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

Kantar, E.N.; Köysal, Y.; Gümüş, S.; Ağar, E.; Soylu, M.S.

doi:10.1107/S160053681201882X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1587

doi:10.1107/S160053681201882X

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

Esen Nur Kantar,^a Yavuz Köysal,^b ^* Sümeyye Gümüş,^c Erbil Ağar ^c and Mustafa Serkan Soylu ^d

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, ^bYesilyurt Demir Celik Vocational School, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, ^cDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, 55139 Samsun, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Giresun University, Giresun, Turkey
^*Correspondence e-mail: yavuzk@omu.edu.tr

(Received 5 April 2012; accepted 26 April 2012; online 2 May 2012)

The title Schiff base, C₁₉H₂₄N₂O₃, exists in the crystal structure in the phenol–imine tautomeric form with an intramolecular O—H⋯N hydrogen bond. The planes of the aromatic rings form a dihedral angle of 36.8 (8)°. The crystal packing is characterized by C—H⋯O hydrogen bonds and π–π stacking interactions [centroid–centroid distance = 3.478 (4)Å].

Related literature

Schiff bases of salicylaldehyde may exhibit thermochromism or photochromism, depending on the planarity or non-planarity, respectively, of the molecule, see: Amimoto & Kawato (2005 ); Schmidt & Cohen (1964 ). For similar structures, see: Ha (2011 ); Asiri et al. (2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₂₄N₂O₃
M_r = 328.40
Monoclinic, P 2₁ /c
a = 7.2028 (3) Å
b = 9.4423 (5) Å
c = 26.050 (2) Å
β = 91.742 (7)°
V = 1770.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.22 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.933, T_max = 1.000
8031 measured reflections
4165 independent reflections
1959 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.164
S = 1.06
4165 reflections
226 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 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
O1—H1⋯N1	0.84 (2)	1.79 (2)	2.575 (3)	153 (4)
C16—H16B⋯O1ⁱ	0.97	2.53	3.491 (4)	172
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S160053681201882X/ld2055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201882X/ld2055Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201882X/ld2055Isup3.cml

checkCIF report

Comment top

We have studied a Schiff base derived from 4-(diethylamino)-2-hydroxybenzaldehyde. It is known that Schiff bases of salicylaldehyde may exhibit thermochromism or photochromism, depending on planarity or non-planarity of the molecule, respectively (Schmidt & Cohen, 1964; Amimoto & Kawato, 2005).

The C10-C9-N1-C5 torsion angle is -169.8 (2)°, that contributes to the general non-planarity of the molecule. The C15-O1 [1.352 (3)Å] bond length is similar to the corresponding distance in 4-Bromo-2- {[(pyridin-3-ylmethyl)imino]-methyl}phenol, [1.352 (4)Å; Ha, 2011] and in the monoclinic modification of 2-[(1,3-benzothiazol-2-yl)iminomethyl]phenol [1.345 (3)Å; Asiri et al., 2010).

Depending on the tautomers, two types of intramolecular hydrogen bonds are observed in Schiff bases: O-H···N in phenol-imine and N-H···O in keto-amine tautomers. Our X-ray investigation shows that the title compound exists in the phenol-imine form. The title compound forms intermolecular C-H···O and a strong intramolecular O-H···N hydrogen bonds, namely C16-H16B···O1 [symmetry code: (i) x-1,y,z] and O1-H1A···N1. The intramolecular hydrogen bonds generates a six membered ring, producing S(6) ring motif (Bernstein, et al., 1995). Weak π-π stacking interactions are observed which may influence crystal stability – the distance between centroids Cg1(C2-C7 ring) to Cg1ⁱⁱ [symmetry code: (ii) 1-x,-y,1-z] is 3.478 (4)Å.

Related literature top

Schiff bases of salicylaldehyde may exhibit thermochromism or photochromism, depending on the planarity or non-planarity, respectively, of the molecule, see: Amimoto & Kawato (2005); Schmidt & Cohen (1964). For similar structures, see: Ha (2011); Asiri et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The 2-{(E)-[(2,4-dimethoxyphenyl)imino]methyl}-5- (pentan-3-yl)phenol was prepared by refluxing a mixture of 4-(diethylamino)-2-hydroxybenzaldehyde (0.011 g 0.057 mmol) in 20 ml of ethanol and 2,4-dimethoxyaniline (0.009 g 0.057 mmol) in 20 ml of ethanol. The mixture was stirred for 1 h under reflux. The crystals of the 2-{(E)-[(2,4-dimethoxyphenyl)imino]methyl}-5-(pentan-3-yl)phenol suitable for X-ray analysis were obtained from ethyl alcohol by slow evaporation (yield %72; m.p. 371–373 °K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); 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 50% probability displacement ellipsoids.

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

Crystal data top

C₁₉H₂₄N₂O₃	F(000) = 704
M_r = 328.40	D_x = 1.232 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.2028 (3) Å	Cell parameters from 1690 reflections
b = 9.4423 (5) Å	θ = 3.2–29.0°
c = 26.050 (2) Å	µ = 0.08 mm⁻¹
β = 91.742 (7)°	T = 293 K
V = 1770.9 (2) Å³	Block, orange
Z = 4	0.22 × 0.15 × 0.10 mm

Data collection top

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer	4165 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1959 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 16.0454 pixels mm^-1	θ_max = 29.1°, θ_min = 3.2°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −9→11
T_min = 0.933, T_max = 1.000	l = −35→33
8031 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) = 0.164	w = 1/[σ²(F_o²) + (0.0373P)² + 0.4437P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4165 reflections	Δρ_max = 0.16 e Å⁻³
226 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (6)

Crystal data top

C₁₉H₂₄N₂O₃	V = 1770.9 (2) Å³
M_r = 328.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2028 (3) Å	µ = 0.08 mm⁻¹
b = 9.4423 (5) Å	T = 293 K
c = 26.050 (2) Å	0.22 × 0.15 × 0.10 mm
β = 91.742 (7)°

Data collection top

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer	4165 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	1959 reflections with I > 2σ(I)
T_min = 0.933, T_max = 1.000	R_int = 0.036
8031 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	1 restraint
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.16 e Å⁻³
4165 reflections	Δρ_min = −0.15 e Å⁻³
226 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.19 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	0.3547 (3)	0.5391 (2)	0.37257 (9)	0.0640 (6)
N1	0.3519 (3)	0.2811 (2)	0.40463 (9)	0.0529 (6)
O3	0.7902 (3)	−0.1820 (2)	0.46150 (9)	0.0732 (7)
C13	−0.1045 (4)	0.6216 (3)	0.31791 (10)	0.0455 (6)
C14	0.0834 (3)	0.6313 (3)	0.33320 (10)	0.0490 (7)
H14	0.1488	0.7136	0.3260	0.059*
O2	0.6402 (3)	0.3076 (2)	0.47090 (8)	0.0650 (6)
C12	−0.1986 (4)	0.4935 (3)	0.32942 (11)	0.0521 (7)
H12	−0.3229	0.4830	0.3195	0.062*
C10	0.0799 (4)	0.3947 (3)	0.37000 (10)	0.0458 (6)
N2	−0.1934 (3)	0.7311 (2)	0.29284 (9)	0.0555 (6)
C15	0.1737 (4)	0.5215 (3)	0.35868 (10)	0.0469 (7)
C11	−0.1092 (4)	0.3860 (3)	0.35480 (10)	0.0502 (7)
H11	−0.1751	0.3043	0.3623	0.060*
C9	0.1748 (4)	0.2768 (3)	0.39315 (10)	0.0505 (7)
H9	0.1083	0.1950	0.4002	0.061*
C7	0.7176 (4)	0.0578 (3)	0.46522 (11)	0.0552 (8)
H7	0.8223	0.0689	0.4866	0.066*
C5	0.4521 (4)	0.1580 (3)	0.41991 (10)	0.0491 (7)
C16	−0.3951 (4)	0.7321 (3)	0.28369 (12)	0.0628 (8)
H16A	−0.4404	0.8283	0.2871	0.075*
H16B	−0.4527	0.6749	0.3097	0.075*
C2	0.6713 (4)	−0.0755 (3)	0.44630 (11)	0.0550 (7)
C4	0.4107 (4)	0.0244 (3)	0.40130 (11)	0.0559 (8)
H4	0.3081	0.0130	0.3791	0.067*
C6	0.6091 (4)	0.1742 (3)	0.45242 (10)	0.0505 (7)
C3	0.5170 (4)	−0.0937 (3)	0.41452 (11)	0.0566 (8)
H3	0.4846	−0.1830	0.4022	0.068*
C18	−0.0953 (4)	0.8577 (3)	0.27682 (12)	0.0652 (9)
H18A	−0.1594	0.8975	0.2469	0.078*
H18B	0.0288	0.8314	0.2669	0.078*
C8	0.7964 (4)	0.3284 (3)	0.50488 (13)	0.0752 (10)
H8A	0.9086	0.3126	0.4867	0.113*
H8B	0.7905	0.2631	0.5330	0.113*
H8C	0.7954	0.4236	0.5178	0.113*
C17	−0.4527 (5)	0.6764 (4)	0.23138 (14)	0.1018 (13)
H17A	−0.3987	0.7341	0.2054	0.153*
H17B	−0.5856	0.6790	0.2274	0.153*
H17C	−0.4103	0.5805	0.2280	0.153*
C19	−0.0808 (5)	0.9695 (3)	0.31823 (14)	0.0801 (11)
H19A	−0.0146	1.0500	0.3056	0.120*
H19B	−0.0154	0.9316	0.3478	0.120*
H19C	−0.2031	0.9981	0.3276	0.120*
C1	0.7411 (5)	−0.3221 (3)	0.44663 (14)	0.0798 (11)
H1A	0.7206	−0.3257	0.4101	0.120*
H1B	0.6296	−0.3496	0.4633	0.120*
H1C	0.8399	−0.3857	0.4565	0.120*
H1	0.388 (5)	0.462 (3)	0.3860 (14)	0.114 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0442 (12)	0.0605 (14)	0.0867 (17)	−0.0032 (10)	−0.0064 (11)	0.0111 (12)
N1	0.0546 (14)	0.0542 (15)	0.0494 (14)	0.0062 (11)	−0.0060 (12)	0.0042 (11)
O3	0.0689 (14)	0.0558 (13)	0.0934 (17)	0.0147 (11)	−0.0204 (13)	−0.0056 (11)
C13	0.0443 (15)	0.0474 (16)	0.0449 (16)	0.0009 (12)	0.0014 (13)	0.0003 (12)
C14	0.0436 (15)	0.0456 (16)	0.0580 (17)	−0.0044 (12)	0.0028 (13)	0.0070 (13)
O2	0.0654 (13)	0.0550 (13)	0.0735 (15)	0.0015 (10)	−0.0157 (12)	−0.0042 (10)
C12	0.0437 (15)	0.0492 (17)	0.0631 (19)	−0.0033 (13)	−0.0024 (14)	−0.0031 (14)
C10	0.0467 (15)	0.0437 (15)	0.0470 (16)	0.0012 (12)	0.0017 (13)	0.0017 (12)
N2	0.0472 (13)	0.0534 (15)	0.0654 (16)	−0.0001 (11)	−0.0068 (12)	0.0108 (12)
C15	0.0406 (15)	0.0517 (17)	0.0486 (16)	−0.0010 (13)	0.0019 (12)	0.0009 (13)
C11	0.0457 (15)	0.0483 (16)	0.0568 (18)	−0.0046 (13)	0.0029 (14)	0.0003 (13)
C9	0.0490 (16)	0.0515 (17)	0.0509 (17)	−0.0007 (13)	0.0031 (14)	0.0018 (13)
C7	0.0530 (17)	0.0609 (19)	0.0510 (18)	0.0062 (15)	−0.0087 (14)	−0.0018 (14)
C5	0.0474 (16)	0.0502 (17)	0.0493 (17)	0.0055 (13)	−0.0031 (13)	0.0036 (13)
C16	0.0574 (19)	0.0621 (19)	0.068 (2)	0.0029 (15)	−0.0073 (16)	0.0068 (16)
C2	0.0499 (17)	0.0593 (19)	0.0557 (18)	0.0098 (14)	−0.0001 (14)	0.0012 (14)
C4	0.0554 (18)	0.0647 (19)	0.0470 (17)	0.0034 (15)	−0.0088 (14)	0.0001 (14)
C6	0.0524 (16)	0.0502 (17)	0.0487 (17)	0.0023 (14)	−0.0002 (14)	0.0012 (13)
C3	0.0610 (18)	0.0526 (17)	0.0556 (18)	0.0064 (15)	−0.0049 (15)	−0.0051 (14)
C18	0.065 (2)	0.0584 (19)	0.072 (2)	−0.0051 (16)	−0.0003 (17)	0.0217 (16)
C8	0.073 (2)	0.072 (2)	0.080 (2)	−0.0082 (18)	−0.021 (2)	−0.0065 (18)
C17	0.102 (3)	0.118 (3)	0.084 (3)	−0.020 (3)	−0.024 (2)	−0.003 (2)
C19	0.077 (2)	0.060 (2)	0.102 (3)	−0.0080 (18)	−0.012 (2)	0.0009 (19)
C1	0.078 (2)	0.060 (2)	0.101 (3)	0.0154 (18)	−0.006 (2)	−0.0072 (19)

Geometric parameters (Å, º) top

O1—C15	1.352 (3)	C5—C4	1.381 (4)
O1—H1	0.843 (18)	C5—C6	1.401 (3)
N1—C9	1.302 (3)	C16—C17	1.507 (4)
N1—C5	1.418 (3)	C16—H16A	0.9700
O3—C2	1.371 (3)	C16—H16B	0.9700
O3—C1	1.420 (3)	C2—C3	1.376 (4)
C13—N2	1.372 (3)	C4—C3	1.390 (3)
C13—C14	1.403 (3)	C4—H4	0.9300
C13—C12	1.423 (3)	C3—H3	0.9300
C14—C15	1.383 (3)	C18—C19	1.511 (4)
C14—H14	0.9300	C18—H18A	0.9700
O2—C6	1.365 (3)	C18—H18B	0.9700
O2—C8	1.424 (3)	C8—H8A	0.9600
C12—C11	1.362 (3)	C8—H8B	0.9600
C12—H12	0.9300	C8—H8C	0.9600
C10—C11	1.410 (3)	C17—H17A	0.9600
C10—C15	1.410 (3)	C17—H17B	0.9600
C10—C9	1.430 (3)	C17—H17C	0.9600
N2—C18	1.456 (3)	C19—H19A	0.9600
N2—C16	1.465 (3)	C19—H19B	0.9600
C11—H11	0.9300	C19—H19C	0.9600
C9—H9	0.9300	C1—H1A	0.9600
C7—C6	1.384 (3)	C1—H1B	0.9600
C7—C2	1.389 (4)	C1—H1C	0.9600
C7—H7	0.9300

C15—O1—H1	105 (3)	O3—C2—C7	114.9 (2)
C9—N1—C5	121.7 (2)	C3—C2—C7	120.5 (3)
C2—O3—C1	117.1 (2)	C5—C4—C3	122.3 (3)
N2—C13—C14	121.2 (2)	C5—C4—H4	118.8
N2—C13—C12	121.5 (2)	C3—C4—H4	118.8
C14—C13—C12	117.3 (2)	O2—C6—C7	124.2 (2)
C15—C14—C13	121.5 (2)	O2—C6—C5	115.8 (2)
C15—C14—H14	119.2	C7—C6—C5	119.9 (2)
C13—C14—H14	119.2	C2—C3—C4	118.6 (3)
C6—O2—C8	117.7 (2)	C2—C3—H3	120.7
C11—C12—C13	121.0 (2)	C4—C3—H3	120.7
C11—C12—H12	119.5	N2—C18—C19	113.1 (3)
C13—C12—H12	119.5	N2—C18—H18A	109.0
C11—C10—C15	117.1 (2)	C19—C18—H18A	109.0
C11—C10—C9	121.2 (2)	N2—C18—H18B	109.0
C15—C10—C9	121.6 (2)	C19—C18—H18B	109.0
C13—N2—C18	122.2 (2)	H18A—C18—H18B	107.8
C13—N2—C16	121.9 (2)	O2—C8—H8A	109.5
C18—N2—C16	115.8 (2)	O2—C8—H8B	109.5
O1—C15—C14	118.2 (2)	H8A—C8—H8B	109.5
O1—C15—C10	120.8 (2)	O2—C8—H8C	109.5
C14—C15—C10	121.0 (2)	H8A—C8—H8C	109.5
C12—C11—C10	122.1 (3)	H8B—C8—H8C	109.5
C12—C11—H11	119.0	C16—C17—H17A	109.5
C10—C11—H11	119.0	C16—C17—H17B	109.5
N1—C9—C10	121.6 (3)	H17A—C17—H17B	109.5
N1—C9—H9	119.2	C16—C17—H17C	109.5
C10—C9—H9	119.2	H17A—C17—H17C	109.5
C6—C7—C2	120.4 (3)	H17B—C17—H17C	109.5
C6—C7—H7	119.8	C18—C19—H19A	109.5
C2—C7—H7	119.8	C18—C19—H19B	109.5
C4—C5—C6	118.3 (2)	H19A—C19—H19B	109.5
C4—C5—N1	123.2 (2)	C18—C19—H19C	109.5
C6—C5—N1	118.3 (2)	H19A—C19—H19C	109.5
N2—C16—C17	112.9 (3)	H19B—C19—H19C	109.5
N2—C16—H16A	109.0	O3—C1—H1A	109.5
C17—C16—H16A	109.0	O3—C1—H1B	109.5
N2—C16—H16B	109.0	H1A—C1—H1B	109.5
C17—C16—H16B	109.0	O3—C1—H1C	109.5
H16A—C16—H16B	107.8	H1A—C1—H1C	109.5
O3—C2—C3	124.6 (3)	H1B—C1—H1C	109.5

N2—C13—C14—C15	179.7 (3)	C13—N2—C16—C17	−95.4 (3)
C12—C13—C14—C15	−0.4 (4)	C18—N2—C16—C17	88.7 (3)
N2—C13—C12—C11	−179.3 (3)	C1—O3—C2—C3	−5.4 (5)
C14—C13—C12—C11	0.8 (4)	C1—O3—C2—C7	175.1 (3)
C14—C13—N2—C18	5.4 (4)	C6—C7—C2—O3	179.7 (3)
C12—C13—N2—C18	−174.5 (3)	C6—C7—C2—C3	0.1 (5)
C14—C13—N2—C16	−170.3 (3)	C6—C5—C4—C3	1.3 (4)
C12—C13—N2—C16	9.8 (4)	N1—C5—C4—C3	176.3 (3)
C13—C14—C15—O1	−179.5 (2)	C8—O2—C6—C7	1.1 (4)
C13—C14—C15—C10	0.4 (4)	C8—O2—C6—C5	178.9 (3)
C11—C10—C15—O1	179.1 (3)	C2—C7—C6—O2	177.3 (3)
C9—C10—C15—O1	−4.5 (4)	C2—C7—C6—C5	−0.4 (5)
C11—C10—C15—C14	−0.8 (4)	C4—C5—C6—O2	−178.1 (3)
C9—C10—C15—C14	175.6 (3)	N1—C5—C6—O2	6.6 (4)
C13—C12—C11—C10	−1.2 (4)	C4—C5—C6—C7	−0.2 (4)
C15—C10—C11—C12	1.2 (4)	N1—C5—C6—C7	−175.5 (3)
C9—C10—C11—C12	−175.2 (3)	O3—C2—C3—C4	−178.6 (3)
C5—N1—C9—C10	−169.8 (2)	C7—C2—C3—C4	0.9 (5)
C11—C10—C9—N1	176.0 (3)	C5—C4—C3—C2	−1.6 (5)
C15—C10—C9—N1	−0.2 (4)	C13—N2—C18—C19	−86.8 (3)
C9—N1—C5—C4	33.2 (4)	C16—N2—C18—C19	89.1 (3)
C9—N1—C5—C6	−151.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84 (2)	1.79 (2)	2.575 (3)	153 (4)
C16—H16B···O1ⁱ	0.97	2.53	3.491 (4)	172

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄N₂O₃
M_r	328.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.2028 (3), 9.4423 (5), 26.050 (2)
β (°)	91.742 (7)
V (Å³)	1770.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.22 × 0.15 × 0.10

Data collection
Diffractometer	Oxford Diffraction SuperNova (single source at offset) Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.933, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8031, 4165, 1959
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.684

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.164, 1.06
No. of reflections	4165
No. of parameters	226
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), 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	0.843 (18)	1.79 (2)	2.575 (3)	153 (4)
C16—H16B···O1ⁱ	0.97	2.53	3.491 (4)	172.0

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Giresun University, Turkey, for the use of the diffractometer.

References

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