(E)-4-[(4-Diethyl­amino-2-hy­droxy­benzyl­idene)amino]­benzoic acid

Kargar, H.; Sharafi, Z.; Kia, R.; Tahir, M.N.

doi:10.1107/S160053681200997X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1036

doi:10.1107/S160053681200997X

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(E)-4-[(4-Diethylamino-2-hydroxybenzylidene)amino]benzoic acid

Hadi Kargar,^a ^* Zahra Sharafi,^b Reza Kia ^c and Muhammad Nawaz Tahir ^d ^*

^aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I. R. of IRAN, ^bDepartment of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran, ^cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^dDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: h.kargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 4 March 2012; accepted 6 March 2012; online 10 March 2012)

In the title compound, C₁₈H₂₀N₂O₃, a potential bidentate N,O-donor Schiff base ligand, the benzene rings are inclined at an angle of 12.25 (19)°. The molecule has an E conformation about the C=N bond. One of the ethyl groups is disordered over two positions, with a refined site-occupancy ratio of 0.55 (1):0.45 (1). An intramolecular O—H⋯N hydrogen bond makes an S(6) ring motif. In the crystal, pairs of O—H⋯O hydrogen bonds link molecules, forming inversion dimers with R₂²(8) ring motifs.

Related literature

For background to Schiff base ligands and their metal complexes, see: Kargar et al. (2011 , 2012 ); Kia et al. (2010 ). For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₃
M_r = 312.36
Monoclinic, P 2₁ /c
a = 12.4216 (8) Å
b = 8.1511 (6) Å
c = 16.0820 (11) Å
β = 93.001 (3)°
V = 1626.06 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.25 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.978, T_max = 0.991
11192 measured reflections
2872 independent reflections
918 reflections with I > 2σ(I)
R_int = 0.097

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.133
S = 0.94
2872 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.14 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
O3—H3⋯N1	0.82	1.88	2.609 (3)	147
O2—H2⋯O1ⁱ	0.82	1.80	2.613 (2)	170
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681200997X/su2388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200997X/su2388Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200997X/su2388Isup3.cml

checkCIF report

Comment top

In continuation of our work on the crystal structure analysis of Schiff base ligands (Kargar et al., 2011, 2012; Kia et al., 2010), we determined the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a potential bidentate N,O-donor Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The intramolecular O3—H3···N1 hydrogen bond (Table 1) makes an S(6) ring motif (Bernstein et al., 1995). The dihedral angle between the benzene rings is 12.25 (19)°, and the molecule has an E conformation about the C8═N1 bond. One of the ethyl groups was disordered over two position with a refined site occupancy ratio of 0.55 (1)/0.45 (1).

In the crystal, pairs of O—H···O hydrogen bonds (Table 1) link molecules into inversion dimers with an R²₂(8) ring motif (Fig. 2).

Related literature top

For background to Schiff base ligands and their metal complexes, see: Kargar et al. (2011, 2012); Kia et al. (2010). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by adding 4-diethylaminosalicylaldehyde (2 mmol) to a solution of 4-carboxyaniline (2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 30 min. The resultant solution was filtered. Pale-yellow single crystals of the title compound, suitable for X-ray structure analysis, were obtained by recrystallization from ethanol, by slow evaporation of the solvents at room temperature over several days.

Structure description top

In continuation of our work on the crystal structure analysis of Schiff base ligands (Kargar et al., 2011, 2012; Kia et al., 2010), we determined the crystal structure of the title compound.

In the crystal, pairs of O—H···O hydrogen bonds (Table 1) link molecules into inversion dimers with an R²₂(8) ring motif (Fig. 2).

For background to Schiff base ligands and their metal complexes, see: Kargar et al. (2011, 2012); Kia et al. (2010). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The open bonds show the minor component of the disordered ethyl group. The dashed lines show the O-H···N hydrogen bond (see Table 1 for details).
	Fig. 2. The crystal packing diagram of the title compound viewed along the b-axis, showing the inversion dimers with an R²₂(8) ring motif. Only the hydrogen atoms involved the hydrogen bonding are shown - see Table 1 for details.

(E)-4-[(4-Diethylamino-2-hydroxybenzylidene)amino]benzoic acid top

Crystal data top

C₁₈H₂₀N₂O₃	F(000) = 664
M_r = 312.36	D_x = 1.276 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3270 reflections
a = 12.4216 (8) Å	θ = 2.8–28.8°
b = 8.1511 (6) Å	µ = 0.09 mm⁻¹
c = 16.0820 (11) Å	T = 296 K
β = 93.001 (3)°	Block, pale-yellow
V = 1626.06 (19) Å³	0.25 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2872 independent reflections
Radiation source: fine-focus sealed tube	918 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
φ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→12
T_min = 0.978, T_max = 0.991	k = −9→9
11192 measured reflections	l = −19→19

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0393P)²] where P = (F_o² + 2F_c²)/3
2872 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₃	V = 1626.06 (19) Å³
M_r = 312.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4216 (8) Å	µ = 0.09 mm⁻¹
b = 8.1511 (6) Å	T = 296 K
c = 16.0820 (11) Å	0.25 × 0.12 × 0.10 mm
β = 93.001 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2872 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	918 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.991	R_int = 0.097
11192 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 0.94	Δρ_max = 0.14 e Å⁻³
2872 reflections	Δρ_min = −0.13 e Å⁻³
219 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	Occ. (<1)
C1	0.9492 (3)	0.4842 (5)	0.8861 (2)	0.0584 (12)
C2	0.9076 (3)	0.4702 (5)	0.7993 (2)	0.0508 (11)
C3	0.8265 (3)	0.3620 (5)	0.7757 (2)	0.0684 (13)
H18	0.7990	0.2917	0.8150	0.082*
C4	0.7858 (3)	0.3574 (5)	0.6946 (2)	0.0703 (13)
H17	0.7299	0.2852	0.6801	0.084*
C5	0.8256 (3)	0.4564 (5)	0.6347 (2)	0.0541 (12)
C6	0.9084 (3)	0.5642 (5)	0.6578 (2)	0.0657 (13)
H10	0.9371	0.6327	0.6184	0.079*
C7	0.9481 (3)	0.5692 (5)	0.7398 (2)	0.0633 (12)
H11	1.0036	0.6416	0.7547	0.076*
C8	0.8135 (3)	0.5152 (5)	0.4913 (2)	0.0627 (13)
H7	0.8806	0.5655	0.4982	0.075*
C9	0.7599 (3)	0.5179 (5)	0.4096 (2)	0.0507 (11)
C10	0.8031 (3)	0.5970 (5)	0.3437 (2)	0.0644 (12)
H5	0.8700	0.6476	0.3520	0.077*
C11	0.7519 (3)	0.6043 (5)	0.2663 (2)	0.0627 (12)
H4	0.7842	0.6589	0.2234	0.075*
C12	0.6503 (4)	0.5293 (5)	0.2515 (2)	0.0655 (13)
C13	0.6062 (3)	0.4454 (5)	0.3171 (2)	0.0696 (14)
H15	0.5408	0.3909	0.3083	0.084*
C14	0.6582 (4)	0.4422 (5)	0.3949 (2)	0.0614 (12)
C15	0.6378 (3)	0.6430 (6)	0.1074 (2)	0.0862 (15)
H2A	0.6707	0.7408	0.1319	0.103*
H2B	0.5769	0.6770	0.0713	0.103*
C16	0.7176 (4)	0.5578 (5)	0.0570 (3)	0.1024 (17)
H1A	0.7796	0.5285	0.0920	0.154*
H1B	0.7391	0.6293	0.0134	0.154*
H1C	0.6856	0.4604	0.0329	0.154*
C17	0.4751 (11)	0.5013 (14)	0.1607 (7)	0.089 (5)	0.549 (11)
H17A	0.4373	0.5097	0.2118	0.107*	0.549 (11)
H17B	0.4407	0.5708	0.1182	0.107*	0.549 (11)
C18	0.4858 (16)	0.3342 (18)	0.1334 (11)	0.111 (6)	0.549 (11)
H18A	0.4156	0.2891	0.1200	0.167*	0.549 (11)
H18B	0.5212	0.2706	0.1771	0.167*	0.549 (11)
H18C	0.5277	0.3313	0.0850	0.167*	0.549 (11)
C17A	0.5142 (16)	0.405 (2)	0.1518 (10)	0.058 (5)	0.451 (11)
H17C	0.5183	0.3745	0.0937	0.070*	0.451 (11)
H17D	0.5286	0.3077	0.1855	0.070*	0.451 (11)
C18A	0.40179 (14)	0.4703 (4)	0.16718 (11)	0.075 (4)	0.451 (11)
H18D	0.3490	0.3878	0.1523	0.112*	0.451 (11)
H18E	0.3880	0.5665	0.1339	0.112*	0.451 (11)
H18F	0.3977	0.4977	0.2250	0.112*	0.451 (11)
N1	0.77425 (12)	0.44793 (19)	0.55449 (9)	0.0639 (11)
N2	0.59881 (15)	0.5375 (3)	0.17449 (16)	0.0925 (14)
O1	1.00875 (12)	0.59948 (19)	0.90912 (8)	0.0827 (10)
O2	0.91877 (12)	0.37246 (19)	0.93606 (10)	0.0889 (10)
H2	0.9476	0.3876	0.9825	0.133*
O3	0.6110 (2)	0.3604 (4)	0.45575 (15)	0.0883 (10)
H3	0.6443	0.3772	0.5003	0.132*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.061 (3)	0.068 (3)	0.045 (3)	0.010 (3)	−0.004 (2)	0.005 (2)
C2	0.049 (3)	0.055 (3)	0.047 (3)	0.003 (2)	−0.007 (2)	−0.001 (2)
C3	0.078 (3)	0.078 (4)	0.049 (3)	−0.012 (3)	−0.002 (2)	0.009 (2)
C4	0.078 (3)	0.078 (4)	0.053 (3)	−0.026 (3)	−0.010 (3)	0.005 (3)
C5	0.065 (3)	0.053 (3)	0.044 (2)	0.003 (2)	−0.005 (2)	−0.004 (2)
C6	0.078 (4)	0.072 (3)	0.046 (3)	−0.016 (3)	−0.001 (2)	0.005 (2)
C7	0.068 (3)	0.066 (3)	0.055 (3)	−0.016 (2)	−0.009 (2)	0.000 (2)
C8	0.069 (3)	0.058 (3)	0.060 (3)	0.004 (2)	−0.007 (3)	−0.013 (2)
C9	0.056 (3)	0.051 (3)	0.044 (3)	0.000 (2)	−0.004 (2)	−0.003 (2)
C10	0.064 (3)	0.076 (3)	0.054 (3)	−0.005 (3)	0.004 (2)	0.003 (3)
C11	0.068 (3)	0.076 (3)	0.043 (3)	−0.010 (3)	−0.005 (2)	0.008 (2)
C12	0.064 (3)	0.081 (4)	0.050 (3)	−0.011 (3)	−0.008 (3)	0.006 (3)
C13	0.073 (3)	0.085 (4)	0.050 (3)	−0.024 (3)	−0.011 (3)	0.007 (3)
C14	0.077 (4)	0.058 (3)	0.049 (3)	−0.011 (3)	0.006 (3)	0.009 (2)
C15	0.076 (4)	0.121 (4)	0.060 (3)	0.000 (3)	−0.011 (3)	0.016 (3)
C16	0.111 (5)	0.116 (5)	0.079 (3)	0.000 (3)	−0.002 (3)	−0.005 (3)
C17	0.112 (15)	0.077 (10)	0.078 (7)	0.023 (9)	0.002 (7)	0.012 (7)
C18	0.138 (15)	0.088 (14)	0.109 (13)	−0.014 (10)	0.007 (9)	−0.011 (9)
C17A	0.076 (11)	0.055 (14)	0.040 (7)	0.008 (10)	−0.024 (7)	−0.009 (9)
C18A	0.034 (7)	0.100 (11)	0.090 (8)	0.013 (6)	0.000 (6)	0.013 (7)
N1	0.080 (3)	0.066 (3)	0.045 (2)	−0.0010 (19)	−0.007 (2)	0.0019 (19)
N2	0.071 (3)	0.155 (4)	0.050 (2)	−0.037 (3)	−0.015 (2)	0.022 (3)
O1	0.097 (2)	0.089 (2)	0.0590 (19)	−0.0284 (19)	−0.0243 (16)	0.0038 (17)
O2	0.124 (3)	0.090 (2)	0.0495 (18)	−0.023 (2)	−0.0197 (17)	0.0063 (17)
O3	0.105 (3)	0.105 (2)	0.0537 (18)	−0.042 (2)	−0.0093 (17)	0.0086 (19)

Geometric parameters (Å, º) top

C1—O1	1.240 (4)	C13—H15	0.9300
C1—O2	1.284 (4)	C14—O3	1.344 (4)
C1—C2	1.468 (4)	C15—N2	1.481 (4)
C2—C7	1.368 (4)	C15—C16	1.485 (5)
C2—C3	1.377 (4)	C15—H2A	0.9700
C3—C4	1.374 (4)	C15—H2B	0.9700
C3—H18	0.9300	C16—H1A	0.9600
C4—C5	1.369 (4)	C16—H1B	0.9600
C4—H17	0.9300	C16—H1C	0.9600
C5—C6	1.389 (4)	C17—C18	1.440 (19)
C5—N1	1.410 (4)	C17—N2	1.569 (14)
C6—C7	1.383 (5)	C17—H17A	0.9700
C6—H10	0.9300	C17—H17B	0.9700
C7—H11	0.9300	C18—H18A	0.9600
C8—N1	1.274 (4)	C18—H18B	0.9600
C8—C9	1.441 (4)	C18—H18C	0.9600
C8—H7	0.9300	C17A—C18A	1.53 (2)
C9—C10	1.374 (4)	C17A—N2	1.538 (15)
C9—C14	1.414 (5)	C17A—H17C	0.9700
C10—C11	1.370 (4)	C17A—H17D	0.9700
C10—H5	0.9300	C18A—H18D	0.9600
C11—C12	1.411 (5)	C18A—H18E	0.9600
C11—H4	0.9300	C18A—H18F	0.9600
C12—N2	1.365 (4)	O2—H2	0.8200
C12—C13	1.394 (5)	O3—H3	0.8200
C13—C14	1.379 (5)

O1—C1—O2	122.8 (3)	O3—C14—C9	121.0 (4)
O1—C1—C2	121.2 (3)	C13—C14—C9	121.1 (4)
O2—C1—C2	116.0 (4)	N2—C15—C16	112.3 (4)
C7—C2—C3	118.4 (3)	N2—C15—H2A	109.1
C7—C2—C1	119.7 (4)	C16—C15—H2A	109.1
C3—C2—C1	121.9 (4)	N2—C15—H2B	109.1
C4—C3—C2	120.4 (4)	C16—C15—H2B	109.1
C4—C3—H18	119.8	H2A—C15—H2B	107.9
C2—C3—H18	119.8	C15—C16—H1A	109.5
C5—C4—C3	121.6 (4)	C15—C16—H1B	109.5
C5—C4—H17	119.2	H1A—C16—H1B	109.5
C3—C4—H17	119.2	C15—C16—H1C	109.5
C4—C5—C6	118.3 (3)	H1A—C16—H1C	109.5
C4—C5—N1	116.9 (4)	H1B—C16—H1C	109.5
C6—C5—N1	124.7 (4)	C18—C17—N2	96.6 (12)
C7—C6—C5	119.7 (4)	C18—C17—H17A	112.4
C7—C6—H10	120.1	N2—C17—H17A	112.4
C5—C6—H10	120.1	C18—C17—H17B	112.4
C2—C7—C6	121.6 (4)	N2—C17—H17B	112.4
C2—C7—H11	119.2	H17A—C17—H17B	110.0
C6—C7—H11	119.2	C18A—C17A—N2	109.6 (11)
N1—C8—C9	123.8 (4)	C18A—C17A—H17C	109.8
N1—C8—H7	118.1	N2—C17A—H17C	109.8
C9—C8—H7	118.1	C18A—C17A—H17D	109.8
C10—C9—C14	117.2 (4)	N2—C17A—H17D	109.8
C10—C9—C8	122.0 (4)	H17C—C17A—H17D	108.2
C14—C9—C8	120.8 (4)	C17A—C18A—H18D	109.5
C11—C10—C9	122.7 (4)	C17A—C18A—H18E	109.5
C11—C10—H5	118.7	H18D—C18A—H18E	109.5
C9—C10—H5	118.7	C17A—C18A—H18F	109.5
C10—C11—C12	120.2 (4)	H18D—C18A—H18F	109.5
C10—C11—H4	119.9	H18E—C18A—H18F	109.5
C12—C11—H4	119.9	C8—N1—C5	122.4 (3)
N2—C12—C13	121.8 (4)	C12—N2—C15	122.2 (3)
N2—C12—C11	120.3 (4)	C12—N2—C17A	117.5 (7)
C13—C12—C11	118.0 (4)	C15—N2—C17A	118.8 (7)
C14—C13—C12	120.8 (4)	C12—N2—C17	121.8 (5)
C14—C13—H15	119.6	C15—N2—C17	111.2 (5)
C12—C13—H15	119.6	C1—O2—H2	109.5
O3—C14—C13	117.9 (4)	C14—O3—H3	109.5

O1—C1—C2—C7	10.7 (6)	C12—C13—C14—C9	−2.7 (6)
O2—C1—C2—C7	−170.5 (3)	C10—C9—C14—O3	179.1 (4)
O1—C1—C2—C3	−167.8 (4)	C8—C9—C14—O3	−2.6 (6)
O2—C1—C2—C3	11.1 (6)	C10—C9—C14—C13	1.2 (6)
C7—C2—C3—C4	−1.5 (6)	C8—C9—C14—C13	179.5 (4)
C1—C2—C3—C4	176.9 (4)	C9—C8—N1—C5	−175.9 (3)
C2—C3—C4—C5	1.4 (6)	C4—C5—N1—C8	−169.4 (3)
C3—C4—C5—C6	−0.5 (6)	C6—C5—N1—C8	14.6 (5)
C3—C4—C5—N1	−176.7 (3)	C13—C12—N2—C15	172.2 (4)
C4—C5—C6—C7	−0.1 (6)	C11—C12—N2—C15	−9.0 (5)
N1—C5—C6—C7	175.8 (3)	C13—C12—N2—C17A	−21.8 (10)
C3—C2—C7—C6	0.9 (6)	C11—C12—N2—C17A	157.0 (9)
C1—C2—C7—C6	−177.6 (4)	C13—C12—N2—C17	18.6 (7)
C5—C6—C7—C2	−0.1 (6)	C11—C12—N2—C17	−162.5 (6)
N1—C8—C9—C10	177.6 (4)	C16—C15—N2—C12	88.2 (4)
N1—C8—C9—C14	−0.6 (6)	C16—C15—N2—C17A	−77.6 (10)
C14—C9—C10—C11	0.0 (6)	C16—C15—N2—C17	−115.7 (5)
C8—C9—C10—C11	−178.2 (4)	C18A—C17A—N2—C12	97.2 (10)
C9—C10—C11—C12	0.2 (6)	C18A—C17A—N2—C15	−96.3 (11)
C10—C11—C12—N2	179.6 (4)	C18A—C17A—N2—C17	−9.9 (8)
C10—C11—C12—C13	−1.5 (6)	C18—C17—N2—C12	−98.4 (11)
N2—C12—C13—C14	−178.3 (4)	C18—C17—N2—C15	105.4 (10)
C11—C12—C13—C14	2.8 (6)	C18—C17—N2—C17A	−4.7 (18)
C12—C13—C14—O3	179.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	1.88	2.609 (3)	147
O2—H2···O1ⁱ	0.82	1.80	2.613 (2)	170

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₃
M_r	312.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.4216 (8), 8.1511 (6), 16.0820 (11)
β (°)	93.001 (3)
V (Å³)	1626.06 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.978, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	11192, 2872, 918
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.133, 0.94
No. of reflections	2872
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.13

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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
O3—H3···N1	0.82	1.88	2.609 (3)	147
O2—H2···O1ⁱ	0.82	1.80	2.613 (2)	170

Symmetry code: (i) −x+2, −y+1, −z+2.

Acknowledgements

HK thanks PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for the research facility.

References

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