1-(2-Bromobenzoyl)-6,7-(methylene-dioxy)isoquinoline.

In the title mol-ecule, C(17)H(10)BrNO(3), the mean planes of tricycle and bromo-phenyl fragments form a dihedral angle of 75.5 (1)°. In the crystal, π-π inter-actions [centroid-centroid distances = 3.556 (2) and 3.898 (8) Å] between the isoquinoline systems link mol-ecules into stacks parallel to the a axis. The crystal packing also exibits weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

The title compound was been obtained during our work on the synthesis of oxoaporphine from isoquinoline for use as a substrate for coupling reactions to obtain an oxoaporphine product, see: Cuny (2004 ▶); Lafrance et al. (2004 ▶). For related structures, see: Orito et al. (2000 ▶).

Experimental

Crystal data

C17H10BrNO3

M = 356.17

Triclinic,

a = 7.6152 (6) Å

b = 7.8130 (6) Å

c = 12.0454 (9) Å

α = 98.339 (2)°

β = 94.982 (1)°

γ = 100.264 (2)°

V = 693.06 (9) Å3

Z = 2

Mo Kα radiation

μ = 2.98 mm−1

T = 298 K

0.16 × 0.13 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

3157 measured reflections

2742 independent reflections

2276 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.04

2742 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.76 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051329/cv5003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051329/cv5003Isup2.hkl

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

C17H10BrNO3	Z = 2
Mr = 356.17	F(000) = 356
Triclinic, P1	Dx = 1.707 Mg m−3
a = 7.6152 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8130 (6) Å	Cell parameters from 25 reflections
c = 12.0454 (9) Å	θ = 25–35°
α = 98.339 (2)°	µ = 2.98 mm−1
β = 94.982 (1)°	T = 298 K
γ = 100.264 (2)°	Needle, colourless
V = 693.06 (9) Å3	0.16 × 0.13 × 0.11 mm

Bruker SMART CCD area-detector diffractometer	2276 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
graphite	θmax = 30.5°, θmin = 2.7°
phi and ω scans	h = −10→7
3157 measured reflections	k = −11→9
2742 independent reflections	l = −16→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0873P)2 + 0.147P] where P = (Fo2 + 2Fc2)/3
2742 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.76 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
Br	0.29325 (5)	0.84480 (4)	0.65647 (3)	0.05585 (17)
O1	1.0229 (3)	0.6977 (3)	1.29657 (19)	0.0484 (6)
O2	1.0035 (3)	0.9486 (3)	1.2189 (2)	0.0489 (6)
O3	0.5942 (4)	0.8829 (3)	0.8581 (2)	0.0533 (6)
N	0.5871 (4)	0.4413 (3)	0.8070 (2)	0.0372 (5)
C1	1.0794 (5)	0.8853 (4)	1.3122 (3)	0.0541 (9)
H1A	1.0405	0.9389	1.3813	0.065*
H1B	1.2094	0.9160	1.3184	0.065*
C2	0.9304 (4)	0.6499 (4)	1.1915 (2)	0.0352 (6)
C3	0.9177 (4)	0.8020 (3)	1.1432 (2)	0.0353 (6)
C4	0.8317 (4)	0.7975 (3)	1.0398 (2)	0.0358 (6)
H4A	0.8249	0.9001	1.0104	0.043*
C5	0.7512 (4)	0.6262 (3)	0.9773 (2)	0.0297 (5)
C6	0.7642 (4)	0.4726 (3)	1.0269 (2)	0.0307 (5)
C7	0.8554 (4)	0.4857 (3)	1.1363 (3)	0.0369 (6)
H7A	0.8636	0.3861	1.1689	0.044*
C8	0.6816 (4)	0.3074 (3)	0.9630 (2)	0.0375 (6)
H8A	0.6847	0.2048	0.9932	0.045*
C9	0.5975 (4)	0.2978 (3)	0.8574 (3)	0.0392 (6)
H9A	0.5441	0.1871	0.8174	0.047*
C10	0.6596 (4)	0.5985 (3)	0.8670 (2)	0.0322 (5)
C11	0.6251 (4)	0.7482 (3)	0.8073 (2)	0.0353 (6)
C12	0.6279 (4)	0.7207 (3)	0.6816 (2)	0.0330 (6)
C13	0.7726 (4)	0.6592 (4)	0.6371 (3)	0.0411 (7)
H13A	0.8574	0.6248	0.6850	0.049*
C14	0.7927 (5)	0.6483 (4)	0.5236 (3)	0.0461 (7)
H14A	0.8929	0.6123	0.4961	0.055*
C15	0.6625 (5)	0.6914 (4)	0.4513 (3)	0.0491 (8)
H15A	0.6734	0.6807	0.3744	0.059*
C16	0.5171 (5)	0.7501 (4)	0.4921 (3)	0.0482 (8)
H16A	0.4299	0.7786	0.4429	0.058*
C17	0.5004 (4)	0.7668 (3)	0.6066 (3)	0.0372 (6)

	U11	U22	U33	U12	U13	U23
Br	0.0385 (2)	0.0639 (2)	0.0752 (3)	0.02005 (16)	0.00774 (18)	0.03108 (17)
O1	0.0518 (15)	0.0501 (11)	0.0419 (13)	0.0091 (10)	−0.0035 (10)	0.0090 (8)
O2	0.0525 (14)	0.0400 (10)	0.0478 (13)	0.0053 (9)	−0.0099 (10)	0.0000 (8)
O3	0.080 (2)	0.0352 (10)	0.0486 (13)	0.0286 (11)	0.0000 (11)	0.0041 (8)
N	0.0442 (14)	0.0287 (10)	0.0383 (13)	0.0081 (9)	0.0022 (10)	0.0042 (8)
C1	0.055 (2)	0.0509 (17)	0.052 (2)	0.0093 (15)	−0.0082 (15)	0.0023 (13)
C2	0.0324 (14)	0.0433 (13)	0.0326 (14)	0.0107 (11)	0.0065 (11)	0.0095 (10)
C3	0.0314 (14)	0.0341 (11)	0.0396 (15)	0.0059 (10)	0.0034 (11)	0.0043 (9)
C4	0.0365 (15)	0.0280 (10)	0.0431 (16)	0.0063 (10)	0.0019 (11)	0.0082 (9)
C5	0.0312 (13)	0.0267 (10)	0.0336 (13)	0.0083 (9)	0.0074 (10)	0.0076 (8)
C6	0.0318 (14)	0.0287 (10)	0.0347 (14)	0.0072 (9)	0.0089 (10)	0.0109 (8)
C7	0.0375 (16)	0.0368 (12)	0.0411 (16)	0.0098 (11)	0.0083 (12)	0.0166 (10)
C8	0.0454 (17)	0.0241 (10)	0.0459 (16)	0.0075 (10)	0.0103 (12)	0.0115 (9)
C9	0.0477 (18)	0.0257 (10)	0.0436 (16)	0.0058 (10)	0.0067 (12)	0.0048 (9)
C10	0.0348 (14)	0.0271 (10)	0.0367 (14)	0.0087 (9)	0.0049 (10)	0.0079 (9)
C11	0.0416 (16)	0.0304 (11)	0.0356 (15)	0.0103 (10)	0.0008 (11)	0.0092 (9)
C12	0.0339 (14)	0.0273 (10)	0.0379 (14)	0.0055 (9)	−0.0004 (11)	0.0095 (8)
C13	0.0434 (18)	0.0409 (13)	0.0393 (16)	0.0088 (12)	0.0000 (12)	0.0092 (10)
C14	0.0449 (19)	0.0476 (15)	0.0464 (19)	0.0103 (13)	0.0082 (14)	0.0064 (12)
C15	0.054 (2)	0.0549 (17)	0.0370 (17)	0.0032 (15)	0.0047 (14)	0.0136 (12)
C16	0.0415 (18)	0.0573 (17)	0.0460 (19)	0.0030 (14)	−0.0057 (14)	0.0229 (13)
C17	0.0309 (14)	0.0344 (12)	0.0473 (17)	0.0035 (10)	0.0005 (11)	0.0166 (10)

Br—C17	1.903 (3)	C6—C7	1.417 (4)
O1—C2	1.361 (4)	C7—H7A	0.9300
O1—C1	1.432 (4)	C8—C9	1.360 (4)
O2—C3	1.378 (3)	C8—H8A	0.9300
O2—C1	1.411 (4)	C9—H9A	0.9300
O3—C11	1.210 (3)	C10—C11	1.509 (3)
N—C10	1.330 (3)	C11—C12	1.501 (4)
N—C9	1.361 (3)	C12—C13	1.396 (5)
C1—H1A	0.9700	C12—C17	1.398 (4)
C1—H1B	0.9700	C13—C14	1.381 (5)
C2—C7	1.356 (4)	C13—H13A	0.9300
C2—C3	1.411 (4)	C14—C15	1.382 (5)
C3—C4	1.349 (4)	C14—H14A	0.9300
C4—C5	1.438 (3)	C15—C16	1.374 (6)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C10	1.414 (4)	C16—C17	1.385 (5)
C5—C6	1.431 (3)	C16—H16A	0.9300
C6—C8	1.412 (3)
Cg1···Cg1i	3.556 (2)	Cg1···Cg2ii	3.898 (8)
C2—O1—C1	106.0 (2)	C6—C8—H8A	119.9
C3—O2—C1	106.2 (2)	C8—C9—N	123.6 (2)
C10—N—C9	117.2 (2)	C8—C9—H9A	118.2
O2—C1—O1	108.9 (2)	N—C9—H9A	118.2
O2—C1—H1A	109.9	N—C10—C5	124.7 (2)
O1—C1—H1A	109.9	N—C10—C11	112.6 (2)
O2—C1—H1B	109.9	C5—C10—C11	122.6 (2)
O1—C1—H1B	109.9	O3—C11—C12	121.7 (2)
H1A—C1—H1B	108.3	O3—C11—C10	121.5 (3)
C7—C2—O1	128.5 (3)	C12—C11—C10	116.8 (2)
C7—C2—C3	121.9 (3)	C13—C12—C17	117.7 (3)
O1—C2—C3	109.6 (2)	C13—C12—C11	118.7 (2)
C4—C3—O2	127.5 (3)	C17—C12—C11	123.4 (3)
C4—C3—C2	123.5 (2)	C14—C13—C12	121.5 (3)
O2—C3—C2	108.9 (2)	C14—C13—H13A	119.2
C3—C4—C5	116.7 (2)	C12—C13—H13A	119.2
C3—C4—H4A	121.6	C13—C14—C15	119.4 (3)
C5—C4—H4A	121.6	C13—C14—H14A	120.3
C10—C5—C6	116.8 (2)	C15—C14—H14A	120.3
C10—C5—C4	123.7 (2)	C16—C15—C14	120.4 (3)
C6—C5—C4	119.4 (2)	C16—C15—H15A	119.8
C8—C6—C7	121.2 (2)	C14—C15—H15A	119.8
C8—C6—C5	117.5 (2)	C15—C16—C17	120.0 (3)
C7—C6—C5	121.3 (2)	C15—C16—H16A	120.0
C2—C7—C6	117.1 (2)	C17—C16—H16A	120.0
C2—C7—H7A	121.5	C16—C17—C12	120.9 (3)
C6—C7—H7A	121.5	C16—C17—Br	117.6 (2)
C9—C8—C6	120.2 (2)	C12—C17—Br	121.5 (2)
C9—C8—H8A	119.9
C3—O2—C1—O1	−5.7 (4)	C9—N—C10—C5	2.2 (5)
C2—O1—C1—O2	5.7 (4)	C9—N—C10—C11	−174.6 (3)
C1—O1—C2—C7	177.5 (3)	C6—C5—C10—N	−0.5 (5)
C1—O1—C2—C3	−3.5 (4)	C4—C5—C10—N	178.7 (3)
C1—O2—C3—C4	−177.3 (3)	C6—C5—C10—C11	175.9 (3)
C1—O2—C3—C2	3.5 (4)	C4—C5—C10—C11	−4.9 (5)
C7—C2—C3—C4	−0.1 (5)	N—C10—C11—O3	141.9 (3)
O1—C2—C3—C4	−179.2 (3)	C5—C10—C11—O3	−34.9 (5)
C7—C2—C3—O2	179.1 (3)	N—C10—C11—C12	−37.1 (4)
O1—C2—C3—O2	0.0 (4)	C5—C10—C11—C12	146.1 (3)
O2—C3—C4—C5	−179.5 (3)	O3—C11—C12—C13	131.7 (3)
C2—C3—C4—C5	−0.4 (5)	C10—C11—C12—C13	−49.3 (3)
C3—C4—C5—C10	−178.6 (3)	O3—C11—C12—C17	−42.9 (4)
C3—C4—C5—C6	0.5 (4)	C10—C11—C12—C17	136.1 (3)
C10—C5—C6—C8	−1.4 (4)	C17—C12—C13—C14	1.7 (4)
C4—C5—C6—C8	179.4 (3)	C11—C12—C13—C14	−173.3 (2)
C10—C5—C6—C7	179.1 (3)	C12—C13—C14—C15	−3.0 (4)
C4—C5—C6—C7	−0.2 (4)	C13—C14—C15—C16	2.1 (5)
O1—C2—C7—C6	179.4 (3)	C14—C15—C16—C17	0.2 (5)
C3—C2—C7—C6	0.5 (5)	C15—C16—C17—C12	−1.5 (4)
C8—C6—C7—C2	−179.9 (3)	C15—C16—C17—Br	−178.9 (2)
C5—C6—C7—C2	−0.3 (4)	C13—C12—C17—C16	0.6 (4)
C7—C6—C8—C9	−178.9 (3)	C11—C12—C17—C16	175.3 (2)
C5—C6—C8—C9	1.6 (5)	C13—C12—C17—Br	177.88 (19)
C6—C8—C9—N	0.1 (5)	C11—C12—C17—Br	−7.4 (3)
C10—N—C9—C8	−2.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O3iii	0.93	2.58	3.239 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O3i	0.93	2.58	3.239 (3)	128

Symmetry code: (i) .