3-(3-Bromo-benz-yl)isoquinolin-1(2H)-one.

In the title compound, C(16)H(12)BrNO, the ring systems subtend an inter-planar dihedral angle of 75.95 (3)°. In the crystal packing, mol-ecules are linked to form centrosymmetric pairs by pairs of classical N-H⋯O hydrogen bonds.

Related literature

For the biological and pharmaceutical properties of isoquinolin-1(2H)-one derivatives, see: Chern & Li (2004 ▶); Coelho et al. (2003 ▶); Jayaraman et al. (2000 ▶); Thompson & Kallmerten (1990 ▶); Ukita et al. (2001 ▶). For the structure of a related isochromene derivative, see: Ali et al. (2009 ▶).

Experimental

Crystal data

C16H12BrNO

M = 314.18

Triclinic,

a = 4.5858 (4) Å

b = 9.4976 (7) Å

c = 14.8296 (11) Å

α = 88.698 (6)°

β = 83.829 (6)°

γ = 86.529 (6)°

V = 640.88 (9) Å3

Z = 2

Cu Kα radiation

μ = 4.28 mm−1

T = 100 K

0.16 × 0.07 × 0.07 mm

Data collection

Oxford Diffraction Nova A diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.817, T max = 1.000

9267 measured reflections

2642 independent reflections

2586 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.068

S = 0.90

2642 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051137/rz2396sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051137/rz2396Isup2.hkl

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

C16H12BrNO	Z = 2
Mr = 314.18	F(000) = 316
Triclinic, P1	Dx = 1.628 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 4.5858 (4) Å	Cell parameters from 9315 reflections
b = 9.4976 (7) Å	θ = 3.0–75.6°
c = 14.8296 (11) Å	µ = 4.28 mm−1
α = 88.698 (6)°	T = 100 K
β = 83.829 (6)°	Prism, colourless
γ = 86.529 (6)°	0.16 × 0.07 × 0.07 mm
V = 640.88 (9) Å3

Oxford Diffraction Nova A diffractometer	2642 independent reflections
Radiation source: Nova (Cu) X-ray Source	2586 reflections with I > 2σ(I)
mirror	Rint = 0.021
Detector resolution: 10.3543 pixels mm-1	θmax = 75.8°, θmin = 3.0°
ω scan	h = −5→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −11→11
Tmin = 0.817, Tmax = 1.000	l = −18→18
9267 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.8338P] where P = (Fo2 + 2Fc2)/3
2642 reflections	(Δ/σ)max = 0.016
176 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.65 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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)- 3.3521 (0.0017) x + 6.0480 (0.0040) y - 1.1834 (0.0042) z = 2.8164 (0.0038)* 0.0154 (0.0011) C10 * -0.0101 (0.0014) C11 * -0.0109 (0.0014) C12 * -0.0098 (0.0015) C13 * 0.0036 (0.0015) C14 * 0.0074 (0.0013) C15 * -0.0053 (0.0014) C16 * 0.0097 (0.0008) BrRms deviation of fitted atoms = 0.00963.3793 (0.0010) x + 4.6226 (0.0023) y + 8.8098 (0.0043) z = 6.7949 (0.0012)Angle to previous plane (with approximate e.s.d.) = 75.95 (0.03)* 0.0161 (0.0013) C10 * -0.0154 (0.0013) N * 0.0007 (0.0011) O * -0.0018 (0.0014) C1 * -0.0080 (0.0015) C2 * -0.0054 (0.0015) C3 * 0.0009 (0.0015) C4 * -0.0003 (0.0014) C5 * -0.0016 (0.0014) C6 * -0.0046 (0.0015) C7 * 0.0104 (0.0015) C8 * 0.0089 (0.0015) C9Rms deviation of fitted atoms = 0.0082

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
Br	0.41731 (5)	0.68583 (2)	−0.065128 (12)	0.03136 (9)
N	0.2730 (3)	0.49455 (15)	0.40535 (10)	0.0155 (3)
H01	0.131 (5)	0.545 (3)	0.4306 (17)	0.025 (6)*
O	0.2033 (3)	0.33201 (12)	0.51915 (8)	0.0187 (2)
C1	0.3423 (4)	0.36850 (17)	0.44644 (11)	0.0159 (3)
C2	0.4140 (4)	0.54534 (17)	0.32544 (11)	0.0155 (3)
C3	0.6381 (4)	0.46744 (18)	0.28064 (11)	0.0168 (3)
H3	0.7347	0.5018	0.2253	0.020*
C4	0.7296 (4)	0.33229 (17)	0.31716 (11)	0.0162 (3)
C5	0.9617 (4)	0.24635 (19)	0.27310 (12)	0.0194 (3)
H5	1.0630	0.2778	0.2178	0.023*
C6	1.0421 (4)	0.11699 (19)	0.30999 (12)	0.0216 (4)
H6	1.1988	0.0603	0.2798	0.026*
C7	0.8955 (4)	0.06803 (18)	0.39159 (12)	0.0216 (4)
H7	0.9509	−0.0217	0.4160	0.026*
C8	0.6701 (4)	0.15123 (18)	0.43607 (12)	0.0190 (3)
H8	0.5721	0.1192	0.4918	0.023*
C9	0.5853 (4)	0.28290 (17)	0.39932 (11)	0.0159 (3)
C10	0.2940 (4)	0.68958 (18)	0.29851 (12)	0.0194 (3)
H10A	0.3169	0.7560	0.3474	0.023*
H10B	0.0811	0.6853	0.2937	0.023*
C11	0.4378 (4)	0.74776 (17)	0.21028 (12)	0.0170 (3)
C12	0.3752 (4)	0.69677 (18)	0.12761 (12)	0.0201 (3)
H12	0.2438	0.6235	0.1261	0.024*
C13	0.5061 (4)	0.75386 (19)	0.04767 (12)	0.0211 (3)
C14	0.6969 (4)	0.8617 (2)	0.04693 (13)	0.0237 (4)
H14	0.7836	0.9000	−0.0086	0.028*
C15	0.7580 (4)	0.91238 (19)	0.12966 (14)	0.0247 (4)
H15	0.8878	0.9864	0.1309	0.030*
C16	0.6308 (4)	0.85559 (18)	0.21038 (12)	0.0195 (3)
H16	0.6758	0.8906	0.2665	0.023*

	U11	U22	U33	U12	U13	U23
Br	0.04174 (14)	0.03719 (14)	0.01477 (12)	0.00054 (9)	−0.00234 (8)	−0.00284 (8)
N	0.0173 (7)	0.0153 (6)	0.0130 (6)	0.0004 (5)	0.0017 (5)	−0.0002 (5)
O	0.0218 (6)	0.0182 (6)	0.0152 (6)	−0.0004 (4)	0.0016 (5)	0.0024 (4)
C1	0.0177 (8)	0.0156 (7)	0.0148 (8)	−0.0021 (6)	−0.0031 (6)	−0.0007 (6)
C2	0.0184 (8)	0.0156 (7)	0.0130 (7)	−0.0029 (6)	−0.0020 (6)	−0.0008 (6)
C3	0.0186 (8)	0.0182 (8)	0.0134 (8)	−0.0027 (6)	−0.0002 (6)	0.0001 (6)
C4	0.0166 (7)	0.0173 (8)	0.0152 (8)	−0.0021 (6)	−0.0031 (6)	−0.0027 (6)
C5	0.0186 (8)	0.0226 (8)	0.0168 (8)	−0.0003 (6)	−0.0013 (6)	−0.0030 (6)
C6	0.0211 (8)	0.0228 (8)	0.0212 (9)	0.0041 (7)	−0.0050 (7)	−0.0066 (7)
C7	0.0270 (9)	0.0175 (8)	0.0211 (9)	0.0031 (7)	−0.0083 (7)	−0.0022 (6)
C8	0.0231 (8)	0.0175 (8)	0.0170 (8)	−0.0015 (6)	−0.0042 (6)	−0.0003 (6)
C9	0.0172 (8)	0.0158 (7)	0.0151 (8)	−0.0013 (6)	−0.0036 (6)	−0.0014 (6)
C10	0.0243 (8)	0.0172 (8)	0.0156 (8)	0.0019 (6)	0.0015 (7)	0.0007 (6)
C11	0.0193 (8)	0.0136 (7)	0.0166 (8)	0.0037 (6)	0.0013 (6)	0.0014 (6)
C12	0.0229 (8)	0.0175 (8)	0.0193 (8)	−0.0007 (6)	−0.0004 (7)	0.0001 (6)
C13	0.0250 (9)	0.0220 (8)	0.0151 (8)	0.0051 (7)	−0.0005 (7)	−0.0001 (6)
C14	0.0246 (9)	0.0243 (9)	0.0202 (9)	0.0016 (7)	0.0045 (7)	0.0073 (7)
C15	0.0250 (9)	0.0205 (8)	0.0280 (10)	−0.0043 (7)	0.0009 (7)	0.0044 (7)
C16	0.0213 (8)	0.0179 (8)	0.0189 (8)	0.0012 (6)	−0.0016 (6)	−0.0003 (6)

Br—C13	1.8997 (18)	C12—C13	1.384 (2)
N—C1	1.367 (2)	C13—C14	1.386 (3)
N—C2	1.379 (2)	C14—C15	1.390 (3)
O—C1	1.245 (2)	C15—C16	1.387 (3)
C1—C9	1.463 (2)	N—H01	0.85 (3)
C2—C3	1.352 (2)	C3—H3	0.9500
C2—C10	1.507 (2)	C5—H5	0.9500
C3—C4	1.438 (2)	C6—H6	0.9500
C4—C9	1.407 (2)	C7—H7	0.9500
C4—C5	1.413 (2)	C8—H8	0.9500
C5—C6	1.379 (3)	C10—H10A	0.9900
C6—C7	1.404 (3)	C10—H10B	0.9900
C7—C8	1.380 (3)	C12—H12	0.9500
C8—C9	1.403 (2)	C14—H14	0.9500
C10—C11	1.509 (2)	C15—H15	0.9500
C11—C16	1.394 (2)	C16—H16	0.9500
C11—C12	1.393 (2)
C1—N—C2	125.36 (14)	C14—C15—C16	120.44 (17)
O—C1—N	120.74 (15)	C15—C16—C11	120.83 (17)
O—C1—C9	123.72 (15)	C1—N—H01	117.5 (16)
N—C1—C9	115.54 (15)	C2—N—H01	117.1 (16)
C3—C2—N	119.97 (15)	C2—C3—H3	120.2
C3—C2—C10	126.87 (15)	C4—C3—H3	120.2
N—C2—C10	113.15 (14)	C6—C5—H5	119.8
C2—C3—C4	119.66 (15)	C4—C5—H5	119.8
C9—C4—C5	118.38 (15)	C5—C6—H6	119.6
C9—C4—C3	119.57 (15)	C7—C6—H6	119.6
C5—C4—C3	122.06 (15)	C8—C7—H7	120.2
C6—C5—C4	120.36 (16)	C6—C7—H7	120.2
C5—C6—C7	120.90 (16)	C7—C8—H8	119.9
C8—C7—C6	119.53 (16)	C9—C8—H8	119.9
C7—C8—C9	120.25 (17)	C2—C10—H10A	108.5
C8—C9—C4	120.57 (16)	C11—C10—H10A	108.5
C8—C9—C1	119.53 (15)	C2—C10—H10B	108.5
C4—C9—C1	119.89 (15)	C11—C10—H10B	108.5
C2—C10—C11	114.88 (14)	H10A—C10—H10B	107.5
C16—C11—C12	119.00 (16)	C13—C12—H12	120.3
C16—C11—C10	120.36 (16)	C11—C12—H12	120.3
C12—C11—C10	120.63 (15)	C13—C14—H14	120.9
C13—C12—C11	119.41 (16)	C15—C14—H14	120.9
C12—C13—C14	122.10 (17)	C16—C15—H15	119.8
C12—C13—Br	119.42 (14)	C14—C15—H15	119.8
C14—C13—Br	118.46 (13)	C15—C16—H16	119.6
C13—C14—C15	118.22 (16)	C11—C16—H16	119.6
C2—N—C1—O	179.43 (15)	O—C1—C9—C8	0.6 (3)
C2—N—C1—C9	−0.6 (2)	N—C1—C9—C8	−179.41 (15)
C1—N—C2—C3	1.0 (3)	O—C1—C9—C4	179.80 (15)
C1—N—C2—C10	−178.22 (15)	N—C1—C9—C4	−0.2 (2)
N—C2—C3—C4	−0.5 (2)	C3—C2—C10—C11	2.2 (3)
C10—C2—C3—C4	178.55 (16)	N—C2—C10—C11	−178.69 (14)
C2—C3—C4—C9	−0.2 (2)	C2—C10—C11—C16	−106.28 (18)
C2—C3—C4—C5	179.80 (16)	C2—C10—C11—C12	75.1 (2)
C9—C4—C5—C6	0.4 (2)	C16—C11—C12—C13	0.1 (2)
C3—C4—C5—C6	−179.64 (16)	C10—C11—C12—C13	178.82 (15)
C4—C5—C6—C7	0.1 (3)	C11—C12—C13—C14	−0.6 (3)
C5—C6—C7—C8	−0.8 (3)	C11—C12—C13—Br	−179.29 (12)
C6—C7—C8—C9	0.9 (3)	C12—C13—C14—C15	0.4 (3)
C7—C8—C9—C4	−0.4 (3)	Br—C13—C14—C15	179.16 (13)
C7—C8—C9—C1	178.80 (15)	C13—C14—C15—C16	0.1 (3)
C5—C4—C9—C8	−0.2 (2)	C14—C15—C16—C11	−0.6 (3)
C3—C4—C9—C8	179.78 (15)	C12—C11—C16—C15	0.4 (3)
C5—C4—C9—C1	−179.46 (15)	C10—C11—C16—C15	−178.27 (16)
C3—C4—C9—C1	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N—H01···Oi	0.85 (3)	1.96 (3)	2.8036 (19)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H01⋯Oi	0.85 (3)	1.96 (3)	2.8036 (19)	176 (2)

Symmetry code: (i) .