
4117 reflections	(Δ/σ)_max = 0.001
319 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₅H₁₅NO	V = 2478.5 (2) Å³
M_r = 225.28	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3161 (4) Å	µ = 0.08 mm⁻¹
b = 12.0287 (7) Å	T = 296 K
c = 28.1634 (15) Å	0.51 × 0.35 × 0.32 mm

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4117 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3381 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.976	R_int = 0.027
39373 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.19 e Å⁻³
4117 reflections	Δρ_min = −0.13 e Å⁻³
319 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
O1A	0.9304 (2)	0.77108 (12)	−0.04120 (5)	0.0671 (4)
N1A	0.7924 (2)	0.91236 (11)	0.01797 (4)	0.0445 (3)
C1A	0.8636 (2)	0.83620 (14)	−0.07601 (5)	0.0485 (3)
C2A	0.8931 (3)	0.80560 (16)	−0.12313 (6)	0.0598 (5)
H2AA	0.9601	0.7419	−0.1301	0.072*
C3A	0.8235 (3)	0.86924 (18)	−0.15938 (6)	0.0656 (5)
H3AA	0.8439	0.8479	−0.1907	0.079*
C4A	0.7240 (3)	0.96424 (17)	−0.15021 (6)	0.0670 (5)
H4AA	0.6766	1.0063	−0.1750	0.080*
C5A	0.6955 (3)	0.99621 (16)	−0.10335 (6)	0.0573 (4)
H5AA	0.6293	1.0604	−0.0969	0.069*
C6A	0.7647 (2)	0.93353 (13)	−0.06593 (5)	0.0446 (3)
C7A	0.7319 (2)	0.96829 (14)	−0.01727 (5)	0.0465 (3)
H7AA	0.6653	1.0328	−0.0116	0.056*
C8A	0.7652 (2)	0.94552 (13)	0.06567 (5)	0.0416 (3)
C9A	0.7052 (3)	1.05078 (14)	0.07882 (5)	0.0505 (4)
H9AA	0.6770	1.1029	0.0556	0.061*
C10A	0.6870 (3)	1.07866 (16)	0.12636 (6)	0.0555 (4)
H10A	0.6461	1.1493	0.1345	0.067*
C11A	0.7287 (3)	1.00352 (17)	0.16175 (5)	0.0521 (4)
C12A	0.7875 (3)	0.89892 (15)	0.14813 (5)	0.0527 (4)
H12A	0.8136	0.8470	0.1716	0.063*
C13A	0.8095 (2)	0.86800 (14)	0.10087 (5)	0.0472 (3)
C14A	0.7152 (3)	1.0353 (2)	0.21353 (6)	0.0696 (6)
H14A	0.6420	0.9815	0.2300	0.104*
H14B	0.6597	1.1073	0.2163	0.104*
H14C	0.8354	1.0373	0.2272	0.104*
C15A	0.8789 (4)	0.75441 (16)	0.08827 (7)	0.0703 (6)
H15A	0.8982	0.7122	0.1168	0.105*
H15B	0.9922	0.7611	0.0713	0.105*
H15C	0.7908	0.7172	0.0686	0.105*
O1B	0.0454 (2)	0.23511 (11)	0.08434 (5)	0.0626 (3)
N1B	0.1838 (2)	0.08482 (12)	0.14035 (5)	0.0500 (3)
C1B	0.0999 (2)	0.16993 (14)	0.04804 (6)	0.0487 (4)
C2B	0.0575 (3)	0.20224 (15)	0.00174 (6)	0.0568 (4)
H2BA	−0.0090	0.2669	−0.0036	0.068*
C3B	0.1143 (3)	0.13803 (17)	−0.03601 (6)	0.0628 (5)
H3BA	0.0864	0.1603	−0.0668	0.075*
C4B	0.2116 (3)	0.04152 (17)	−0.02891 (6)	0.0620 (5)
H4BA	0.2514	−0.0001	−0.0548	0.074*
C5B	0.2499 (3)	0.00667 (16)	0.01675 (6)	0.0551 (4)
H5BA	0.3128	−0.0596	0.0215	0.066*
C6B	0.1953 (2)	0.06990 (13)	0.05584 (5)	0.0460 (3)
C7B	0.2336 (2)	0.03067 (14)	0.10346 (6)	0.0497 (4)
H7BA	0.2965	−0.0359	0.1073	0.060*
C8B	0.2118 (2)	0.04277 (15)	0.18674 (5)	0.0494 (4)
C9B	0.2152 (3)	−0.06991 (16)	0.19735 (6)	0.0582 (4)
H9BA	0.2036	−0.1216	0.1730	0.070*
C10B	0.2357 (3)	−0.10637 (17)	0.24352 (6)	0.0660 (5)
H10B	0.2388	−0.1823	0.2497	0.079*
C11B	0.2515 (3)	−0.03198 (19)	0.28073 (6)	0.0628 (5)
C12B	0.2454 (3)	0.07986 (19)	0.26989 (6)	0.0649 (5)
H12B	0.2544	0.1309	0.2946	0.078*
C13B	0.2264 (3)	0.11976 (16)	0.22389 (6)	0.0583 (4)
C14B	0.2744 (4)	−0.0720 (2)	0.33137 (6)	0.0847 (7)
H14D	0.3425	−0.1402	0.3315	0.127*
H14E	0.1563	−0.0843	0.3453	0.127*
H14F	0.3389	−0.0168	0.3494	0.127*
C15B	0.2263 (5)	0.24280 (17)	0.21427 (8)	0.0910 (9)
H15D	0.2594	0.2820	0.2427	0.137*
H15E	0.1065	0.2655	0.2043	0.137*
H15F	0.3130	0.2593	0.1897	0.137*
H1OA	0.906 (4)	0.802 (2)	−0.0136 (8)	0.092 (8)*
H1OB	0.068 (4)	0.201 (2)	0.1120 (8)	0.090 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0892 (11)	0.0605 (7)	0.0517 (7)	0.0224 (8)	0.0009 (7)	−0.0004 (6)
N1A	0.0474 (7)	0.0463 (6)	0.0398 (6)	−0.0021 (6)	0.0024 (5)	−0.0014 (5)
C1A	0.0499 (8)	0.0489 (8)	0.0468 (8)	0.0004 (7)	0.0029 (7)	−0.0026 (6)
C2A	0.0665 (11)	0.0597 (10)	0.0532 (9)	0.0045 (9)	0.0070 (9)	−0.0120 (8)
C3A	0.0806 (14)	0.0739 (12)	0.0423 (8)	−0.0055 (11)	0.0055 (9)	−0.0090 (8)
C4A	0.0892 (15)	0.0693 (11)	0.0425 (8)	0.0027 (12)	−0.0034 (10)	0.0049 (8)
C5A	0.0730 (12)	0.0515 (8)	0.0475 (8)	0.0059 (9)	−0.0037 (9)	0.0005 (7)
C6A	0.0463 (8)	0.0476 (7)	0.0400 (7)	−0.0031 (7)	0.0008 (6)	−0.0021 (6)
C7A	0.0478 (8)	0.0484 (8)	0.0431 (7)	0.0021 (7)	0.0013 (6)	−0.0035 (6)
C8A	0.0401 (7)	0.0463 (7)	0.0384 (6)	−0.0028 (6)	0.0010 (6)	0.0001 (5)
C9A	0.0607 (9)	0.0476 (8)	0.0433 (7)	0.0029 (8)	−0.0003 (7)	0.0000 (6)
C10A	0.0637 (11)	0.0546 (9)	0.0481 (8)	0.0020 (9)	0.0027 (8)	−0.0074 (7)
C11A	0.0475 (8)	0.0673 (10)	0.0415 (7)	−0.0101 (8)	0.0026 (7)	−0.0053 (7)
C12A	0.0562 (9)	0.0599 (9)	0.0421 (7)	−0.0050 (8)	−0.0023 (7)	0.0070 (7)
C13A	0.0473 (8)	0.0489 (8)	0.0454 (7)	−0.0010 (7)	−0.0018 (7)	0.0022 (6)
C14A	0.0711 (12)	0.0956 (15)	0.0420 (8)	−0.0062 (13)	0.0044 (9)	−0.0117 (9)
C15A	0.0933 (16)	0.0566 (10)	0.0609 (10)	0.0196 (11)	−0.0087 (11)	0.0030 (8)
O1B	0.0783 (9)	0.0510 (6)	0.0586 (7)	0.0045 (7)	0.0039 (7)	−0.0023 (6)
N1B	0.0519 (8)	0.0539 (7)	0.0441 (6)	−0.0028 (7)	0.0005 (6)	0.0005 (6)
C1B	0.0487 (8)	0.0459 (7)	0.0516 (8)	−0.0080 (7)	0.0021 (7)	0.0006 (6)
C2B	0.0579 (10)	0.0540 (9)	0.0586 (9)	−0.0074 (8)	−0.0019 (8)	0.0120 (8)
C3B	0.0713 (12)	0.0709 (11)	0.0462 (8)	−0.0168 (10)	−0.0020 (8)	0.0085 (8)
C4B	0.0735 (12)	0.0650 (10)	0.0474 (8)	−0.0088 (10)	0.0080 (9)	−0.0035 (8)
C5B	0.0594 (10)	0.0540 (8)	0.0519 (8)	−0.0034 (8)	0.0074 (8)	−0.0017 (7)
C6B	0.0465 (8)	0.0477 (8)	0.0437 (7)	−0.0073 (7)	0.0023 (6)	0.0014 (6)
C7B	0.0511 (8)	0.0508 (8)	0.0471 (8)	−0.0019 (7)	0.0017 (7)	0.0023 (7)
C8B	0.0472 (8)	0.0584 (9)	0.0426 (7)	−0.0024 (8)	0.0015 (7)	−0.0010 (7)
C9B	0.0698 (12)	0.0562 (9)	0.0487 (8)	−0.0041 (9)	0.0006 (8)	−0.0015 (7)
C10B	0.0784 (14)	0.0643 (11)	0.0555 (9)	−0.0025 (11)	0.0019 (10)	0.0104 (8)
C11B	0.0599 (11)	0.0837 (13)	0.0449 (8)	0.0007 (11)	0.0037 (8)	0.0048 (8)
C12B	0.0729 (13)	0.0749 (11)	0.0470 (8)	0.0052 (11)	0.0024 (9)	−0.0097 (8)
C13B	0.0664 (11)	0.0595 (9)	0.0490 (8)	0.0038 (9)	0.0036 (8)	−0.0060 (7)
C14B	0.0918 (17)	0.1126 (19)	0.0496 (10)	0.0030 (17)	0.0001 (11)	0.0142 (11)
C15B	0.143 (3)	0.0597 (11)	0.0709 (12)	0.0069 (16)	0.0003 (17)	−0.0125 (10)

Geometric parameters (Å, º) top

O1A—C1A	1.346 (2)	O1B—C1B	1.349 (2)
O1A—H1OA	0.88 (3)	O1B—H1OB	0.89 (2)
N1A—C7A	1.278 (2)	N1B—C7B	1.279 (2)
N1A—C8A	1.4155 (18)	N1B—C8B	1.416 (2)
C1A—C2A	1.394 (2)	C1B—C2B	1.395 (2)
C1A—C6A	1.405 (2)	C1B—C6B	1.408 (2)
C2A—C3A	1.374 (3)	C2B—C3B	1.378 (3)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.379 (3)	C3B—C4B	1.376 (3)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.390 (2)	C4B—C5B	1.382 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.391 (2)	C5B—C6B	1.396 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.453 (2)	C6B—C7B	1.449 (2)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.390 (2)	C8B—C9B	1.388 (3)
C8A—C13A	1.399 (2)	C8B—C13B	1.401 (2)
C9A—C10A	1.387 (2)	C9B—C10B	1.380 (2)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.379 (3)	C10B—C11B	1.383 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.384 (3)	C11B—C12B	1.380 (3)
C11A—C14A	1.511 (2)	C11B—C14B	1.514 (2)
C12A—C13A	1.391 (2)	C12B—C13B	1.389 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C15A	1.500 (2)	C13B—C15B	1.505 (3)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600

C1A—O1A—H1OA	109.1 (17)	C1B—O1B—H1OB	110.0 (17)
C7A—N1A—C8A	122.67 (14)	C7B—N1B—C8B	121.75 (15)
O1A—C1A—C2A	118.90 (16)	O1B—C1B—C2B	118.72 (16)
O1A—C1A—C6A	121.63 (14)	O1B—C1B—C6B	121.66 (15)
C2A—C1A—C6A	119.47 (15)	C2B—C1B—C6B	119.61 (16)
C3A—C2A—C1A	120.19 (17)	C3B—C2B—C1B	119.84 (18)
C3A—C2A—H2AA	119.9	C3B—C2B—H2BA	120.1
C1A—C2A—H2AA	119.9	C1B—C2B—H2BA	120.1
C2A—C3A—C4A	121.21 (16)	C4B—C3B—C2B	121.10 (17)
C2A—C3A—H3AA	119.4	C4B—C3B—H3BA	119.4
C4A—C3A—H3AA	119.4	C2B—C3B—H3BA	119.4
C3A—C4A—C5A	119.07 (18)	C3B—C4B—C5B	119.74 (18)
C3A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.1
C5A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.1
C4A—C5A—C6A	120.98 (18)	C4B—C5B—C6B	120.70 (18)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.6
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.6
C5A—C6A—C1A	119.08 (14)	C5B—C6B—C1B	118.96 (15)
C5A—C6A—C7A	119.90 (15)	C5B—C6B—C7B	119.78 (16)
C1A—C6A—C7A	121.02 (14)	C1B—C6B—C7B	121.24 (15)
N1A—C7A—C6A	121.58 (15)	N1B—C7B—C6B	122.04 (16)
N1A—C7A—H7AA	119.2	N1B—C7B—H7BA	119.0
C6A—C7A—H7AA	119.2	C6B—C7B—H7BA	119.0
C9A—C8A—C13A	119.42 (14)	C9B—C8B—C13B	118.89 (16)
C9A—C8A—N1A	123.64 (14)	C9B—C8B—N1B	123.37 (15)
C13A—C8A—N1A	116.88 (14)	C13B—C8B—N1B	117.64 (16)
C10A—C9A—C8A	120.51 (15)	C10B—C9B—C8B	121.00 (17)
C10A—C9A—H9AA	119.7	C10B—C9B—H9BA	119.5
C8A—C9A—H9AA	119.7	C8B—C9B—H9BA	119.5
C11A—C10A—C9A	121.19 (17)	C9B—C10B—C11B	121.15 (18)
C11A—C10A—H10A	119.4	C9B—C10B—H10B	119.4
C9A—C10A—H10A	119.4	C11B—C10B—H10B	119.4
C10A—C11A—C12A	117.65 (15)	C12B—C11B—C10B	117.41 (17)
C10A—C11A—C14A	121.14 (18)	C12B—C11B—C14B	121.42 (19)
C12A—C11A—C14A	121.19 (17)	C10B—C11B—C14B	121.2 (2)
C11A—C12A—C13A	122.96 (16)	C11B—C12B—C13B	123.12 (18)
C11A—C12A—H12A	118.5	C11B—C12B—H12B	118.4
C13A—C12A—H12A	118.5	C13B—C12B—H12B	118.4
C12A—C13A—C8A	118.23 (15)	C12B—C13B—C8B	118.42 (18)
C12A—C13A—C15A	120.59 (15)	C12B—C13B—C15B	120.53 (18)
C8A—C13A—C15A	121.18 (14)	C8B—C13B—C15B	121.03 (16)
C11A—C14A—H14A	109.5	C11B—C14B—H14D	109.5
C11A—C14A—H14B	109.5	C11B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C11A—C14A—H14C	109.5	C11B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C13A—C15A—H15A	109.5	C13B—C15B—H15D	109.5
C13A—C15A—H15B	109.5	C13B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C13A—C15A—H15C	109.5	C13B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5

O1A—C1A—C2A—C3A	178.71 (19)	O1B—C1B—C2B—C3B	178.93 (17)
C6A—C1A—C2A—C3A	−1.0 (3)	C6B—C1B—C2B—C3B	−2.1 (3)
C1A—C2A—C3A—C4A	0.1 (3)	C1B—C2B—C3B—C4B	0.5 (3)
C2A—C3A—C4A—C5A	0.6 (3)	C2B—C3B—C4B—C5B	1.5 (3)
C3A—C4A—C5A—C6A	−0.4 (3)	C3B—C4B—C5B—C6B	−1.8 (3)
C4A—C5A—C6A—C1A	−0.4 (3)	C4B—C5B—C6B—C1B	0.1 (3)
C4A—C5A—C6A—C7A	−179.54 (19)	C4B—C5B—C6B—C7B	178.76 (17)
O1A—C1A—C6A—C5A	−178.57 (17)	O1B—C1B—C6B—C5B	−179.27 (16)
C2A—C1A—C6A—C5A	1.1 (3)	C2B—C1B—C6B—C5B	1.8 (2)
O1A—C1A—C6A—C7A	0.5 (3)	O1B—C1B—C6B—C7B	2.1 (2)
C2A—C1A—C6A—C7A	−179.75 (17)	C2B—C1B—C6B—C7B	−176.81 (16)
C8A—N1A—C7A—C6A	178.82 (15)	C8B—N1B—C7B—C6B	176.07 (15)
C5A—C6A—C7A—N1A	179.56 (17)	C5B—C6B—C7B—N1B	−178.89 (17)
C1A—C6A—C7A—N1A	0.5 (3)	C1B—C6B—C7B—N1B	−0.3 (3)
C7A—N1A—C8A—C9A	−13.7 (2)	C7B—N1B—C8B—C9B	−29.7 (3)
C7A—N1A—C8A—C13A	169.08 (15)	C7B—N1B—C8B—C13B	153.98 (18)
C13A—C8A—C9A—C10A	−0.8 (3)	C13B—C8B—C9B—C10B	−1.1 (3)
N1A—C8A—C9A—C10A	−177.94 (16)	N1B—C8B—C9B—C10B	−177.34 (19)
C8A—C9A—C10A—C11A	0.4 (3)	C8B—C9B—C10B—C11B	0.7 (4)
C9A—C10A—C11A—C12A	−0.6 (3)	C9B—C10B—C11B—C12B	0.2 (4)
C9A—C10A—C11A—C14A	177.81 (18)	C9B—C10B—C11B—C14B	−179.9 (2)
C10A—C11A—C12A—C13A	1.3 (3)	C10B—C11B—C12B—C13B	−0.7 (4)
C14A—C11A—C12A—C13A	−177.09 (19)	C14B—C11B—C12B—C13B	179.3 (2)
C11A—C12A—C13A—C8A	−1.7 (3)	C11B—C12B—C13B—C8B	0.3 (3)
C11A—C12A—C13A—C15A	178.23 (19)	C11B—C12B—C13B—C15B	−178.2 (3)
C9A—C8A—C13A—C12A	1.4 (2)	C9B—C8B—C13B—C12B	0.6 (3)
N1A—C8A—C13A—C12A	178.78 (15)	N1B—C8B—C13B—C12B	177.06 (18)
C9A—C8A—C13A—C15A	−178.55 (18)	C9B—C8B—C13B—C15B	179.1 (2)
N1A—C8A—C13A—C15A	−1.2 (2)	N1B—C8B—C13B—C15B	−4.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N1A	0.88 (2)	1.80 (2)	2.5854 (19)	147 (2)
O1B—H1OB···N1B	0.90 (2)	1.82 (2)	2.604 (2)	145 (2)
C5A—H5AA···O1Bⁱ	0.93	2.56	3.455 (2)	162

Symmetry code: (i) x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO
M_r	225.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	7.3161 (4), 12.0287 (7), 28.1634 (15)
V (Å³)	2478.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.51 × 0.35 × 0.32

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.963, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	39373, 4117, 3381
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.122, 1.02
No. of reflections	4117
No. of parameters	319
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.13

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
O1A—H1OA···N1A	0.88 (2)	1.80 (2)	2.5854 (19)	147 (2)
O1B—H1OB···N1B	0.90 (2)	1.82 (2)	2.604 (2)	145 (2)
C5A—H5AA···O1Bⁱ	0.93	2.56	3.455 (2)	162

Symmetry code: (i) x+1/2, −y+3/2, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

References

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