3-(3,4-Dimeth-oxy-phen-yl)-4-(2-meth-oxy-anilino)furan-2(5H)-one.

In the title compound, C(19)H(19)NO(5), the furan-one unit makes a dihedral angle of 30.93 (6)° with the benzene ring and a dihedral angle of 9.51 (6)° with the aniline ring. In the crystal, inter-molecular C-H⋯O hydrogen bonds and C-H⋯π contacts link the mol-ecules into sheets. A weak intramolecular hydrogen bond is also observed.

Related literature

For the biological activity of furan-2(5H)-one derivatives, see: Xiao, He et al. (2011 ▶). For related structures, see: Xiao et al. (2010 ▶); Xiao, Peng et al. (2011 ▶).

Experimental

Crystal data

C19H19NO5

M = 341.35

Orthorhombic,

a = 7.4932 (5) Å

b = 11.5862 (7) Å

c = 18.5744 (12) Å

V = 1612.59 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.980

10601 measured reflections

3940 independent reflections

3732 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.121

S = 1.09

3940 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031266/pv2437sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031266/pv2437Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031266/pv2437Isup3.cml

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

C19H19NO5	F(000) = 720
Mr = 341.35	Dx = 1.406 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3629 reflections
a = 7.4932 (5) Å	θ = 2.4–27.8°
b = 11.5862 (7) Å	µ = 0.10 mm−1
c = 18.5744 (12) Å	T = 298 K
V = 1612.59 (18) Å3	Block, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Bruker SMART APEX CCD diffractometer	3940 independent reflections
Radiation source: fine-focus sealed tube	3732 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.970, Tmax = 0.980	k = −14→15
10601 measured reflections	l = −19→24

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0689P)2 + 0.1364P] where P = (Fo2 + 2Fc2)/3
3940 reflections	(Δ/σ)max = 0.001
233 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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
C1	0.1004 (2)	0.78788 (13)	0.96299 (8)	0.0298 (3)
C2	0.1438 (2)	0.90439 (13)	0.96587 (9)	0.0357 (3)
H2	0.1580	0.9453	0.9232	0.043*
C3	0.1665 (2)	0.96090 (14)	1.03105 (10)	0.0386 (4)
H3	0.1968	1.0387	1.0314	0.046*
C4	0.1447 (2)	0.90327 (15)	1.09529 (9)	0.0380 (4)
C5	0.0948 (2)	0.78615 (14)	1.09393 (9)	0.0354 (3)
C6	0.0722 (2)	0.73015 (13)	1.02868 (8)	0.0325 (3)
H6	0.0379	0.6530	1.0283	0.039*
C7	0.0929 (2)	0.72736 (13)	0.89352 (8)	0.0306 (3)
C8	0.0519 (2)	0.78617 (14)	0.82608 (9)	0.0375 (4)
C9	0.1286 (3)	0.60193 (14)	0.79642 (8)	0.0410 (4)
H9A	0.2447	0.5807	0.7774	0.049*
H9B	0.0429	0.5428	0.7833	0.049*
C10	0.1364 (2)	0.61684 (14)	0.87662 (8)	0.0313 (3)
C11	0.2423 (2)	0.41733 (13)	0.91057 (9)	0.0327 (3)
C12	0.3074 (2)	0.35932 (13)	0.97200 (9)	0.0337 (3)
C13	0.3749 (2)	0.24856 (14)	0.96556 (10)	0.0423 (4)
H13	0.4209	0.2110	1.0057	0.051*
C14	0.3739 (3)	0.19349 (15)	0.89930 (12)	0.0478 (4)
H14	0.4209	0.1195	0.8951	0.057*
C15	0.3044 (3)	0.24702 (15)	0.84022 (11)	0.0452 (4)
H15	0.3022	0.2087	0.7962	0.054*
C16	0.2368 (2)	0.35889 (15)	0.84532 (9)	0.0401 (4)
H16	0.1880	0.3944	0.8050	0.048*
C17	0.3697 (3)	0.37008 (17)	1.09825 (10)	0.0503 (5)
H17A	0.2980	0.3053	1.1125	0.075*
H17B	0.3706	0.4264	1.1362	0.075*
H17C	0.4895	0.3447	1.0890	0.075*
C18	0.0450 (3)	0.61586 (16)	1.16219 (10)	0.0514 (5)
H18A	−0.0672	0.5970	1.1402	0.077*
H18B	0.0447	0.5905	1.2114	0.077*
H18C	0.1398	0.5780	1.1366	0.077*
C19	0.2239 (3)	1.06783 (16)	1.16409 (12)	0.0539 (5)
H19A	0.3331	1.0760	1.1375	0.081*
H19B	0.2431	1.0908	1.2131	0.081*
H19C	0.1336	1.1158	1.1429	0.081*
H1	0.210 (3)	0.5550 (18)	0.9629 (12)	0.046 (6)*
N1	0.1861 (2)	0.53176 (12)	0.92278 (7)	0.0360 (3)
O1	0.0054 (2)	0.88447 (10)	0.81447 (7)	0.0520 (4)
O2	0.0742 (2)	0.71219 (10)	0.76969 (6)	0.0484 (3)
O3	0.29681 (17)	0.42052 (10)	1.03438 (6)	0.0398 (3)
O4	0.0713 (2)	0.73683 (11)	1.15974 (7)	0.0529 (4)
O5	0.1675 (2)	0.95037 (11)	1.16213 (7)	0.0532 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0314 (7)	0.0298 (7)	0.0282 (7)	0.0035 (5)	0.0000 (5)	0.0007 (6)
C2	0.0432 (8)	0.0308 (7)	0.0331 (7)	0.0034 (6)	0.0009 (7)	0.0070 (6)
C3	0.0450 (9)	0.0253 (7)	0.0456 (9)	0.0010 (6)	−0.0016 (8)	−0.0022 (6)
C4	0.0433 (9)	0.0358 (8)	0.0349 (8)	0.0017 (7)	−0.0039 (7)	−0.0054 (7)
C5	0.0440 (9)	0.0337 (7)	0.0284 (7)	−0.0004 (7)	−0.0007 (6)	0.0006 (6)
C6	0.0395 (8)	0.0287 (7)	0.0292 (7)	−0.0005 (6)	−0.0007 (6)	0.0010 (6)
C7	0.0365 (8)	0.0314 (7)	0.0240 (7)	0.0013 (6)	−0.0001 (5)	0.0044 (5)
C8	0.0483 (9)	0.0369 (8)	0.0272 (7)	0.0023 (7)	−0.0013 (6)	0.0050 (6)
C9	0.0625 (10)	0.0341 (8)	0.0264 (7)	0.0028 (8)	−0.0008 (7)	0.0022 (6)
C10	0.0357 (7)	0.0334 (7)	0.0248 (7)	−0.0007 (6)	−0.0003 (5)	0.0020 (6)
C11	0.0332 (7)	0.0292 (7)	0.0359 (8)	0.0002 (6)	0.0017 (6)	0.0016 (6)
C12	0.0348 (7)	0.0299 (7)	0.0365 (8)	−0.0035 (6)	−0.0008 (6)	0.0037 (6)
C13	0.0447 (9)	0.0294 (8)	0.0528 (10)	0.0015 (7)	−0.0034 (8)	0.0102 (7)
C14	0.0501 (10)	0.0269 (7)	0.0664 (12)	0.0017 (7)	0.0047 (9)	−0.0025 (8)
C15	0.0519 (10)	0.0340 (8)	0.0496 (10)	−0.0034 (8)	0.0080 (8)	−0.0089 (8)
C16	0.0472 (9)	0.0360 (8)	0.0369 (9)	−0.0010 (7)	−0.0001 (7)	−0.0015 (7)
C17	0.0676 (12)	0.0442 (10)	0.0392 (9)	−0.0006 (9)	−0.0172 (9)	0.0095 (7)
C18	0.0718 (13)	0.0466 (10)	0.0357 (9)	−0.0087 (9)	−0.0026 (9)	0.0116 (8)
C19	0.0584 (12)	0.0448 (10)	0.0586 (12)	−0.0023 (9)	−0.0102 (10)	−0.0203 (9)
N1	0.0534 (9)	0.0302 (6)	0.0245 (6)	0.0080 (6)	−0.0046 (6)	−0.0010 (5)
O1	0.0830 (10)	0.0373 (6)	0.0358 (7)	0.0139 (7)	−0.0052 (6)	0.0104 (5)
O2	0.0808 (10)	0.0388 (6)	0.0256 (5)	0.0069 (6)	−0.0025 (6)	0.0060 (5)
O3	0.0528 (7)	0.0350 (6)	0.0315 (6)	0.0025 (5)	−0.0074 (5)	0.0055 (4)
O4	0.0895 (10)	0.0430 (7)	0.0262 (6)	−0.0069 (7)	−0.0014 (6)	−0.0004 (5)
O5	0.0796 (10)	0.0422 (7)	0.0378 (7)	−0.0057 (6)	−0.0079 (7)	−0.0112 (5)

C1—C2	1.390 (2)	C11—C12	1.411 (2)
C1—C6	1.407 (2)	C12—O3	1.3607 (19)
C1—C7	1.470 (2)	C12—C13	1.384 (2)
C2—C3	1.387 (2)	C13—C14	1.386 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.377 (2)	C14—C15	1.364 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—O5	1.367 (2)	C15—C16	1.395 (2)
C4—C5	1.408 (2)	C15—H15	0.9300
C5—O4	1.361 (2)	C16—H16	0.9300
C5—C6	1.385 (2)	C17—O3	1.431 (2)
C6—H6	0.9300	C17—H17A	0.9600
C7—C10	1.358 (2)	C17—H17B	0.9600
C7—C8	1.459 (2)	C17—H17C	0.9600
C8—O1	1.210 (2)	C18—O4	1.416 (2)
C8—O2	1.364 (2)	C18—H18A	0.9600
C9—O2	1.4299 (19)	C18—H18B	0.9600
C9—C10	1.501 (2)	C18—H18C	0.9600
C9—H9A	0.9700	C19—O5	1.425 (2)
C9—H9B	0.9700	C19—H19A	0.9600
C10—N1	1.359 (2)	C19—H19B	0.9600
C11—C16	1.389 (2)	C19—H19C	0.9600
C11—N1	1.4093 (19)	N1—H1	0.81 (2)
C2—C1—C6	117.60 (13)	C13—C12—C11	119.85 (15)
C2—C1—C7	120.42 (13)	C12—C13—C14	120.10 (16)
C6—C1—C7	121.92 (13)	C12—C13—H13	120.0
C3—C2—C1	121.40 (14)	C14—C13—H13	120.0
C3—C2—H2	119.3	C15—C14—C13	120.47 (16)
C1—C2—H2	119.3	C15—C14—H14	119.8
C4—C3—C2	120.86 (14)	C13—C14—H14	119.8
C4—C3—H3	119.6	C14—C15—C16	120.44 (17)
C2—C3—H3	119.6	C14—C15—H15	119.8
O5—C4—C3	125.35 (15)	C16—C15—H15	119.8
O5—C4—C5	115.74 (15)	C11—C16—C15	120.10 (16)
C3—C4—C5	118.91 (14)	C11—C16—H16	119.9
O4—C5—C6	125.00 (14)	C15—C16—H16	119.9
O4—C5—C4	115.02 (14)	O3—C17—H17A	109.5
C6—C5—C4	119.98 (14)	O3—C17—H17B	109.5
C5—C6—C1	121.18 (14)	H17A—C17—H17B	109.5
C5—C6—H6	119.4	O3—C17—H17C	109.5
C1—C6—H6	119.4	H17A—C17—H17C	109.5
C10—C7—C8	107.00 (13)	H17B—C17—H17C	109.5
C10—C7—C1	130.07 (13)	O4—C18—H18A	109.5
C8—C7—C1	122.63 (14)	O4—C18—H18B	109.5
O1—C8—O2	119.34 (14)	H18A—C18—H18B	109.5
O1—C8—C7	130.77 (16)	O4—C18—H18C	109.5
O2—C8—C7	109.89 (13)	H18A—C18—H18C	109.5
O2—C9—C10	104.64 (13)	H18B—C18—H18C	109.5
O2—C9—H9A	110.8	O5—C19—H19A	109.5
C10—C9—H9A	110.8	O5—C19—H19B	109.5
O2—C9—H9B	110.8	H19A—C19—H19B	109.5
C10—C9—H9B	110.8	O5—C19—H19C	109.5
H9A—C9—H9B	108.9	H19A—C19—H19C	109.5
C7—C10—N1	127.16 (14)	H19B—C19—H19C	109.5
C7—C10—C9	109.19 (13)	C10—N1—C11	131.53 (14)
N1—C10—C9	123.60 (15)	C10—N1—H1	113.5 (15)
C16—C11—N1	126.17 (15)	C11—N1—H1	113.1 (15)
C16—C11—C12	118.92 (14)	C8—O2—C9	109.26 (12)
N1—C11—C12	114.91 (14)	C12—O3—C17	118.09 (13)
O3—C12—C13	125.31 (14)	C5—O4—C18	117.54 (14)
O3—C12—C11	114.83 (13)	C4—O5—C19	116.20 (15)
C6—C1—C2—C3	2.8 (2)	O2—C9—C10—N1	−178.82 (16)
C7—C1—C2—C3	−174.47 (14)	C16—C11—C12—O3	−175.81 (14)
C1—C2—C3—C4	−0.7 (2)	N1—C11—C12—O3	3.5 (2)
C2—C3—C4—O5	178.57 (16)	C16—C11—C12—C13	4.0 (2)
C2—C3—C4—C5	−1.4 (2)	N1—C11—C12—C13	−176.63 (15)
O5—C4—C5—O4	1.8 (2)	O3—C12—C13—C14	178.05 (16)
C3—C4—C5—O4	−178.21 (16)	C11—C12—C13—C14	−1.8 (3)
O5—C4—C5—C6	−178.62 (15)	C12—C13—C14—C15	−0.9 (3)
C3—C4—C5—C6	1.4 (2)	C13—C14—C15—C16	1.3 (3)
O4—C5—C6—C1	−179.67 (16)	N1—C11—C16—C15	177.11 (17)
C4—C5—C6—C1	0.8 (2)	C12—C11—C16—C15	−3.6 (2)
C2—C1—C6—C5	−2.8 (2)	C14—C15—C16—C11	1.0 (3)
C7—C1—C6—C5	174.39 (15)	C7—C10—N1—C11	−176.24 (17)
C2—C1—C7—C10	145.33 (17)	C9—C10—N1—C11	1.2 (3)
C6—C1—C7—C10	−31.8 (3)	C16—C11—N1—C10	−9.3 (3)
C2—C1—C7—C8	−27.5 (2)	C12—C11—N1—C10	171.42 (17)
C6—C1—C7—C8	155.39 (16)	O1—C8—O2—C9	−179.88 (18)
C10—C7—C8—O1	179.3 (2)	C7—C8—O2—C9	0.6 (2)
C1—C7—C8—O1	−6.4 (3)	C10—C9—O2—C8	0.2 (2)
C10—C7—C8—O2	−1.2 (2)	C13—C12—O3—C17	3.7 (2)
C1—C7—C8—O2	173.04 (15)	C11—C12—O3—C17	−176.45 (15)
C8—C7—C10—N1	179.05 (16)	C6—C5—O4—C18	8.8 (3)
C1—C7—C10—N1	5.4 (3)	C4—C5—O4—C18	−171.59 (17)
C8—C7—C10—C9	1.34 (19)	C3—C4—O5—C19	−2.1 (3)
C1—C7—C10—C9	−172.34 (16)	C5—C4—O5—C19	177.94 (16)
O2—C9—C10—C7	−1.0 (2)

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.43	3.006 (2)	121.
C17—H17B···O1i	0.96	2.58	3.428 (2)	147.
C17—H17C···Cgii	0.96	2.94	3.847 (2)	158
C19—H19C···Cgiii	0.96	2.77	3.695 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.43	3.006 (2)	121
C17—H17B⋯O1i	0.96	2.58	3.428 (2)	147
C17—H17C⋯Cgii	0.96	2.94	3.847 (2)	158
C19—H19C⋯Cgiii	0.96	2.77	3.695 (2)	162

Symmetry codes: (i) ; (ii) ; (iii) .