4-Bromo-3-hy-droxy-3-(4-hy-droxy-2-oxo-2H-chromen-3-yl)indolin-2-one.

In the mol-ecule of the title compound, C(17)H(10)BrNO(5), the indoline system and the attached coumarin ring are each essentially planar with maximum deviations of 0.074 (2) and 0.062 (2) Å, respectively. The dihedral angle between them is 85.09 (3)°. In the crystal, all heteroatoms (except for the coumarin oxo O atoms) are involved in intra- and inter-molecular hydrogen bonds. An intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked through O-H⋯O, N-H⋯O and C-H⋯O contacts, forming a complex three-dimensional structure.

Related literature

For general background to indoles and their biological activity, see: Da-Silva et al. (2001 ▶); Joshi & Chand (1982 ▶). Coumarin and its derivatives are important in the perfume, cosmetic and pharmaceutical industries, see: Soine (1964 ▶). For the synthesis of indole and coumarin derivatives in water, see: Zhu (2008 ▶).

Experimental

Crystal data

C17H10BrNO5

M = 388.17

Monoclinic,

a = 11.358 (3) Å

b = 13.428 (3) Å

c = 10.360 (2) Å

β = 113.307 (3)°

V = 1451.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.86 mm−1

T = 153 K

0.78 × 0.36 × 0.35 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.173, T max = 0.366

13755 measured reflections

2655 independent reflections

2544 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.059

S = 1.08

2655 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000213/bh2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000213/bh2329Isup2.hkl

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

C17H10BrNO5	F(000) = 776
Mr = 388.17	Dx = 1.777 Mg m−3
Monoclinic, P21/c	Melting point = 469–471 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71070 Å
a = 11.358 (3) Å	Cell parameters from 5845 reflections
b = 13.428 (3) Å	θ = 3.0–25.3°
c = 10.360 (2) Å	µ = 2.86 mm−1
β = 113.307 (3)°	T = 153 K
V = 1451.1 (5) Å3	Block, colourless
Z = 4	0.78 × 0.36 × 0.35 mm

Rigaku Mercury diffractometer	2655 independent reflections
Radiation source: fine-focus sealed tube	2544 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 7.31 pixels mm-1	θmax = 25.4°, θmin = 3.0°
ω scans	h = −13→11
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −16→16
Tmin = 0.173, Tmax = 0.366	l = −12→12
13755 measured reflections

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0278P)2 + 1.0659P] where P = (Fo2 + 2Fc2)/3
2655 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.42 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Br1	0.618858 (19)	0.424530 (16)	−0.05888 (2)	0.02468 (8)
O1	0.81967 (12)	0.24579 (9)	0.19817 (13)	0.0150 (3)
H1	0.8602	0.2544	0.1466	0.023*
O2	0.93364 (12)	0.28564 (10)	0.50987 (13)	0.0165 (3)
O3	0.55747 (12)	0.43528 (9)	0.37776 (13)	0.0147 (3)
O4	0.75296 (12)	0.48622 (9)	0.41805 (13)	0.0170 (3)
O5	0.58573 (13)	0.20063 (10)	0.13673 (14)	0.0195 (3)
H5	0.6572	0.1978	0.1306	0.029*
N1	1.01146 (14)	0.40717 (11)	0.40768 (16)	0.0144 (3)
H1A	1.0875	0.4158	0.4757	0.017*
C1	0.81079 (17)	0.33888 (13)	0.26299 (18)	0.0122 (4)
C2	0.92400 (17)	0.33989 (13)	0.41181 (19)	0.0130 (4)
C3	0.96558 (18)	0.46179 (14)	0.28075 (19)	0.0149 (4)
C4	0.84479 (18)	0.42644 (13)	0.19296 (19)	0.0131 (4)
C5	0.78170 (18)	0.47149 (14)	0.06449 (19)	0.0169 (4)
C6	0.8382 (2)	0.55024 (15)	0.0235 (2)	0.0223 (4)
H6	0.7943	0.5817	−0.0648	0.027*
C7	0.9589 (2)	0.58249 (15)	0.1123 (2)	0.0239 (5)
H7	0.9975	0.6359	0.0832	0.029*
C8	1.02526 (19)	0.53885 (15)	0.2429 (2)	0.0196 (4)
H8	1.1081	0.5613	0.3034	0.023*
C9	0.68273 (17)	0.34335 (13)	0.27623 (18)	0.0124 (4)
C10	0.66978 (17)	0.42446 (13)	0.35962 (19)	0.0124 (4)
C11	0.45996 (17)	0.36647 (14)	0.32443 (18)	0.0135 (4)
C12	0.46973 (17)	0.28643 (14)	0.24491 (18)	0.0139 (4)
C13	0.58467 (17)	0.27702 (14)	0.21777 (18)	0.0136 (4)
C14	0.37095 (18)	0.21509 (15)	0.20037 (19)	0.0176 (4)
H14	0.3758	0.1597	0.1457	0.021*
C15	0.26732 (18)	0.22596 (16)	0.2364 (2)	0.0203 (4)
H15	0.2014	0.1772	0.2084	0.024*
C16	0.25902 (18)	0.30829 (16)	0.3140 (2)	0.0214 (4)
H16	0.1864	0.3156	0.3370	0.026*
C17	0.35425 (18)	0.37954 (15)	0.35806 (19)	0.0178 (4)
H17	0.3476	0.4360	0.4100	0.021*

	U11	U22	U33	U12	U13	U23
Br1	0.02298 (13)	0.02838 (13)	0.01533 (12)	−0.00237 (8)	−0.00025 (9)	0.00135 (8)
O1	0.0179 (7)	0.0140 (7)	0.0178 (7)	−0.0007 (5)	0.0120 (5)	−0.0031 (5)
O2	0.0181 (7)	0.0185 (7)	0.0146 (6)	0.0034 (5)	0.0084 (5)	0.0029 (5)
O3	0.0115 (6)	0.0166 (7)	0.0166 (7)	−0.0005 (5)	0.0061 (5)	−0.0045 (5)
O4	0.0156 (7)	0.0151 (7)	0.0192 (7)	−0.0024 (5)	0.0058 (5)	−0.0056 (5)
O5	0.0166 (7)	0.0213 (7)	0.0231 (7)	−0.0047 (6)	0.0106 (6)	−0.0118 (6)
N1	0.0099 (7)	0.0185 (8)	0.0131 (8)	−0.0012 (6)	0.0028 (6)	−0.0004 (6)
C1	0.0130 (9)	0.0116 (9)	0.0125 (9)	−0.0004 (7)	0.0057 (7)	−0.0017 (7)
C2	0.0125 (9)	0.0130 (9)	0.0157 (9)	0.0032 (7)	0.0078 (7)	−0.0013 (7)
C3	0.0159 (9)	0.0154 (9)	0.0153 (9)	0.0010 (7)	0.0082 (7)	−0.0021 (8)
C4	0.0153 (9)	0.0122 (9)	0.0143 (9)	−0.0005 (7)	0.0085 (8)	−0.0019 (7)
C5	0.0192 (10)	0.0174 (10)	0.0139 (9)	0.0005 (8)	0.0064 (8)	−0.0024 (8)
C6	0.0326 (12)	0.0192 (10)	0.0158 (10)	0.0000 (9)	0.0101 (9)	0.0038 (8)
C7	0.0338 (12)	0.0179 (10)	0.0256 (11)	−0.0060 (9)	0.0177 (10)	0.0002 (8)
C8	0.0204 (10)	0.0182 (10)	0.0226 (10)	−0.0061 (8)	0.0113 (8)	−0.0035 (8)
C9	0.0121 (9)	0.0136 (9)	0.0112 (9)	0.0009 (7)	0.0045 (7)	−0.0002 (7)
C10	0.0114 (9)	0.0141 (9)	0.0110 (9)	0.0008 (7)	0.0038 (7)	0.0018 (7)
C11	0.0111 (9)	0.0177 (9)	0.0089 (8)	−0.0008 (7)	0.0010 (7)	0.0011 (7)
C12	0.0128 (9)	0.0173 (9)	0.0102 (8)	0.0001 (7)	0.0031 (7)	0.0021 (7)
C13	0.0164 (9)	0.0137 (9)	0.0103 (8)	0.0012 (7)	0.0048 (7)	−0.0003 (7)
C14	0.0176 (9)	0.0185 (10)	0.0155 (9)	−0.0021 (8)	0.0051 (8)	−0.0023 (8)
C15	0.0129 (9)	0.0272 (11)	0.0191 (10)	−0.0068 (8)	0.0045 (8)	−0.0005 (8)
C16	0.0138 (9)	0.0339 (12)	0.0181 (10)	0.0004 (8)	0.0080 (8)	0.0008 (9)
C17	0.0153 (9)	0.0238 (10)	0.0143 (9)	0.0033 (8)	0.0056 (8)	−0.0016 (8)

Br1—C5	1.8925 (19)	C6—C7	1.384 (3)
O1—C1	1.441 (2)	C6—H6	0.9500
O1—H1	0.8400	C7—C8	1.392 (3)
O2—C2	1.219 (2)	C7—H7	0.9500
O3—C10	1.369 (2)	C8—H8	0.9500
O3—C11	1.379 (2)	C9—C13	1.366 (3)
O4—C10	1.222 (2)	C9—C10	1.434 (2)
O5—C13	1.329 (2)	C11—C12	1.385 (3)
O5—H5	0.8400	C11—C17	1.387 (3)
N1—C2	1.356 (2)	C12—C14	1.407 (3)
N1—C3	1.413 (2)	C12—C13	1.446 (3)
N1—H1A	0.8800	C14—C15	1.376 (3)
C1—C4	1.510 (2)	C14—H14	0.9500
C1—C9	1.515 (2)	C15—C16	1.392 (3)
C1—C2	1.569 (2)	C15—H15	0.9500
C3—C8	1.376 (3)	C16—C17	1.379 (3)
C3—C4	1.395 (3)	C16—H16	0.9500
C4—C5	1.377 (3)	C17—H17	0.9500
C5—C6	1.388 (3)
C1—O1—H1	109.5	C3—C8—C7	117.08 (18)
C10—O3—C11	121.22 (14)	C3—C8—H8	121.5
C13—O5—H5	109.5	C7—C8—H8	121.5
C2—N1—C3	111.72 (15)	C13—C9—C10	120.16 (16)
C2—N1—H1A	124.1	C13—C9—C1	125.27 (16)
C3—N1—H1A	124.1	C10—C9—C1	114.56 (15)
O1—C1—C4	111.91 (14)	O4—C10—O3	116.09 (16)
O1—C1—C9	108.86 (14)	O4—C10—C9	124.78 (17)
C4—C1—C9	116.74 (15)	O3—C10—C9	119.13 (15)
O1—C1—C2	106.50 (14)	O3—C11—C12	121.17 (16)
C4—C1—C2	101.50 (14)	O3—C11—C17	116.90 (16)
C9—C1—C2	110.71 (14)	C12—C11—C17	121.91 (17)
O2—C2—N1	126.80 (17)	C11—C12—C14	118.83 (16)
O2—C2—C1	125.59 (16)	C11—C12—C13	118.33 (16)
N1—C2—C1	107.49 (15)	C14—C12—C13	122.75 (17)
C8—C3—C4	122.56 (18)	O5—C13—C9	125.02 (16)
C8—C3—N1	127.83 (17)	O5—C13—C12	115.15 (16)
C4—C3—N1	109.61 (16)	C9—C13—C12	119.82 (16)
C5—C4—C3	118.82 (17)	C15—C14—C12	119.70 (18)
C5—C4—C1	132.24 (17)	C15—C14—H14	120.2
C3—C4—C1	108.91 (16)	C12—C14—H14	120.2
C4—C5—C6	120.25 (18)	C14—C15—C16	120.10 (18)
C4—C5—Br1	120.15 (14)	C14—C15—H15	120.0
C6—C5—Br1	119.59 (15)	C16—C15—H15	120.0
C7—C6—C5	119.43 (19)	C17—C16—C15	121.25 (18)
C7—C6—H6	120.3	C17—C16—H16	119.4
C5—C6—H6	120.3	C15—C16—H16	119.4
C6—C7—C8	121.85 (19)	C16—C17—C11	118.19 (18)
C6—C7—H7	119.1	C16—C17—H17	120.9
C8—C7—H7	119.1	C11—C17—H17	120.9
C3—N1—C2—O2	−176.25 (17)	C2—C1—C9—C13	−125.59 (19)
C3—N1—C2—C1	7.53 (19)	O1—C1—C9—C10	170.24 (14)
O1—C1—C2—O2	−67.8 (2)	C4—C1—C9—C10	−61.9 (2)
C4—C1—C2—O2	175.02 (17)	C2—C1—C9—C10	53.5 (2)
C9—C1—C2—O2	50.4 (2)	C11—O3—C10—O4	−175.77 (15)
O1—C1—C2—N1	108.53 (15)	C11—O3—C10—C9	3.9 (2)
C4—C1—C2—N1	−8.69 (17)	C13—C9—C10—O4	178.59 (17)
C9—C1—C2—N1	−133.29 (15)	C1—C9—C10—O4	−0.5 (3)
C2—N1—C3—C8	176.71 (18)	C13—C9—C10—O3	−1.0 (3)
C2—N1—C3—C4	−3.0 (2)	C1—C9—C10—O3	179.82 (15)
C8—C3—C4—C5	−1.2 (3)	C10—O3—C11—C12	−3.1 (2)
N1—C3—C4—C5	178.55 (16)	C10—O3—C11—C17	174.87 (16)
C8—C3—C4—C1	177.16 (17)	O3—C11—C12—C14	176.13 (16)
N1—C3—C4—C1	−3.1 (2)	C17—C11—C12—C14	−1.7 (3)
O1—C1—C4—C5	71.8 (2)	O3—C11—C12—C13	−0.6 (3)
C9—C1—C4—C5	−54.5 (3)	C17—C11—C12—C13	−178.41 (17)
C2—C1—C4—C5	−174.98 (19)	C10—C9—C13—O5	178.61 (17)
O1—C1—C4—C3	−106.26 (17)	C1—C9—C13—O5	−2.4 (3)
C9—C1—C4—C3	127.40 (17)	C10—C9—C13—C12	−2.5 (3)
C2—C1—C4—C3	6.96 (18)	C1—C9—C13—C12	176.51 (16)
C3—C4—C5—C6	0.4 (3)	C11—C12—C13—O5	−177.70 (16)
C1—C4—C5—C6	−177.55 (18)	C14—C12—C13—O5	5.8 (3)
C3—C4—C5—Br1	179.05 (13)	C11—C12—C13—C9	3.3 (3)
C1—C4—C5—Br1	1.1 (3)	C14—C12—C13—C9	−173.22 (17)
C4—C5—C6—C7	0.6 (3)	C11—C12—C14—C15	−0.1 (3)
Br1—C5—C6—C7	−178.13 (15)	C13—C12—C14—C15	176.45 (17)
C5—C6—C7—C8	−0.7 (3)	C12—C14—C15—C16	1.4 (3)
C4—C3—C8—C7	1.0 (3)	C14—C15—C16—C17	−1.0 (3)
N1—C3—C8—C7	−178.66 (18)	C15—C16—C17—C11	−0.8 (3)
C6—C7—C8—C3	−0.1 (3)	O3—C11—C17—C16	−175.81 (16)
O1—C1—C9—C13	−8.8 (2)	C12—C11—C17—C16	2.1 (3)
C4—C1—C9—C13	119.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.98	2.7672 (17)	155
O5—H5···O1	0.84	1.81	2.5486 (19)	145
N1—H1A···O4ii	0.88	2.16	2.940 (2)	148
C7—H7···O2iii	0.95	2.49	3.429 (2)	172
C8—H8···O1iii	0.95	2.61	3.217 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.98	2.7672 (17)	155
O5—H5⋯O1	0.84	1.81	2.5486 (19)	145
N1—H1A⋯O4ii	0.88	2.16	2.940 (2)	148
C7—H7⋯O2iii	0.95	2.49	3.429 (2)	172
C8—H8⋯O1iii	0.95	2.61	3.217 (2)	122

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