8-[(1E)-1-(2-Aminophenyl­iminio)eth­yl]-2-oxo-2H-chromen-7-olate

Aazam, E.S.; El Husseiny, A.F.; Al-Amri, H.M.; Büyükgüngör, O.

doi:10.1107/S1600536810023093

organic compounds

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Volume 66| Part 7| July 2010| Page o1796

doi:10.1107/S1600536810023093

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8-[(1E)-1-(2-Aminophenyliminio)ethyl]-2-oxo-2H-chromen-7-olate

E. S. Aazam,^a ^* A. F. El Husseiny,^b H. M. Al-Amri ^a and Orhan Büyükgüngör ^c

^aDepartment of Chemistry, Girls Section, University of King Abdulaziz, PO Box 6171, Jeddah 21442, Saudi Arabia, ^bDepartment of Chemistry, Faculty of Science, Alexandria University, Egypt, and ^cDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
^*Correspondence e-mail: wayfield8@yahoo.com

(Received 4 June 2010; accepted 15 June 2010; online 26 June 2010)

The title Schiff base, C₁₇H₁₄N₂O₃, exists as an NH tautomer with the H atom of the phenol group transferred to the imine N atom. The iminium H atom is involved in a strong intramolecular N⁺—H⋯O⁻ hydrogen bond to the phenolate O atom, forming an S(6) motif. In the crystal structure, N—H⋯O hydrogen bonds form a C(9) chain parallel to [100] and a C(11) chain parallel to [010], while C—H⋯O hydrogen bonds form a C(11) chain parallel to [010]. The combination of N—H⋯O and C—H⋯O hydrogen bonds generates R₄³(30) rings parallel to the ab plane

Related literature

For related structures, see: Patil et al. (2010 ); Aazam et al. (2006 ); Filarowski (2005 ); El Husseiny et al. (2008 ); Aazam et al. (2008 ); Karabıyık et al. (2008 ). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₄N₂O₃
M_r = 294.30
Orthorhombic, P b c a
a = 7.5462 (3) Å
b = 18.9324 (11) Å
c = 20.0445 (9) Å
V = 2863.7 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.44 × 0.29 × 0.20 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.962, T_max = 0.984
25561 measured reflections
2868 independent reflections
1972 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.095
S = 1.00
2868 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 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
N1—H1⋯O1	0.95 (2)	1.56 (2)	2.4534 (17)	155 (2)
N2—H2A⋯O1ⁱ	0.92 (2)	2.13 (2)	2.9933 (19)	154.7 (15)
N2—H2B⋯O2ⁱⁱ	0.91 (2)	2.37 (2)	3.1203 (19)	138.7 (17)
C5—H5⋯O2ⁱⁱⁱ	0.93	2.48	3.242 (2)	139
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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/S1600536810023093/gk2282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023093/gk2282Isup2.hkl

checkCIF report

Comment top

Coumarin and its derivatives have been a subject of numerous investigations due to their diverse biological activities, interesting photophysical, photochemical and metal binding properties. Schiff base complexes play an important role in coordination chemistry (Patil et al., 2010). We have recently reported synthesis, single-crystal X-ray diffraction studies, characterization and antibacterial activity of a Schiff-base ligand incorporating coumarin moiety and their metal complexes (Aazam et al., 2006; El Husseiny, et al., 2008; Aazam et al., 2008). In this work, we would like to present an X-ray investigation of a newly synthesized coumarin Schiff base derived from 8-acetyl-7-hydroxycoumarin and o-phenylenediamine. We report here the crystal structure of (I) (Figure 1).

Schiff bases exhibit two well known tautomeric forms viz. OH and NH tautomers. NH tautomers can be regarded as a resonance hybrid of two canonical structures the non-charged quinoid and ionic zwitterionic forms. Our investigations show that compound (I) formula can be given as a combination of two canonical forms: phenolate with negative charge predominantly at the phenolate O atom or as chromen-8-ide with negative charge at the C atom. Compound I is a hyprid of two zwitterionic canonical forms (Fig. 2) having N⁺—H bond (0.952 Å) longer than standared interatomic separations observed in neutral N—H bonds (0.878 Å)(Karabıyık et al., 2008). Compound (I) crystallizes in the orthorhombic space group Pbca (No. 61) with one molecule per asymmetric unit. The iminium H atom is almost coplanar with the coumarin ring (deviation from the coumarin plane 0.0444 Å) and on the same side of the molecule as the phenolic O atom, allowing the formation of an intramolecular N—H···O hydrogen bond. A summary of bond lengths and angles of the ketoimine system is presented in Table 1.

In order to compare the bond lengths found in (I) with other molecules containing similar functional groups, a comparison with a previous search in the Cambridge Structural Database (CSD) was performed (Filarowski, 2005). The comparison with the mean bond lengths of similar molecules clearly tends to confirm that (I) is cis-ketoimine tauutomer and that the C7—N1 in agreement with double-bond character, the C10—O1 is 1.3040 Å, this bond is not double (keto group) and is one of the longest among similar iminium derivatives, also C7—C9 bond length is not a typical single-bond. Moreover C9—C14 ring is in agreement with the cyclohexadienide bond character. The intramolecular hydrogen bond produces S(6) motif (Bernstein et al., 1995). The amino atom N2 in the molecule at (x, y, z) acts as a hydrogen-bond donor (Table 1) to atom O1ⁱ so forming a C(9) chain running parallel to the [100] direction. Amino atom N2 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom O2ⁱⁱ so forming a C(11) chain running parallel to the [010] direction. Similarly, atom C5 in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom O2ⁱⁱⁱ so forming a C(11) chain running parallel to the [010] direction. The combination of N—H···O and C—H···O hydrogen bonds generates R₄³(30) rings parallel to the ab plane (Fig. 3).

Related literature top

For related structures, see: Patil et al. (2010); Aazam et al. (2006); Filarowski (2005); El Husseiny et al. (2008); Aazam et al. (2008); Karabıyık et al. (2008). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995).

Experimental top

A clear solution of o-phenylenediamine (0.26 g, 2.5 mmol) in 10 ml of ethanol was added to a warm solution of 8-acetyl-7-hydroxy coumarin (0.5 g, 2.5 mmol) in the same solvent (30 ml). The resulting mixture was refluxed for 2–3 h. The yellow product was precipitated, filtered off and washed with ethanol followed by diethyl ether, dried in a vacuum desiccator and crystallized from chloroform/ethanol (2:1). Single crystals were obtained by slow evaporation of dichloromethane solution of I at room temperature; Yield (75%), m.p. 480 K. Purity of the ligand was checked using TLC; (methanol: benzene, 1:4).

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 one molecule of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are indicated by dashed lines.
	Fig. 2. Zwitterionic canonical forms of I.
	Fig. 3. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded sheet built from C(9) and C(11) chains. For the sake of clarity, H atoms not involved in the motif shown have been omitted.

8-[(1E)-1-(2-Aminophenyliminio)ethyl]-2-oxo-2H-chromen-7-olate top

Crystal data top

C₁₇H₁₄N₂O₃	F(000) = 1232
M_r = 294.30	D_x = 1.365 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25561 reflections
a = 7.5462 (3) Å	θ = 2.0–26.7°
b = 18.9324 (11) Å	µ = 0.10 mm⁻¹
c = 20.0445 (9) Å	T = 296 K
V = 2863.7 (2) Å³	Prism, yellow
Z = 8	0.44 × 0.29 × 0.20 mm

Data collection top

Stoe IPDS 2 diffractometer	2868 independent reflections
Radiation source: fine-focus sealed tube	1972 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
rotation method scans	θ_max = 26.2°, θ_min = 2.0°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −9→9
T_min = 0.962, T_max = 0.984	k = −23→23
25561 measured reflections	l = −24→24

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0515P)² + ] where P = (F_o² + 2F_c²)/3
2868 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.11 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O₃	V = 2863.7 (2) Å³
M_r = 294.30	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.5462 (3) Å	µ = 0.10 mm⁻¹
b = 18.9324 (11) Å	T = 296 K
c = 20.0445 (9) Å	0.44 × 0.29 × 0.20 mm

Data collection top

Stoe IPDS 2 diffractometer	2868 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1972 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.984	R_int = 0.039
25561 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.11 e Å⁻³
2868 reflections	Δρ_min = −0.15 e Å⁻³
212 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	0.3733 (2)	0.81253 (7)	0.38471 (7)	0.0462 (4)
C2	0.5193 (2)	0.83854 (7)	0.41971 (8)	0.0487 (4)
C3	0.4876 (2)	0.89106 (8)	0.46724 (8)	0.0584 (4)
H3	0.5822	0.9095	0.4914	0.070*
C4	0.3197 (3)	0.91605 (8)	0.47909 (9)	0.0632 (5)
H4	0.3019	0.9507	0.5113	0.076*
C5	0.1777 (3)	0.89021 (9)	0.44379 (9)	0.0646 (5)
H5	0.0642	0.9073	0.4519	0.077*
C6	0.2051 (2)	0.83870 (8)	0.39613 (9)	0.0581 (4)
H6	0.1098	0.8215	0.3716	0.070*
C7	0.44310 (18)	0.69702 (7)	0.33766 (7)	0.0446 (3)
C8	0.4588 (2)	0.66606 (8)	0.40572 (8)	0.0602 (4)
H8A	0.4121	0.6987	0.4379	0.072*
H8B	0.5813	0.6569	0.4154	0.072*
H8C	0.3932	0.6227	0.4077	0.072*
C9	0.47034 (19)	0.65822 (7)	0.27529 (7)	0.0442 (3)
C10	0.4368 (2)	0.69219 (7)	0.21251 (8)	0.0491 (4)
C11	0.4623 (2)	0.65452 (8)	0.15220 (8)	0.0584 (4)
H11	0.4402	0.6767	0.1117	0.070*
C12	0.5186 (2)	0.58675 (8)	0.15284 (9)	0.0587 (4)
H12	0.5332	0.5630	0.1126	0.070*
C13	0.5555 (2)	0.55134 (7)	0.21273 (8)	0.0525 (4)
C14	0.53174 (19)	0.58766 (7)	0.27212 (8)	0.0455 (4)
C15	0.6172 (2)	0.48034 (8)	0.21610 (10)	0.0641 (5)
H15	0.6307	0.4548	0.1768	0.077*
C16	0.6561 (2)	0.44943 (8)	0.27412 (10)	0.0671 (5)
H16	0.6943	0.4027	0.2746	0.081*
C17	0.6397 (2)	0.48719 (7)	0.33552 (10)	0.0588 (4)
N1	0.39971 (17)	0.76316 (6)	0.33146 (7)	0.0488 (3)
N2	0.68956 (19)	0.81302 (8)	0.41013 (8)	0.0631 (4)
O1	0.38245 (16)	0.75749 (5)	0.20935 (6)	0.0603 (3)
O2	0.67878 (17)	0.46798 (5)	0.39135 (7)	0.0735 (4)
O3	0.57044 (14)	0.55503 (5)	0.33133 (5)	0.0541 (3)
H1	0.390 (3)	0.7742 (10)	0.2853 (8)	0.087 (6)*
H2A	0.715 (2)	0.7907 (9)	0.3703 (10)	0.071 (5)*
H2B	0.772 (3)	0.8469 (11)	0.4178 (11)	0.099 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0615 (9)	0.0363 (7)	0.0409 (9)	−0.0009 (6)	0.0025 (7)	0.0007 (6)
C2	0.0586 (9)	0.0435 (7)	0.0439 (9)	−0.0018 (7)	0.0053 (7)	−0.0002 (6)
C3	0.0700 (11)	0.0557 (8)	0.0494 (10)	−0.0061 (8)	0.0042 (8)	−0.0116 (7)
C4	0.0844 (13)	0.0537 (9)	0.0515 (10)	0.0048 (8)	0.0143 (9)	−0.0090 (7)
C5	0.0651 (10)	0.0662 (10)	0.0623 (12)	0.0133 (8)	0.0086 (9)	−0.0029 (9)
C6	0.0586 (10)	0.0577 (9)	0.0579 (11)	0.0039 (7)	−0.0008 (8)	−0.0007 (8)
C7	0.0490 (8)	0.0393 (7)	0.0454 (9)	−0.0045 (6)	−0.0014 (7)	0.0024 (6)
C8	0.0889 (12)	0.0459 (8)	0.0459 (10)	0.0056 (8)	0.0010 (9)	0.0037 (7)
C9	0.0483 (8)	0.0397 (7)	0.0446 (9)	−0.0056 (6)	−0.0026 (6)	−0.0011 (6)
C10	0.0563 (9)	0.0455 (7)	0.0454 (9)	−0.0067 (6)	−0.0048 (7)	0.0001 (6)
C11	0.0734 (11)	0.0588 (9)	0.0431 (10)	−0.0053 (8)	−0.0043 (8)	−0.0011 (7)
C12	0.0681 (10)	0.0594 (9)	0.0486 (11)	−0.0077 (8)	0.0003 (8)	−0.0134 (7)
C13	0.0544 (9)	0.0465 (8)	0.0565 (11)	−0.0054 (6)	−0.0008 (7)	−0.0097 (7)
C14	0.0474 (8)	0.0411 (7)	0.0480 (10)	−0.0076 (6)	−0.0040 (7)	0.0001 (6)
C15	0.0686 (11)	0.0489 (8)	0.0749 (13)	−0.0011 (8)	−0.0002 (10)	−0.0181 (8)
C16	0.0724 (11)	0.0416 (8)	0.0874 (15)	0.0047 (7)	−0.0082 (10)	−0.0091 (9)
C17	0.0586 (10)	0.0384 (7)	0.0795 (14)	−0.0011 (7)	−0.0101 (9)	0.0018 (8)
N1	0.0667 (8)	0.0393 (6)	0.0403 (8)	0.0007 (5)	−0.0026 (6)	−0.0012 (5)
N2	0.0562 (8)	0.0674 (9)	0.0659 (10)	−0.0034 (7)	0.0055 (8)	−0.0179 (8)
O1	0.0862 (8)	0.0476 (6)	0.0472 (7)	0.0064 (5)	−0.0074 (6)	0.0060 (5)
O2	0.0904 (9)	0.0482 (6)	0.0820 (10)	0.0054 (6)	−0.0181 (8)	0.0106 (6)
O3	0.0671 (7)	0.0391 (5)	0.0560 (7)	0.0035 (5)	−0.0068 (5)	0.0008 (5)

Geometric parameters (Å, º) top

C1—C6	1.381 (2)	C9—C10	1.436 (2)
C1—C2	1.396 (2)	C10—O1	1.3040 (17)
C1—N1	1.4327 (18)	C10—C11	1.417 (2)
C2—N2	1.386 (2)	C11—C12	1.351 (2)
C2—C3	1.398 (2)	C11—H11	0.9300
C3—C4	1.373 (2)	C12—C13	1.403 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.374 (3)	C13—C14	1.386 (2)
C4—H4	0.9300	C13—C15	1.424 (2)
C5—C6	1.381 (2)	C14—O3	1.3695 (17)
C5—H5	0.9300	C15—C16	1.334 (2)
C6—H6	0.9300	C15—H15	0.9300
C7—N1	1.3004 (17)	C16—C17	1.429 (3)
C7—C9	1.464 (2)	C16—H16	0.9300
C7—C8	1.490 (2)	C17—O2	1.213 (2)
C8—H8A	0.9600	C17—O3	1.3893 (17)
C8—H8B	0.9600	N1—H1	0.952 (15)
C8—H8C	0.9600	N2—H2A	0.92 (2)
C9—C14	1.4153 (19)	N2—H2B	0.91 (2)

C6—C1—C2	121.01 (14)	O1—C10—C9	121.51 (13)
C6—C1—N1	119.04 (14)	C11—C10—C9	119.89 (13)
C2—C1—N1	119.65 (13)	C12—C11—C10	120.84 (16)
N2—C2—C1	122.62 (14)	C12—C11—H11	119.6
N2—C2—C3	120.05 (15)	C10—C11—H11	119.6
C1—C2—C3	117.31 (14)	C11—C12—C13	121.61 (15)
C4—C3—C2	121.38 (16)	C11—C12—H12	119.2
C4—C3—H3	119.3	C13—C12—H12	119.2
C2—C3—H3	119.3	C14—C13—C12	118.17 (13)
C3—C4—C5	120.51 (15)	C14—C13—C15	118.01 (16)
C3—C4—H4	119.7	C12—C13—C15	123.82 (16)
C5—C4—H4	119.7	O3—C14—C13	119.53 (13)
C4—C5—C6	119.43 (16)	O3—C14—C9	117.17 (13)
C4—C5—H5	120.3	C13—C14—C9	123.30 (14)
C6—C5—H5	120.3	C16—C15—C13	121.81 (16)
C5—C6—C1	120.36 (16)	C16—C15—H15	119.1
C5—C6—H6	119.8	C13—C15—H15	119.1
C1—C6—H6	119.8	C15—C16—C17	120.82 (15)
N1—C7—C9	115.89 (13)	C15—C16—H16	119.6
N1—C7—C8	119.11 (13)	C17—C16—H16	119.6
C9—C7—C8	124.99 (12)	O2—C17—O3	115.12 (15)
C7—C8—H8A	109.5	O2—C17—C16	128.58 (15)
C7—C8—H8B	109.5	O3—C17—C16	116.29 (16)
H8A—C8—H8B	109.5	C7—N1—C1	126.31 (13)
C7—C8—H8C	109.5	C7—N1—H1	108.9 (11)
H8A—C8—H8C	109.5	C1—N1—H1	124.8 (11)
H8B—C8—H8C	109.5	C2—N2—H2A	118.0 (11)
C14—C9—C10	116.18 (13)	C2—N2—H2B	111.5 (13)
C14—C9—C7	123.89 (13)	H2A—N2—H2B	109.3 (17)
C10—C9—C7	119.92 (12)	C14—O3—C17	123.35 (13)
O1—C10—C11	118.60 (14)

C6—C1—C2—N2	179.24 (15)	C11—C12—C13—C15	−179.15 (16)
N1—C1—C2—N2	−7.1 (2)	C12—C13—C14—O3	−178.55 (13)
C6—C1—C2—C3	1.0 (2)	C15—C13—C14—O3	1.0 (2)
N1—C1—C2—C3	174.61 (13)	C12—C13—C14—C9	0.8 (2)
N2—C2—C3—C4	−178.25 (16)	C15—C13—C14—C9	−179.68 (14)
C1—C2—C3—C4	0.0 (2)	C10—C9—C14—O3	177.82 (12)
C2—C3—C4—C5	−0.5 (3)	C7—C9—C14—O3	−1.3 (2)
C3—C4—C5—C6	0.0 (3)	C10—C9—C14—C13	−1.5 (2)
C4—C5—C6—C1	1.0 (3)	C7—C9—C14—C13	179.41 (14)
C2—C1—C6—C5	−1.5 (2)	C14—C13—C15—C16	−1.7 (2)
N1—C1—C6—C5	−175.19 (14)	C12—C13—C15—C16	177.81 (17)
N1—C7—C9—C14	174.71 (14)	C13—C15—C16—C17	−1.0 (3)
C8—C7—C9—C14	−6.3 (2)	C15—C16—C17—O2	−175.59 (18)
N1—C7—C9—C10	−4.4 (2)	C15—C16—C17—O3	4.2 (3)
C8—C7—C9—C10	174.68 (14)	C9—C7—N1—C1	−177.28 (14)
C14—C9—C10—O1	−178.93 (14)	C8—C7—N1—C1	3.6 (2)
C7—C9—C10—O1	0.2 (2)	C6—C1—N1—C7	−112.84 (17)
C14—C9—C10—C11	1.2 (2)	C2—C1—N1—C7	73.42 (19)
C7—C9—C10—C11	−179.71 (14)	C13—C14—O3—C17	2.5 (2)
O1—C10—C11—C12	179.96 (15)	C9—C14—O3—C17	−176.83 (13)
C9—C10—C11—C12	−0.1 (2)	O2—C17—O3—C14	174.78 (14)
C10—C11—C12—C13	−0.7 (3)	C16—C17—O3—C14	−5.1 (2)
C11—C12—C13—C14	0.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.95 (2)	1.56 (2)	2.4534 (17)	155 (2)
N2—H2A···O1ⁱ	0.92 (2)	2.13 (2)	2.9933 (19)	154.7 (15)
N2—H2B···O2ⁱⁱ	0.91 (2)	2.37 (2)	3.1203 (19)	138.7 (17)
C5—H5···O2ⁱⁱⁱ	0.93	2.48	3.242 (2)	139

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₃
M_r	294.30
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	7.5462 (3), 18.9324 (11), 20.0445 (9)
V (Å³)	2863.7 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.44 × 0.29 × 0.20

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.962, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	25561, 2868, 1972
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.095, 1.00
No. of reflections	2868
No. of parameters	212
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)	0.11, −0.15

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
N1—H1···O1	0.952 (15)	1.556 (16)	2.4534 (17)	155.4 (17)
N2—H2A···O1ⁱ	0.92 (2)	2.13 (2)	2.9933 (19)	154.7 (15)
N2—H2B···O2ⁱⁱ	0.91 (2)	2.37 (2)	3.1203 (19)	138.7 (17)
C5—H5···O2ⁱⁱⁱ	0.93	2.48	3.242 (2)	139

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

Acknowledgements

The authors acknowledge King Abdulaziz University for financial support and the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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