2-(6-Oxo-3,4-diphenyl-1,6-dihydro­pyridazin-1-yl)acetic acid

Aydın, A.; Doğruer, D.S.; Akkurt, M.; Büyükgüngör, O.

doi:10.1107/S1600536807053172

2-(6-Oxo-3,4-diphenyl-1,6-dihydropyridazin-1-yl)acetic acid

A. Aydın, D. S. Doğruer, M. Akkurt and O. Büyükgüngör

In the title compound, C₁₈H₁₄N₂O₃, the pyridazine ring makes dihedral angles of 72.73 (11) and 49.97 (10)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 52.42 (12)°. The crystal structure is stabilized by intermolecular O—H

O and C—H

O hydrogen-bonding interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053172/hg2323sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053172/hg2323Isup2.hkl Contains datablock I

CCDC reference: 672800

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R factor = 0.055
wR factor = 0.150
Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTY03_ALERT_1_C  The _exptl_absorpt_correction_type has been given as none.
            However values have been given for Tmin and Tmax. Remove
            these if an absorption correction has not been applied.
  From the CIF: _exptl_absorpt_correction_T_min   0.965
  From the CIF: _exptl_absorpt_correction_T_max   0.968
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.101
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

2-[5,6-Diphenyl-3(2H)-pyridazinone-2-yl]acetic acid was used as starting material to synthesize 2-[5,6-Diphenyl-3(2H)-pyridazinone-2-yl]acetamide derivatives with analgesic and anti-Inflammatory effects. This compound was synthesized for first time by (Doğruer et al., 2007).

All bond lengths and angles in the title compound (I) (Fig. 1) are normal (Allen et al., 1987). The bond lengths for C2═C3, 1.359 (3) Å, C4═N2, 1.306 (3) Å, N1—N2, 1.359 (2) Å and C1═O1, 1.251 (2) Å are comparable with published values for other pyridazinones (Moreau et al., 1995; Prout et al., 1994). In (I), the pyridazine ring (C1–C4/N1/N2) makes dihedral angles of 72.73 (11)° and 49.97 (10)° with two phenyl rings (C5–C10) and (C11—C16), respectively. The dihedral angle between two phenyl rings is 52.42 (12)°.

The quantum-chemical calculation, using the CNDO (Pople et al., 1970) aproximation showed that the charges at atoms C1, C4, C18, N1, N2, O1, O2 and O3 are 0.331, 0.109, 0.403, -0.127, -0.094, -0.367, -0.312 and -0.268 e^-, respectively. The spatial view of the calculated molecule is shown in Fig. 2. The HOMO and LUMO energy levels are -10.4162 and 0.8511 eV, respectively. The calculated molecule dipole moment of (I) is 3.795 Debye (1 D = 3.33564 × 10–30 Cm). Due to the lack of the strong intermolecular interactions in the crystal structure of (I), the theoretical CNDO and experimental X-rays values of the geometric parameters in (I) are almost comparable within the experimental error interval.

The crystal structure of (I) is stabilized by intermolecular O—H···O and C—H···O hydrogen bonding interactions (Table 1, Fig. 3).

Related literature top

For related literature, see: Allen et al. (1987); Doğruer et al. (2007); Moreau et al. (1995); Pople & Beveridge (1970); Prout et al. (1994).

Experimental top

0.01 mol of ethyl 2-[5,6-Diphenyl-3(2H)-pyridazinone-2-yl]acetate in 100 ml 10% NaOH was hydrolyzed for 4 h. After cooling to 278 K, the reaction mixture was acidified 20% HCl. The precipitate was filtered, washed with water to neutral pH and dried and crystallized from 2-propanol (m.p. 491 K, yield 80%), IR v_max(cm^-1) (KBr): 3100–2100 (OH), 1725 (CO acid), 1627 (CO amide) (Doğruer et al., 2007).

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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. ORTEP-3 drawings of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The spatial view of the title molecule calculated by the CNDO approximation.
	Fig. 3. View of the hydrogen bonding interactions (dash lines) of the title compound in the unit cell. H atoms not involved in hydrogen bonding interactions have been omitted for clarity.

2-(6-Oxo-3,4-diphenyl-1,6-dihydropyridazin-1-yl)acetic acid top

Crystal data top

C₁₈H₁₄N₂O₃	F(000) = 640
M_r = 306.31	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 37146 reflections
a = 10.3646 (11) Å	θ = 2.0–28.0°
b = 10.3410 (9) Å	µ = 0.09 mm⁻¹
c = 15.5884 (17) Å	T = 296 K
β = 109.721 (8)°	Prism, colourless
V = 1572.8 (3) Å³	0.40 × 0.38 × 0.37 mm
Z = 4

Data collection top

Stoe IPDS-2 diffractometer	2225 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	R_int = 0.101
Plane graphite monochromator	θ_max = 27.8°, θ_min = 2.1°
Detector resolution: 6.67 pixels mm^-1	h = −13→13
ω scans	k = −13→13
21463 measured reflections	l = −20→20
3658 independent 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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.0634P)² + 0.0964P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3658 reflections	Δρ_max = 0.19 e Å⁻³
209 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

Crystal data top

C₁₈H₁₄N₂O₃	V = 1572.8 (3) Å³
M_r = 306.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3646 (11) Å	µ = 0.09 mm⁻¹
b = 10.3410 (9) Å	T = 296 K
c = 15.5884 (17) Å	0.40 × 0.38 × 0.37 mm
β = 109.721 (8)°

Data collection top

Stoe IPDS-2 diffractometer	2225 reflections with I > 2σ(I)
21463 measured reflections	R_int = 0.101
3658 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
3658 reflections	Δρ_min = −0.16 e Å⁻³
209 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.94042 (12)	0.14434 (14)	0.76943 (10)	0.0709 (5)
O2	0.92925 (14)	−0.17253 (16)	0.77544 (10)	0.0781 (5)
O3	1.08356 (16)	−0.13826 (18)	0.91244 (11)	0.0929 (6)
N1	0.77229 (14)	0.02608 (16)	0.79118 (11)	0.0570 (5)
N2	0.64208 (15)	−0.01944 (16)	0.76872 (11)	0.0599 (5)
C1	0.81545 (17)	0.11781 (19)	0.74420 (13)	0.0575 (6)
C2	0.71116 (18)	0.17567 (19)	0.66976 (13)	0.0590 (6)
C3	0.57856 (17)	0.13681 (18)	0.64688 (12)	0.0533 (6)
C4	0.54875 (17)	0.03339 (19)	0.69902 (13)	0.0544 (6)
C5	0.40883 (18)	−0.0228 (2)	0.67529 (14)	0.0606 (7)
C6	0.3823 (2)	−0.1430 (2)	0.63435 (16)	0.0743 (8)
C7	0.2494 (3)	−0.1894 (3)	0.60170 (19)	0.0942 (10)
C8	0.1447 (3)	−0.1187 (4)	0.6128 (2)	0.1068 (13)
C9	0.1710 (2)	−0.0024 (4)	0.6561 (2)	0.1076 (15)
C10	0.3029 (2)	0.0472 (3)	0.68677 (19)	0.0836 (9)
C11	0.46957 (17)	0.20112 (19)	0.57093 (13)	0.0545 (6)
C12	0.37528 (19)	0.1305 (2)	0.50165 (13)	0.0658 (7)
C13	0.2768 (2)	0.1926 (3)	0.43160 (16)	0.0779 (9)
C14	0.2698 (2)	0.3255 (3)	0.42961 (17)	0.0814 (9)
C15	0.3612 (2)	0.3964 (2)	0.49734 (17)	0.0764 (8)
C16	0.46225 (19)	0.3345 (2)	0.56787 (15)	0.0657 (7)
C17	0.8709 (2)	−0.0297 (2)	0.87331 (14)	0.0654 (7)
C18	0.97349 (19)	−0.1186 (2)	0.85540 (14)	0.0619 (7)
H2	0.73400	0.24090	0.63640	0.0710*
H2A	0.98900	−0.21990	0.76920	0.1170*
H6	0.45380	−0.19270	0.62870	0.0890*
H7	0.23120	−0.26890	0.57210	0.1130*
H8	0.05540	−0.15010	0.59070	0.1280*
H9	0.09990	0.04410	0.66520	0.1290*
H10	0.31980	0.12760	0.71500	0.1000*
H12	0.37890	0.04060	0.50280	0.0790*
H13	0.21480	0.14460	0.38540	0.0940*
H14	0.20290	0.36710	0.38230	0.0980*
H15	0.35570	0.48620	0.49620	0.0920*
H16	0.52510	0.38310	0.61310	0.0790*
H17A	0.82130	−0.07720	0.90590	0.0790*
H17B	0.91970	0.04000	0.91250	0.0790*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0406 (7)	0.0780 (9)	0.0799 (10)	−0.0027 (6)	0.0016 (6)	0.0080 (7)
O2	0.0593 (8)	0.0896 (11)	0.0671 (9)	0.0188 (7)	−0.0026 (7)	−0.0126 (8)
O3	0.0646 (9)	0.1135 (13)	0.0735 (10)	0.0284 (9)	−0.0123 (8)	−0.0078 (9)
N1	0.0416 (7)	0.0679 (10)	0.0542 (9)	0.0041 (6)	0.0065 (7)	0.0057 (7)
N2	0.0473 (8)	0.0704 (10)	0.0580 (9)	0.0011 (7)	0.0124 (7)	0.0059 (8)
C1	0.0432 (9)	0.0610 (11)	0.0609 (11)	0.0004 (8)	0.0078 (8)	−0.0009 (9)
C2	0.0450 (9)	0.0654 (12)	0.0595 (11)	−0.0005 (8)	0.0083 (9)	0.0074 (9)
C3	0.0427 (9)	0.0615 (11)	0.0513 (10)	0.0020 (7)	0.0102 (8)	−0.0003 (8)
C4	0.0430 (9)	0.0651 (12)	0.0515 (10)	0.0026 (7)	0.0111 (8)	0.0013 (8)
C5	0.0475 (10)	0.0738 (13)	0.0567 (11)	−0.0050 (9)	0.0126 (9)	0.0052 (9)
C6	0.0679 (13)	0.0788 (15)	0.0744 (14)	−0.0130 (11)	0.0218 (11)	0.0034 (12)
C7	0.0831 (17)	0.1003 (19)	0.0899 (18)	−0.0398 (15)	0.0171 (15)	0.0045 (15)
C8	0.0551 (14)	0.134 (3)	0.118 (2)	−0.0281 (16)	0.0119 (15)	0.027 (2)
C9	0.0529 (13)	0.129 (3)	0.144 (3)	−0.0006 (15)	0.0375 (16)	0.013 (2)
C10	0.0563 (12)	0.0979 (18)	0.0993 (18)	−0.0012 (11)	0.0300 (13)	−0.0025 (14)
C11	0.0402 (8)	0.0671 (12)	0.0531 (10)	0.0029 (8)	0.0117 (8)	0.0041 (9)
C12	0.0498 (10)	0.0822 (14)	0.0553 (11)	0.0011 (9)	0.0046 (9)	0.0010 (10)
C13	0.0549 (11)	0.1049 (19)	0.0602 (13)	0.0027 (11)	0.0013 (10)	0.0049 (12)
C14	0.0530 (11)	0.113 (2)	0.0688 (14)	0.0168 (12)	0.0081 (11)	0.0239 (14)
C15	0.0608 (12)	0.0790 (15)	0.0858 (16)	0.0142 (10)	0.0199 (12)	0.0218 (12)
C16	0.0504 (10)	0.0720 (13)	0.0681 (13)	0.0019 (9)	0.0113 (10)	0.0069 (10)
C17	0.0551 (11)	0.0790 (14)	0.0524 (11)	0.0101 (9)	0.0053 (9)	0.0082 (10)
C18	0.0489 (10)	0.0696 (13)	0.0565 (11)	0.0043 (9)	0.0037 (9)	0.0053 (9)

Geometric parameters (Å, º) top

O1—C1	1.251 (2)	C11—C12	1.394 (3)
O2—C18	1.300 (3)	C12—C13	1.376 (3)
O3—C18	1.204 (3)	C13—C14	1.376 (4)
O2—H2A	0.8200	C14—C15	1.369 (4)
N1—C1	1.363 (3)	C15—C16	1.392 (3)
N1—C17	1.461 (3)	C17—C18	1.501 (3)
N1—N2	1.359 (2)	C2—H2	0.9300
N2—C4	1.306 (3)	C6—H6	0.9300
C1—C2	1.424 (3)	C7—H7	0.9300
C2—C3	1.359 (3)	C8—H8	0.9300
C3—C4	1.439 (3)	C9—H9	0.9300
C3—C11	1.489 (3)	C10—H10	0.9300
C4—C5	1.489 (3)	C12—H12	0.9300
C5—C10	1.376 (3)	C13—H13	0.9300
C5—C6	1.382 (3)	C14—H14	0.9300
C6—C7	1.383 (4)	C15—H15	0.9300
C7—C8	1.367 (5)	C16—H16	0.9300
C8—C9	1.361 (6)	C17—H17A	0.9700
C9—C10	1.386 (4)	C17—H17B	0.9700
C11—C16	1.381 (3)

O1···C18	3.000 (3)	C12···C10	3.331 (3)
O1···C8ⁱ	3.354 (4)	C13···O2^iv	3.220 (3)
O1···O2ⁱⁱ	2.557 (2)	C15···C15^x	3.566 (3)
O2···O1ⁱⁱⁱ	2.557 (2)	C16···N2ⁱ	3.435 (3)
O2···C1	3.202 (3)	C18···O1	3.000 (3)
O2···N1	2.682 (2)	C1···H2Aⁱⁱ	2.6900
O2···C13^iv	3.220 (3)	C2···H16	2.8200
O3···C7^v	3.378 (3)	C4···H12	2.9700
O1···H2Aⁱⁱ	1.7800	C5···H12	2.6800
O1···H9^vi	2.8700	C6···H12	2.7900
O1···H17B	2.5500	C15···H17Aⁱ	2.8000
O1···H14^vii	2.7000	C16···H15^x	3.0400
O2···H13^iv	2.4600	C16···H2	2.8200
O3···H2ⁱⁱⁱ	2.5900	H2···C16	2.8200
O3···H7^v	2.6200	H2···H16	2.5400
N1···O2	2.682 (2)	H2···O3ⁱⁱ	2.5900
N1···C7ⁱ	3.428 (3)	H2A···O1ⁱⁱⁱ	1.7800
N2···C16^viii	3.435 (3)	H2A···C1ⁱⁱⁱ	2.6900
C1···O2	3.202 (3)	H7···H17B^viii	2.5800
C1···C7ⁱ	3.360 (4)	H7···O3^ix	2.6200
C1···C8ⁱ	3.456 (4)	H9···O1^xi	2.8700
C5···C12	3.054 (3)	H12···C4	2.9700
C6···C12	3.490 (3)	H12···C5	2.6800
C7···C1^viii	3.360 (4)	H12···C6	2.7900
C7···N1^viii	3.428 (3)	H13···O2^iv	2.4600
C7···O3^ix	3.378 (3)	H14···O1^xii	2.7000
C8···C1^viii	3.456 (4)	H15···C16^x	3.0400
C8···O1^viii	3.354 (4)	H16···C2	2.8200
C10···C12	3.331 (3)	H16···H2	2.5400
C10···C11	3.299 (3)	H17A···C15^viii	2.8000
C11···C10	3.299 (3)	H17B···O1	2.5500
C12···C6	3.490 (3)	H17B···H7ⁱ	2.5800
C12···C5	3.054 (3)

C18—O2—H2A	109.00	N1—C17—C18	114.13 (17)
N2—N1—C17	115.43 (16)	O2—C18—C17	113.47 (18)
C1—N1—C17	119.11 (16)	O3—C18—C17	121.35 (19)
N2—N1—C1	125.46 (16)	O2—C18—O3	125.2 (2)
N1—N2—C4	117.51 (16)	C1—C2—H2	120.00
O1—C1—C2	125.81 (18)	C3—C2—H2	120.00
N1—C1—C2	115.72 (17)	C5—C6—H6	120.00
O1—C1—N1	118.47 (17)	C7—C6—H6	120.00
C1—C2—C3	120.81 (18)	C6—C7—H7	120.00
C2—C3—C4	117.55 (17)	C8—C7—H7	120.00
C4—C3—C11	122.09 (17)	C7—C8—H8	120.00
C2—C3—C11	120.35 (17)	C9—C8—H8	120.00
N2—C4—C3	122.76 (17)	C8—C9—H9	120.00
C3—C4—C5	121.79 (17)	C10—C9—H9	120.00
N2—C4—C5	115.44 (17)	C5—C10—H10	120.00
C4—C5—C6	119.42 (18)	C9—C10—H10	120.00
C4—C5—C10	121.0 (2)	C11—C12—H12	120.00
C6—C5—C10	119.3 (2)	C13—C12—H12	120.00
C5—C6—C7	120.0 (2)	C12—C13—H13	120.00
C6—C7—C8	120.2 (3)	C14—C13—H13	120.00
C7—C8—C9	120.1 (3)	C13—C14—H14	120.00
C8—C9—C10	120.5 (3)	C15—C14—H14	120.00
C5—C10—C9	119.9 (3)	C14—C15—H15	120.00
C3—C11—C12	121.84 (18)	C16—C15—H15	120.00
C3—C11—C16	119.44 (18)	C11—C16—H16	120.00
C12—C11—C16	118.72 (18)	C15—C16—H16	120.00
C11—C12—C13	120.6 (2)	N1—C17—H17A	109.00
C12—C13—C14	120.2 (2)	N1—C17—H17B	109.00
C13—C14—C15	120.0 (2)	C18—C17—H17A	109.00
C14—C15—C16	120.2 (2)	C18—C17—H17B	109.00
C11—C16—C15	120.28 (19)	H17A—C17—H17B	108.00

C1—N1—N2—C4	−3.7 (3)	N2—C4—C5—C10	112.0 (2)
C17—N1—N2—C4	175.89 (17)	N2—C4—C5—C6	−73.2 (3)
N2—N1—C1—O1	−175.38 (17)	C3—C4—C5—C6	105.4 (2)
C17—N1—C1—O1	5.1 (3)	C3—C4—C5—C10	−69.4 (3)
N2—N1—C1—C2	4.9 (3)	C4—C5—C6—C7	−172.0 (2)
C17—N1—C1—C2	−174.62 (17)	C6—C5—C10—C9	−1.0 (4)
N2—N1—C17—C18	109.0 (2)	C4—C5—C10—C9	173.8 (2)
C1—N1—C17—C18	−71.4 (2)	C10—C5—C6—C7	2.9 (4)
N1—N2—C4—C3	−0.6 (3)	C5—C6—C7—C8	−2.4 (4)
N1—N2—C4—C5	178.03 (16)	C6—C7—C8—C9	0.0 (5)
N1—C1—C2—C3	−2.0 (3)	C7—C8—C9—C10	2.0 (5)
O1—C1—C2—C3	178.26 (19)	C8—C9—C10—C5	−1.5 (5)
C1—C2—C3—C4	−1.6 (3)	C3—C11—C12—C13	−179.09 (19)
C1—C2—C3—C11	177.87 (17)	C12—C11—C16—C15	0.8 (3)
C11—C3—C4—C5	5.1 (3)	C16—C11—C12—C13	0.0 (3)
C2—C3—C11—C12	130.3 (2)	C3—C11—C16—C15	179.9 (2)
C4—C3—C11—C12	−50.3 (3)	C11—C12—C13—C14	−0.5 (3)
C4—C3—C11—C16	130.7 (2)	C12—C13—C14—C15	0.2 (3)
C2—C3—C11—C16	−48.7 (3)	C13—C14—C15—C16	0.6 (4)
C11—C3—C4—N2	−176.41 (18)	C14—C15—C16—C11	−1.2 (3)
C2—C3—C4—N2	3.0 (3)	N1—C17—C18—O2	−26.4 (3)
C2—C3—C4—C5	−175.47 (18)	N1—C17—C18—O3	155.6 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+1, −y, −z+1; (v) x+1, −y−1/2, z+1/2; (vi) x+1, y, z; (vii) x+1, −y+1/2, z+1/2; (viii) −x+1, y−1/2, −z+3/2; (ix) x−1, −y−1/2, z−1/2; (x) −x+1, −y+1, −z+1; (xi) x−1, y, z; (xii) x−1, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱⁱⁱ	0.82	1.78	2.557 (2)	157
C2—H2···O3ⁱⁱ	0.93	2.59	3.422 (3)	150
C13—H13···O2^iv	0.93	2.46	3.220 (3)	138

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₂O₃
M_r	306.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.3646 (11), 10.3410 (9), 15.5884 (17)
β (°)	109.721 (8)
V (Å³)	1572.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.38 × 0.37

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21463, 3658, 2225
R_int	0.101
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.151, 1.04
No. of reflections	3658
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).