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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o112
https://doi.org/10.1107/S1600536810051329

1-(2-Bromo­benzoyl)-6,7-(methylene­di­oxy)iso­quinoline

Supakit Achiwawanich,a Nisachon Khunnawutmanotham,b Supanna Techasakul,a Narongsuk Chaichitc and Sutatip Siripaisarnpipata*

aCenter of Excellence in Functional Materials, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand, bChulabhorn Research Institute, Vibhavadee–Rangsit Highway, Laksi, Bangkok 10210, Thailand., and cDepartment of Physics, Faculty of Science, Thammasart University, Vibhavadee–Rangsit Highway, Bangkok, Thailand.
*Correspondence e-mail: fscists@ku.ac.th

(Received 18 November 2010; accepted 7 December 2010; online 11 December 2010)

In the title mol­ecule, C17H10BrNO3, the mean planes of tricycle and bromo­phenyl fragments form a dihedral angle of 75.5 (1)°. In the crystal, π–π inter­actions [centroid–centroid distances = 3.556 (2) and 3.898 (8) Å] between the isoquinoline systems link mol­ecules into stacks parallel to the a axis. The crystal packing also exibits weak inter­molecular 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[Cuny, G. D. (2004). Tetrahedron Lett. 45, 5167-5170.]); Lafrance et al. (2004[Lafrance, M., Blaquiere, N. & Fagnou, K. (2004). Chem. Commun. pp. 2874-2875.]). For related structures, see: Orito et al. (2000[Orito, K., Uchiito, S., Satoh, Y., Tatsuzawa, T., Harada, R. & Tokuda, M. (2000). Org. Lett. 2, 307-310.]).

[Scheme 1]

Experimental

Crystal data

  • C17H10BrNO3

  • Mr = 356.17

  • Triclinic, [P \overline 1]

  • 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)

  • Rint = 0.015
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 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

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) x, y-1, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051329/cv5003Isup2.hkl

checkCIF report


Comment top

The title compound (I) has been obtained in the framework of our work directed to the synthesis of oxoaporphine from isoquinoline to use it as a substrate for coupling reaction to reach an oxoaporphine product (Cuny et al., 2004; Lafrance et al., 2004).

In (I) (Fig. 1), all bond lengths and angles are normal and comparable with those observed in related compounds (Orito et al., 2000). The C11—O3 bond length is 1.210 (3) Å - typical for carbonyl group. The mean planes of tricycle and bromophenyl fragments form a dihedral angle of 75.5 (1)°. The C5-C10-C11-C12 torsion angle is 146.1 (3)°.

In the crystal structure, weak intermolecular π-π interactions between the isoquinoline systems (Table 1) link the molecules into stacks parallel to the axis a. The crystal packing exibits also weak intermolecular C—H···O hydrogen bonds (Table 2).

Related literature top

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 et al. (2004); Lafrance et al. (2004). For related structures, see: Orito et al. (2000).

Experimental top

The title compound was synthesized from piperonal in five steps. The 3,4-methylenedioxypiperonal was converted into phenylethylamine by the reaction with CH3NO2, NH4OAc and acetic acid at 90°C for 2 h.The phenylethylamine was then treated with 4-nitrobenzenesulfonyl chloride at room temperature for 40 h yielding sulfonamide. The sulfonamide further reacted with glyoxal compound at room temperature for 46 h. The resulting product, tetrahydroisoquinoline, was dehydrogenated under basic condition giving the title compound as pale yellow needles.

Refinement top

All H atoms were geometrically positioned (C—H 0.93-0.97 Å), and refined as riding, with Uiso(H) = 1.2-1.5 Ueq of the parent atom.

Structure description top

The title compound (I) has been obtained in the framework of our work directed to the synthesis of oxoaporphine from isoquinoline to use it as a substrate for coupling reaction to reach an oxoaporphine product (Cuny et al., 2004; Lafrance et al., 2004).

In (I) (Fig. 1), all bond lengths and angles are normal and comparable with those observed in related compounds (Orito et al., 2000). The C11—O3 bond length is 1.210 (3) Å - typical for carbonyl group. The mean planes of tricycle and bromophenyl fragments form a dihedral angle of 75.5 (1)°. The C5-C10-C11-C12 torsion angle is 146.1 (3)°.

In the crystal structure, weak intermolecular π-π interactions between the isoquinoline systems (Table 1) link the molecules into stacks parallel to the axis a. The crystal packing exibits also weak intermolecular C—H···O hydrogen bonds (Table 2).

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 et al. (2004); Lafrance et al. (2004). For related structures, see: Orito et al. (2000).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probabilty displacement ellipsoids.
(2-Bromophenyl)(2H-naphtho[2,3-d][1,3]dioxol-5-yl)methanone top
Crystal data top
C17H10BrNO3Z = 2
Mr = 356.17F(000) = 356
Triclinic, P1Dx = 1.707 Mg m−3
a = 7.6152 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.8130 (6) ÅCell parameters from 25 reflections
c = 12.0454 (9) Åθ = 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) Å30.16 × 0.13 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		2276 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
Graphite monochromatorθmax = 30.5°, θmin = 2.7°
phi and ω scansh = −10→7
3157 measured reflectionsk = −11→9
2742 independent reflectionsl = −16→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-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 parametersΔρmax = 0.64 e Å−3
0 restraintsΔρmin = −0.76 e Å−3
Crystal data top
C17H10BrNO3γ = 100.264 (2)°
Mr = 356.17V = 693.06 (9) Å3
Triclinic, P1Z = 2
a = 7.6152 (6) ÅMo Kα radiation
b = 7.8130 (6) ŵ = 2.98 mm−1
c = 12.0454 (9) ÅT = 298 K
α = 98.339 (2)°0.16 × 0.13 × 0.11 mm
β = 94.982 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2276 reflections with I > 2σ(I)
3157 measured reflectionsRint = 0.015
2742 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 1.04Δρmax = 0.64 e Å−3
2742 reflectionsΔρmin = −0.76 e Å−3
199 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br0.29325 (5)0.84480 (4)0.65647 (3)0.05585 (17)
O11.0229 (3)0.6977 (3)1.29657 (19)0.0484 (6)
O21.0035 (3)0.9486 (3)1.2189 (2)0.0489 (6)
O30.5942 (4)0.8829 (3)0.8581 (2)0.0533 (6)
N0.5871 (4)0.4413 (3)0.8070 (2)0.0372 (5)
C11.0794 (5)0.8853 (4)1.3122 (3)0.0541 (9)
H1A1.04050.93891.38130.065*
H1B1.20940.91601.31840.065*
C20.9304 (4)0.6499 (4)1.1915 (2)0.0352 (6)
C30.9177 (4)0.8020 (3)1.1432 (2)0.0353 (6)
C40.8317 (4)0.7975 (3)1.0398 (2)0.0358 (6)
H4A0.82490.90011.01040.043*
C50.7512 (4)0.6262 (3)0.9773 (2)0.0297 (5)
C60.7642 (4)0.4726 (3)1.0269 (2)0.0307 (5)
C70.8554 (4)0.4857 (3)1.1363 (3)0.0369 (6)
H7A0.86360.38611.16890.044*
C80.6816 (4)0.3074 (3)0.9630 (2)0.0375 (6)
H8A0.68470.20480.99320.045*
C90.5975 (4)0.2978 (3)0.8574 (3)0.0392 (6)
H9A0.54410.18710.81740.047*
C100.6596 (4)0.5985 (3)0.8670 (2)0.0322 (5)
C110.6251 (4)0.7482 (3)0.8073 (2)0.0353 (6)
C120.6279 (4)0.7207 (3)0.6816 (2)0.0330 (6)
C130.7726 (4)0.6592 (4)0.6371 (3)0.0411 (7)
H13A0.85740.62480.68500.049*
C140.7927 (5)0.6483 (4)0.5236 (3)0.0461 (7)
H14A0.89290.61230.49610.055*
C150.6625 (5)0.6914 (4)0.4513 (3)0.0491 (8)
H15A0.67340.68070.37440.059*
C160.5171 (5)0.7501 (4)0.4921 (3)0.0482 (8)
H16A0.42990.77860.44290.058*
C170.5004 (4)0.7668 (3)0.6066 (3)0.0372 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0385 (2)0.0639 (2)0.0752 (3)0.02005 (16)0.00774 (18)0.03108 (17)
O10.0518 (15)0.0501 (11)0.0419 (13)0.0091 (10)−0.0035 (10)0.0090 (8)
O20.0525 (14)0.0400 (10)0.0478 (13)0.0053 (9)−0.0099 (10)0.0000 (8)
O30.080 (2)0.0352 (10)0.0486 (13)0.0286 (11)0.0000 (11)0.0041 (8)
N0.0442 (14)0.0287 (10)0.0383 (13)0.0081 (9)0.0022 (10)0.0042 (8)
C10.055 (2)0.0509 (17)0.052 (2)0.0093 (15)−0.0082 (15)0.0023 (13)
C20.0324 (14)0.0433 (13)0.0326 (14)0.0107 (11)0.0065 (11)0.0095 (10)
C30.0314 (14)0.0341 (11)0.0396 (15)0.0059 (10)0.0034 (11)0.0043 (9)
C40.0365 (15)0.0280 (10)0.0431 (16)0.0063 (10)0.0019 (11)0.0082 (9)
C50.0312 (13)0.0267 (10)0.0336 (13)0.0083 (9)0.0074 (10)0.0076 (8)
C60.0318 (14)0.0287 (10)0.0347 (14)0.0072 (9)0.0089 (10)0.0109 (8)
C70.0375 (16)0.0368 (12)0.0411 (16)0.0098 (11)0.0083 (12)0.0166 (10)
C80.0454 (17)0.0241 (10)0.0459 (16)0.0075 (10)0.0103 (12)0.0115 (9)
C90.0477 (18)0.0257 (10)0.0436 (16)0.0058 (10)0.0067 (12)0.0048 (9)
C100.0348 (14)0.0271 (10)0.0367 (14)0.0087 (9)0.0049 (10)0.0079 (9)
C110.0416 (16)0.0304 (11)0.0356 (15)0.0103 (10)0.0008 (11)0.0092 (9)
C120.0339 (14)0.0273 (10)0.0379 (14)0.0055 (9)−0.0004 (11)0.0095 (8)
C130.0434 (18)0.0409 (13)0.0393 (16)0.0088 (12)0.0000 (12)0.0092 (10)
C140.0449 (19)0.0476 (15)0.0464 (19)0.0103 (13)0.0082 (14)0.0064 (12)
C150.054 (2)0.0549 (17)0.0370 (17)0.0032 (15)0.0047 (14)0.0136 (12)
C160.0415 (18)0.0573 (17)0.0460 (19)0.0030 (14)−0.0057 (14)0.0229 (13)
C170.0309 (14)0.0344 (12)0.0473 (17)0.0035 (10)0.0005 (11)0.0166 (10)
Geometric parameters (Å, º) top
Br—C171.903 (3)C6—C71.417 (4)
O1—C21.361 (4)C7—H7A0.9300
O1—C11.432 (4)C8—C91.360 (4)
O2—C31.378 (3)C8—H8A0.9300
O2—C11.411 (4)C9—H9A0.9300
O3—C111.210 (3)C10—C111.509 (3)
N—C101.330 (3)C11—C121.501 (4)
N—C91.361 (3)C12—C131.396 (5)
C1—H1A0.9700C12—C171.398 (4)
C1—H1B0.9700C13—C141.381 (5)
C2—C71.356 (4)C13—H13A0.9300
C2—C31.411 (4)C14—C151.382 (5)
C3—C41.349 (4)C14—H14A0.9300
C4—C51.438 (3)C15—C161.374 (6)
C4—H4A0.9300C15—H15A0.9300
C5—C101.414 (4)C16—C171.385 (5)
C5—C61.431 (3)C16—H16A0.9300
C6—C81.412 (3)
Cg1···Cg1i3.556 (2)Cg1···Cg2ii3.898 (8)
C2—O1—C1106.0 (2)C6—C8—H8A119.9
C3—O2—C1106.2 (2)C8—C9—N123.6 (2)
C10—N—C9117.2 (2)C8—C9—H9A118.2
O2—C1—O1108.9 (2)N—C9—H9A118.2
O2—C1—H1A109.9N—C10—C5124.7 (2)
O1—C1—H1A109.9N—C10—C11112.6 (2)
O2—C1—H1B109.9C5—C10—C11122.6 (2)
O1—C1—H1B109.9O3—C11—C12121.7 (2)
H1A—C1—H1B108.3O3—C11—C10121.5 (3)
C7—C2—O1128.5 (3)C12—C11—C10116.8 (2)
C7—C2—C3121.9 (3)C13—C12—C17117.7 (3)
O1—C2—C3109.6 (2)C13—C12—C11118.7 (2)
C4—C3—O2127.5 (3)C17—C12—C11123.4 (3)
C4—C3—C2123.5 (2)C14—C13—C12121.5 (3)
O2—C3—C2108.9 (2)C14—C13—H13A119.2
C3—C4—C5116.7 (2)C12—C13—H13A119.2
C3—C4—H4A121.6C13—C14—C15119.4 (3)
C5—C4—H4A121.6C13—C14—H14A120.3
C10—C5—C6116.8 (2)C15—C14—H14A120.3
C10—C5—C4123.7 (2)C16—C15—C14120.4 (3)
C6—C5—C4119.4 (2)C16—C15—H15A119.8
C8—C6—C7121.2 (2)C14—C15—H15A119.8
C8—C6—C5117.5 (2)C15—C16—C17120.0 (3)
C7—C6—C5121.3 (2)C15—C16—H16A120.0
C2—C7—C6117.1 (2)C17—C16—H16A120.0
C2—C7—H7A121.5C16—C17—C12120.9 (3)
C6—C7—H7A121.5C16—C17—Br117.6 (2)
C9—C8—C6120.2 (2)C12—C17—Br121.5 (2)
C9—C8—H8A119.9
C3—O2—C1—O1−5.7 (4)C9—N—C10—C52.2 (5)
C2—O1—C1—O25.7 (4)C9—N—C10—C11−174.6 (3)
C1—O1—C2—C7177.5 (3)C6—C5—C10—N−0.5 (5)
C1—O1—C2—C3−3.5 (4)C4—C5—C10—N178.7 (3)
C1—O2—C3—C4−177.3 (3)C6—C5—C10—C11175.9 (3)
C1—O2—C3—C23.5 (4)C4—C5—C10—C11−4.9 (5)
C7—C2—C3—C4−0.1 (5)N—C10—C11—O3141.9 (3)
O1—C2—C3—C4−179.2 (3)C5—C10—C11—O3−34.9 (5)
C7—C2—C3—O2179.1 (3)N—C10—C11—C12−37.1 (4)
O1—C2—C3—O20.0 (4)C5—C10—C11—C12146.1 (3)
O2—C3—C4—C5−179.5 (3)O3—C11—C12—C13131.7 (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—C60.5 (4)C10—C11—C12—C17136.1 (3)
C10—C5—C6—C8−1.4 (4)C17—C12—C13—C141.7 (4)
C4—C5—C6—C8179.4 (3)C11—C12—C13—C14−173.3 (2)
C10—C5—C6—C7179.1 (3)C12—C13—C14—C15−3.0 (4)
C4—C5—C6—C7−0.2 (4)C13—C14—C15—C162.1 (5)
O1—C2—C7—C6179.4 (3)C14—C15—C16—C170.2 (5)
C3—C2—C7—C60.5 (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—C160.6 (4)
C7—C6—C8—C9−178.9 (3)C11—C12—C17—C16175.3 (2)
C5—C6—C8—C91.6 (5)C13—C12—C17—Br177.88 (19)
C6—C8—C9—N0.1 (5)C11—C12—C17—Br−7.4 (3)
C10—N—C9—C8−2.0 (5)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O3iii0.932.583.239 (3)128
Symmetry code: (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC17H10BrNO3
Mr356.17
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.6152 (6), 7.8130 (6), 12.0454 (9)
α, β, γ (°)98.339 (2), 94.982 (1), 100.264 (2)
V (Å3)693.06 (9)
Z2
Radiation typeMo Kα
µ (mm−1)2.98
Crystal size (mm)0.16 × 0.13 × 0.11
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		3157, 2742, 2276
Rint0.015
(sin θ/λ)max (Å−1)0.713
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.130, 1.04
No. of reflections2742
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.64, −0.76

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O3i0.932.583.239 (3)128
Symmetry code: (i) x, y−1, z.
 

Acknowledgements

The authors thank the Chulabhorn Research Institute and the Department of Chemistry, Faculty of Science, Kasetsart University, for financial support.

References

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o112
https://doi.org/10.1107/S1600536810051329
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