3-(3-Bromo-benz-yl)-1H-isochromen-1-one.

In the title compound, C(16)H(11)BrO(2), the isocoumarin ring system is planar (r.m.s. deviation = 0.015 Å) and subtends a dihedral angle of 88.90 (2)° with the bromo-benzene ring. In the crystal, mol-ecules are linked, forming a three-dimensional packing pattern involving C-H⋯O inter-actions, Br⋯O contacts [3.4734 (10) Å] and π-π stacking inter-actions with centroid-centroid distances ranging from 3.667 (2) to 3.765 (2) Å.

Related literature

For the properties and applications of isocoumarins and 3,4-dihydro­isocoumarins, see: Chinworrungsee et al. (2002 ▶); Devienne et al. (2002 ▶); Mali & Babu (1998 ▶); Rama et al. (1998 ▶); Waters & Kozlowski (2001 ▶). For related structures, see: Abid et al. (2008 ▶); Babar et al. (2008 ▶).

Experimental

Crystal data

C16H11BrO2

M = 315.16

Triclinic,

a = 7.4508 (5) Å

b = 8.1824 (6) Å

c = 11.3663 (8) Å

α = 90.130 (6)°

β = 98.392 (7)°

γ = 113.844 (8)°

V = 625.58 (8) Å3

Z = 2

Mo Kα radiation

μ = 3.28 mm−1

T = 103 K

0.25 × 0.25 × 0.20 mm

Data collection

Oxford Xcalibur E diffractometer

Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction 2009 ▶) T min = 0.922, T max = 1.000

16250 measured reflections

3449 independent reflections

2899 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.045

S = 0.97

3449 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; 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/S1600536809037246/rz2357sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037246/rz2357Isup2.hkl

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

C16H11BrO2	Z = 2
Mr = 315.16	F(000) = 316
Triclinic, P1	Dx = 1.673 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4508 (5) Å	Cell parameters from 9750 reflections
b = 8.1824 (6) Å	θ = 2.7–30.7°
c = 11.3663 (8) Å	µ = 3.28 mm−1
α = 90.130 (6)°	T = 103 K
β = 98.392 (7)°	Block, colourless
γ = 113.844 (8)°	0.25 × 0.25 × 0.20 mm
V = 625.58 (8) Å3

Oxford Xcalibur E diffractometer	3449 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2899 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 16.1419 pixels mm-1	θmax = 29.6°, θmin = 3.0°
ω scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction 2009)	k = −11→11
Tmin = 0.922, Tmax = 1.000	l = −15→15
16250 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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.045	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0233P)2] where P = (Fo2 + 2Fc2)/3
3449 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.25 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.Non-bonded contact:3.4734 (0.0010) Br - O2_$5 157.19 (0.04) C13 - Br - O2_$5 144.68 (0.08) Br - O2_$5 - C1_$5 Operator for generating equivalent atoms: $5 x - 1, y, z - 1Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)- 1.8912 (0.0020) x + 7.3803 (0.0014) y + 4.4053 (0.0037) z = 0.7728 (0.0010)* 0.0088 (0.0008) C10 * -0.0063 (0.0011) C11 * 0.0058 (0.0010) C12 * 0.0167 (0.0011) C13 * 0.0215 (0.0010) C14 * -0.0036 (0.0009) C15 * -0.0224 (0.0011) C16 * -0.0204 (0.0006) BrRms deviation of fitted atoms = 0.01517.0134 (0.0011) x - 0.6456 (0.0018) y - 2.6242 (0.0032) z = 3.6495 (0.0018)Angle to previous plane (with approximate e.s.d.) = 88.90 (0.02)* -0.0183 (0.0009) C10 * -0.0095 (0.0009) O1 * 0.0027 (0.0011) C1 * -0.0081 (0.0008) O2 * 0.0273 (0.0011) C3 * 0.0129 (0.0012) C4 * -0.0052 (0.0011) C5 * -0.0241 (0.0011) C6 * -0.0078 (0.0012) C7 * 0.0144 (0.0012) C8 * 0.0159 (0.0012) C9Rms deviation of fitted atoms = 0.0152

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	0.13942 (2)	0.205557 (19)	−0.113746 (13)	0.02023 (5)
O1	0.70881 (14)	0.19099 (12)	0.46026 (8)	0.0146 (2)
O2	0.78538 (15)	0.22208 (13)	0.65672 (8)	0.0195 (2)
C1	0.75969 (19)	0.29281 (17)	0.56653 (12)	0.0141 (3)
C2	0.67678 (19)	0.25762 (17)	0.35091 (11)	0.0128 (3)
C3	0.69140 (19)	0.42394 (17)	0.34239 (11)	0.0136 (3)
H3	0.6699	0.4662	0.2661	0.016*
C4	0.73964 (18)	0.54146 (17)	0.44789 (11)	0.0124 (3)
C5	0.7521 (2)	0.71742 (18)	0.44484 (12)	0.0170 (3)
H5	0.7288	0.7643	0.3706	0.020*
C6	0.7982 (2)	0.82214 (18)	0.54931 (13)	0.0182 (3)
H6	0.8045	0.9404	0.5465	0.022*
C7	0.8354 (2)	0.75669 (19)	0.65887 (13)	0.0185 (3)
H7	0.8683	0.8306	0.7301	0.022*
C8	0.8248 (2)	0.58509 (18)	0.66416 (12)	0.0162 (3)
H8	0.8507	0.5406	0.7389	0.019*
C9	0.77565 (19)	0.47639 (17)	0.55899 (11)	0.0126 (3)
C10	0.6231 (2)	0.11432 (17)	0.25339 (11)	0.0161 (3)
H10A	0.4972	0.0138	0.2639	0.019*
H10B	0.7280	0.0682	0.2602	0.019*
C11	0.5989 (2)	0.17984 (17)	0.12982 (11)	0.0144 (3)
C12	0.4136 (2)	0.16677 (17)	0.07491 (11)	0.0146 (3)
H12	0.3011	0.1147	0.1140	0.018*
C13	0.39414 (19)	0.23009 (17)	−0.03706 (12)	0.0143 (3)
C14	0.5553 (2)	0.30743 (18)	−0.09635 (12)	0.0155 (3)
H14	0.5401	0.3518	−0.1726	0.019*
C15	0.7391 (2)	0.31864 (17)	−0.04193 (12)	0.0165 (3)
H15	0.8510	0.3704	−0.0815	0.020*
C16	0.7613 (2)	0.25498 (17)	0.06999 (12)	0.0157 (3)
H16	0.8880	0.2627	0.1061	0.019*

	U11	U22	U33	U12	U13	U23
Br	0.01563 (7)	0.02239 (8)	0.02281 (8)	0.00845 (6)	0.00152 (5)	0.00243 (6)
O1	0.0220 (5)	0.0115 (5)	0.0106 (5)	0.0075 (4)	0.0015 (4)	0.0015 (4)
O2	0.0273 (6)	0.0183 (5)	0.0130 (5)	0.0098 (5)	0.0022 (4)	0.0048 (4)
C1	0.0134 (6)	0.0152 (7)	0.0135 (7)	0.0051 (6)	0.0033 (5)	0.0009 (5)
C2	0.0130 (6)	0.0147 (6)	0.0106 (6)	0.0051 (5)	0.0027 (5)	0.0033 (5)
C3	0.0162 (7)	0.0141 (7)	0.0107 (6)	0.0065 (6)	0.0016 (5)	0.0022 (5)
C4	0.0109 (6)	0.0123 (6)	0.0145 (7)	0.0046 (5)	0.0033 (5)	0.0014 (5)
C5	0.0191 (7)	0.0163 (7)	0.0170 (7)	0.0087 (6)	0.0031 (5)	0.0034 (6)
C6	0.0188 (7)	0.0124 (7)	0.0246 (8)	0.0069 (6)	0.0053 (6)	−0.0005 (6)
C7	0.0181 (7)	0.0183 (7)	0.0183 (7)	0.0062 (6)	0.0045 (6)	−0.0049 (6)
C8	0.0164 (7)	0.0187 (7)	0.0123 (7)	0.0054 (6)	0.0039 (5)	0.0009 (5)
C9	0.0111 (6)	0.0130 (6)	0.0138 (7)	0.0045 (5)	0.0034 (5)	0.0013 (5)
C10	0.0218 (7)	0.0117 (6)	0.0141 (7)	0.0060 (6)	0.0028 (5)	0.0010 (5)
C11	0.0208 (7)	0.0089 (6)	0.0124 (7)	0.0053 (6)	0.0014 (5)	−0.0030 (5)
C12	0.0173 (7)	0.0119 (6)	0.0140 (7)	0.0046 (6)	0.0052 (5)	−0.0014 (5)
C13	0.0147 (6)	0.0121 (6)	0.0155 (7)	0.0058 (5)	0.0001 (5)	−0.0032 (5)
C14	0.0196 (7)	0.0137 (7)	0.0131 (7)	0.0068 (6)	0.0021 (5)	0.0004 (5)
C15	0.0170 (7)	0.0149 (7)	0.0170 (7)	0.0051 (6)	0.0055 (5)	0.0019 (6)
C16	0.0159 (7)	0.0145 (7)	0.0154 (7)	0.0057 (6)	0.0002 (5)	−0.0012 (5)

Br—C13	1.9001 (13)	C11—C16	1.3947 (19)
O1—C1	1.3796 (15)	C12—C13	1.3854 (18)
O1—C2	1.3859 (15)	C13—C14	1.3859 (19)
O2—C1	1.2073 (15)	C14—C15	1.3842 (18)
C1—C9	1.4618 (18)	C15—C16	1.3887 (18)
C2—C3	1.3256 (18)	C3—H3	0.9500
C2—C10	1.4996 (18)	C5—H5	0.9500
C3—C4	1.4426 (18)	C6—H6	0.9500
C4—C9	1.4035 (18)	C7—H7	0.9500
C4—C5	1.4056 (18)	C8—H8	0.9500
C5—C6	1.3787 (19)	C10—H10A	0.9900
C6—C7	1.392 (2)	C10—H10B	0.9900
C7—C8	1.3759 (19)	C12—H12	0.9500
C8—C9	1.3994 (18)	C14—H14	0.9500
C10—C11	1.5166 (18)	C15—H15	0.9500
C11—C12	1.3911 (18)	C16—H16	0.9500
C1—O1—C2	122.56 (10)	C15—C14—C13	118.52 (13)
O2—C1—O1	117.22 (12)	C14—C15—C16	120.63 (13)
O2—C1—C9	126.19 (12)	C15—C16—C11	120.46 (13)
O1—C1—C9	116.59 (11)	C2—C3—H3	119.7
C3—C2—O1	121.65 (12)	C4—C3—H3	119.7
C3—C2—C10	128.78 (12)	C6—C5—H5	119.9
O1—C2—C10	109.56 (11)	C4—C5—H5	119.9
C2—C3—C4	120.62 (12)	C5—C6—H6	119.6
C9—C4—C5	118.50 (12)	C7—C6—H6	119.6
C9—C4—C3	118.22 (12)	C8—C7—H7	119.9
C5—C4—C3	123.28 (12)	C6—C7—H7	119.9
C6—C5—C4	120.19 (13)	C7—C8—H8	120.1
C5—C6—C7	120.77 (13)	C9—C8—H8	120.1
C8—C7—C6	120.14 (13)	C2—C10—H10A	109.0
C7—C8—C9	119.74 (13)	C11—C10—H10A	109.0
C8—C9—C4	120.65 (12)	C2—C10—H10B	109.0
C8—C9—C1	119.01 (12)	C11—C10—H10B	109.0
C4—C9—C1	120.34 (12)	H10A—C10—H10B	107.8
C2—C10—C11	112.98 (11)	C13—C12—H12	120.2
C12—C11—C16	119.06 (12)	C11—C12—H12	120.2
C12—C11—C10	120.17 (12)	C15—C14—H14	120.7
C16—C11—C10	120.77 (12)	C13—C14—H14	120.7
C13—C12—C11	119.64 (12)	C14—C15—H15	119.7
C12—C13—C14	121.67 (13)	C16—C15—H15	119.7
C12—C13—Br	119.50 (10)	C15—C16—H16	119.8
C14—C13—Br	118.81 (10)	C11—C16—H16	119.8
C2—O1—C1—O2	−179.57 (11)	O2—C1—C9—C8	−0.1 (2)
C2—O1—C1—C9	0.95 (17)	O1—C1—C9—C8	179.34 (11)
C1—O1—C2—C3	−0.72 (19)	O2—C1—C9—C4	−179.30 (13)
C1—O1—C2—C10	−179.69 (11)	O1—C1—C9—C4	0.14 (18)
O1—C2—C3—C4	−0.6 (2)	C3—C2—C10—C11	5.0 (2)
C10—C2—C3—C4	178.12 (13)	O1—C2—C10—C11	−176.15 (11)
C2—C3—C4—C9	1.66 (19)	C2—C10—C11—C12	−90.92 (15)
C2—C3—C4—C5	−178.28 (13)	C2—C10—C11—C16	88.60 (15)
C9—C4—C5—C6	−0.22 (19)	C16—C11—C12—C13	−0.72 (19)
C3—C4—C5—C6	179.72 (13)	C10—C11—C12—C13	178.81 (11)
C4—C5—C6—C7	0.9 (2)	C11—C12—C13—C14	−0.27 (19)
C5—C6—C7—C8	−0.6 (2)	C11—C12—C13—Br	178.14 (9)
C6—C7—C8—C9	−0.2 (2)	C12—C13—C14—C15	0.9 (2)
C7—C8—C9—C4	0.9 (2)	Br—C13—C14—C15	−177.54 (10)
C7—C8—C9—C1	−178.34 (13)	C13—C14—C15—C16	−0.50 (19)
C5—C4—C9—C8	−0.63 (19)	C14—C15—C16—C11	−0.5 (2)
C3—C4—C9—C8	179.43 (12)	C12—C11—C16—C15	1.09 (19)
C5—C4—C9—C1	178.56 (12)	C10—C11—C16—C15	−178.44 (12)
C3—C4—C9—C1	−1.38 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.95	2.58	3.4666 (16)	155
C10—H10A···O2ii	0.99	2.50	3.4685 (17)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.58	3.4666 (16)	155
C10—H10A⋯O2ii	0.99	2.50	3.4685 (17)	166

Symmetry codes: (i) ; (ii) .