3-(4-Bromo-phen-yl)-4-(4-hy-droxy-anilino)furan-2(5H)-one.

In the title compound, C(16)H(12)BrNO(3), the butyrolactone core adopts the furan-2(5H)-one structure and forms dihedral angles of 44.80 (17) and 65.73 (18)° with the bromo-benzene and phenol rings, respectively. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules, generating R(4) (3)(26) loops The edge-fused rings extend to form a chain running along the b-axis direction and C-H⋯π contacts help to consolidate the packing.

Related literature

For biological background to furan-2(5H)-one derivatives, see: Bailly et al. (2008 ▶); Weber et al. (2005 ▶); Xiao et al. (2011a ▶,b ▶). For related structures, see: Xiao et al. (2010 ▶, 2011c ▶).

Experimental

Crystal data

C16H12BrNO3

M = 346.18

Monoclinic,

a = 11.2418 (10) Å

b = 8.0545 (7) Å

c = 16.1138 (13) Å

β = 100.244 (4)°

V = 1435.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.87 mm−1

T = 296 K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.597, T max = 0.762

7599 measured reflections

2725 independent reflections

1650 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.01

2725 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.59 e Å−3

Data collection: SMART (Bruker, 2000) ▶; cell refinement: SAINT (Bruker, 2000) ▶; 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031849/hb6341sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031849/hb6341Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031849/hb6341Isup3.cml

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

C16H12BrNO3	F(000) = 696
Mr = 346.18	Dx = 1.601 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1582 reflections
a = 11.2418 (10) Å	θ = 2.1–25.1°
b = 8.0545 (7) Å	µ = 2.87 mm−1
c = 16.1138 (13) Å	T = 296 K
β = 100.244 (4)°	Block, colorless
V = 1435.8 (2) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Bruker APEX CCD diffractometer	2725 independent reflections
Radiation source: fine-focus sealed tube	1650 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 25.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
Tmin = 0.597, Tmax = 0.762	k = −9→9
7599 measured reflections	l = −18→19

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0519P)2 + 0.1637P] where P = (Fo2 + 2Fc2)/3
2725 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.59 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
Br1	−0.33348 (4)	0.01420 (6)	−0.05871 (2)	0.0870 (2)
C1	−0.0793 (3)	0.0631 (4)	0.2028 (2)	0.0449 (8)
C2	−0.1939 (3)	−0.0066 (4)	0.1953 (2)	0.0506 (8)
H2	−0.2201	−0.0450	0.2435	0.061*
C3	−0.2695 (3)	−0.0201 (4)	0.1185 (2)	0.0544 (9)
H3	−0.3466	−0.0647	0.1148	0.065*
C4	−0.2294 (3)	0.0333 (4)	0.0473 (2)	0.0512 (9)
C5	−0.1167 (3)	0.1009 (4)	0.0516 (2)	0.0549 (9)
H5	−0.0908	0.1361	0.0028	0.066*
C6	−0.0417 (3)	0.1162 (4)	0.1293 (2)	0.0522 (8)
H6	0.0347	0.1625	0.1324	0.063*
C7	−0.0029 (3)	0.0832 (4)	0.28604 (19)	0.0452 (8)
C8	−0.0498 (3)	0.1479 (4)	0.3561 (2)	0.0548 (9)
C9	0.1485 (3)	0.0909 (4)	0.4049 (2)	0.0549 (9)
H9A	0.1731	−0.0102	0.4360	0.066*
H9B	0.2132	0.1718	0.4172	0.066*
C10	0.1178 (3)	0.0571 (4)	0.31223 (19)	0.0447 (8)
C11	0.3288 (3)	0.0027 (4)	0.3037 (2)	0.0485 (8)
C12	0.3717 (3)	−0.1054 (4)	0.3681 (2)	0.0632 (10)
H12	0.3191	−0.1784	0.3879	0.076*
C13	0.4933 (3)	−0.1054 (5)	0.4032 (2)	0.0690 (10)
H13	0.5224	−0.1783	0.4469	0.083*
C14	0.5709 (3)	0.0011 (5)	0.3740 (2)	0.0603 (10)
C15	0.5287 (3)	0.1075 (5)	0.3088 (2)	0.0575 (9)
H15	0.5817	0.1787	0.2881	0.069*
C16	0.4072 (3)	0.1084 (4)	0.27397 (19)	0.0517 (8)
H16	0.3784	0.1810	0.2301	0.062*
N1	0.2020 (3)	0.0087 (4)	0.2687 (2)	0.0594 (8)
O1	−0.1497 (2)	0.2035 (4)	0.36051 (14)	0.0755 (8)
O2	0.03891 (19)	0.1547 (3)	0.42643 (13)	0.0621 (6)
O3	0.6898 (2)	−0.0049 (4)	0.4118 (2)	0.0954 (10)
H3A	0.7279	0.0661	0.3911	0.143*
H1	0.187 (3)	−0.027 (4)	0.224 (2)	0.062 (13)*

	U11	U22	U33	U12	U13	U23
Br1	0.0902 (4)	0.1047 (4)	0.0567 (3)	−0.0269 (2)	−0.0122 (2)	0.0012 (2)
C1	0.0419 (18)	0.0458 (18)	0.0469 (18)	−0.0003 (14)	0.0078 (14)	−0.0035 (15)
C2	0.046 (2)	0.057 (2)	0.0502 (19)	−0.0069 (16)	0.0130 (15)	0.0000 (16)
C3	0.047 (2)	0.057 (2)	0.058 (2)	−0.0081 (16)	0.0074 (16)	−0.0011 (17)
C4	0.057 (2)	0.043 (2)	0.051 (2)	0.0020 (16)	0.0011 (16)	−0.0051 (15)
C5	0.061 (2)	0.060 (2)	0.0455 (19)	−0.0004 (18)	0.0133 (16)	0.0042 (16)
C6	0.0436 (18)	0.060 (2)	0.055 (2)	−0.0065 (16)	0.0131 (15)	0.0012 (17)
C7	0.0409 (18)	0.0498 (19)	0.0460 (18)	−0.0022 (15)	0.0109 (14)	−0.0043 (15)
C8	0.045 (2)	0.070 (2)	0.049 (2)	−0.0012 (18)	0.0066 (16)	−0.0012 (17)
C9	0.046 (2)	0.060 (2)	0.057 (2)	0.0035 (17)	0.0053 (16)	−0.0054 (18)
C10	0.0414 (19)	0.0432 (18)	0.0503 (19)	−0.0064 (14)	0.0100 (15)	−0.0048 (14)
C11	0.0401 (19)	0.054 (2)	0.0519 (19)	0.0012 (16)	0.0089 (15)	−0.0112 (17)
C12	0.055 (2)	0.050 (2)	0.088 (3)	−0.0011 (17)	0.021 (2)	0.0051 (19)
C13	0.060 (2)	0.070 (3)	0.077 (3)	0.019 (2)	0.013 (2)	0.016 (2)
C14	0.039 (2)	0.080 (3)	0.062 (2)	0.0043 (18)	0.0085 (17)	0.003 (2)
C15	0.0407 (19)	0.078 (3)	0.055 (2)	−0.0114 (17)	0.0119 (16)	0.0001 (19)
C16	0.050 (2)	0.066 (2)	0.0410 (18)	0.0016 (18)	0.0111 (15)	−0.0016 (16)
N1	0.0412 (17)	0.079 (2)	0.058 (2)	−0.0017 (14)	0.0086 (15)	−0.0229 (18)
O1	0.0518 (15)	0.115 (2)	0.0616 (16)	0.0171 (14)	0.0139 (12)	−0.0101 (14)
O2	0.0556 (14)	0.0847 (18)	0.0457 (13)	0.0084 (12)	0.0087 (11)	−0.0092 (12)
O3	0.0431 (16)	0.147 (3)	0.091 (2)	0.0103 (15)	−0.0021 (14)	0.0237 (18)

Br1—C4	1.897 (3)	C9—H9A	0.9700
C1—C2	1.391 (4)	C9—H9B	0.9700
C1—C6	1.394 (4)	C10—N1	1.332 (4)
C1—C7	1.467 (4)	C11—C16	1.371 (4)
C2—C3	1.376 (5)	C11—C12	1.375 (5)
C2—H2	0.9300	C11—N1	1.437 (4)
C3—C4	1.373 (5)	C12—C13	1.384 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.369 (5)	C13—C14	1.366 (5)
C5—C6	1.384 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—O3	1.368 (4)
C6—H6	0.9300	C14—C15	1.373 (5)
C7—C10	1.364 (4)	C15—C16	1.381 (4)
C7—C8	1.428 (4)	C15—H15	0.9300
C8—O1	1.222 (4)	C16—H16	0.9300
C8—O2	1.371 (3)	N1—H1	0.76 (4)
C9—O2	1.433 (4)	O3—H3A	0.8200
C9—C10	1.497 (4)
C2—C1—C6	117.8 (3)	C10—C9—H9B	110.8
C2—C1—C7	120.4 (3)	H9A—C9—H9B	108.9
C6—C1—C7	121.8 (3)	N1—C10—C7	130.0 (3)
C3—C2—C1	121.6 (3)	N1—C10—C9	121.3 (3)
C3—C2—H2	119.2	C7—C10—C9	108.7 (3)
C1—C2—H2	119.2	C16—C11—C12	119.7 (3)
C4—C3—C2	119.0 (3)	C16—C11—N1	119.8 (3)
C4—C3—H3	120.5	C12—C11—N1	120.5 (3)
C2—C3—H3	120.5	C11—C12—C13	119.8 (3)
C5—C4—C3	121.4 (3)	C11—C12—H12	120.1
C5—C4—Br1	119.6 (3)	C13—C12—H12	120.1
C3—C4—Br1	119.0 (3)	C14—C13—C12	120.2 (3)
C4—C5—C6	119.3 (3)	C14—C13—H13	119.9
C4—C5—H5	120.3	C12—C13—H13	119.9
C6—C5—H5	120.3	C13—C14—O3	117.2 (3)
C5—C6—C1	120.9 (3)	C13—C14—C15	120.1 (3)
C5—C6—H6	119.6	O3—C14—C15	122.7 (3)
C1—C6—H6	119.6	C14—C15—C16	119.7 (3)
C10—C7—C8	107.4 (3)	C14—C15—H15	120.1
C10—C7—C1	130.9 (3)	C16—C15—H15	120.1
C8—C7—C1	121.6 (3)	C11—C16—C15	120.4 (3)
O1—C8—O2	118.6 (3)	C11—C16—H16	119.8
O1—C8—C7	130.7 (3)	C15—C16—H16	119.8
O2—C8—C7	110.6 (3)	C10—N1—C11	123.4 (3)
O2—C9—C10	104.5 (2)	C10—N1—H1	123 (3)
O2—C9—H9A	110.8	C11—N1—H1	113 (3)
C10—C9—H9A	110.8	C8—O2—C9	108.4 (2)
O2—C9—H9B	110.8	C14—O3—H3A	109.5
C6—C1—C2—C3	−1.3 (5)	C1—C7—C10—C9	−177.8 (3)
C7—C1—C2—C3	177.0 (3)	O2—C9—C10—N1	174.5 (3)
C1—C2—C3—C4	1.5 (5)	O2—C9—C10—C7	−6.0 (4)
C2—C3—C4—C5	−0.7 (5)	C16—C11—C12—C13	0.9 (5)
C2—C3—C4—Br1	179.8 (2)	N1—C11—C12—C13	−177.6 (3)
C3—C4—C5—C6	−0.2 (5)	C11—C12—C13—C14	−0.3 (6)
Br1—C4—C5—C6	179.3 (2)	C12—C13—C14—O3	179.7 (4)
C4—C5—C6—C1	0.3 (5)	C12—C13—C14—C15	−0.8 (6)
C2—C1—C6—C5	0.4 (5)	C13—C14—C15—C16	1.2 (5)
C7—C1—C6—C5	−177.9 (3)	O3—C14—C15—C16	−179.3 (3)
C2—C1—C7—C10	138.5 (4)	C12—C11—C16—C15	−0.5 (5)
C6—C1—C7—C10	−43.2 (5)	N1—C11—C16—C15	178.0 (3)
C2—C1—C7—C8	−45.2 (4)	C14—C15—C16—C11	−0.5 (5)
C6—C1—C7—C8	133.1 (3)	C7—C10—N1—C11	173.4 (3)
C10—C7—C8—O1	172.4 (4)	C9—C10—N1—C11	−7.2 (5)
C1—C7—C8—O1	−4.6 (6)	C16—C11—N1—C10	−113.5 (4)
C10—C7—C8—O2	−2.9 (4)	C12—C11—N1—C10	64.9 (5)
C1—C7—C8—O2	−180.0 (3)	O1—C8—O2—C9	−177.0 (3)
C8—C7—C10—N1	−175.1 (3)	C7—C8—O2—C9	−1.0 (4)
C1—C7—C10—N1	1.6 (6)	C10—C9—O2—C8	4.2 (3)
C8—C7—C10—C9	5.5 (4)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.76 (4)	2.56 (4)	3.207 (4)	144 (4)
O3—H3A···O1ii	0.82	1.90	2.700 (4)	165.
C12—H12···Cg1i	0.93	2.86	3.723 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.76 (4)	2.56 (4)	3.207 (4)	144 (4)
O3—H3A⋯O1ii	0.82	1.90	2.700 (4)	165
C12—H12⋯Cg1i	0.93	2.86	3.723 (4)	155

Symmetry codes: (i) ; (ii) .