4-(4-Nitro­phen­yl)-3-phenoxy­azetidin-2-one

Akkurt, M.; Yalçın, Ş.P.; Jarrahpour, A.A.; Nazari, M.; Büyükgüngör, O.

doi:10.1107/S1600536807038354

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4-(4-Nitrophenyl)-3-phenoxyazetidin-2-one

M. Akkurt, Ş.P. Yalçın, A. A. Jarrahpour, M. Nazari and O. Büyükgüngör

The title compound, C₁₅H₁₂N₂O₄, contains a nearly planar four-membered β-lactam ring, making dihedral angles of 67.01 (13) and 75.21 (11)° with the phenyl and the benzene rings, respectively. A single N—H

O hydrogen bond links molecules into centrosymmetric dimers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038354/bh2126sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038354/bh2126Isup2.hkl Contains datablock I

CCDC reference: 660226

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.043
wR factor = 0.116
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.77 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        900 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C9     = ...          S

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

   4 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
   1 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

β-Lactams are one of the best known and most extensively studied class of compounds due to their biological activity (Bruggink, 2001; Morin & Gorman, 1982; Katritzky et al., 1996; Georg, 1993). The β-lactam class of drugs have revolutionized treatment in medicine (Coyne et al., 2007). In the late 1970's and early 1980's, the first classes of the monocyclic β-lactam antibacterial agents were found in natural sources (Dobrowolski et al., 2004). All β-lactams are based on a β-lactam ring responsible for the antibacterial activity and variable side chains that account for the major differences in their chemical and pharmacological properties (Cha et al., 2006). Monocyclic β-lactams such as nocardicins (Kamiya et al., 1982) and monobactams (Koster et al., 1982) are of interest as they have been found to exhibit antibiotic properties. These compounds can be synthesized by various routes, although the preparation of a N-unsubstituted β-lactam is a common feature (Chan et al., 1995). Apart from their clinical interest, the use of β-lactams as versatile synthons for the preparation of compounds of biological relevance, such as α- and β-amino acids, alkaloids, heterocycles, and taxoids, has triggered a renewed interest in the building of new β-lactam systems (Alcaide et al., 2007). In solution-phase syntheses, CAN has been utilized to remove the p-methoxyphenyl group from the amide nitrogen of β-lactams to generate corresponding N-unsubstituted analogs (Fukuyama et al., 1980; Kronenthal et al., 1982; Jarrahpour & Zarei, 2006). Jarrahpour and coworkers have synthesized some sugar-based monocyclic β-lactams (Jarrahpour & Alvand, 2007). We herein report on the crystal and molecular structures of the title compound, (I).

In (I) (Fig. 1), the four-membered β-lactam ring is nearly planar, with a maximum deviation of 0.013 (1) Å for atom N1. Within the lactam ring, the bond lengths are similar to those observed in our previous studies (Pınar et al., 2006; Akkurt et al., 2006). The four-membered β-lactam ring (N1/C7/C8/C9) in (I) makes dihedral angles of 67.01 (13) and 75.21 (11)°, respectively, with the C1···C6 phenyl and the C10···C15 benzene rings.

A single N—H···O hydrogen bond (Fig. 2) links molecules into centrosymmetric dimers, forming a R₂²(8) motif (Bernstein et al., 1995).

Related literature top

For related literature, see: Akkurt et al. (2006); Alcaide et al. (2007); Bernstein et al. (1995); Bruggink (2001); Cha et al. (2006); Chan et al. (1995); Coyne et al. (2007); Dobrowolski et al. (2004); Fukuyama et al. (1980); Georg (1993); Jarrahpour & Alvand (2007); Jarrahpour & Zarei (2006); Kamiya et al. (1982); Katritzky et al. (1996); Koster et al. (1982); Kronenthal et al. (1982); Morin & Gorman (1982); Pınar et al. (2006).

Experimental top

Treatment of 1-(4-methoxyphenyl)-4-(4-nitrophenyl)-3-phenoxyazetidin-2-one with ceric ammonium nitrate (CAN) at 273 K in acetonitrile gave the title N-unsubstituted monocyclic β-lactam (Jarrahpour et al., 2006). Compound (I) was recrystallized from dichloromethane to give light yellow single crystals. The IR spectrum showed the characteristic absorption of β-lactam carbonyl at 1755 cm^-1 and the lactam NH at 3383.9 cm^-1. The ¹H NMR spectrum showed the β-lactam H-4 proton as a doublet at 5.11 p.p.m. (J = 5.50 Hz) and the H-3 proton also as a doublet at 5.71 p.p.m. (J = 5.50 Hz), NH at 6.76 p.p.m. and aromatic H protons at 6.59–8.21 p.p.m.. The ¹³C NMR spectrum exhibited the following signals: β-lactam C-4 at 55.11, β-lactam C-3 at 88.76, aromatic carbons at 114.23–158.13, and CO of β-lactam at 167.56 p.p.m.·The mass spectrum showed the molecular ion at m/e 284 and the base peak at m/e 191.

Structure description top

A single N—H···O hydrogen bond (Fig. 2) links molecules into centrosymmetric dimers, forming a R₂²(8) motif (Bernstein et al., 1995).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; 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. An ORTEP drawing of the title compound, with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. View of the packing of (I), showing the formation of centrosymmetric dimers, down the a axis in the unit cell. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

4-(4-Nitrophenyl)-3-phenoxyazetidin-2-one top

Crystal data top

C₁₅H₁₂N₂O₄	Z = 2
M_r = 284.27	F(000) = 296
Triclinic, P1	D_x = 1.383 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1548 (7) Å	Cell parameters from 3067 reflections
b = 9.8007 (11) Å	θ = 2.1–27.9°
c = 11.9296 (13) Å	µ = 0.10 mm⁻¹
α = 80.552 (9)°	T = 296 K
β = 75.167 (9)°	Prism, light yellow
γ = 82.188 (9)°	0.77 × 0.41 × 0.22 mm
V = 682.86 (14) Å³

Data collection top

Stoe IPDS2 diffractometer	2635 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2047 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.032
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ω scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.925, T_max = 0.978	l = −14→14
5874 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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0485P)² + 0.1246P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2635 reflections	Δρ_max = 0.19 e Å⁻³
195 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (4)

Crystal data top

C₁₅H₁₂N₂O₄	γ = 82.188 (9)°
M_r = 284.27	V = 682.86 (14) Å³
Triclinic, P1	Z = 2
a = 6.1548 (7) Å	Mo Kα radiation
b = 9.8007 (11) Å	µ = 0.10 mm⁻¹
c = 11.9296 (13) Å	T = 296 K
α = 80.552 (9)°	0.77 × 0.41 × 0.22 mm
β = 75.167 (9)°

Data collection top

Stoe IPDS2 diffractometer	2635 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2047 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.978	R_int = 0.032
5874 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.19 e Å⁻³
2635 reflections	Δρ_min = −0.24 e Å⁻³
195 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.43673 (18)	0.16127 (12)	0.32486 (10)	0.0569 (4)
O2	0.31243 (19)	−0.00746 (14)	0.15344 (12)	0.0669 (5)
O3	1.0921 (4)	0.7129 (2)	0.1750 (2)	0.1277 (10)
O4	0.7998 (4)	0.78343 (17)	0.11047 (19)	0.1150 (9)
N1	0.6469 (2)	0.09919 (15)	0.07432 (14)	0.0586 (5)
N2	0.9265 (4)	0.69132 (18)	0.14639 (16)	0.0798 (7)
C1	0.5052 (3)	0.19644 (19)	0.41665 (15)	0.0587 (6)
C2	0.6992 (4)	0.1401 (2)	0.44995 (19)	0.0765 (8)
C3	0.7471 (5)	0.1856 (3)	0.5453 (2)	0.1007 (11)
C4	0.6077 (7)	0.2836 (4)	0.6032 (2)	0.1137 (13)
C5	0.4185 (6)	0.3397 (3)	0.5681 (2)	0.1074 (13)
C6	0.3640 (4)	0.2961 (2)	0.47587 (18)	0.0797 (8)
C7	0.5801 (3)	0.06734 (16)	0.25548 (15)	0.0529 (5)
C8	0.4792 (3)	0.04325 (17)	0.15693 (16)	0.0540 (5)
C9	0.7757 (3)	0.12692 (17)	0.15498 (15)	0.0529 (5)
C10	0.8109 (2)	0.27613 (16)	0.15189 (14)	0.0467 (5)
C11	0.9911 (3)	0.30699 (18)	0.19038 (16)	0.0548 (5)
C12	1.0272 (3)	0.44190 (18)	0.19040 (16)	0.0587 (6)
C13	0.8818 (3)	0.54697 (17)	0.15168 (14)	0.0551 (5)
C14	0.6991 (3)	0.52079 (18)	0.11567 (15)	0.0598 (6)
C15	0.6654 (3)	0.38471 (17)	0.11566 (15)	0.0549 (6)
H1	0.684 (3)	0.091 (2)	−0.0023 (19)	0.075 (6)*
H2	0.79660	0.07320	0.41010	0.0920*
H3	0.87740	0.14780	0.56940	0.1210*
H4	0.64140	0.31240	0.66680	0.1360*
H5	0.32430	0.40860	0.60680	0.1290*
H6	0.23200	0.33390	0.45360	0.0960*
H7	0.62810	−0.01890	0.30100	0.0630*
H9	0.91710	0.06610	0.14960	0.0640*
H11	1.08870	0.23500	0.21660	0.0660*
H12	1.14830	0.46180	0.21620	0.0700*
H14	0.60000	0.59340	0.09170	0.0720*
H15	0.54260	0.36560	0.09090	0.0660*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0555 (6)	0.0631 (7)	0.0574 (7)	−0.0073 (5)	−0.0158 (5)	−0.0182 (5)
O2	0.0579 (7)	0.0690 (8)	0.0845 (9)	−0.0143 (6)	−0.0215 (6)	−0.0274 (7)
O3	0.1617 (18)	0.0836 (12)	0.166 (2)	−0.0607 (12)	−0.0640 (16)	−0.0180 (12)
O4	0.1542 (17)	0.0467 (9)	0.1371 (17)	0.0001 (10)	−0.0286 (13)	−0.0104 (9)
N1	0.0623 (8)	0.0590 (9)	0.0615 (9)	−0.0137 (7)	−0.0132 (7)	−0.0248 (7)
N2	0.1102 (14)	0.0526 (10)	0.0743 (11)	−0.0222 (10)	−0.0060 (10)	−0.0157 (8)
C1	0.0706 (10)	0.0604 (10)	0.0480 (9)	−0.0262 (8)	−0.0115 (8)	−0.0039 (7)
C2	0.0866 (13)	0.0816 (14)	0.0718 (13)	−0.0252 (11)	−0.0342 (11)	−0.0021 (10)
C3	0.124 (2)	0.113 (2)	0.0853 (17)	−0.0509 (17)	−0.0543 (16)	0.0080 (15)
C4	0.177 (3)	0.121 (2)	0.0630 (15)	−0.071 (2)	−0.0369 (18)	−0.0102 (15)
C5	0.154 (3)	0.107 (2)	0.0636 (14)	−0.0338 (19)	−0.0079 (16)	−0.0303 (14)
C6	0.0971 (15)	0.0826 (14)	0.0591 (12)	−0.0178 (11)	−0.0053 (10)	−0.0225 (10)
C7	0.0549 (9)	0.0428 (8)	0.0668 (11)	−0.0061 (7)	−0.0212 (8)	−0.0124 (7)
C8	0.0528 (8)	0.0444 (8)	0.0711 (11)	−0.0040 (7)	−0.0185 (8)	−0.0210 (7)
C9	0.0474 (8)	0.0475 (9)	0.0691 (11)	−0.0023 (7)	−0.0169 (7)	−0.0199 (8)
C10	0.0433 (7)	0.0473 (8)	0.0512 (9)	−0.0043 (6)	−0.0088 (6)	−0.0156 (7)
C11	0.0444 (8)	0.0517 (9)	0.0726 (11)	−0.0020 (7)	−0.0184 (7)	−0.0158 (8)
C12	0.0522 (9)	0.0596 (10)	0.0701 (11)	−0.0150 (8)	−0.0137 (8)	−0.0190 (9)
C13	0.0673 (10)	0.0476 (9)	0.0493 (9)	−0.0132 (7)	−0.0035 (7)	−0.0140 (7)
C14	0.0720 (11)	0.0496 (9)	0.0580 (10)	0.0049 (8)	−0.0202 (8)	−0.0094 (7)
C15	0.0555 (9)	0.0563 (10)	0.0590 (10)	−0.0020 (7)	−0.0223 (7)	−0.0149 (8)

Geometric parameters (Å, º) top

O1—C1	1.377 (2)	C10—C15	1.382 (2)
O1—C7	1.402 (2)	C10—C11	1.389 (2)
O2—C8	1.212 (2)	C11—C12	1.370 (3)
O3—N2	1.209 (4)	C12—C13	1.371 (3)
O4—N2	1.208 (3)	C13—C14	1.370 (3)
N1—C8	1.339 (2)	C14—C15	1.377 (2)
N1—C9	1.471 (2)	C2—H2	0.9300
N2—C13	1.466 (3)	C3—H3	0.9300
N1—H1	0.90 (2)	C4—H4	0.9300
C1—C6	1.375 (3)	C5—H5	0.9300
C1—C2	1.371 (3)	C6—H6	0.9300
C2—C3	1.398 (3)	C7—H7	0.9800
C3—C4	1.351 (5)	C9—H9	0.9800
C4—C5	1.354 (5)	C11—H11	0.9300
C5—C6	1.374 (4)	C12—H12	0.9300
C7—C8	1.526 (3)	C14—H14	0.9300
C7—C9	1.565 (3)	C15—H15	0.9300
C9—C10	1.500 (2)

O1···O2	3.1236 (18)	C12···C14^vii	3.589 (3)
O1···N1	3.063 (2)	C14···C12^vii	3.589 (3)
O1···C15	3.202 (2)	C15···O1	3.202 (2)
O2···C9ⁱ	3.383 (2)	C2···H7	2.7000
O2···O1	3.1236 (18)	C3···H7^ix	3.0400
O2···O3ⁱⁱ	3.165 (3)	C4···H7^ix	3.0600
O2···N1ⁱⁱⁱ	2.940 (2)	C7···H2	2.5500
O3···O2^iv	3.165 (3)	C8···H1ⁱⁱⁱ	2.87 (2)
O4···C8^v	3.037 (3)	C8···H11ⁱ	2.8500
O4···N1^v	3.103 (2)	C9···H2	3.0400
O1···H11ⁱ	2.7300	C13···H5^x	2.9100
O2···H9ⁱ	2.4500	H1···O2ⁱⁱⁱ	2.09 (2)
O2···H11ⁱ	2.7000	H1···O3^vii	2.79 (2)
O2···H1ⁱⁱⁱ	2.09 (2)	H1···C8ⁱⁱⁱ	2.87 (2)
O3···H4^vi	2.7600	H2···C7	2.5500
O3···H12	2.4200	H2···C9	3.0400
O3···H1^vii	2.79 (2)	H2···H7	2.2200
O4···H14	2.4400	H4···O3^vi	2.7600
N1···O1	3.063 (2)	H5···C13^x	2.9100
N1···O4^viii	3.103 (2)	H7···C2	2.7000
N1···O2ⁱⁱⁱ	2.940 (2)	H7···H2	2.2200
N1···H15	2.6300	H7···C3^ix	3.0400
C1···C10	3.267 (2)	H7···C4^ix	3.0600
C2···C9	3.450 (3)	H9···O2^xi	2.4500
C2···C10	3.512 (3)	H9···H11	2.4200
C2···C11	3.432 (3)	H11···O1^xi	2.7300
C3···C7^ix	3.581 (3)	H11···O2^xi	2.7000
C5···C5^x	3.445 (4)	H11···C8^xi	2.8500
C7···C3^ix	3.581 (3)	H11···H9	2.4200
C8···O4^viii	3.037 (3)	H12···O3	2.4200
C9···C2	3.450 (3)	H14···O4	2.4400
C9···O2^xi	3.383 (2)	H14···H15^xii	2.5000
C10···C2	3.512 (3)	H15···N1	2.6300
C10···C1	3.267 (2)	H15···H14^xii	2.5000
C11···C2	3.432 (3)

C1—O1—C7	118.37 (14)	N2—C13—C14	119.22 (17)
C8—N1—C9	96.21 (14)	N2—C13—C12	118.87 (18)
O3—N2—O4	122.8 (2)	C12—C13—C14	121.90 (16)
O3—N2—C13	118.55 (19)	C13—C14—C15	118.61 (17)
O4—N2—C13	118.6 (2)	C10—C15—C14	121.12 (17)
C9—N1—H1	133.2 (13)	C1—C2—H2	121.00
C8—N1—H1	127.4 (13)	C3—C2—H2	121.00
O1—C1—C6	115.25 (17)	C2—C3—H3	119.00
O1—C1—C2	124.64 (17)	C4—C3—H3	119.00
C2—C1—C6	120.10 (18)	C3—C4—H4	120.00
C1—C2—C3	118.4 (2)	C5—C4—H4	120.00
C2—C3—C4	121.3 (3)	C4—C5—H5	120.00
C3—C4—C5	119.6 (3)	C6—C5—H5	120.00
C4—C5—C6	120.8 (3)	C1—C6—H6	120.00
C1—C6—C5	119.8 (2)	C5—C6—H6	120.00
O1—C7—C8	111.02 (15)	O1—C7—H7	113.00
O1—C7—C9	117.47 (13)	C8—C7—H7	113.00
C8—C7—C9	85.24 (13)	C9—C7—H7	113.00
O2—C8—N1	133.27 (18)	N1—C9—H9	112.00
N1—C8—C7	92.45 (14)	C7—C9—H9	112.00
O2—C8—C7	134.29 (17)	C10—C9—H9	112.00
N1—C9—C10	116.21 (14)	C10—C11—H11	120.00
C7—C9—C10	116.46 (14)	C12—C11—H11	119.00
N1—C9—C7	86.05 (13)	C11—C12—H12	121.00
C11—C10—C15	118.48 (15)	C13—C12—H12	121.00
C9—C10—C11	119.25 (14)	C13—C14—H14	121.00
C9—C10—C15	122.23 (14)	C15—C14—H14	121.00
C10—C11—C12	121.01 (17)	C10—C15—H15	119.00
C11—C12—C13	118.85 (18)	C14—C15—H15	119.00

C7—O1—C1—C2	−3.9 (3)	C8—C7—C9—N1	1.65 (12)
C7—O1—C1—C6	175.69 (16)	C8—C7—C9—C10	119.04 (15)
C1—O1—C7—C8	−178.78 (14)	O1—C7—C8—N1	115.82 (15)
C1—O1—C7—C9	−83.06 (19)	O1—C7—C9—C10	7.8 (2)
C9—N1—C8—O2	−177.7 (2)	C9—C7—C8—O2	177.9 (2)
C8—N1—C9—C10	−119.51 (16)	C9—C7—C8—N1	−1.81 (13)
C9—N1—C8—C7	1.93 (14)	O1—C7—C9—N1	−109.59 (16)
C8—N1—C9—C7	−1.89 (13)	N1—C9—C10—C15	25.4 (2)
O3—N2—C13—C12	0.9 (3)	C7—C9—C10—C11	104.01 (19)
O4—N2—C13—C14	0.2 (3)	C7—C9—C10—C15	−73.7 (2)
O4—N2—C13—C12	178.9 (2)	N1—C9—C10—C11	−156.84 (16)
O3—N2—C13—C14	−177.8 (2)	C9—C10—C11—C12	−179.13 (16)
O1—C1—C6—C5	−179.2 (2)	C15—C10—C11—C12	−1.3 (3)
C6—C1—C2—C3	0.6 (3)	C9—C10—C15—C14	178.79 (16)
O1—C1—C2—C3	−179.8 (2)	C11—C10—C15—C14	1.0 (3)
C2—C1—C6—C5	0.4 (3)	C10—C11—C12—C13	0.0 (3)
C1—C2—C3—C4	−0.6 (4)	C11—C12—C13—N2	−177.11 (17)
C2—C3—C4—C5	−0.4 (5)	C11—C12—C13—C14	1.5 (3)
C3—C4—C5—C6	1.4 (5)	N2—C13—C14—C15	176.84 (16)
C4—C5—C6—C1	−1.4 (4)	C12—C13—C14—C15	−1.8 (3)
O1—C7—C8—O2	−64.5 (2)	C13—C14—C15—C10	0.5 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱⁱⁱ	0.90 (2)	2.09 (2)	2.940 (2)	156.9 (18)
C9—H9···O2^xi	0.98	2.45	3.383 (2)	159

Symmetry codes: (iii) −x+1, −y, −z; (xi) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O₄
M_r	284.27
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.1548 (7), 9.8007 (11), 11.9296 (13)
α, β, γ (°)	80.552 (9), 75.167 (9), 82.188 (9)
V (Å³)	682.86 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.77 × 0.41 × 0.22

Data collection
Diffractometer	Stoe IPDS2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.925, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	5874, 2635, 2047
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.116, 1.03
No. of reflections	2635
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), 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···O2ⁱ	0.90 (2)	2.09 (2)	2.940 (2)	156.9 (18)
C9—H9···O2ⁱⁱ	0.98	2.45	3.383 (2)	159

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

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