Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054335/sj2397sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054335/sj2397Isup2.hkl |
CCDC reference: 672831
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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).
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.
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).
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).
C13H8Br3NO | Z = 2 |
Mr = 433.90 | F(000) = 412 |
Triclinic, P1 | Dx = 2.162 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.985 (3) Å | Cell parameters from 1206 reflections |
b = 8.594 (3) Å | θ = 2.9–26.2° |
c = 11.020 (4) Å | µ = 9.07 mm−1 |
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 |
Bruker SMART CCD area-detector diffractometer | 2309 independent reflections |
Radiation source: fine-focus sealed tube | 1471 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→9 |
Tmin = 0.202, Tmax = 0.339 | k = −6→10 |
3322 measured reflections | l = −12→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-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 parameters | Δρmax = 0.86 e Å−3 |
0 restraints | Δρmin = −1.27 e Å−3 |
C13H8Br3NO | γ = 65.180 (5)° |
Mr = 433.90 | V = 666.5 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.985 (3) Å | Mo Kα radiation |
b = 8.594 (3) Å | µ = 9.07 mm−1 |
c = 11.020 (4) Å | T = 294 K |
α = 87.801 (6)° | 0.24 × 0.16 × 0.12 mm |
β = 76.688 (7)° |
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 = 0.339 | Rint = 0.065 |
3322 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.86 e Å−3 |
2309 reflections | Δρmin = −1.27 e Å−3 |
163 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.12496 (17) | 0.33749 (14) | 0.12113 (9) | 0.0560 (4) | |
Br2 | 0.69858 (18) | 0.14000 (16) | 0.98515 (10) | 0.0616 (5) | |
Br3 | −0.19458 (18) | 1.03572 (14) | 0.29251 (11) | 0.0597 (5) | |
O1 | 0.2910 (9) | 0.2930 (9) | 0.3421 (6) | 0.0451 (18) | |
H1 | 0.2990 | 0.2748 | 0.4146 | 0.054* | |
N1 | 0.3470 (10) | 0.3870 (10) | 0.5425 (7) | 0.0350 (19) | |
C1 | 0.1501 (12) | 0.5864 (12) | 0.4244 (8) | 0.032 (2) | |
C2 | 0.1817 (12) | 0.4586 (11) | 0.3349 (8) | 0.030 (2) | |
C3 | 0.0952 (13) | 0.5088 (13) | 0.2346 (8) | 0.035 (2) | |
C4 | −0.0163 (12) | 0.6781 (11) | 0.2222 (8) | 0.030 (2) | |
H4 | −0.0730 | 0.7103 | 0.1549 | 0.036* | |
C5 | −0.0428 (12) | 0.8008 (12) | 0.3121 (9) | 0.034 (2) | |
C6 | 0.0394 (13) | 0.7551 (12) | 0.4103 (8) | 0.035 (2) | |
H6 | 0.0203 | 0.8394 | 0.4690 | 0.042* | |
C7 | 0.2360 (13) | 0.5403 (13) | 0.5293 (9) | 0.037 (2) | |
H7 | 0.2093 | 0.6258 | 0.5894 | 0.044* | |
C8 | 0.4295 (12) | 0.3389 (12) | 0.6481 (8) | 0.032 (2) | |
C9 | 0.5304 (14) | 0.1652 (12) | 0.6570 (9) | 0.041 (2) | |
H9 | 0.5436 | 0.0877 | 0.5950 | 0.049* | |
C10 | 0.6116 (15) | 0.1055 (14) | 0.7560 (10) | 0.049 (3) | |
H10 | 0.6817 | −0.0116 | 0.7603 | 0.059* | |
C11 | 0.5887 (13) | 0.2199 (13) | 0.8488 (9) | 0.042 (3) | |
C12 | 0.4891 (15) | 0.3947 (14) | 0.8395 (9) | 0.048 (3) | |
H12 | 0.4767 | 0.4728 | 0.9009 | 0.057* | |
C13 | 0.4093 (13) | 0.4518 (12) | 0.7400 (8) | 0.037 (2) | |
H13 | 0.3405 | 0.5690 | 0.7348 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0849 (8) | 0.0393 (7) | 0.0331 (6) | −0.0047 (5) | −0.0351 (6) | −0.0061 (5) |
Br2 | 0.0917 (9) | 0.0532 (8) | 0.0349 (7) | −0.0119 (6) | −0.0432 (6) | 0.0077 (5) |
Br3 | 0.0896 (9) | 0.0281 (7) | 0.0566 (8) | −0.0077 (6) | −0.0431 (6) | 0.0098 (5) |
O1 | 0.061 (4) | 0.039 (4) | 0.023 (4) | −0.001 (3) | −0.026 (3) | 0.003 (3) |
N1 | 0.044 (4) | 0.033 (5) | 0.028 (4) | −0.011 (4) | −0.022 (3) | 0.006 (4) |
C1 | 0.044 (5) | 0.034 (5) | 0.018 (5) | −0.014 (4) | −0.015 (4) | 0.007 (4) |
C2 | 0.039 (5) | 0.024 (5) | 0.017 (4) | −0.001 (4) | −0.011 (4) | 0.000 (4) |
C3 | 0.047 (5) | 0.047 (7) | 0.017 (5) | −0.020 (5) | −0.016 (4) | 0.005 (4) |
C4 | 0.045 (5) | 0.030 (5) | 0.014 (4) | −0.010 (4) | −0.017 (4) | 0.006 (4) |
C5 | 0.044 (5) | 0.026 (5) | 0.039 (6) | −0.015 (4) | −0.020 (4) | 0.016 (4) |
C6 | 0.060 (6) | 0.027 (6) | 0.025 (5) | −0.018 (5) | −0.022 (4) | 0.005 (4) |
C7 | 0.053 (6) | 0.035 (6) | 0.032 (5) | −0.020 (5) | −0.024 (4) | 0.003 (4) |
C8 | 0.037 (5) | 0.045 (6) | 0.014 (4) | −0.014 (4) | −0.014 (4) | 0.007 (4) |
C9 | 0.062 (6) | 0.029 (6) | 0.036 (6) | −0.015 (5) | −0.030 (5) | 0.001 (4) |
C10 | 0.067 (7) | 0.031 (6) | 0.046 (6) | −0.006 (5) | −0.037 (5) | 0.002 (5) |
C11 | 0.050 (6) | 0.043 (6) | 0.026 (5) | −0.007 (5) | −0.021 (4) | 0.005 (4) |
C12 | 0.077 (7) | 0.041 (7) | 0.032 (6) | −0.022 (6) | −0.034 (5) | 0.013 (5) |
C13 | 0.053 (5) | 0.021 (5) | 0.028 (5) | −0.004 (4) | −0.017 (4) | −0.003 (4) |
Br1—C3 | 1.870 (10) | C5—C6 | 1.354 (12) |
Br2—C11 | 1.876 (9) | C6—H6 | 0.9300 |
Br3—C5 | 1.904 (9) | C7—H7 | 0.9300 |
O1—C2 | 1.332 (11) | C8—C13 | 1.365 (13) |
O1—H1 | 0.8200 | C8—C9 | 1.379 (13) |
N1—C7 | 1.268 (12) | C9—C10 | 1.371 (13) |
N1—C8 | 1.431 (10) | C9—H9 | 0.9300 |
C1—C6 | 1.370 (13) | C10—C11 | 1.373 (14) |
C1—C2 | 1.406 (13) | C10—H10 | 0.9300 |
C1—C7 | 1.437 (12) | C11—C12 | 1.387 (15) |
C2—C3 | 1.397 (12) | C12—C13 | 1.367 (13) |
C3—C4 | 1.372 (13) | C12—H12 | 0.9300 |
C4—C5 | 1.390 (13) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | ||
C2—O1—H1 | 109.4 | N1—C7—H7 | 118.9 |
C7—N1—C8 | 122.6 (8) | C1—C7—H7 | 118.9 |
C6—C1—C2 | 119.8 (8) | C13—C8—C9 | 119.3 (8) |
C6—C1—C7 | 120.1 (9) | C13—C8—N1 | 124.5 (8) |
C2—C1—C7 | 120.1 (8) | C9—C8—N1 | 116.2 (8) |
O1—C2—C3 | 119.2 (8) | C10—C9—C8 | 120.8 (9) |
O1—C2—C1 | 122.6 (8) | C10—C9—H9 | 119.6 |
C3—C2—C1 | 118.2 (8) | C8—C9—H9 | 119.6 |
C4—C3—C2 | 121.3 (8) | C9—C10—C11 | 119.6 (10) |
C4—C3—Br1 | 120.5 (6) | C9—C10—H10 | 120.2 |
C2—C3—Br1 | 118.2 (7) | C11—C10—H10 | 120.2 |
C3—C4—C5 | 118.7 (8) | C10—C11—C12 | 119.8 (9) |
C3—C4—H4 | 120.6 | C10—C11—Br2 | 120.0 (8) |
C5—C4—H4 | 120.6 | C12—C11—Br2 | 120.1 (8) |
C6—C5—C4 | 121.0 (8) | C13—C12—C11 | 119.8 (10) |
C6—C5—Br3 | 120.6 (8) | C13—C12—H12 | 120.1 |
C4—C5—Br3 | 118.4 (6) | C11—C12—H12 | 120.1 |
C5—C6—C1 | 120.9 (9) | C8—C13—C12 | 120.8 (9) |
C5—C6—H6 | 119.5 | C8—C13—H13 | 119.6 |
C1—C6—H6 | 119.5 | C12—C13—H13 | 119.6 |
N1—C7—C1 | 122.2 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.93 | 2.574 (10) | 135 |
C10—H10···O1i | 0.93 | 2.61 | 3.341 (13) | 136 |
C10—H10···Br1i | 0.93 | 2.99 | 3.866 (10) | 157 |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H8Br3NO |
Mr | 433.90 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 666.5 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 9.07 |
Crystal size (mm) | 0.24 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.202, 0.339 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3322, 2309, 1471 |
Rint | 0.065 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.199, 0.98 |
No. of reflections | 2309 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.86, −1.27 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.93 | 2.574 (10) | 134.6 |
C10—H10···O1i | 0.93 | 2.61 | 3.341 (13) | 135.7 |
C10—H10···Br1i | 0.93 | 2.99 | 3.866 (10) | 157.2 |
Symmetry code: (i) −x+1, −y, −z+1. |
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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.