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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 4| April 2011| Page o755
doi:10.1107/S160053681100715X

4-Bromo-N-(4-bromo­phen­yl)aniline

Michelle M. Duonga and Joseph M. Tanskia*

aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
*Correspondence e-mail: jotanski@vassar.edu

(Received 14 February 2011; accepted 24 February 2011; online 2 March 2011)

In the title compound, C12H9Br2N, the dihedral angle between the benzene rings is 47.32 (5)°, whereas the pitch angles, or the angles between the mean plane of each aryl group `propeller blade' and the plane defined by the aryl bridging C—N—C angle, are 18.1 (2) and 31.7 (2)°. No inter­molecular N—H hydrogen bonding is present in the crystal; however, there is a short inter­molecular Br⋯Br contact of 3.568 (1) Å.

Related literature

The title compound is an amine analogue of brominated diphenyl ether flame retardant materials commonly used in household items. For information on environmental and health concerns related to brominated flame retardants, see: de Wit (2002)[Wit, C. A. de (2002). Chemosphere, 46, 583-624.]; Lunder et al. (2010[Lunder, S., Hovander, L., Athanassiadis, I. & Bergman, A. (2010). Environ. Sci. Technol. 44, 5256-5262.]). For the synthesis of the title compound, see: Crounse & Raiford (1945[Crounse, N. & Raiford, C. (1945). J. Am. Chem. Soc. 67, 875-876.]); Galatis & Megaloikonomos (1934[Galatis, L. & Megaloikonomos, J. (1934). Prakt. Akad. Atkenon, 9, 20-21.]); He et al. (2008[He, C., Chen, C., Cheng, J., Liu, C., Liu, W., Li, Q. & Lei, A. (2008). Angew. Chem. Int. Ed. 47, 6414-6417.]). For related structures, see: Eriksson et al. (2004[Eriksson, L., Eriksson, J. & Hu, J. (2004). Acta Cryst. B60, 734-738.]); Plieth & Ruban (1961[Plieth, K. & Ruban, G. (1961). Z. Kristallogr. 116, 161-172.]); Li et al. (2010[Li, H., Quiang, L.-M., Si, J.-L. & Mao, D.-B. (2010). Z. Kristallogr. New Cryst. Struct. 225, 1-2.]). For the van der Waals radius of Br and inter­molecular Br⋯Br contacts, see: Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-451.]); Medlycott et al. (2007[Medlycott, E. A., Udachin, K. A. & Hanan, G. S. (2007). Dalton Trans. pp. 430-438.]). For a description of the pitch angle, see: Lim & Tanski (2007[Lim, C. F. & Tanski, J. M. (2007). J. Chem. Crystallogr. 37, 587-595.]).

[Scheme 1]

Experimental

Crystal data

  • C12H9Br2N

  • Mr = 327.02

  • Monoclinic, P 21 /c

  • a = 5.9993 (12) Å

  • b = 13.032 (3) Å

  • c = 14.228 (3) Å

  • β = 96.967 (3)°

  • V = 1104.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 7.30 mm−1

  • T = 125 K

  • 0.30 × 0.30 × 0.17 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.218, Tmax = 0.370

  • 17275 measured reflections

  • 3373 independent reflections

  • 2786 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.064

  • S = 1.02

  • 3373 reflections

  • 139 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.94 e Å−3

  • Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SADABS 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: 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: 10.1107/S160053681100715X/si2339sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100715X/si2339Isup2.hkl

checkCIF report


Comment top

The title compound, 4-bromo-N-(4-bromophenyl)aniline, C12H9Br2N (I), was first synthesized by Galatis & Megaloikonomos (1934) via the direct bromination of diphenylamine, and the structure was corroborated by Crounse & Raiford (1945) in their study of the hydrolysis of the benzoyl derivative. More recently, halogenated diphenylamines have been prepared by copper catalyzed coupling reactions (He et al., 2008). The crystal structure of the chloride analogue is known (Plieth & Ruban, 1961), and an analogous structure with an oxygen bridge has also been reported (Eriksson et al., 2004). The title compound is an amine analogues of a class of brominated diphenyl ether materials (de Wit, 2002). Polybrominated diphenyl ethers are commonly used as flame retardants (Eriksson et al., 2004) in consumer products and electronics and have been found in humans (Lunder et al., 2010).

Compound (I) is a dibrominated diphenyl amine derivative with a "propeller blade" disposition of the benzene rings about the bridging nitrogen atom. The structure reveals that there is no intermolecular hydrogen bonding, although there are significant intermolecular Br···Br contacts (Medlycott et al. , 2007) at a distance of 3.568 (1) Å, which is shorter than the sum of the van der Waals radius of bromine, 1.85Å (Bondi, 1964), at 3.7 Å. The aryl-bridging C4—N—C7 angle in (I) is 128.5 (2)°, somewhat smaller than the C—N—C bond angle of 133.8° found in the isomorphous dichloro analog (Plieth & Ruban, 1961), but similar to the C—N—C bond angle of 128.1° in another similar structure, N-4-(bromophenyl)-4-nitroaniline, which contains one bromo and one nitro group (Li et al., 2010).

The dihedral angle in (I) is found to be 47.32 (5)°, whereas the pitch angles are 18.1 (2)° and 31.7 (2)°. The pitch angles are the angles between the mean plane of each aryl group "propeller blade" and the plane defined by the aryl bridging C4—N—C7 angle. The pitch angles are metrical parameters that describe the dispostion of the benzene rings about the bridging atom with greater detail than the dihedral angle; structures with equivalent dihedral angles may exhibit dramatically different orientations of the benzene rings about the bridging group (Lim & Tanski, 2007). In the isomorphous dichloro analog to the title compound, the dihedral angle is found to be significantly larger, 56.5°, as are the pitch angles of 22.1° and 39.1°. In another similar bromo compound, N-4-(bromophenyl)-4-nitroaniline, where the dihedral angle of 44.8° is more similar to that of the title compound, the pitch angles are found to be 12.6° and 35.1°.

Related literature top

The title compound is an amine analogue of brominated diphenyl ether flame retardant materials commonly used in household items. For information on environmental and health concerns related to brominated flame retardants, see: de Wit (2002); Lunder et al. (2010). For he synthesis of the title compound, see: Crounse & Raiford (1945); Galatis & Megaloikonomos (1934); He et al. (2008). For related structures, see: Eriksson et al. (2004); Plieth & Ruban (1961); Li et al. (2010). For the van der Waals radius of Br and intermolecular Br···Br contacts, see: Bondi (1964); Medlycott et al. (2007). For a description of the pitch angle, see: Lim & Tanski (2007).

Experimental top

Crystalline 4-bromo-N-(4-bromophenyl)aniline (I) was purchase from Aldrich Chemical Company, USA.

Refinement top

All non-hydrogen atoms were refined anisotropically. The hydrogen atoms on carbon were included in calculated positions and were refined using a riding model at C–H = 0.95Å and Uiso(H) = 1.2 × Ueq(C) of the aryl C-atoms. T hydrogen atom on nitrogen was refined semifreely with the help of a distance restraint, d(N–H) = 0.835 (16) Å and Uiso(H) = 1.2 × Ueq(N). The extinction parameter (EXTI) refined to zero and was removed from the refinement.

Computing details top

Data collection: APEX2 (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of compound (I), with displacement ellipsoids shown at the 50% probability level.
4-Bromo-N-(4-bromophenyl)aniline top
Crystal data top
C12H9Br2NF(000) = 632
Mr = 327.02Dx = 1.967 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8371 reflections
a = 5.9993 (12) Åθ = 2.9–30.4°
b = 13.032 (3) ŵ = 7.30 mm−1
c = 14.228 (3) ÅT = 125 K
β = 96.967 (3)°Plate, colourless
V = 1104.2 (4) Å30.30 × 0.30 × 0.17 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		3373 independent reflections
Radiation source: fine-focus sealed tube2786 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 30.6°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker 2007)		h = −8→8
Tmin = 0.218, Tmax = 0.370k = −18→18
17275 measured reflectionsl = −20→20
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0365P)2]
where P = (Fo2 + 2Fc2)/3
3373 reflections(Δ/σ)max = 0.001
139 parametersΔρmax = 0.94 e Å−3
1 restraintΔρmin = −0.45 e Å−3
Crystal data top
C12H9Br2NV = 1104.2 (4) Å3
Mr = 327.02Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.9993 (12) ŵ = 7.30 mm−1
b = 13.032 (3) ÅT = 125 K
c = 14.228 (3) Å0.30 × 0.30 × 0.17 mm
β = 96.967 (3)°
Data collection top
Bruker APEXII CCD
diffractometer		3373 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker 2007)		2786 reflections with I > 2σ(I)
Tmin = 0.218, Tmax = 0.370Rint = 0.038
17275 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0261 restraint
wR(F2) = 0.064H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.94 e Å−3
3373 reflectionsΔρmin = −0.45 e Å−3
139 parameters
Special details top

Experimental. A suitable crystal was mounted in a nylon loop with Paratone-N cryoprotectant oil and data was collected on a Bruker APEX 2 CCD platform diffractometer. The structure was solved using direct methods and standard difference map techniques, and was refined by full-matrix least-squares procedures on F2 with SHELXTL Version 6.14 (Sheldrick, 2008).

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
Br10.35642 (4)0.125752 (16)0.143618 (15)0.02649 (7)
Br2−0.19656 (3)0.946875 (15)0.134200 (15)0.02372 (7)
N0.4407 (3)0.58823 (13)0.10486 (13)0.0224 (4)
H10.566 (3)0.6043 (18)0.0893 (16)0.027*
C10.3790 (3)0.27103 (16)0.13498 (13)0.0200 (4)
C20.5839 (3)0.31866 (15)0.16241 (14)0.0229 (4)
H2A0.71140.27930.18650.027*
C30.5998 (3)0.42427 (15)0.15413 (14)0.0215 (4)
H3A0.73910.45730.17330.026*
C40.4131 (3)0.48316 (15)0.11792 (13)0.0186 (4)
C50.2092 (3)0.43296 (15)0.09209 (14)0.0204 (4)
H5A0.08060.47190.06850.025*
C60.1911 (3)0.32763 (15)0.10030 (14)0.0209 (4)
H6A0.05140.29440.08240.025*
C70.2844 (3)0.66694 (15)0.10980 (14)0.0188 (4)
C80.0933 (3)0.65683 (15)0.15638 (14)0.0192 (4)
H8A0.06210.59310.18450.023*
C9−0.0513 (3)0.73940 (15)0.16173 (13)0.0194 (4)
H9A−0.18220.73180.19250.023*
C10−0.0044 (3)0.83266 (14)0.12218 (14)0.0191 (4)
C110.1859 (3)0.84517 (15)0.07631 (14)0.0208 (4)
H11A0.21790.90960.04970.025*
C120.3281 (3)0.76224 (15)0.06992 (13)0.0202 (4)
H12A0.45720.77010.03800.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03250 (12)0.01599 (11)0.03174 (12)0.00176 (8)0.00695 (9)−0.00159 (8)
Br20.02408 (11)0.01647 (10)0.03091 (12)0.00214 (7)0.00456 (8)−0.00193 (7)
N0.0179 (8)0.0174 (8)0.0330 (10)0.0004 (7)0.0076 (7)0.0013 (7)
C10.0219 (9)0.0166 (9)0.0217 (9)0.0016 (7)0.0039 (7)−0.0020 (7)
C20.0197 (9)0.0232 (10)0.0253 (10)0.0046 (8)0.0008 (8)0.0007 (8)
C30.0144 (9)0.0215 (10)0.0283 (10)−0.0001 (7)0.0012 (7)−0.0016 (8)
C40.0203 (9)0.0182 (9)0.0180 (9)−0.0002 (7)0.0051 (7)−0.0009 (7)
C50.0184 (9)0.0210 (10)0.0212 (9)0.0031 (7)−0.0006 (7)−0.0014 (7)
C60.0189 (9)0.0225 (10)0.0211 (9)−0.0008 (7)0.0020 (7)−0.0033 (7)
C70.0192 (9)0.0167 (9)0.0205 (9)−0.0008 (7)0.0019 (7)0.0001 (7)
C80.0204 (9)0.0155 (9)0.0219 (9)−0.0030 (7)0.0038 (7)0.0002 (7)
C90.0176 (9)0.0207 (10)0.0206 (9)−0.0031 (7)0.0049 (7)−0.0008 (7)
C100.0192 (9)0.0150 (9)0.0227 (9)0.0017 (7)0.0005 (7)−0.0019 (7)
C110.0239 (10)0.0156 (9)0.0232 (10)−0.0042 (7)0.0038 (8)0.0009 (7)
C120.0193 (9)0.0210 (9)0.0210 (9)−0.0027 (7)0.0049 (7)−0.0007 (7)
Geometric parameters (Å, º) top
Br1—C11.903 (2)C5—H5A0.9500
Br2—C101.9031 (19)C6—H6A0.9500
N—C41.394 (3)C7—C81.399 (3)
N—C71.397 (3)C7—C121.403 (3)
N—H10.835 (16)C8—C91.390 (3)
C1—C61.387 (3)C8—H8A0.9500
C1—C21.390 (3)C9—C101.383 (3)
C2—C31.386 (3)C9—H9A0.9500
C2—H2A0.9500C10—C111.391 (3)
C3—C41.403 (3)C11—C121.387 (3)
C3—H3A0.9500C11—H11A0.9500
C4—C51.397 (3)C12—H12A0.9500
C5—C61.383 (3)
C4—N—C7128.53 (17)C1—C6—H6A120.4
C4—N—H1114.0 (17)N—C7—C8123.26 (17)
C7—N—H1117.4 (17)N—C7—C12118.05 (17)
C6—C1—C2121.03 (19)C8—C7—C12118.62 (18)
C6—C1—Br1119.41 (15)C9—C8—C7120.40 (18)
C2—C1—Br1119.56 (15)C9—C8—H8A119.8
C3—C2—C1119.14 (18)C7—C8—H8A119.8
C3—C2—H2A120.4C10—C9—C8119.93 (18)
C1—C2—H2A120.4C10—C9—H9A120.0
C2—C3—C4120.97 (18)C8—C9—H9A120.0
C2—C3—H3A119.5C9—C10—C11120.87 (18)
C4—C3—H3A119.5C9—C10—Br2119.70 (15)
N—C4—C5122.64 (18)C11—C10—Br2119.40 (14)
N—C4—C3118.93 (17)C12—C11—C10119.05 (18)
C5—C4—C3118.36 (18)C12—C11—H11A120.5
C6—C5—C4121.20 (18)C10—C11—H11A120.5
C6—C5—H5A119.4C11—C12—C7121.13 (18)
C4—C5—H5A119.4C11—C12—H12A119.4
C5—C6—C1119.28 (19)C7—C12—H12A119.4
C5—C6—H6A120.4
C6—C1—C2—C3−0.5 (3)C4—N—C7—C820.0 (3)
Br1—C1—C2—C3178.75 (15)C4—N—C7—C12−163.25 (19)
C1—C2—C3—C4−0.5 (3)N—C7—C8—C9177.59 (18)
C7—N—C4—C533.3 (3)C12—C7—C8—C90.8 (3)
C7—N—C4—C3−149.9 (2)C7—C8—C9—C10−1.1 (3)
C2—C3—C4—N−175.67 (18)C8—C9—C10—C110.4 (3)
C2—C3—C4—C51.3 (3)C8—C9—C10—Br2−177.49 (14)
N—C4—C5—C6175.75 (18)C9—C10—C11—C120.5 (3)
C3—C4—C5—C6−1.1 (3)Br2—C10—C11—C12178.40 (15)
C4—C5—C6—C10.1 (3)C10—C11—C12—C7−0.8 (3)
C2—C1—C6—C50.7 (3)N—C7—C12—C11−176.84 (18)
Br1—C1—C6—C5−178.55 (14)C8—C7—C12—C110.1 (3)

Experimental details

Crystal data
Chemical formulaC12H9Br2N
Mr327.02
Crystal system, space groupMonoclinic, P21/c
Temperature (K)125
a, b, c (Å)5.9993 (12), 13.032 (3), 14.228 (3)
β (°) 96.967 (3)
V (Å3)1104.2 (4)
Z4
Radiation typeMo Kα
µ (mm−1)7.30
Crystal size (mm)0.30 × 0.30 × 0.17
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker 2007)
Tmin, Tmax0.218, 0.370
No. of measured, independent and
observed [I > 2σ(I)] reflections		17275, 3373, 2786
Rint0.038
(sin θ/λ)max (Å−1)0.717
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.064, 1.02
No. of reflections3373
No. of parameters139
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.94, −0.45

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

References

First citationBondi, A. (1964). J. Phys. Chem. 68, 441–451.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCrounse, N. & Raiford, C. (1945). J. Am. Chem. Soc. 67, 875–876.  CrossRef CAS Google Scholar
 First citationEriksson, L., Eriksson, J. & Hu, J. (2004). Acta Cryst. B60, 734–738.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationGalatis, L. & Megaloikonomos, J. (1934). Prakt. Akad. Atkenon, 9, 20–21.  CAS Google Scholar
 First citationHe, C., Chen, C., Cheng, J., Liu, C., Liu, W., Li, Q. & Lei, A. (2008). Angew. Chem. Int. Ed. 47, 6414–6417.  CrossRef CAS Google Scholar
 First citationLi, H., Quiang, L.-M., Si, J.-L. & Mao, D.-B. (2010). Z. Kristallogr. New Cryst. Struct. 225, 1–2.  Google Scholar
 First citationLim, C. F. & Tanski, J. M. (2007). J. Chem. Crystallogr. 37, 587–595.  Web of Science CSD CrossRef CAS Google Scholar
 First citationLunder, S., Hovander, L., Athanassiadis, I. & Bergman, A. (2010). Environ. Sci. Technol. 44, 5256–5262.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationMedlycott, E. A., Udachin, K. A. & Hanan, G. S. (2007). Dalton Trans. pp. 430–438.  Web of Science CSD CrossRef Google Scholar
 First citationPlieth, K. & Ruban, G. (1961). Z. Kristallogr. 116, 161–172.  CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWit, C. A. de (2002). Chemosphere, 46, 583–624.  Web of Science PubMed Google Scholar

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Page o755
doi:10.1107/S160053681100715X
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