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In the title compound, C13H8Br3NO, the two aromatic substituents lie trans to each other across the C=N bond. The mol­ecule is almost planar, with a dihedral angle of 3.6 (5)° between the aromatic rings. Intra­molecular O—H...N hydrogen bonding generates an S(6) ring motif, while short inter­molecular C—H...O, C—H...Br and Br...Br contacts [Br...Br distance 3.669 (2) Å] link the mol­ecules into a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054335/sj2397sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054335/sj2397Isup2.hkl
Contains datablock I

CCDC reference: 672831

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.014 Å
  • R factor = 0.066
  • wR factor = 0.199
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.83 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 14 PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. O1 .. 2.61 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. BR1 .. 2.99 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Schiff bases are important in diverse fields of chemistry and biochemistry owing to their biological activity, photochromism and related properties (Yeap et al., 2003). In view of the importance and also the usefulness of these compounds, chemists are prompted to generate the new derivatives by introducing different substituents into the existing skeleton of the molecule (Zheng et al., 2005;Özek et al., 2007; Guo, 2007). Here, we report the structure of the title compound, (I), Fig. 1, a new Schiff base, which was prepared by reaction of 3,5-dibromo-2-hydroxybenzaldehyde with 4-bromobenzenamine. The planarity of the molecule is supported by the conjugation of the imino group and the aromatic system, together with a resonance-assisted intramolecular O1—H1···N1 hydrogen bond (Table 1). The dihedral angle between the aromatic rings is 3.6 (5)°.

In addition to the intramolecular hydrogen bond, some short intermolecular contacts, C10—H10···Oi (see Table 1 for symmetry codes), C10—H10···Br1i and Br3···Br2ii (d[Br2—Br3] = 3.669 (2) Å, symmetry code: (ii) 1 + x,-1 + y,1 + z), were observed in the crystal structure. These link the molecules into a two-dimensional network, Fig. 2.

Related literature top

For the background to Schiff base chemistry, see: Yeap, et al. (2003) and for related structures, see: Zheng et al. (2005); Özek et al., (2007) and Guo (2007).

Experimental top

The title compound, (I), was prepared by reaction of 3,5-dibromo-2-hydroxybenzaldehyde (1.4 g, 5 mmol) with 4-bromobenzenamine (0.95 g 5.5 mol) in 30 ml of 95% ethanol. The mixture was stirred and heated in air at reflux temperature for 30 min, after which 40 ml distilled water was added, the resulting product was separated by filtration (1.8 g, yield 83.1%). The pure product (0.5 g) was heated and dissolved in 15 ml of 95% ethanol. Single crystals were obtained from this solution by slow evaporation over a period of 2 days at room temperature.

Refinement top

The H atom involved in the O–H···N hydrogen bond was found in a difference Fourier map, but was fixed during refinement with d(O—H) = 0.82 Å and Uiso(H) = 1.2 Ueq (O). H atoms bound to C atoms were included in the refinement in the riding model approximation, with C–H = 0.93 Å and Uiso (H) = 1.2 Ueq (C atom).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. A view of the structure of (I), showing the atom-numbering Scheme and the O1—H1···N1 hydrogen bond (dashed line); displacement ellipsoids were drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of (I) viewed down the c axis, showing hydrogen bonds and short intermolecular contacts as dashed lines.
2,4-Dibromo-6-(4-bromophenyliminomethyl)phenol top
Crystal data top
C13H8Br3NOZ = 2
Mr = 433.90F(000) = 412
Triclinic, P1Dx = 2.162 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.985 (3) ÅCell parameters from 1206 reflections
b = 8.594 (3) Åθ = 2.9–26.2°
c = 11.020 (4) ŵ = 9.07 mm1
α = 87.801 (6)°T = 294 K
β = 76.688 (7)°Prism, red
γ = 65.180 (5)°0.24 × 0.16 × 0.12 mm
V = 666.5 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2309 independent reflections
Radiation source: fine-focus sealed tube1471 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 79
Tmin = 0.202, Tmax = 0.339k = 610
3322 measured reflectionsl = 1213
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.1123P)2]
where P = (Fo2 + 2Fc2)/3
2309 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.86 e Å3
0 restraintsΔρmin = 1.27 e Å3
Crystal data top
C13H8Br3NOγ = 65.180 (5)°
Mr = 433.90V = 666.5 (4) Å3
Triclinic, P1Z = 2
a = 7.985 (3) ÅMo Kα radiation
b = 8.594 (3) ŵ = 9.07 mm1
c = 11.020 (4) ÅT = 294 K
α = 87.801 (6)°0.24 × 0.16 × 0.12 mm
β = 76.688 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2309 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1471 reflections with I > 2σ(I)
Tmin = 0.202, Tmax = 0.339Rint = 0.065
3322 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.199H-atom parameters constrained
S = 0.98Δρmax = 0.86 e Å3
2309 reflectionsΔρmin = 1.27 e Å3
163 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
Br10.12496 (17)0.33749 (14)0.12113 (9)0.0560 (4)
Br20.69858 (18)0.14000 (16)0.98515 (10)0.0616 (5)
Br30.19458 (18)1.03572 (14)0.29251 (11)0.0597 (5)
O10.2910 (9)0.2930 (9)0.3421 (6)0.0451 (18)
H10.29900.27480.41460.054*
N10.3470 (10)0.3870 (10)0.5425 (7)0.0350 (19)
C10.1501 (12)0.5864 (12)0.4244 (8)0.032 (2)
C20.1817 (12)0.4586 (11)0.3349 (8)0.030 (2)
C30.0952 (13)0.5088 (13)0.2346 (8)0.035 (2)
C40.0163 (12)0.6781 (11)0.2222 (8)0.030 (2)
H40.07300.71030.15490.036*
C50.0428 (12)0.8008 (12)0.3121 (9)0.034 (2)
C60.0394 (13)0.7551 (12)0.4103 (8)0.035 (2)
H60.02030.83940.46900.042*
C70.2360 (13)0.5403 (13)0.5293 (9)0.037 (2)
H70.20930.62580.58940.044*
C80.4295 (12)0.3389 (12)0.6481 (8)0.032 (2)
C90.5304 (14)0.1652 (12)0.6570 (9)0.041 (2)
H90.54360.08770.59500.049*
C100.6116 (15)0.1055 (14)0.7560 (10)0.049 (3)
H100.68170.01160.76030.059*
C110.5887 (13)0.2199 (13)0.8488 (9)0.042 (3)
C120.4891 (15)0.3947 (14)0.8395 (9)0.048 (3)
H120.47670.47280.90090.057*
C130.4093 (13)0.4518 (12)0.7400 (8)0.037 (2)
H130.34050.56900.73480.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0849 (8)0.0393 (7)0.0331 (6)0.0047 (5)0.0351 (6)0.0061 (5)
Br20.0917 (9)0.0532 (8)0.0349 (7)0.0119 (6)0.0432 (6)0.0077 (5)
Br30.0896 (9)0.0281 (7)0.0566 (8)0.0077 (6)0.0431 (6)0.0098 (5)
O10.061 (4)0.039 (4)0.023 (4)0.001 (3)0.026 (3)0.003 (3)
N10.044 (4)0.033 (5)0.028 (4)0.011 (4)0.022 (3)0.006 (4)
C10.044 (5)0.034 (5)0.018 (5)0.014 (4)0.015 (4)0.007 (4)
C20.039 (5)0.024 (5)0.017 (4)0.001 (4)0.011 (4)0.000 (4)
C30.047 (5)0.047 (7)0.017 (5)0.020 (5)0.016 (4)0.005 (4)
C40.045 (5)0.030 (5)0.014 (4)0.010 (4)0.017 (4)0.006 (4)
C50.044 (5)0.026 (5)0.039 (6)0.015 (4)0.020 (4)0.016 (4)
C60.060 (6)0.027 (6)0.025 (5)0.018 (5)0.022 (4)0.005 (4)
C70.053 (6)0.035 (6)0.032 (5)0.020 (5)0.024 (4)0.003 (4)
C80.037 (5)0.045 (6)0.014 (4)0.014 (4)0.014 (4)0.007 (4)
C90.062 (6)0.029 (6)0.036 (6)0.015 (5)0.030 (5)0.001 (4)
C100.067 (7)0.031 (6)0.046 (6)0.006 (5)0.037 (5)0.002 (5)
C110.050 (6)0.043 (6)0.026 (5)0.007 (5)0.021 (4)0.005 (4)
C120.077 (7)0.041 (7)0.032 (6)0.022 (6)0.034 (5)0.013 (5)
C130.053 (5)0.021 (5)0.028 (5)0.004 (4)0.017 (4)0.003 (4)
Geometric parameters (Å, º) top
Br1—C31.870 (10)C5—C61.354 (12)
Br2—C111.876 (9)C6—H60.9300
Br3—C51.904 (9)C7—H70.9300
O1—C21.332 (11)C8—C131.365 (13)
O1—H10.8200C8—C91.379 (13)
N1—C71.268 (12)C9—C101.371 (13)
N1—C81.431 (10)C9—H90.9300
C1—C61.370 (13)C10—C111.373 (14)
C1—C21.406 (13)C10—H100.9300
C1—C71.437 (12)C11—C121.387 (15)
C2—C31.397 (12)C12—C131.367 (13)
C3—C41.372 (13)C12—H120.9300
C4—C51.390 (13)C13—H130.9300
C4—H40.9300
C2—O1—H1109.4N1—C7—H7118.9
C7—N1—C8122.6 (8)C1—C7—H7118.9
C6—C1—C2119.8 (8)C13—C8—C9119.3 (8)
C6—C1—C7120.1 (9)C13—C8—N1124.5 (8)
C2—C1—C7120.1 (8)C9—C8—N1116.2 (8)
O1—C2—C3119.2 (8)C10—C9—C8120.8 (9)
O1—C2—C1122.6 (8)C10—C9—H9119.6
C3—C2—C1118.2 (8)C8—C9—H9119.6
C4—C3—C2121.3 (8)C9—C10—C11119.6 (10)
C4—C3—Br1120.5 (6)C9—C10—H10120.2
C2—C3—Br1118.2 (7)C11—C10—H10120.2
C3—C4—C5118.7 (8)C10—C11—C12119.8 (9)
C3—C4—H4120.6C10—C11—Br2120.0 (8)
C5—C4—H4120.6C12—C11—Br2120.1 (8)
C6—C5—C4121.0 (8)C13—C12—C11119.8 (10)
C6—C5—Br3120.6 (8)C13—C12—H12120.1
C4—C5—Br3118.4 (6)C11—C12—H12120.1
C5—C6—C1120.9 (9)C8—C13—C12120.8 (9)
C5—C6—H6119.5C8—C13—H13119.6
C1—C6—H6119.5C12—C13—H13119.6
N1—C7—C1122.2 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.932.574 (10)135
C10—H10···O1i0.932.613.341 (13)136
C10—H10···Br1i0.932.993.866 (10)157
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC13H8Br3NO
Mr433.90
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)7.985 (3), 8.594 (3), 11.020 (4)
α, β, γ (°)87.801 (6), 76.688 (7), 65.180 (5)
V3)666.5 (4)
Z2
Radiation typeMo Kα
µ (mm1)9.07
Crystal size (mm)0.24 × 0.16 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.202, 0.339
No. of measured, independent and
observed [I > 2σ(I)] reflections
3322, 2309, 1471
Rint0.065
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.199, 0.98
No. of reflections2309
No. of parameters163
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.86, 1.27

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.932.574 (10)134.6
C10—H10···O1i0.932.613.341 (13)135.7
C10—H10···Br1i0.932.993.866 (10)157.2
Symmetry code: (i) x+1, y, z+1.
 

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