3-Bromo-4-dibenzyl-amino-5-methoxy-furan-2(5H)-one.

In the the title compound, C(19)H(18)BrNO(3), the furan-one ring is almost planar [maximum atomic deviation = 0.019 (3) Å] and is nearly perpendicular to the two phenyl rings, making dihedral angles of 88.96 (17) and 87.71 (17)°. Inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

2(5H)-Furan­one is the simplest sub-unit of a large class of five-membered heterocyclic carbonyl compounds, see: Reva et al. (2008 ▶). The title compound is a derivative of 4-amino-2(5H)-furan­one. For the biological activity of 4-amino-2(5H)-furan­ones, see: Kimura et al. (2000 ▶); Tanoury et al. (2008 ▶). For the synthesis, see: Toshiyuki & Yoshikazu (1955 ▶).

Experimental

Crystal data

C19H18BrNO3

M = 388.25

Orthorhombic,

a = 15.756 (2) Å

b = 11.2475 (14) Å

c = 19.779 (3) Å

V = 3505.2 (8) Å3

Z = 8

Mo Kα radiation

μ = 2.36 mm−1

T = 298 K

0.23 × 0.20 × 0.16 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.613, T max = 0.704

18029 measured reflections

3429 independent reflections

2028 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.089

S = 1.00

3429 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008007/xu2724sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008007/xu2724Isup2.hkl

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

C19H18BrNO3	F(000) = 1584
Mr = 388.25	Dx = 1.471 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2798 reflections
a = 15.756 (2) Å	θ = 2.5–21.2°
b = 11.2475 (14) Å	µ = 2.36 mm−1
c = 19.779 (3) Å	T = 298 K
V = 3505.2 (8) Å3	Block, colourless
Z = 8	0.23 × 0.20 × 0.16 mm

Bruker APEXII area-detector diffractometer	3429 independent reflections
Radiation source: fine-focus sealed tube	2028 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scan	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→18
Tmin = 0.613, Tmax = 0.704	k = −13→13
18029 measured reflections	l = −10→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0297P)2 + 1.9449P] where P = (Fo2 + 2Fc2)/3
3429 reflections	(Δ/σ)max = 0.002
218 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. 1H NMR (400 MHz, CDCl3, TMS): 3.52 (3H, s, CH, CH3), 4.53 (2H, d, CH, CH2), 4.90 (2H, d, CH, CH2), 5.74 (1H, s, CH), 7.21-7.42 (10H, m, CH, Ar-H);

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.09981 (2)	1.14889 (3)	0.35209 (2)	0.07708 (16)
C9	0.24254 (19)	0.8956 (3)	0.36299 (14)	0.0447 (7)
C5	0.29710 (17)	0.8590 (3)	0.16073 (14)	0.0440 (7)
C8	0.25104 (19)	0.9658 (3)	0.29832 (14)	0.0506 (8)
H8A	0.2423	1.0493	0.3083	0.061*
H8B	0.3085	0.9570	0.2815	0.061*
C6	0.3624 (2)	0.7779 (3)	0.15594 (17)	0.0689 (10)
H6	0.3598	0.7075	0.1805	0.083*
C7	0.22153 (18)	0.8294 (2)	0.20442 (15)	0.0495 (8)
H7A	0.1754	0.8027	0.1757	0.059*
H7B	0.2365	0.7644	0.2344	0.059*
C10	0.1799 (2)	0.8127 (3)	0.37322 (17)	0.0618 (9)
H10	0.1395	0.7997	0.3398	0.074*
C4	0.3031 (2)	0.9608 (3)	0.12329 (18)	0.0674 (10)
H4	0.2598	1.0168	0.1252	0.081*
C14	0.3011 (2)	0.9133 (3)	0.41324 (17)	0.0625 (9)
H14	0.3436	0.9696	0.4072	0.075*
C11	0.1764 (2)	0.7486 (3)	0.43241 (19)	0.0750 (11)
H11	0.1335	0.6928	0.4388	0.090*
C13	0.2981 (3)	0.8493 (4)	0.47231 (18)	0.0828 (12)
H13	0.3385	0.8623	0.5058	0.099*
C12	0.2358 (3)	0.7666 (4)	0.48199 (18)	0.0806 (11)
H12	0.2337	0.7230	0.5219	0.097*
C2	0.4371 (3)	0.9017 (4)	0.0793 (2)	0.0818 (12)
H2	0.4844	0.9168	0.0525	0.098*
C1	0.4314 (2)	0.7997 (4)	0.1153 (2)	0.0858 (12)
H1	0.4747	0.7438	0.1125	0.103*
C3	0.3730 (3)	0.9814 (4)	0.0826 (2)	0.0840 (12)
H3	0.3760	1.0509	0.0573	0.101*
N1	0.19202 (15)	0.9304 (2)	0.24524 (12)	0.0448 (6)
O1	0.08872 (13)	0.95812 (19)	0.12416 (10)	0.0558 (6)
O3	−0.06901 (14)	1.1434 (2)	0.26344 (12)	0.0691 (6)
O2	−0.02363 (12)	0.99727 (18)	0.19541 (10)	0.0532 (5)
C16	0.05326 (18)	0.9313 (3)	0.18643 (14)	0.0434 (7)
H16	0.0426	0.8457	0.1904	0.052*
C18	0.11283 (18)	0.9735 (2)	0.24190 (14)	0.0400 (7)
C20	−0.0134 (2)	1.0746 (3)	0.24854 (16)	0.0497 (8)
C19	0.06917 (18)	1.0562 (2)	0.27812 (14)	0.0446 (7)
C15	0.0499 (3)	0.8984 (4)	0.07008 (18)	0.0898 (13)
H15A	0.0518	0.8142	0.0780	0.135*
H15B	0.0794	0.9166	0.0289	0.135*
H15C	−0.0082	0.9235	0.0663	0.135*

	U11	U22	U33	U12	U13	U23
Br1	0.0724 (3)	0.0756 (3)	0.0833 (3)	0.0017 (2)	−0.0117 (2)	−0.0326 (2)
C9	0.0377 (17)	0.0467 (16)	0.0498 (19)	0.0101 (14)	−0.0009 (15)	−0.0007 (14)
C5	0.0398 (17)	0.0478 (17)	0.0445 (18)	0.0011 (15)	−0.0038 (13)	0.0051 (15)
C8	0.0364 (17)	0.0554 (19)	0.060 (2)	−0.0035 (15)	−0.0035 (15)	0.0059 (16)
C6	0.059 (2)	0.074 (2)	0.073 (2)	0.0192 (19)	0.0072 (19)	0.026 (2)
C7	0.0452 (18)	0.0435 (18)	0.060 (2)	0.0056 (14)	0.0007 (15)	0.0084 (15)
C10	0.053 (2)	0.075 (2)	0.057 (2)	−0.0080 (18)	−0.0030 (16)	0.0139 (18)
C4	0.060 (2)	0.057 (2)	0.085 (3)	0.0059 (17)	0.0155 (19)	0.020 (2)
C14	0.061 (2)	0.068 (2)	0.059 (2)	0.0024 (18)	−0.0100 (18)	−0.0032 (19)
C11	0.079 (3)	0.081 (3)	0.066 (2)	−0.006 (2)	0.005 (2)	0.017 (2)
C13	0.088 (3)	0.102 (3)	0.058 (3)	0.008 (3)	−0.022 (2)	−0.005 (2)
C12	0.097 (3)	0.091 (3)	0.054 (2)	0.015 (3)	0.002 (2)	0.019 (2)
C2	0.059 (2)	0.103 (3)	0.083 (3)	−0.005 (2)	0.023 (2)	0.006 (3)
C1	0.060 (2)	0.102 (3)	0.095 (3)	0.026 (2)	0.024 (2)	0.017 (3)
C3	0.080 (3)	0.075 (3)	0.098 (3)	−0.007 (2)	0.026 (2)	0.030 (2)
N1	0.0362 (14)	0.0476 (14)	0.0506 (15)	−0.0009 (12)	−0.0020 (11)	0.0026 (12)
O1	0.0549 (13)	0.0668 (14)	0.0457 (13)	−0.0002 (11)	0.0038 (11)	0.0049 (11)
O3	0.0516 (13)	0.0647 (14)	0.0909 (18)	0.0162 (12)	0.0008 (12)	−0.0133 (13)
O2	0.0393 (12)	0.0610 (13)	0.0594 (14)	0.0064 (10)	−0.0041 (10)	−0.0071 (11)
C16	0.0411 (17)	0.0447 (17)	0.0442 (18)	−0.0011 (14)	0.0014 (14)	0.0013 (14)
C18	0.0381 (17)	0.0366 (16)	0.0452 (17)	−0.0082 (13)	0.0016 (13)	0.0085 (13)
C20	0.048 (2)	0.0440 (18)	0.057 (2)	−0.0009 (16)	0.0058 (16)	0.0004 (16)
C19	0.0427 (17)	0.0406 (16)	0.0506 (18)	−0.0044 (14)	−0.0017 (14)	−0.0012 (14)
C15	0.086 (3)	0.133 (4)	0.050 (2)	−0.001 (3)	0.004 (2)	−0.015 (2)

Br1—C19	1.860 (3)	C11—H11	0.9300
C9—C14	1.371 (4)	C13—C12	1.366 (5)
C9—C10	1.372 (4)	C13—H13	0.9300
C9—C8	1.509 (4)	C12—H12	0.9300
C5—C4	1.367 (4)	C2—C3	1.351 (5)
C5—C6	1.378 (4)	C2—C1	1.353 (5)
C5—C7	1.508 (4)	C2—H2	0.9300
C8—N1	1.458 (3)	C1—H1	0.9300
C8—H8A	0.9700	C3—H3	0.9300
C8—H8B	0.9700	N1—C18	1.340 (3)
C6—C1	1.374 (5)	O1—C16	1.386 (3)
C6—H6	0.9300	O1—C15	1.404 (4)
C7—N1	1.469 (3)	O3—C20	1.206 (3)
C7—H7A	0.9700	O2—C20	1.374 (3)
C7—H7B	0.9700	O2—C16	1.432 (3)
C10—C11	1.376 (4)	C16—C18	1.520 (4)
C10—H10	0.9300	C16—H16	0.9800
C4—C3	1.383 (5)	C18—C19	1.361 (4)
C4—H4	0.9300	C20—C19	1.441 (4)
C14—C13	1.373 (5)	C15—H15A	0.9600
C14—H14	0.9300	C15—H15B	0.9600
C11—C12	1.371 (5)	C15—H15C	0.9600
C14—C9—C10	118.4 (3)	C13—C12—H12	120.3
C14—C9—C8	118.6 (3)	C11—C12—H12	120.3
C10—C9—C8	123.0 (3)	C3—C2—C1	119.1 (4)
C4—C5—C6	117.7 (3)	C3—C2—H2	120.4
C4—C5—C7	123.4 (3)	C1—C2—H2	120.4
C6—C5—C7	118.9 (3)	C2—C1—C6	120.8 (4)
N1—C8—C9	114.3 (2)	C2—C1—H1	119.6
N1—C8—H8A	108.7	C6—C1—H1	119.6
C9—C8—H8A	108.7	C2—C3—C4	120.8 (4)
N1—C8—H8B	108.7	C2—C3—H3	119.6
C9—C8—H8B	108.7	C4—C3—H3	119.6
H8A—C8—H8B	107.6	C18—N1—C8	122.1 (2)
C1—C6—C5	120.8 (3)	C18—N1—C7	123.2 (2)
C1—C6—H6	119.6	C8—N1—C7	113.9 (2)
C5—C6—H6	119.6	C16—O1—C15	113.4 (2)
N1—C7—C5	113.2 (2)	C20—O2—C16	108.9 (2)
N1—C7—H7A	108.9	O1—C16—O2	109.8 (2)
C5—C7—H7A	108.9	O1—C16—C18	108.9 (2)
N1—C7—H7B	108.9	O2—C16—C18	105.7 (2)
C5—C7—H7B	108.9	O1—C16—H16	110.7
H7A—C7—H7B	107.7	O2—C16—H16	110.7
C9—C10—C11	120.7 (3)	C18—C16—H16	110.7
C9—C10—H10	119.6	N1—C18—C19	133.8 (3)
C11—C10—H10	119.6	N1—C18—C16	119.9 (2)
C5—C4—C3	120.7 (3)	C19—C18—C16	106.3 (2)
C5—C4—H4	119.7	O3—C20—O2	120.5 (3)
C3—C4—H4	119.7	O3—C20—C19	130.5 (3)
C9—C14—C13	121.2 (3)	O2—C20—C19	109.0 (3)
C9—C14—H14	119.4	C18—C19—C20	109.9 (3)
C13—C14—H14	119.4	C18—C19—Br1	131.8 (2)
C12—C11—C10	120.2 (4)	C20—C19—Br1	118.2 (2)
C12—C11—H11	119.9	O1—C15—H15A	109.5
C10—C11—H11	119.9	O1—C15—H15B	109.5
C12—C13—C14	120.0 (4)	H15A—C15—H15B	109.5
C12—C13—H13	120.0	O1—C15—H15C	109.5
C14—C13—H13	120.0	H15A—C15—H15C	109.5
C13—C12—C11	119.4 (4)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O3i	0.98	2.49	3.396 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O3i	0.98	2.49	3.396 (4)	154

Symmetry code: (i) .