5-Diethyl­amino-2-[(E)-(4-eth­oxy­phen­yl)imino­meth­yl]phenol

Soydemir, E.; Büyükgüngör, O.; Albayrak, Ç.; Odabaşoğlu, M.

doi:10.1107/S1600536811004533

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o599-o600

doi:10.1107/S1600536811004533

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5-Diethylamino-2-[(E)-(4-ethoxyphenyl)iminomethyl]phenol

Erkan Soydemir,^a Orhan Büyükgüngör,^a ^* Çiğdem Albayrak ^b and Mustafa Odabaşoğlu ^c

^aDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, ^bSinop Faculty of Education, Sinop University, Sinop, Turkey, and ^cChemistry Programme, Denizli Higher Vocational School, Pamukkale University, TR-20159 Denizli, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 24 January 2011; accepted 7 February 2011; online 12 February 2011)

The title compound, C₁₉H₂₄N₂O₂, adopts the phenol–imine tautomeric form. An intramolecular O—H⋯N hydrogen bond results in the formation of a six-membered ring. The aromatic rings are oriented at a dihedral angle of 17.33 (16)°. Intermolecular C—H⋯π interactions occur in the crystal.

Related literature

For general background to Schiff bases, see: Hadjoudis et al. (1987 ); Hodnett & Dunn (1970 ); Misra et al. (1981 ); Agarwal et al. (1983 ); Varma et al. (1986 ); Singh & Dash (1988 ); Pandeya et al. (1999 ); El-Masry et al. (2000 ); Cohen et al. (1964 ); Moustakali-Mavridis et al. (1978 ) Kaitner & Pavlovic (1996 ); Yıldız et al. (1998 ). For related structures, see: Odabaşoğlu et al. (2003 ); Hökelek et al. (2000 ); Bingöl Alpaslan et al. (2010 ).

Experimental

Crystal data

C₁₉H₂₄N₂O₂
M_r = 312.40
Monoclinic, C 2/c
a = 29.4936 (13) Å
b = 7.8546 (2) Å
c = 16.7146 (7) Å
β = 115.093 (3)°
V = 3506.7 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.76 × 0.59 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.944, T_max = 0.979
22701 measured reflections
3625 independent reflections
2383 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.260
S = 1.10
3625 reflections
208 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.610 (3)	148
C2—H2⋯Cg1ⁱ	0.93	2.85	3.681 (4)	149
C17—H17A⋯Cg1ⁱⁱ	0.96	2.97	3.763 (6)	140
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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/S1600536811004533/fj2390sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004533/fj2390Isup2.hkl

checkCIF report

Comment top

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives are also known to have biological activities such as antimicrobial (El-Masry et al., 2000; Pandeya et al., 1999); antifungal (Singh & Dash 1988; Varma et al., 1986) and antitumor (Hodnett & Dunn 1970; Misra et al., 1981; Agarwal et al., 1983). There are two characteristic properties of Schiff bases, viz. photochromism and thermochromism (Cohen et al., 1964; Moustakali-Mavridis et al., 1978). Schiff bases display two possible tautomeric form, namely the phenol-imine (O—H···N) and keto-amine (N—H···O) forms. In the solid state, the keto-amine tautomer has been found in naphthaldimines (Hökelek et al., 2000; Odabaşoğlu et al., 2003), while the phenol-imine form exists in salicylaldimine Schiff bases (Kaitner & Pavlovic, 1996; Yıldız et al., 1998).

In the title compound, (I), the phenol-imine tautomer is favoured over the keto-amine form, and there is an intramolecular O—H···N hydrogen bond (Fig. 1 and Table 1). It is known that Schiff bases may exhibit thermochromism or photochromism, depending on the planarity or non-planarity of the molecule, respectively. This planarity of the molecule allows the H atom to be transferred through the hydrogen bond in the ground state with a low energy requirement (Hadjoudis et al., 1987). Therefore, one can expect thermochromic properties in (I) caused by planarity of the molecule: the dihedral angle between rings A (C1—C6) and B (C8—C13) is 17.33 (16)° (Fig. 1). In (I), the C8—C7, C4—N1, C7=N1 and O1—C13 bond lengths of 1.441 (4), 1.417 (3), 1.263 (3) and 1.338 (3) Å, respectively are in good agreement with those observed in (E)-2[(3-Fluoropheng)iminomethy]-4-(trifluoromethoxy)phenol [1.447 (4), 1.420 (3), 1.268 (3) and 1.343 (3) Å, Bingöl Alpaslan et al., 2010]. The C5—C4—N1=C7 and N1=C7—C8—C13 torsion angles are -19.0 (5)° and 1.2 (5)°, respectively. In crystal packing, the interactions [C2—H2···Cg1(x, 1 - y, z - 1/2)] and [C17—H17A···Cg1(1/2 - x, 1/2 + y, 3/2 - z)] are effective (Table 1 and Fig. 2.)

Related literature top

For general background to Schiff bases, see: Hadjoudis et al. (1987); Hodnett & Dunn (1970); Misra et al. (1981); Agarwal et al. (1983); Varma et al. (1986); Singh & Dash (1988); Pandeya et al. (1999); El-Masry et al. (2000); Cohen et al. (1964); Moustakali-Mavridis et al. (1978) Kaitner & Pavlovic (1996); Yıldız et al. (1998). For related structures, see: Odabaşoğlu et al. (2003); Hökelek et al. (2000); Bingöl Alpaslan et al. (2010).

Experimental top

The title compound was prepared by refluxing a mixture of a solution containing 5-(diethylamino)-2-hydroxybenzaldehyde (0.5 g, 2.59 mmol) in 20 ml e thanol and a solution containing 4-ethoxyaniline (0.4 g, 2.59 mmol) in 20 ml e thanol. The reaction mixture was stirred for 1 h under reflux. The crystals of (E)-5-(diethylamino)-2-[(4-ethoxyphenylimino)methyl]phenol suitable for x-ray analysis were obtained by slow evaporation from ethyl alcohol (yield % 82;).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (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. The dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. A packing diagram for (I). C—H···π interactions are drawn as dashed lines. [Symmetry codes: (i) x, 1 - y, -1/2 + z; (ii) 1/2 - x, 1/2 + y, 3/2 - z]

5-Diethylamino-2-[(E)-(4-ethoxyphenyl)iminomethyl]phenol top

Crystal data top

C₁₉H₂₄N₂O₂	F(000) = 1344
M_r = 312.40	D_x = 1.183 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 18643 reflections
a = 29.4936 (13) Å	θ = 1.5–28.0°
b = 7.8546 (2) Å	µ = 0.08 mm⁻¹
c = 16.7146 (7) Å	T = 296 K
β = 115.093 (3)°	Prism, yellow
V = 3506.7 (2) Å³	0.76 × 0.59 × 0.28 mm
Z = 8

Data collection top

Stoe IPDS 2 diffractometer	3625 independent reflections
Radiation source: fine-focus sealed tube	2383 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.5°
rotation method scans	h = −36→36
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
T_min = 0.944, T_max = 0.979	l = −20→20
22701 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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.260	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.1257P)² + 1.7422P] where P = (F_o² + 2F_c²)/3
3625 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.56 e Å⁻³
4 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₉H₂₄N₂O₂	V = 3506.7 (2) Å³
M_r = 312.40	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.4936 (13) Å	µ = 0.08 mm⁻¹
b = 7.8546 (2) Å	T = 296 K
c = 16.7146 (7) Å	0.76 × 0.59 × 0.28 mm
β = 115.093 (3)°

Data collection top

Stoe IPDS 2 diffractometer	3625 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2383 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.979	R_int = 0.073
22701 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	4 restraints
wR(F²) = 0.260	H-atom parameters constrained
S = 1.10	Δρ_max = 0.56 e Å⁻³
3625 reflections	Δρ_min = −0.28 e Å⁻³
208 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	0.55509 (10)	0.2708 (3)	0.09804 (16)	0.0622 (7)
C2	0.59206 (13)	0.3870 (4)	0.14442 (19)	0.0790 (9)
H2	0.6032	0.4636	0.1143	0.095*
C3	0.61234 (13)	0.3892 (4)	0.23535 (19)	0.0788 (9)
H3	0.6374	0.4677	0.2658	0.095*
C4	0.59672 (10)	0.2789 (4)	0.28250 (17)	0.0633 (7)
C5	0.55981 (11)	0.1594 (4)	0.23483 (18)	0.0700 (7)
H5	0.5489	0.0815	0.2648	0.084*
C6	0.53963 (10)	0.1569 (4)	0.14410 (17)	0.0688 (7)
H6	0.5152	0.0770	0.1133	0.083*
C7	0.60388 (11)	0.2229 (4)	0.42580 (18)	0.0677 (7)
H7	0.5730	0.1684	0.3999	0.081*
C8	0.62939 (10)	0.2270 (3)	0.52080 (17)	0.0634 (7)
C9	0.60954 (11)	0.1486 (4)	0.57326 (18)	0.0734 (8)
H9	0.5786	0.0950	0.5459	0.088*
C10	0.63345 (11)	0.1467 (4)	0.66328 (18)	0.0706 (8)
H10	0.6190	0.0904	0.6957	0.085*
C11	0.68015 (11)	0.2300 (4)	0.70765 (17)	0.0663 (7)
C12	0.69978 (11)	0.3123 (4)	0.65580 (18)	0.0737 (8)
H12	0.7299	0.3706	0.6832	0.088*
C13	0.67567 (11)	0.3099 (4)	0.56443 (17)	0.0668 (7)
C14	0.68851 (12)	0.1161 (5)	0.85131 (19)	0.0863 (10)
H14A	0.7178	0.0829	0.9037	0.104*
H14B	0.6739	0.0137	0.8179	0.104*
C15	0.65140 (15)	0.1970 (5)	0.8787 (3)	0.1017 (12)
H15A	0.6427	0.1182	0.9139	0.153*
H15B	0.6219	0.2272	0.8271	0.153*
H15C	0.6658	0.2975	0.9127	0.153*
C16	0.74589 (14)	0.3596 (6)	0.8467 (2)	0.1112 (14)
H16A	0.7407	0.4619	0.8114	0.133*
H16B	0.7453	0.3906	0.9024	0.133*
C17	0.79396 (19)	0.2842 (7)	0.8626 (3)	0.1395 (18)
H17A	0.8202	0.3645	0.8931	0.209*
H17B	0.7944	0.2546	0.8073	0.209*
H17C	0.7990	0.1836	0.8981	0.209*
C18	0.54784 (14)	0.3722 (5)	−0.04086 (19)	0.0911 (10)
H18A	0.5835	0.3629	−0.0240	0.109*
H18B	0.5406	0.4877	−0.0293	0.109*
C19	0.51921 (17)	0.3309 (6)	−0.1370 (2)	0.1181 (15)
H19A	0.5286	0.4088	−0.1716	0.177*
H19B	0.4840	0.3409	−0.1531	0.177*
H19C	0.5267	0.2167	−0.1478	0.177*
N1	0.62123 (9)	0.2895 (3)	0.37583 (14)	0.0701 (6)
N2	0.70399 (10)	0.2291 (4)	0.79754 (15)	0.0912 (9)
O1	0.69745 (9)	0.3886 (3)	0.51884 (14)	0.1011 (9)
H1	0.6798	0.3787	0.4658	0.152*
O2	0.53303 (8)	0.2546 (3)	0.00831 (12)	0.0780 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0630 (15)	0.0717 (16)	0.0496 (13)	0.0059 (13)	0.0218 (11)	−0.0012 (11)
C2	0.100 (2)	0.0798 (19)	0.0593 (16)	−0.0170 (17)	0.0355 (16)	0.0001 (13)
C3	0.093 (2)	0.0834 (19)	0.0564 (15)	−0.0248 (17)	0.0281 (14)	−0.0084 (14)
C4	0.0642 (15)	0.0705 (16)	0.0532 (14)	0.0001 (13)	0.0230 (12)	−0.0035 (11)
C5	0.0692 (16)	0.0829 (18)	0.0597 (15)	−0.0066 (14)	0.0291 (13)	0.0031 (13)
C6	0.0581 (15)	0.0851 (19)	0.0577 (15)	−0.0057 (13)	0.0191 (12)	−0.0052 (13)
C7	0.0663 (16)	0.0733 (17)	0.0603 (15)	−0.0030 (13)	0.0237 (13)	−0.0049 (13)
C8	0.0670 (16)	0.0653 (15)	0.0553 (14)	0.0001 (12)	0.0232 (12)	−0.0032 (11)
C9	0.0678 (17)	0.088 (2)	0.0616 (16)	−0.0118 (15)	0.0251 (13)	−0.0030 (14)
C10	0.0711 (17)	0.0843 (19)	0.0556 (14)	−0.0087 (14)	0.0260 (13)	0.0004 (13)
C11	0.0744 (17)	0.0709 (16)	0.0517 (14)	−0.0023 (13)	0.0249 (13)	−0.0013 (12)
C12	0.0741 (18)	0.0820 (19)	0.0599 (16)	−0.0155 (15)	0.0234 (14)	−0.0037 (14)
C13	0.0798 (18)	0.0651 (15)	0.0578 (15)	−0.0106 (13)	0.0315 (14)	−0.0003 (12)
C14	0.085 (2)	0.109 (2)	0.0555 (15)	−0.0049 (18)	0.0209 (15)	0.0098 (16)
C15	0.124 (3)	0.105 (3)	0.089 (2)	−0.011 (2)	0.058 (2)	0.000 (2)
C16	0.088 (2)	0.166 (4)	0.0653 (19)	−0.036 (2)	0.0193 (17)	0.011 (2)
C17	0.133 (4)	0.130 (4)	0.129 (4)	0.008 (3)	0.030 (3)	0.023 (3)
C18	0.109 (3)	0.106 (2)	0.0574 (16)	−0.002 (2)	0.0342 (17)	0.0046 (16)
C19	0.136 (3)	0.154 (4)	0.0554 (18)	−0.009 (3)	0.031 (2)	0.001 (2)
N1	0.0841 (16)	0.0725 (14)	0.0520 (12)	−0.0050 (12)	0.0273 (12)	−0.0018 (10)
N2	0.0797 (16)	0.137 (2)	0.0484 (13)	−0.0196 (15)	0.0187 (11)	0.0094 (13)
O1	0.1140 (18)	0.1272 (19)	0.0608 (12)	−0.0550 (16)	0.0358 (12)	−0.0062 (12)
O2	0.0849 (14)	0.0925 (14)	0.0498 (10)	−0.0046 (11)	0.0220 (9)	0.0006 (9)

Geometric parameters (Å, º) top

C1—O2	1.364 (3)	C12—H12	0.9300
C1—C6	1.378 (4)	C13—O1	1.338 (3)
C1—C2	1.381 (4)	C14—N2	1.467 (4)
C2—C3	1.377 (4)	C14—C15	1.495 (5)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.375 (4)	C14—H14B	0.9700
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.402 (4)	C15—H15B	0.9600
C4—N1	1.417 (3)	C15—H15C	0.9600
C5—C6	1.374 (4)	C16—C17	1.453 (5)
C5—H5	0.9300	C16—N2	1.547 (5)
C6—H6	0.9300	C16—H16A	0.9700
C7—N1	1.263 (4)	C16—H16B	0.9700
C7—C8	1.441 (4)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—C9	1.388 (4)	C17—H17C	0.9600
C8—C13	1.405 (4)	C18—O2	1.423 (4)
C9—C10	1.364 (4)	C18—C19	1.499 (4)
C9—H9	0.9300	C18—H18A	0.9700
C10—C11	1.417 (4)	C18—H18B	0.9700
C10—H10	0.9300	C19—H19A	0.9600
C11—N2	1.362 (3)	C19—H19B	0.9600
C11—C12	1.389 (4)	C19—H19C	0.9600
C12—C13	1.385 (4)	O1—H1	0.8200

O2—C1—C6	115.9 (2)	C15—C14—H14A	109.0
O2—C1—C2	125.0 (3)	N2—C14—H14B	109.0
C6—C1—C2	119.0 (2)	C15—C14—H14B	109.0
C3—C2—C1	119.9 (3)	H14A—C14—H14B	107.8
C3—C2—H2	120.1	C14—C15—H15A	109.5
C1—C2—H2	120.1	C14—C15—H15B	109.5
C4—C3—C2	122.0 (3)	H15A—C15—H15B	109.5
C4—C3—H3	119.0	C14—C15—H15C	109.5
C2—C3—H3	119.0	H15A—C15—H15C	109.5
C3—C4—C5	117.7 (2)	H15B—C15—H15C	109.5
C3—C4—N1	117.1 (2)	C17—C16—N2	109.0 (4)
C5—C4—N1	125.2 (3)	C17—C16—H16A	109.9
C6—C5—C4	120.4 (3)	N2—C16—H16A	109.9
C6—C5—H5	119.8	C17—C16—H16B	109.9
C4—C5—H5	119.8	N2—C16—H16B	109.9
C5—C6—C1	121.1 (3)	H16A—C16—H16B	108.3
C5—C6—H6	119.5	C16—C17—H17A	109.5
C1—C6—H6	119.5	C16—C17—H17B	109.5
N1—C7—C8	123.4 (3)	H17A—C17—H17B	109.5
N1—C7—H7	118.3	C16—C17—H17C	109.5
C8—C7—H7	118.3	H17A—C17—H17C	109.5
C9—C8—C13	117.1 (2)	H17B—C17—H17C	109.5
C9—C8—C7	121.6 (3)	O2—C18—C19	107.9 (3)
C13—C8—C7	121.4 (3)	O2—C18—H18A	110.1
C10—C9—C8	122.8 (3)	C19—C18—H18A	110.1
C10—C9—H9	118.6	O2—C18—H18B	110.1
C8—C9—H9	118.6	C19—C18—H18B	110.1
C9—C10—C11	120.3 (3)	H18A—C18—H18B	108.4
C9—C10—H10	119.8	C18—C19—H19A	109.5
C11—C10—H10	119.8	C18—C19—H19B	109.5
N2—C11—C12	122.3 (3)	H19A—C19—H19B	109.5
N2—C11—C10	120.5 (3)	C18—C19—H19C	109.5
C12—C11—C10	117.3 (2)	H19A—C19—H19C	109.5
C13—C12—C11	121.8 (3)	H19B—C19—H19C	109.5
C13—C12—H12	119.1	C7—N1—C4	122.9 (3)
C11—C12—H12	119.1	C11—N2—C14	122.0 (3)
O1—C13—C12	118.4 (3)	C11—N2—C16	120.3 (3)
O1—C13—C8	120.9 (2)	C14—N2—C16	117.5 (2)
C12—C13—C8	120.7 (3)	C13—O1—H1	109.5
N2—C14—C15	112.9 (3)	C1—O2—C18	117.0 (2)
N2—C14—H14A	109.0

O2—C1—C2—C3	−178.6 (3)	C11—C12—C13—C8	1.7 (5)
C6—C1—C2—C3	−1.0 (5)	C9—C8—C13—O1	179.9 (3)
C1—C2—C3—C4	−0.4 (5)	C7—C8—C13—O1	0.3 (4)
C2—C3—C4—C5	1.5 (5)	C9—C8—C13—C12	−0.2 (4)
C2—C3—C4—N1	178.2 (3)	C7—C8—C13—C12	−179.8 (3)
C3—C4—C5—C6	−1.3 (4)	C8—C7—N1—C4	177.4 (3)
N1—C4—C5—C6	−177.8 (3)	C3—C4—N1—C7	164.5 (3)
C4—C5—C6—C1	0.0 (5)	C5—C4—N1—C7	−19.0 (5)
O2—C1—C6—C5	179.0 (3)	C12—C11—N2—C14	−167.9 (3)
C2—C1—C6—C5	1.1 (4)	C10—C11—N2—C14	12.7 (5)
N1—C7—C8—C9	−178.4 (3)	C12—C11—N2—C16	17.2 (5)
N1—C7—C8—C13	1.2 (5)	C10—C11—N2—C16	−162.2 (3)
C13—C8—C9—C10	−1.4 (4)	C15—C14—N2—C11	−92.0 (4)
C7—C8—C9—C10	178.3 (3)	C15—C14—N2—C16	83.0 (4)
C8—C9—C10—C11	1.4 (5)	C17—C16—N2—C11	−93.3 (4)
C9—C10—C11—N2	179.6 (3)	C17—C16—N2—C14	91.6 (4)
C9—C10—C11—C12	0.2 (4)	C6—C1—O2—C18	179.2 (3)
N2—C11—C12—C13	178.9 (3)	C2—C1—O2—C18	−3.1 (4)
C10—C11—C12—C13	−1.7 (5)	C19—C18—O2—C1	179.9 (3)
C11—C12—C13—O1	−178.4 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.610 (3)	148
C2—H2···Cg1ⁱ	0.93	2.85	3.681 (4)	149
C17—H17A···Cg1ⁱⁱ	0.96	2.97	3.763 (6)	140

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄N₂O₂
M_r	312.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	29.4936 (13), 7.8546 (2), 16.7146 (7)
β (°)	115.093 (3)
V (Å³)	3506.7 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.76 × 0.59 × 0.28

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.944, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	22701, 3625, 2383
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.260, 1.10
No. of reflections	3625
No. of parameters	208
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.28

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.610 (3)	148
C2—H2···Cg1ⁱ	0.93	2.85	3.681 (4)	149
C17—H17A···Cg1ⁱⁱ	0.96	2.97	3.763 (6)	140

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

Acknowledgements

The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant No. F279 of the University Research Fund).

References

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Volume 67| Part 3| March 2011| Pages o599-o600

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