5-Amino-4-bromo-2,3-dihydro-1H-inden-1-one.

In the title compound, C(9)H(8)BrNO, the non-H-atom framework is essentially planar, with a maximum deviation of 0.087 (3) Å. In the crystal, mol-ecules are inter-connected into a three-dimensional network by C-H⋯O and N-H⋯O hydrogen bonds. In addition, C-H⋯π inter-actions and a π-π stacking inter-action, with a centroid-centroid distance of 3.5535 (19) Å, are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H8BrNO

M = 226.06

Monoclinic,

a = 12.6362 (4) Å

b = 8.3655 (2) Å

c = 17.4913 (5) Å

β = 113.128 (4)°

V = 1700.37 (10) Å3

Z = 8

Cu Kα radiation

μ = 6.16 mm−1

T = 297 K

0.77 × 0.60 × 0.08 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.031, T max = 0.616

3085 measured reflections

1594 independent reflections

1544 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.134

S = 1.06

1594 reflections

117 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.31 e Å−3

Δρmin = −0.89 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007489/fj2519sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007489/fj2519Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007489/fj2519Isup3.cml

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

C9H8BrNO	F(000) = 896
Mr = 226.06	Dx = 1.766 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 2518 reflections
a = 12.6362 (4) Å	θ = 5.5–70.2°
b = 8.3655 (2) Å	µ = 6.16 mm−1
c = 17.4913 (5) Å	T = 297 K
β = 113.128 (4)°	Plate, colourless
V = 1700.37 (10) Å3	0.77 × 0.60 × 0.08 mm
Z = 8

Agilent Xcalibur Ruby Gemini diffractometer	1594 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1544 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.2673 pixels mm-1	θmax = 70.4°, θmin = 5.5°
ω scans	h = −13→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −6→10
Tmin = 0.031, Tmax = 0.616	l = −19→21
3085 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.1063P)2 + 1.0273P] where P = (Fo2 + 2Fc2)/3
1594 reflections	(Δ/σ)max = 0.001
117 parameters	Δρmax = 1.31 e Å−3
3 restraints	Δρmin = −0.89 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.52857 (3)	0.21900 (4)	0.63347 (2)	0.0470 (2)
O1	0.2303 (2)	0.4628 (3)	0.26770 (13)	0.0544 (8)
N1	0.3501 (3)	0.4337 (4)	0.66390 (17)	0.0535 (9)
C1	0.3037 (3)	0.4330 (4)	0.41603 (17)	0.0381 (8)
C2	0.2318 (3)	0.5262 (4)	0.44160 (18)	0.0422 (8)
C3	0.2489 (3)	0.5253 (4)	0.5240 (2)	0.0431 (9)
C4	0.3357 (3)	0.4322 (4)	0.58293 (17)	0.0399 (8)
C5	0.4086 (2)	0.3422 (3)	0.55556 (16)	0.0368 (8)
C6	0.3917 (2)	0.3426 (3)	0.47291 (16)	0.0345 (8)
C7	0.4597 (3)	0.2542 (4)	0.4321 (2)	0.0430 (9)
C8	0.4016 (3)	0.3016 (4)	0.3399 (2)	0.0493 (10)
C9	0.3006 (3)	0.4086 (4)	0.33249 (17)	0.0425 (8)
H1N	0.301 (3)	0.472 (5)	0.679 (3)	0.062 (12)*
H2	0.17350	0.58760	0.40350	0.0510*
H2N	0.387 (4)	0.369 (6)	0.701 (3)	0.10 (2)*
H3	0.20180	0.58790	0.54150	0.0520*
H7A	0.45550	0.13960	0.43890	0.0520*
H7B	0.53980	0.28670	0.45540	0.0520*
H8A	0.45530	0.35870	0.32260	0.0590*
H8B	0.37490	0.20740	0.30530	0.0590*

	U11	U22	U33	U12	U13	U23
Br1	0.0466 (3)	0.0552 (4)	0.0315 (3)	0.0060 (1)	0.0070 (2)	0.0028 (1)
O1	0.0541 (13)	0.0741 (16)	0.0303 (10)	−0.0051 (12)	0.0114 (10)	0.0072 (10)
N1	0.0619 (17)	0.0712 (18)	0.0322 (13)	0.0012 (15)	0.0237 (13)	−0.0070 (12)
C1	0.0412 (14)	0.0433 (13)	0.0290 (13)	−0.0056 (12)	0.0128 (11)	0.0001 (10)
C2	0.0393 (14)	0.0471 (15)	0.0368 (15)	0.0014 (12)	0.0114 (12)	0.0050 (12)
C3	0.0443 (15)	0.0451 (14)	0.0443 (16)	0.0013 (13)	0.0221 (13)	−0.0033 (12)
C4	0.0444 (14)	0.0451 (14)	0.0305 (14)	−0.0062 (12)	0.0152 (12)	−0.0046 (11)
C5	0.0386 (13)	0.0414 (14)	0.0274 (12)	−0.0026 (12)	0.0098 (10)	−0.0017 (10)
C6	0.0371 (13)	0.0362 (13)	0.0298 (13)	−0.0009 (10)	0.0126 (11)	−0.0008 (10)
C7	0.0438 (17)	0.0496 (13)	0.0376 (17)	0.0024 (14)	0.0182 (14)	−0.0045 (13)
C8	0.0578 (19)	0.0602 (18)	0.0344 (16)	−0.0064 (15)	0.0230 (15)	−0.0064 (13)
C9	0.0474 (15)	0.0501 (15)	0.0299 (14)	−0.0140 (13)	0.0151 (12)	−0.0006 (11)

Br1—C5	1.896 (3)	C5—C6	1.376 (4)
O1—C9	1.220 (4)	C6—C7	1.509 (5)
N1—C4	1.355 (4)	C7—C8	1.539 (5)
N1—H1N	0.83 (4)	C8—C9	1.522 (5)
N1—H2N	0.83 (5)	C2—H2	0.9300
C1—C9	1.461 (4)	C3—H3	0.9300
C1—C2	1.397 (5)	C7—H7A	0.9700
C1—C6	1.389 (4)	C7—H7B	0.9700
C2—C3	1.371 (4)	C8—H8A	0.9700
C3—C4	1.409 (5)	C8—H8B	0.9700
C4—C5	1.411 (5)
H1N—N1—H2N	105 (5)	C7—C8—C9	106.3 (3)
C4—N1—H1N	122 (3)	O1—C9—C1	126.9 (3)
C4—N1—H2N	128 (3)	O1—C9—C8	125.3 (3)
C2—C1—C6	120.9 (3)	C1—C9—C8	107.8 (3)
C2—C1—C9	129.3 (3)	C1—C2—H2	121.00
C6—C1—C9	109.9 (3)	C3—C2—H2	121.00
C1—C2—C3	118.7 (3)	C2—C3—H3	119.00
C2—C3—C4	121.9 (3)	C4—C3—H3	119.00
C3—C4—C5	118.1 (3)	C6—C7—H7A	111.00
N1—C4—C5	121.5 (3)	C6—C7—H7B	111.00
N1—C4—C3	120.4 (3)	C8—C7—H7A	111.00
Br1—C5—C4	119.4 (2)	C8—C7—H7B	111.00
Br1—C5—C6	120.5 (2)	H7A—C7—H7B	109.00
C4—C5—C6	120.2 (2)	C7—C8—H8A	110.00
C1—C6—C5	120.3 (3)	C7—C8—H8B	111.00
C1—C6—C7	111.9 (3)	C9—C8—H8A	110.00
C5—C6—C7	127.9 (3)	C9—C8—H8B	110.00
C6—C7—C8	104.1 (3)	H8A—C8—H8B	109.00
C6—C1—C2—C3	−0.8 (5)	N1—C4—C5—Br1	0.6 (4)
C9—C1—C2—C3	177.4 (4)	N1—C4—C5—C6	179.8 (3)
C2—C1—C6—C5	0.7 (5)	C3—C4—C5—Br1	178.7 (2)
C2—C1—C6—C7	−178.9 (3)	C3—C4—C5—C6	−2.1 (5)
C9—C1—C6—C5	−177.8 (3)	Br1—C5—C6—C1	180.0 (2)
C9—C1—C6—C7	2.7 (4)	Br1—C5—C6—C7	−0.5 (4)
C2—C1—C9—O1	−2.6 (6)	C4—C5—C6—C1	0.8 (4)
C2—C1—C9—C8	177.6 (4)	C4—C5—C6—C7	−179.7 (3)
C6—C1—C9—O1	175.7 (3)	C1—C6—C7—C8	−0.1 (4)
C6—C1—C9—C8	−4.1 (4)	C5—C6—C7—C8	−179.7 (3)
C1—C2—C3—C4	−0.7 (5)	C6—C7—C8—C9	−2.4 (3)
C2—C3—C4—N1	−179.8 (4)	C7—C8—C9—O1	−175.9 (3)
C2—C3—C4—C5	2.1 (5)	C7—C8—C9—C1	4.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (4)	2.14 (5)	2.915 (4)	155 (4)
N1—H2N···Br1	0.83 (5)	2.80 (5)	3.088 (4)	103 (4)
C8—H8B···O1ii	0.97	2.50	3.448 (4)	166
C7—H7B···Cg2iii	0.97	2.85	3.659 (4)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (4)	2.14 (5)	2.915 (4)	155 (4)
C8—H8B⋯O1ii	0.97	2.50	3.448 (4)	166
C7—H7B⋯Cg2iii	0.97	2.85	3.659 (4)	141

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