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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2875.
Published online 2009 October 28. doi:  10.1107/S1600536809043426
PMCID: PMC2971125

5-Amino-7-(4-bromo­phen­yl)indane-4,6-dicarbonitrile

Abstract

In the title mol­ecule, C17H12BrN3, the mean planes of the bicyclic system and the attached aromatic ring form a dihedral angle of 63.12 (7)°. In the crystal structure, weak inter­molecular N—H(...)N hydrogen bonds link adjacent mol­ecules into ribbons extending along [010].

Related literature

Analogous compounds have been synthesized and reported by Hafidh et al. (2002 [triangle]) and Hafidh & Zantour (2003 [triangle]). For a related structure, see Mereiter et al. (2000 [triangle]).

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Object name is e-65-o2875-scheme1.jpg

Experimental

Crystal data

  • C17H12BrN3
  • M r = 338.21
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2875-efi1.jpg
  • a = 7.5655 (14) Å
  • b = 11.811 (2) Å
  • c = 16.490 (3) Å
  • V = 1473.5 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.79 mm−1
  • T = 298 K
  • 0.35 × 0.28 × 0.20 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.442, T max = 0.606
  • 7199 measured reflections
  • 2708 independent reflections
  • 2171 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.063
  • S = 0.95
  • 2708 reflections
  • 198 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.24 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1253 Friedel pairs
  • Flack parameter: 0.008 (10)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043426/cv2633sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043426/cv2633Isup2.hkl

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

supplementary crystallographic information

Comment

indanee derivatives have attracted some attention in a search of novel functional compounds (Hafidh et al. 2002; Hafidh & Zantour, 2003). As our contribution to this field, we present here the title compound, (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related compound (Mereiter et al., 2000). The mean plane of the bicycle system (C7/C8/C10/C11/C13-C17) and attached aromatic ring (C1-C6) form a dihedral angle of 63.12 (7)°.

In the crystal structure, weak intermolecular N—H···N hydrogen bonds (Table 1) link adjacent molecules into ribbons extended in direction [010].

Experimental

The malononitrile (1.32 g,20 mmol) was added into the mixture of 4-bromobenzaldehyde (1.85 g,10 mmol) and cyclopentanone (0.84 g,10 mmol) in 1-butyl-3-methylimidazol-3-ium tetrafluoroborate (20 ml), and has stirred for three hours at 388 K. The solution was allowed to stand for 2 weeks, whereupon the crystals suitable for the X-ray study was obtained. Yield: 1.047 g, 31%. Anal. for C17H12BrN3: Calc. C, 60.37; H, 3.58; N, 12.42; Found: C, 60.54; H, 3.71; N, 12.54%. The No. of CCDC: 750008.

Refinement

C-bound H atoms were placed in geometrically idealized positions (C—H 0.93-0.97 Å) and treated as riding on their parent atoms , with Uiso(H)=1.2Ueq(C). Amino H atoms were located on a difference map and refined isotropically with the bond restraint of N—H = 0.84 (3) Å.

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C17H12BrN3Dx = 1.525 Mg m3
Mr = 338.21Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 2622 reflections
a = 7.5655 (14) Åθ = 2.5–23.4°
b = 11.811 (2) ŵ = 2.79 mm1
c = 16.490 (3) ÅT = 298 K
V = 1473.5 (5) Å3Block, colourless
Z = 40.35 × 0.28 × 0.20 mm
F(000) = 680

Data collection

Bruker SMART 1000 CCD area-detector diffractometer2708 independent reflections
Radiation source: fine-focus sealed tube2171 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] and ω scansθmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→8
Tmin = 0.442, Tmax = 0.606k = −14→9
7199 measured reflectionsl = −15→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063w = 1/[σ2(Fo2) + (0.0269P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
2708 reflectionsΔρmax = 0.41 e Å3
198 parametersΔρmin = −0.24 e Å3
0 restraintsAbsolute structure: Flack (1983), 1253 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.008 (10)

Special details

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)

xyzUiso*/Ueq
Br10.61120 (5)0.10058 (3)0.17284 (2)0.06606 (14)
C10.6025 (5)0.2417 (2)0.11713 (14)0.0449 (7)
C20.7401 (4)0.2717 (3)0.06832 (18)0.0530 (8)
H20.83830.22490.06330.064*
C30.7311 (4)0.3727 (3)0.02640 (18)0.0484 (8)
H30.82430.3937−0.00720.058*
C40.5870 (4)0.4429 (2)0.03340 (15)0.0396 (7)
C50.4503 (4)0.4104 (3)0.08498 (17)0.0501 (7)
H50.35330.45790.09180.060*
C60.4572 (4)0.3083 (3)0.12627 (18)0.0521 (8)
H60.36430.28570.15950.062*
C70.5761 (4)0.5533 (2)−0.00930 (15)0.0374 (6)
C80.5789 (4)0.5572 (2)−0.09608 (16)0.0390 (7)
C90.5889 (4)0.4534 (2)−0.14014 (16)0.0418 (7)
C100.5655 (4)0.6602 (2)−0.13850 (16)0.0398 (7)
C110.5607 (4)0.7613 (2)−0.09254 (16)0.0405 (7)
C120.5519 (4)0.8699 (3)−0.13046 (17)0.0449 (8)
C130.5621 (4)0.7567 (2)−0.00771 (16)0.0403 (7)
C140.5666 (3)0.6538 (2)0.03272 (15)0.0399 (7)
C150.5628 (4)0.6735 (3)0.12311 (16)0.0524 (8)
H15A0.66290.63730.14920.063*
H15B0.45460.64410.14660.063*
C160.5724 (5)0.8015 (3)0.13270 (18)0.0554 (9)
H16A0.47620.82780.16670.066*
H16B0.68320.82280.15800.066*
C170.5589 (4)0.8542 (3)0.04933 (17)0.0507 (8)
H17A0.44980.89660.04380.061*
H17B0.65780.90450.03930.061*
H1A0.557 (3)0.605 (3)−0.2469 (16)0.042 (8)*
H1B0.538 (4)0.724 (3)−0.2445 (18)0.052 (10)*
N10.5612 (4)0.6630 (3)−0.22009 (15)0.0564 (8)
N20.5985 (4)0.3714 (2)−0.17670 (16)0.0587 (7)
N30.5450 (4)0.9583 (2)−0.15788 (15)0.0635 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1015 (3)0.04187 (17)0.05480 (18)0.0033 (2)0.0026 (2)0.01060 (16)
C10.067 (2)0.0317 (15)0.0355 (14)0.0015 (18)−0.0058 (16)0.0039 (11)
C20.060 (2)0.046 (2)0.0525 (19)0.0155 (17)0.0067 (16)0.0055 (16)
C30.0497 (19)0.046 (2)0.0489 (18)0.0075 (15)0.0097 (14)0.0064 (15)
C40.0448 (18)0.0371 (15)0.0368 (14)−0.0012 (15)0.0014 (14)−0.0036 (12)
C50.0471 (18)0.0439 (18)0.0593 (18)0.0037 (15)0.0043 (14)0.0052 (16)
C60.058 (2)0.049 (2)0.0496 (18)−0.0066 (17)0.0089 (15)0.0064 (15)
C70.0343 (16)0.0352 (15)0.0428 (15)−0.0003 (13)−0.0004 (12)0.0031 (12)
C80.0408 (17)0.0320 (14)0.0443 (15)0.0018 (13)−0.0001 (13)−0.0031 (12)
C90.0455 (18)0.0389 (17)0.0412 (15)0.0004 (17)−0.0042 (14)0.0032 (14)
C100.0401 (18)0.0361 (16)0.0431 (15)−0.0013 (14)−0.0004 (13)0.0014 (13)
C110.0409 (18)0.0325 (15)0.0481 (16)−0.0012 (13)−0.0022 (13)−0.0009 (13)
C120.055 (2)0.0398 (18)0.0402 (16)−0.0030 (14)−0.0039 (14)0.0005 (14)
C130.0423 (18)0.0380 (16)0.0405 (15)0.0023 (14)0.0009 (13)−0.0014 (13)
C140.0408 (17)0.0400 (16)0.0389 (15)0.0048 (13)0.0018 (13)0.0001 (13)
C150.066 (2)0.052 (2)0.0387 (15)0.0052 (17)0.0024 (15)−0.0013 (14)
C160.069 (2)0.0491 (19)0.0478 (16)0.0015 (18)0.0004 (16)−0.0055 (15)
C170.062 (2)0.0390 (16)0.0510 (17)0.0047 (15)−0.0014 (15)−0.0112 (14)
N10.099 (3)0.0337 (16)0.0359 (16)0.0023 (17)−0.0036 (15)−0.0014 (13)
N20.0819 (18)0.0439 (15)0.0501 (14)0.0088 (15)−0.0110 (17)−0.0058 (13)
N30.096 (2)0.0393 (16)0.0557 (16)−0.0058 (15)−0.0125 (15)0.0036 (13)

Geometric parameters (Å, °)

Br1—C11.905 (3)C10—C111.415 (4)
C1—C61.360 (4)C11—C131.400 (4)
C1—C21.363 (4)C11—C121.428 (4)
C2—C31.381 (4)C12—N31.139 (4)
C2—H20.9300C13—C141.387 (4)
C3—C41.375 (4)C13—C171.487 (4)
C3—H30.9300C14—C151.509 (4)
C4—C51.393 (4)C15—C161.521 (4)
C4—C71.484 (4)C15—H15A0.9700
C5—C61.386 (4)C15—H15B0.9700
C5—H50.9300C16—C171.513 (4)
C6—H60.9300C16—H16A0.9700
C7—C141.376 (4)C16—H16B0.9700
C7—C81.432 (4)C17—H17A0.9700
C8—C101.408 (4)C17—H17B0.9700
C8—C91.426 (4)N1—H1A0.82 (3)
C9—N21.144 (3)N1—H1B0.85 (3)
C10—N11.346 (4)
C6—C1—C2122.2 (3)C10—C11—C12121.6 (2)
C6—C1—Br1118.7 (2)N3—C12—C11177.4 (3)
C2—C1—Br1119.1 (3)C14—C13—C11121.0 (3)
C1—C2—C3118.8 (3)C14—C13—C17112.0 (2)
C1—C2—H2120.6C11—C13—C17127.0 (3)
C3—C2—H2120.6C7—C14—C13121.0 (2)
C4—C3—C2121.2 (3)C7—C14—C15129.2 (3)
C4—C3—H3119.4C13—C14—C15109.8 (2)
C2—C3—H3119.4C14—C15—C16104.8 (2)
C3—C4—C5118.3 (3)C14—C15—H15A110.8
C3—C4—C7122.3 (2)C16—C15—H15A110.8
C5—C4—C7119.4 (3)C14—C15—H15B110.8
C6—C5—C4120.8 (3)C16—C15—H15B110.8
C6—C5—H5119.6H15A—C15—H15B108.9
C4—C5—H5119.6C17—C16—C15108.1 (2)
C1—C6—C5118.6 (3)C17—C16—H16A110.1
C1—C6—H6120.7C15—C16—H16A110.1
C5—C6—H6120.7C17—C16—H16B110.1
C14—C7—C8118.5 (2)C15—C16—H16B110.1
C14—C7—C4121.4 (2)H16A—C16—H16B108.4
C8—C7—C4120.1 (2)C13—C17—C16104.8 (2)
C10—C8—C9119.6 (2)C13—C17—H17A110.8
C10—C8—C7121.5 (2)C16—C17—H17A110.8
C9—C8—C7118.9 (2)C13—C17—H17B110.8
N2—C9—C8178.7 (3)C16—C17—H17B110.8
N1—C10—C8121.3 (3)H17A—C17—H17B108.9
N1—C10—C11121.0 (3)C10—N1—H1A121 (2)
C8—C10—C11117.7 (2)C10—N1—H1B120 (2)
C13—C11—C10120.1 (3)H1A—N1—H1B117 (3)
C13—C11—C12118.3 (3)
C6—C1—C2—C3−0.4 (5)N1—C10—C11—C13178.8 (3)
Br1—C1—C2—C3178.3 (2)C8—C10—C11—C13−2.5 (4)
C1—C2—C3—C40.2 (5)N1—C10—C11—C12−0.2 (5)
C2—C3—C4—C50.9 (4)C8—C10—C11—C12178.4 (3)
C2—C3—C4—C7178.4 (3)C13—C11—C12—N32(8)
C3—C4—C5—C6−2.0 (4)C10—C11—C12—N3−179 (100)
C7—C4—C5—C6−179.5 (3)C10—C11—C13—C14−0.5 (4)
C2—C1—C6—C5−0.6 (5)C12—C11—C13—C14178.6 (3)
Br1—C1—C6—C5−179.3 (2)C10—C11—C13—C17179.5 (3)
C4—C5—C6—C11.8 (4)C12—C11—C13—C17−1.4 (5)
C3—C4—C7—C14−116.8 (3)C8—C7—C14—C13−0.8 (4)
C5—C4—C7—C1460.6 (4)C4—C7—C14—C13178.0 (3)
C3—C4—C7—C862.0 (4)C8—C7—C14—C15−179.7 (3)
C5—C4—C7—C8−120.6 (3)C4—C7—C14—C15−0.9 (5)
C14—C7—C8—C10−2.4 (4)C11—C13—C14—C72.3 (4)
C4—C7—C8—C10178.8 (3)C17—C13—C14—C7−177.8 (3)
C14—C7—C8—C9179.9 (3)C11—C13—C14—C15−178.7 (3)
C4—C7—C8—C91.1 (4)C17—C13—C14—C151.3 (3)
C10—C8—C9—N228 (15)C7—C14—C15—C16173.9 (3)
C7—C8—C9—N2−154 (15)C13—C14—C15—C16−5.0 (3)
C9—C8—C10—N10.3 (5)C14—C15—C16—C176.8 (3)
C7—C8—C10—N1−177.4 (3)C14—C13—C17—C163.1 (3)
C9—C8—C10—C11−178.3 (3)C11—C13—C17—C16−177.0 (3)
C7—C8—C10—C114.0 (4)C15—C16—C17—C13−6.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···N2i0.85 (3)2.40 (3)3.227 (4)165 (3)
N1—H1A···N3ii0.82 (3)2.46 (3)3.247 (4)161 (2)

Symmetry codes: (i) −x+1, y+1/2, −z−1/2; (ii) −x+1, y−1/2, −z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2633).

References

  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Hafidh, A. & Zantour, H. (2003). J. Soc. Alger. Chim.13, 1–3.
  • Hafidh, A., Zantour, H. & Jouini, T. (2002). J. Soc. Alger. Chim.12, 171–173.
  • Mereiter, K., Gaith, A. H. & Frohlich, J. (2000). Private Communication (refcode QAJTUQ). CCDC, Cambridge, England.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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