N,N′-Bis(4-bromo­benzyl­idene)biphenyl-2,2′-diamine

Dehghanpour, S.; Asadizadeh, S.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536809000993

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o306

doi:10.1107/S1600536809000993

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N,N′-Bis(4-bromobenzylidene)biphenyl-2,2′-diamine

Saeed Dehghanpour,^a ^* Saeedeh Asadizadeh,^a Shan Gao ^b and Seik Weng Ng ^c

^aDepartment of Chemistry, Alzahra University, Vanak, Tehran, Iran, ^bSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: dehganpour_farasha@yahoo.com

(Received 7 January 2009; accepted 8 January 2009; online 14 January 2009)

The complete molecule of the title Schiff base, C₂₆H₁₈Br₂N₂, is generated by crystallographic twofold symmetry. The aromatic rings of the biphenylene portion of the molecule are twisted, as shown by the dihedral of 61.8 (1)° formed between them.

Related literature

There are relatively few crystallographic reports of Schiff bases formed by condensing biphenyl-2,2′-diamine with aldehydes or ketones. See: Alajarín et al. (2007 ); Coxall et al. (2003 ); Cunningham et al. (2004 ); Finder et al. (1973 ); Pruszynski et al. (1992 ).

Experimental

Crystal data

C₂₆H₁₈Br₂N₂
M_r = 518.24
Orthorhombic, A b a 2
a = 15.9691 (10) Å
b = 8.3482 (5) Å
c = 16.7767 (11) Å
V = 2236.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 3.64 mm⁻¹
T = 295 (2) K
0.28 × 0.25 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.429, T_max = 0.545 (expected range = 0.394–0.501)
10424 measured reflections
2542 independent reflections
1333 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.116
S = 0.98
2542 reflections
136 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ), 1209 Friedel pairs
Flack parameter: −0.013 (15)

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000993/tk2356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000993/tk2356Isup2.hkl

checkCIF report

Related literature top

There are relatively few crystallographic reports of Schiff bases formed by condensing biphenyl-2,2'-diamine with aldehydes or ketones. See: Alajarín et al. (2007); Coxall et al. (2003); Cunningham et al. (2004); Finder et al. (1973); Pruszynski et al. (1992).

Experimental top

Biphenyl-2,2'-diamine (5 mmol) and 4-bromobenzaldehyde (10 mmol) were dissolved in ethanol (50 ml). The solution was heated for 5 h; the solid that separated from the cooled solution was collected and recrystallized from chloroform; a second recrystallization was effected with ethanol. The yield as 90%. Analysis found: C 60.20, H 3.54, N 5.43; C₂₆H₁₈Br₂N₂ requires: C 60.26, H 3.50, N 5.41.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001); displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. (Symmetry code: i = 2 - x, 3 - y, z).

N,N'-Bis(4-bromobenzylidene)biphenyl-2,2'-diamine top

Crystal data top

C₂₆H₁₈Br₂N₂	F(000) = 1032
M_r = 518.24	D_x = 1.539 Mg m⁻³
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 5898 reflections
a = 15.9691 (10) Å	θ = 3.0–27.4°
b = 8.3482 (5) Å	µ = 3.64 mm⁻¹
c = 16.7767 (11) Å	T = 295 K
V = 2236.6 (2) Å³	Cuboid, light yellow
Z = 4	0.28 × 0.25 × 0.19 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2542 independent reflections
Radiation source: fine-focus sealed tube	1333 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.4°, θ_min = 3.0°
ω scans	h = −18→20
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
T_min = 0.429, T_max = 0.545	l = −21→21
10424 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0547P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
2542 reflections	Δρ_max = 0.28 e Å⁻³
136 parameters	Δρ_min = −0.36 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1209 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.013 (15)

Crystal data top

C₂₆H₁₈Br₂N₂	V = 2236.6 (2) Å³
M_r = 518.24	Z = 4
Orthorhombic, Aba2	Mo Kα radiation
a = 15.9691 (10) Å	µ = 3.64 mm⁻¹
b = 8.3482 (5) Å	T = 295 K
c = 16.7767 (11) Å	0.28 × 0.25 × 0.19 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2542 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1333 reflections with I > 2σ(I)
T_min = 0.429, T_max = 0.545	R_int = 0.040
10424 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.116	Δρ_max = 0.28 e Å⁻³
S = 0.98	Δρ_min = −0.36 e Å⁻³
2542 reflections	Absolute structure: Flack (1983), 1209 Friedel pairs
136 parameters	Absolute structure parameter: −0.013 (15)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.89090 (4)	0.63217 (6)	0.50003 (6)	0.1058 (3)
N1	0.8979 (2)	1.3119 (4)	0.7320 (3)	0.0604 (9)
C1	0.8877 (2)	1.4642 (5)	0.7689 (3)	0.0555 (10)
C2	0.9576 (2)	1.5394 (4)	0.8036 (2)	0.0537 (9)
C3	0.9461 (3)	1.6846 (5)	0.8415 (3)	0.0650 (11)
H3	0.9920	1.7371	0.8636	0.078*
C4	0.8672 (3)	1.7534 (6)	0.8471 (4)	0.0676 (13)
H4	0.8605	1.8514	0.8727	0.081*
C5	0.7989 (3)	1.6768 (5)	0.8150 (3)	0.0685 (12)
H5	0.7459	1.7214	0.8205	0.082*
C6	0.8087 (2)	1.5347 (5)	0.7748 (3)	0.0656 (12)
H6	0.7626	1.4854	0.7514	0.079*
C7	0.8654 (3)	1.2832 (7)	0.6649 (3)	0.0633 (12)
H7	0.8381	1.3663	0.6387	0.076*
C8	0.8685 (3)	1.1275 (5)	0.6264 (3)	0.0597 (11)
C9	0.8443 (3)	1.1094 (5)	0.5480 (3)	0.0818 (14)
H9	0.8236	1.1973	0.5202	0.098*
C10	0.8505 (3)	0.9629 (6)	0.5101 (4)	0.0891 (14)
H10	0.8346	0.9518	0.4570	0.107*
C11	0.8805 (3)	0.8339 (6)	0.5523 (3)	0.0714 (13)
C12	0.9015 (3)	0.8464 (5)	0.6305 (3)	0.0703 (13)
H12	0.9195	0.7566	0.6585	0.084*
C13	0.8961 (2)	0.9926 (5)	0.6683 (3)	0.0646 (11)
H13	0.9108	1.0016	0.7217	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1445 (6)	0.0704 (3)	0.1026 (5)	−0.0098 (2)	0.0284 (5)	−0.0131 (4)
N1	0.058 (2)	0.0512 (18)	0.072 (3)	−0.0048 (15)	0.0000 (19)	−0.0029 (19)
C1	0.050 (3)	0.058 (2)	0.058 (3)	0.0000 (18)	0.0025 (18)	0.009 (2)
C2	0.054 (2)	0.052 (2)	0.056 (2)	−0.0007 (16)	0.0007 (19)	0.0069 (19)
C3	0.063 (3)	0.064 (2)	0.067 (3)	−0.001 (2)	−0.005 (2)	−0.004 (2)
C4	0.081 (4)	0.057 (3)	0.065 (3)	0.004 (2)	−0.002 (3)	−0.002 (2)
C5	0.059 (3)	0.064 (2)	0.082 (3)	0.017 (2)	0.008 (2)	0.008 (2)
C6	0.052 (3)	0.065 (3)	0.080 (3)	−0.0025 (19)	0.000 (2)	0.014 (2)
C7	0.066 (3)	0.066 (3)	0.058 (3)	0.000 (2)	−0.007 (2)	0.010 (2)
C8	0.062 (2)	0.065 (3)	0.052 (3)	−0.0084 (18)	−0.002 (2)	0.001 (2)
C9	0.111 (4)	0.068 (3)	0.066 (3)	0.004 (3)	−0.020 (3)	0.002 (2)
C10	0.127 (4)	0.075 (3)	0.066 (3)	−0.001 (3)	−0.024 (4)	0.010 (3)
C11	0.065 (3)	0.084 (3)	0.065 (3)	−0.006 (2)	0.008 (2)	0.004 (3)
C12	0.070 (3)	0.058 (2)	0.083 (4)	−0.0047 (19)	−0.004 (3)	0.015 (2)
C13	0.074 (3)	0.060 (3)	0.059 (3)	0.001 (2)	−0.008 (2)	0.006 (2)

Geometric parameters (Å, º) top

Br1—C11	1.906 (5)	C6—H6	0.9300
N1—C7	1.262 (6)	C7—C8	1.452 (7)
N1—C1	1.424 (6)	C7—H7	0.9300
C1—C6	1.395 (5)	C8—C9	1.378 (7)
C1—C2	1.407 (6)	C8—C13	1.399 (6)
C2—C3	1.381 (6)	C9—C10	1.383 (6)
C2—C2ⁱ	1.506 (7)	C9—H9	0.9300
C3—C4	1.389 (6)	C10—C11	1.376 (7)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.373 (7)	C11—C12	1.358 (8)
C4—H4	0.9300	C12—C13	1.378 (6)
C5—C6	1.374 (6)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300

C7—N1—C1	120.7 (4)	N1—C7—H7	118.2
C6—C1—C2	120.0 (4)	C8—C7—H7	118.2
C6—C1—N1	120.8 (4)	C9—C8—C13	118.6 (4)
C2—C1—N1	119.2 (3)	C9—C8—C7	120.9 (4)
C3—C2—C1	118.5 (4)	C13—C8—C7	120.5 (5)
C3—C2—C2ⁱ	120.2 (4)	C8—C9—C10	121.1 (4)
C1—C2—C2ⁱ	121.2 (4)	C8—C9—H9	119.5
C2—C3—C4	121.0 (4)	C10—C9—H9	119.5
C2—C3—H3	119.5	C9—C10—C11	118.7 (5)
C4—C3—H3	119.5	C9—C10—H10	120.7
C5—C4—C3	120.1 (4)	C11—C10—H10	120.7
C5—C4—H4	120.0	C12—C11—C10	121.6 (5)
C3—C4—H4	120.0	C12—C11—Br1	119.4 (4)
C6—C5—C4	120.3 (4)	C10—C11—Br1	119.0 (4)
C6—C5—H5	119.8	C11—C12—C13	119.8 (5)
C4—C5—H5	119.8	C11—C12—H12	120.1
C5—C6—C1	120.1 (4)	C13—C12—H12	120.1
C5—C6—H6	119.9	C12—C13—C8	120.1 (5)
C1—C6—H6	119.9	C12—C13—H13	119.9
N1—C7—C8	123.6 (5)	C8—C13—H13	119.9

C7—N1—C1—C6	48.5 (6)	C1—N1—C7—C8	−175.6 (4)
C7—N1—C1—C2	−135.0 (5)	N1—C7—C8—C9	−169.2 (5)
C6—C1—C2—C3	−1.4 (6)	N1—C7—C8—C13	10.8 (7)
N1—C1—C2—C3	−177.9 (4)	C13—C8—C9—C10	−2.8 (8)
C6—C1—C2—C2ⁱ	175.4 (3)	C7—C8—C9—C10	177.2 (5)
N1—C1—C2—C2ⁱ	−1.1 (5)	C8—C9—C10—C11	0.6 (8)
C1—C2—C3—C4	1.6 (6)	C9—C10—C11—C12	2.1 (7)
C2ⁱ—C2—C3—C4	−175.3 (4)	C9—C10—C11—Br1	−179.0 (4)
C2—C3—C4—C5	0.2 (8)	C10—C11—C12—C13	−2.7 (7)
C3—C4—C5—C6	−2.2 (8)	Br1—C11—C12—C13	178.5 (3)
C4—C5—C6—C1	2.4 (7)	C11—C12—C13—C8	0.4 (7)
C2—C1—C6—C5	−0.6 (7)	C9—C8—C13—C12	2.2 (7)
N1—C1—C6—C5	175.9 (4)	C7—C8—C13—C12	−177.8 (4)

Symmetry code: (i) −x+2, −y+3, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈Br₂N₂
M_r	518.24
Crystal system, space group	Orthorhombic, Aba2
Temperature (K)	295
a, b, c (Å)	15.9691 (10), 8.3482 (5), 16.7767 (11)
V (Å³)	2236.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.64
Crystal size (mm)	0.28 × 0.25 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.429, 0.545
No. of measured, independent and observed [I > 2σ(I)] reflections	10424, 2542, 1333
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.116, 0.98
No. of reflections	2542
No. of parameters	136
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.36
Absolute structure	Flack (1983), 1209 Friedel pairs
Absolute structure parameter	−0.013 (15)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the Alzahra University Research Council and Natural Resources, and the University of Malaya for supporting this study.

References

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