4-(4-Methoxy-phen-yl)-3-methyl-1,6-di-oxa-2,8-diaza-s-indacen-5(7H)-one.

In the mol-ecule of the title compound, C(16)H(12)N(2)O(4), the pyridine ring is oriented at the same dihedral angle of 2.92 (3)° with respect to the furan and isoxazole rings, while the dihedral angle between furan and isoxazole rings is 1.34 (3)°. The dihedral angle between the benzene and pyridine rings is 53.23 (3)°. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules into chains. Weak π-π contacts between isoxazole and benzene rings [centroid-centroid distance = 3.969 (3) Å] may further stabilize the structure.

Related literature

For general background to isoxazoles, see: Pinho & Teresa (2005 ▶); Shin et al. (2005 ▶); Tatee et al. (1987 ▶). For a related structure, see: Chande et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H12N2O4

M = 296.28

Monoclinic,

a = 13.8513 (16) Å

b = 7.6116 (11) Å

c = 12.6732 (15) Å

β = 95.592 (1)°

V = 1329.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.14 × 0.11 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.985, T max = 0.995

6625 measured reflections

2333 independent reflections

1267 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.093

S = 1.03

2333 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013373/hk2664sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013373/hk2664Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H12N2O4	F(000) = 616
Mr = 296.28	Dx = 1.480 Mg m−3
Monoclinic, P21/c	Melting point = 504–506 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.8513 (16) Å	Cell parameters from 1263 reflections
b = 7.6116 (11) Å	θ = 3.0–27.5°
c = 12.6732 (15) Å	µ = 0.11 mm−1
β = 95.592 (1)°	T = 298 K
V = 1329.8 (3) Å3	Block, colorless
Z = 4	0.14 × 0.11 × 0.05 mm

Bruker SMART CCD area-detector diffractometer	2333 independent reflections
Radiation source: fine-focus sealed tube	1267 reflections with I > 2σ(I)
graphite	Rint = 0.085
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.985, Tmax = 0.995	k = −5→9
6625 measured reflections	l = −15→15

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0242P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2333 reflections	Δρmax = 0.14 e Å−3
201 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
N1	0.19564 (17)	−0.0001 (3)	0.93775 (17)	0.0496 (6)
N2	0.42384 (17)	−0.1679 (3)	0.8929 (2)	0.0646 (7)
O1	−0.00728 (12)	0.1886 (3)	0.77882 (13)	0.0530 (5)
O2	0.03096 (12)	0.1945 (3)	0.61265 (14)	0.0561 (5)
O3	0.35098 (14)	−0.1183 (3)	0.95948 (14)	0.0625 (6)
O4	0.30666 (13)	0.0742 (2)	0.28784 (14)	0.0553 (6)
C1	0.1314 (2)	0.0595 (3)	0.8621 (2)	0.0413 (7)
C2	0.03488 (19)	0.1313 (4)	0.8820 (2)	0.0545 (8)
H2A	−0.0049	0.0415	0.9106	0.065*
H2B	0.0418	0.2291	0.9312	0.065*
C3	0.05378 (18)	0.1546 (4)	0.7033 (2)	0.0431 (7)
C4	0.14180 (18)	0.0708 (3)	0.75423 (18)	0.0371 (6)
C5	0.22780 (17)	0.0190 (3)	0.71290 (19)	0.0364 (6)
C6	0.29723 (19)	−0.0463 (3)	0.7918 (2)	0.0411 (7)
C7	0.2760 (2)	−0.0493 (4)	0.8971 (2)	0.0461 (7)
C8	0.3921 (2)	−0.1270 (4)	0.7960 (2)	0.0496 (7)
C9	0.45235 (19)	−0.1739 (4)	0.7089 (2)	0.0653 (9)
H9A	0.4837	−0.0703	0.6857	0.098*
H9B	0.4117	−0.2232	0.6507	0.098*
H9C	0.5006	−0.2584	0.7344	0.098*
C10	0.24536 (17)	0.0332 (3)	0.60100 (18)	0.0366 (6)
C11	0.18199 (17)	−0.0388 (3)	0.52099 (19)	0.0410 (7)
H11	0.1263	−0.0955	0.5385	0.049*
C12	0.19987 (17)	−0.0281 (3)	0.41641 (19)	0.0424 (7)
H12	0.1567	−0.0784	0.3642	0.051*
C13	0.28166 (18)	0.0570 (4)	0.3886 (2)	0.0411 (7)
C14	0.34544 (18)	0.1327 (3)	0.4676 (2)	0.0438 (7)
H14	0.4002	0.1921	0.4498	0.053*
C15	0.32724 (17)	0.1194 (3)	0.5715 (2)	0.0420 (7)
H15	0.3706	0.1691	0.6237	0.050*
C16	0.2431 (2)	0.0018 (4)	0.2031 (2)	0.0576 (8)
H16A	0.2355	−0.1219	0.2145	0.086*
H16B	0.2703	0.0203	0.1371	0.086*
H16C	0.1810	0.0584	0.2008	0.086*

	U11	U22	U33	U12	U13	U23
N1	0.0622 (16)	0.0493 (17)	0.0355 (14)	−0.0014 (14)	−0.0045 (12)	0.0028 (12)
N2	0.0610 (16)	0.0695 (19)	0.0598 (18)	0.0076 (15)	−0.0117 (14)	0.0066 (14)
O1	0.0524 (11)	0.0708 (14)	0.0364 (12)	0.0069 (11)	0.0064 (9)	0.0018 (10)
O2	0.0512 (11)	0.0798 (15)	0.0365 (12)	0.0089 (11)	0.0012 (9)	0.0128 (11)
O3	0.0690 (13)	0.0704 (16)	0.0447 (13)	0.0046 (12)	−0.0123 (11)	0.0081 (11)
O4	0.0597 (12)	0.0746 (15)	0.0319 (12)	−0.0042 (11)	0.0065 (10)	−0.0003 (10)
C1	0.0515 (16)	0.0396 (18)	0.0320 (16)	−0.0066 (14)	−0.0008 (13)	−0.0008 (13)
C2	0.0623 (19)	0.067 (2)	0.0340 (17)	−0.0022 (17)	0.0060 (14)	−0.0004 (15)
C3	0.0476 (17)	0.048 (2)	0.0345 (17)	−0.0057 (15)	0.0068 (14)	−0.0007 (14)
C4	0.0417 (15)	0.0376 (17)	0.0311 (16)	−0.0049 (13)	−0.0001 (12)	0.0018 (12)
C5	0.0430 (15)	0.0349 (17)	0.0294 (15)	−0.0061 (13)	−0.0056 (12)	−0.0006 (12)
C6	0.0458 (16)	0.0413 (18)	0.0351 (17)	−0.0052 (14)	−0.0020 (13)	−0.0021 (13)
C7	0.0537 (18)	0.0376 (19)	0.0431 (19)	−0.0019 (15)	−0.0154 (15)	0.0031 (14)
C8	0.0483 (17)	0.049 (2)	0.0489 (19)	−0.0036 (16)	−0.0102 (14)	−0.0005 (15)
C9	0.0561 (18)	0.069 (2)	0.069 (2)	0.0130 (18)	−0.0001 (16)	0.0028 (17)
C10	0.0384 (15)	0.0395 (18)	0.0310 (16)	0.0010 (13)	−0.0012 (12)	0.0006 (12)
C11	0.0371 (15)	0.0471 (19)	0.0385 (18)	−0.0041 (13)	0.0015 (12)	0.0026 (13)
C12	0.0411 (16)	0.050 (2)	0.0339 (17)	−0.0022 (15)	−0.0058 (13)	−0.0066 (13)
C13	0.0441 (16)	0.0436 (19)	0.0355 (17)	0.0061 (14)	0.0030 (13)	−0.0004 (13)
C14	0.0389 (15)	0.051 (2)	0.0418 (18)	−0.0034 (14)	0.0049 (13)	0.0020 (14)
C15	0.0380 (15)	0.0470 (19)	0.0393 (17)	−0.0039 (14)	−0.0052 (12)	−0.0028 (14)
C16	0.080 (2)	0.057 (2)	0.0342 (17)	0.0050 (18)	−0.0010 (15)	−0.0030 (15)

N1—C1	1.324 (3)	C6—C8	1.446 (3)
N1—C7	1.325 (3)	C8—C9	1.490 (4)
N2—C8	1.302 (3)	C9—H9A	0.9600
N2—O3	1.428 (3)	C9—H9B	0.9600
O1—C3	1.363 (3)	C9—H9C	0.9600
O1—C2	1.446 (3)	C10—C11	1.388 (3)
O2—C3	1.200 (3)	C10—C15	1.393 (3)
O3—C7	1.349 (3)	C11—C12	1.374 (3)
O4—C13	1.361 (3)	C11—H11	0.9300
O4—C16	1.431 (3)	C12—C13	1.380 (3)
C1—C4	1.391 (3)	C12—H12	0.9300
C1—C2	1.488 (3)	C13—C14	1.394 (3)
C2—H2A	0.9700	C14—C15	1.368 (3)
C2—H2B	0.9700	C14—H14	0.9300
C3—C4	1.469 (3)	C15—H15	0.9300
C4—C5	1.404 (3)	C16—H16A	0.9600
C5—C6	1.409 (3)	C16—H16B	0.9600
C5—C10	1.466 (3)	C16—H16C	0.9600
C6—C7	1.395 (3)
C1—N1—C7	110.3 (2)	C6—C8—C9	130.3 (3)
C8—N2—O3	107.5 (2)	C8—C9—H9A	109.5
C3—O1—C2	110.7 (2)	C8—C9—H9B	109.5
C7—O3—N2	107.8 (2)	H9A—C9—H9B	109.5
C13—O4—C16	118.2 (2)	C8—C9—H9C	109.5
N1—C1—C4	127.3 (3)	H9A—C9—H9C	109.5
N1—C1—C2	123.7 (2)	H9B—C9—H9C	109.5
C4—C1—C2	109.0 (2)	C11—C10—C15	117.6 (2)
O1—C2—C1	104.4 (2)	C11—C10—C5	121.7 (2)
O1—C2—H2A	110.9	C15—C10—C5	120.7 (2)
C1—C2—H2A	110.9	C12—C11—C10	121.4 (2)
O1—C2—H2B	110.9	C12—C11—H11	119.3
C1—C2—H2B	110.9	C10—C11—H11	119.3
H2A—C2—H2B	108.9	C11—C12—C13	120.2 (2)
O2—C3—O1	120.0 (2)	C11—C12—H12	119.9
O2—C3—C4	131.4 (2)	C13—C12—H12	119.9
O1—C3—C4	108.6 (2)	O4—C13—C12	125.1 (2)
C1—C4—C5	121.5 (2)	O4—C13—C14	115.6 (2)
C1—C4—C3	107.3 (2)	C12—C13—C14	119.3 (2)
C5—C4—C3	131.0 (2)	C15—C14—C13	119.8 (2)
C4—C5—C6	112.3 (2)	C15—C14—H14	120.1
C4—C5—C10	124.6 (2)	C13—C14—H14	120.1
C6—C5—C10	123.1 (2)	C14—C15—C10	121.7 (2)
C7—C6—C5	119.5 (3)	C14—C15—H15	119.2
C7—C6—C8	103.5 (2)	C10—C15—H15	119.2
C5—C6—C8	136.9 (3)	O4—C16—H16A	109.5
N1—C7—O3	120.7 (3)	O4—C16—H16B	109.5
N1—C7—C6	129.1 (3)	H16A—C16—H16B	109.5
O3—C7—C6	110.2 (3)	O4—C16—H16C	109.5
N2—C8—C6	111.0 (2)	H16A—C16—H16C	109.5
N2—C8—C9	118.6 (3)	H16B—C16—H16C	109.5
C8—N2—O3—C7	0.6 (3)	N2—O3—C7—C6	−1.7 (3)
C7—N1—C1—C4	0.6 (4)	C5—C6—C7—N1	1.1 (4)
C7—N1—C1—C2	−177.6 (2)	C8—C6—C7—N1	−176.1 (3)
C3—O1—C2—C1	1.0 (3)	C5—C6—C7—O3	179.2 (2)
N1—C1—C2—O1	176.8 (2)	C8—C6—C7—O3	2.0 (3)
C4—C1—C2—O1	−1.6 (3)	O3—N2—C8—C6	0.7 (3)
C2—O1—C3—O2	−179.5 (2)	O3—N2—C8—C9	−176.8 (2)
C2—O1—C3—C4	0.0 (3)	C7—C6—C8—N2	−1.7 (3)
N1—C1—C4—C5	−1.1 (4)	C5—C6—C8—N2	−178.1 (3)
C2—C1—C4—C5	177.3 (2)	C7—C6—C8—C9	175.4 (3)
N1—C1—C4—C3	−176.8 (3)	C5—C6—C8—C9	−1.0 (5)
C2—C1—C4—C3	1.7 (3)	C4—C5—C10—C11	−53.8 (4)
O2—C3—C4—C1	178.3 (3)	C6—C5—C10—C11	127.3 (3)
O1—C3—C4—C1	−1.1 (3)	C4—C5—C10—C15	126.5 (3)
O2—C3—C4—C5	3.2 (5)	C6—C5—C10—C15	−52.4 (4)
O1—C3—C4—C5	−176.1 (2)	C15—C10—C11—C12	1.0 (4)
C1—C4—C5—C6	1.4 (3)	C5—C10—C11—C12	−178.7 (2)
C3—C4—C5—C6	175.9 (3)	C10—C11—C12—C13	−0.7 (4)
C1—C4—C5—C10	−177.6 (2)	C16—O4—C13—C12	1.1 (4)
C3—C4—C5—C10	−3.1 (4)	C16—O4—C13—C14	−179.0 (2)
C4—C5—C6—C7	−1.4 (3)	C11—C12—C13—O4	179.5 (2)
C10—C5—C6—C7	177.7 (2)	C11—C12—C13—C14	−0.4 (4)
C4—C5—C6—C8	174.6 (3)	O4—C13—C14—C15	−178.8 (2)
C10—C5—C6—C8	−6.4 (5)	C12—C13—C14—C15	1.1 (4)
C1—N1—C7—O3	−178.5 (2)	C13—C14—C15—C10	−0.8 (4)
C1—N1—C7—C6	−0.6 (4)	C11—C10—C15—C14	−0.3 (4)
N2—O3—C7—N1	176.5 (2)	C5—C10—C15—C14	179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2i	0.97	2.39	3.215 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O2i	0.97	2.39	3.215 (3)	143

Symmetry code: (i) .