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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 65| Part 11| November 2009| Page o2875
https://doi.org/10.1107/S1600536809043426

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

Cunlan Zhanga*

aDepartment of Chemistry, Dezhou University, Dezhou 253023, People's Republic of China
*Correspondence e-mail: cunlanzhang@126.com

(Received 15 October 2009; accepted 21 October 2009; online 28 October 2009)

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[Hafidh, A., Zantour, H. & Jouini, T. (2002). J. Soc. Alger. Chim. 12, 171-173.]) and Hafidh & Zantour (2003[Hafidh, A. & Zantour, H. (2003). J. Soc. Alger. Chim. 13, 1-3.]). For a related structure, see Mereiter et al. (2000[Mereiter, K., Gaith, A. H. & Frohlich, J. (2000). Private Communication (refcode QAJTUQ). CCDC, Cambridge, England.]).

[Scheme 1]

Experimental

Crystal data

  • C17H12BrN3

  • Mr = 338.21

  • Orthorhombic, P 21 21 21

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.442, Tmax = 0.606

  • 7199 measured reflections

  • 2708 independent reflections

  • 2171 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1253 Friedel pairs

  • Flack parameter: 0.008 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1B⋯N2i 0.85 (3) 2.40 (3) 3.227 (4) 165 (3)
N1—H1A⋯N3ii 0.82 (3) 2.46 (3) 3.247 (4) 161 (2)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043426/cv2633Isup2.hkl

checkCIF report


Comment top

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].

Related literature top

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

Experimental top

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 top

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.

Structure description top

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].

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
5-Amino-7-(4-bromophenyl)indane-4,6-dicarbonitrile top
Crystal data top
C17H12BrN3Dx = 1.525 Mg m−3
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 mm−1
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 top
Bruker SMART 1000 CCD area-detector
diffractometer		2708 independent reflections
Radiation source: fine-focus sealed tube2171 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ 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 top
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) = 0.063 w = 1/[σ2(Fo2) + (0.0269P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
2708 reflectionsΔρmax = 0.41 e Å−3
198 parametersΔρmin = −0.24 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1253 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.008 (10)
Crystal data top
C17H12BrN3V = 1473.5 (5) Å3
Mr = 338.21Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.5655 (14) ŵ = 2.79 mm−1
b = 11.811 (2) ÅT = 298 K
c = 16.490 (3) Å0.35 × 0.28 × 0.20 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2708 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2171 reflections with I > 2σ(I)
Tmin = 0.442, Tmax = 0.606Rint = 0.027
7199 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063Δρmax = 0.41 e Å−3
S = 0.95Δρmin = −0.24 e Å−3
2708 reflectionsAbsolute structure: Flack (1983), 1253 Friedel pairs
198 parametersAbsolute structure parameter: 0.008 (10)
0 restraints
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
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC17H12BrN3
Mr338.21
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)7.5655 (14), 11.811 (2), 16.490 (3)
V (Å3)1473.5 (5)
Z4
Radiation typeMo Kα
µ (mm−1)2.79
Crystal size (mm)0.35 × 0.28 × 0.20
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.442, 0.606
No. of measured, independent and
observed [I > 2σ(I)] reflections		7199, 2708, 2171
Rint0.027
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.063, 0.95
No. of reflections2708
No. of parameters198
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.41, −0.24
Absolute structureFlack (1983), 1253 Friedel pairs
Absolute structure parameter0.008 (10)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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.
 

References

First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2875
https://doi.org/10.1107/S1600536809043426
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