Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055675/cv2344sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055675/cv2344Isup2.hkl |
CCDC reference: 672892
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.014 Å
- R factor = 0.067
- wR factor = 0.197
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.21 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 14
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related crystal structures, see: Zheng et al. (2005); Özek et al. (2007); Guo (2007). For general background, see: Yeap et al. (2003).
The title compound, (I), was prepared by reaction of 3,5-dibromo-2-hydroxybenzaldehyde (1.4 g, 5 mmol) with 4-iodobenzenamine (1.2 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 (2.2 g, yield 91.7%). The pure product (0.5 g) was heated and dissolved in 20 ml of 1,2-dichloroethane. Single crystals were obtained from this solution by slow evaporation over a period of 2 days at room temperature.
Atom H1 was found in difference Fourier map, but placed in idealized position with O—H = 0.82 Å and refined as riding, with Uiso(H) = 1.5 Ueq (O). C-bound H atoms were geometrically positioned (C—H 0.93 Å) and refined as riding, with Uiso(H) = 1.2 Ueq(C).
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).
Fig. 1. The molecular structure of (I) with the atomic numbering and displacement ellipsoids drawn at the 30% probability level. Dashed line indicates hydrogen bond. |
C13H8Br2INO | Z = 2 |
Mr = 480.92 | F(000) = 448 |
Triclinic, P1 | Dx = 2.309 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0213 (17) Å | Cell parameters from 1701 reflections |
b = 8.5936 (18) Å | θ = 2.6–26.4° |
c = 11.290 (2) Å | µ = 8.08 mm−1 |
α = 87.066 (3)° | T = 294 K |
β = 76.541 (4)° | Prism, red |
γ = 66.203 (3)° | 0.14 × 0.12 × 0.10 mm |
V = 691.7 (2) Å3 |
Bruker SMART CCD area-detector diffractometer | 2455 independent reflections |
Radiation source: fine-focus sealed tube | 1802 reflections with I > 2σ |
Graphite monochromator | Rint = 0.043 |
ϕ and ω scans | θmax = 25.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→9 |
Tmin = 0.334, Tmax = 0.447 | k = −9→10 |
3478 measured reflections | l = −10→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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1364P)2] where P = (Fo2 + 2Fc2)/3 |
2455 reflections | (Δ/σ)max < 0.001 |
164 parameters | Δρmax = 2.19 e Å−3 |
0 restraints | Δρmin = −2.26 e Å−3 |
C13H8Br2INO | γ = 66.203 (3)° |
Mr = 480.92 | V = 691.7 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.0213 (17) Å | Mo Kα radiation |
b = 8.5936 (18) Å | µ = 8.08 mm−1 |
c = 11.290 (2) Å | T = 294 K |
α = 87.066 (3)° | 0.14 × 0.12 × 0.10 mm |
β = 76.541 (4)° |
Bruker SMART CCD area-detector diffractometer | 2455 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1802 reflections with I > 2σ |
Tmin = 0.334, Tmax = 0.447 | Rint = 0.043 |
3478 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.00 | Δρmax = 2.19 e Å−3 |
2455 reflections | Δρmin = −2.26 e Å−3 |
164 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 | ||
I1 | 0.29339 (10) | 0.87433 (9) | 0.00531 (6) | 0.0523 (3) | |
N1 | 0.6493 (10) | 0.6165 (10) | 0.4578 (7) | 0.0363 (18) | |
O1 | 0.7096 (10) | 0.7011 (8) | 0.6555 (6) | 0.0471 (17) | |
H1 | 0.7162 | 0.7249 | 0.5837 | 0.071* | |
Br1 | 0.87718 (17) | 0.65091 (14) | 0.87405 (10) | 0.0578 (4) | |
Br2 | 1.19331 (18) | −0.03821 (13) | 0.69717 (11) | 0.0579 (4) | |
C1 | 0.8181 (11) | 0.5375 (11) | 0.6621 (8) | 0.0313 (19) | |
C2 | 0.9089 (13) | 0.4830 (12) | 0.7589 (8) | 0.038 (2) | |
C3 | 1.0183 (13) | 0.3134 (12) | 0.7704 (8) | 0.037 (2) | |
H3 | 1.0751 | 0.2788 | 0.8357 | 0.044* | |
C4 | 1.0406 (13) | 0.1962 (12) | 0.6813 (8) | 0.039 (2) | |
C5 | 0.9571 (14) | 0.2448 (13) | 0.5844 (9) | 0.043 (2) | |
H5 | 0.9754 | 0.1635 | 0.5260 | 0.052* | |
C6 | 0.8464 (12) | 0.4136 (12) | 0.5735 (8) | 0.033 (2) | |
C7 | 0.7600 (13) | 0.4619 (13) | 0.4687 (8) | 0.038 (2) | |
H7 | 0.7859 | 0.3793 | 0.4091 | 0.046* | |
C8 | 0.5710 (11) | 0.6631 (11) | 0.3539 (8) | 0.0306 (19) | |
C9 | 0.5922 (14) | 0.5538 (13) | 0.2609 (9) | 0.043 (2) | |
H9 | 0.6612 | 0.4377 | 0.2648 | 0.052* | |
C10 | 0.5139 (14) | 0.6122 (13) | 0.1631 (9) | 0.044 (2) | |
H10 | 0.5266 | 0.5363 | 0.1024 | 0.053* | |
C11 | 0.4142 (13) | 0.7881 (12) | 0.1555 (8) | 0.038 (2) | |
C12 | 0.3925 (14) | 0.8980 (12) | 0.2458 (9) | 0.043 (2) | |
H12 | 0.3259 | 1.0143 | 0.2409 | 0.052* | |
C13 | 0.4693 (13) | 0.8370 (13) | 0.3450 (9) | 0.041 (2) | |
H13 | 0.4531 | 0.9130 | 0.4067 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0699 (5) | 0.0484 (5) | 0.0438 (5) | −0.0146 (4) | −0.0420 (4) | 0.0128 (3) |
N1 | 0.044 (4) | 0.038 (5) | 0.036 (4) | −0.018 (4) | −0.026 (3) | 0.012 (3) |
O1 | 0.064 (4) | 0.029 (4) | 0.046 (4) | −0.004 (3) | −0.035 (3) | 0.003 (3) |
Br1 | 0.0766 (8) | 0.0456 (7) | 0.0464 (7) | −0.0061 (6) | −0.0382 (6) | −0.0035 (5) |
Br2 | 0.0851 (8) | 0.0310 (6) | 0.0618 (7) | −0.0127 (6) | −0.0468 (6) | 0.0138 (5) |
C1 | 0.033 (4) | 0.028 (5) | 0.034 (4) | −0.010 (4) | −0.016 (4) | 0.006 (4) |
C2 | 0.045 (5) | 0.044 (6) | 0.035 (5) | −0.018 (4) | −0.028 (4) | 0.014 (4) |
C3 | 0.048 (5) | 0.039 (6) | 0.031 (4) | −0.019 (4) | −0.023 (4) | 0.008 (4) |
C4 | 0.043 (5) | 0.037 (5) | 0.038 (5) | −0.010 (4) | −0.027 (4) | 0.015 (4) |
C5 | 0.059 (6) | 0.039 (6) | 0.048 (5) | −0.026 (5) | −0.037 (5) | 0.015 (4) |
C6 | 0.036 (4) | 0.036 (5) | 0.036 (5) | −0.015 (4) | −0.024 (4) | 0.016 (4) |
C7 | 0.050 (5) | 0.041 (6) | 0.039 (5) | −0.025 (5) | −0.029 (4) | 0.012 (4) |
C8 | 0.032 (4) | 0.031 (5) | 0.034 (5) | −0.012 (4) | −0.021 (4) | 0.009 (4) |
C9 | 0.055 (6) | 0.034 (5) | 0.041 (5) | −0.010 (5) | −0.026 (5) | 0.007 (4) |
C10 | 0.053 (6) | 0.037 (6) | 0.038 (5) | −0.008 (5) | −0.025 (4) | 0.001 (4) |
C11 | 0.043 (5) | 0.043 (6) | 0.034 (5) | −0.015 (4) | −0.025 (4) | 0.011 (4) |
C12 | 0.059 (6) | 0.028 (5) | 0.051 (6) | −0.014 (4) | −0.039 (5) | 0.014 (4) |
C13 | 0.053 (5) | 0.036 (5) | 0.039 (5) | −0.012 (4) | −0.030 (4) | 0.002 (4) |
I1—C11 | 2.102 (9) | C5—H5 | 0.9300 |
N1—C7 | 1.285 (12) | C6—C7 | 1.467 (11) |
N1—C8 | 1.423 (10) | C7—H7 | 0.9300 |
O1—C1 | 1.331 (10) | C8—C9 | 1.378 (13) |
O1—H1 | 0.8200 | C8—C13 | 1.396 (13) |
Br1—C2 | 1.892 (10) | C9—C10 | 1.370 (13) |
Br2—C4 | 1.914 (9) | C9—H9 | 0.9300 |
C1—C2 | 1.409 (12) | C10—C11 | 1.406 (13) |
C1—C6 | 1.411 (13) | C10—H10 | 0.9300 |
C2—C3 | 1.383 (13) | C11—C12 | 1.359 (14) |
C3—C4 | 1.390 (14) | C12—C13 | 1.381 (12) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.374 (12) | C13—H13 | 0.9300 |
C5—C6 | 1.379 (13) | ||
C7—N1—C8 | 120.7 (8) | N1—C7—H7 | 119.4 |
C1—O1—H1 | 109.5 | C6—C7—H7 | 119.4 |
O1—C1—C2 | 120.4 (8) | C9—C8—C13 | 118.1 (8) |
O1—C1—C6 | 121.7 (8) | C9—C8—N1 | 126.1 (8) |
C2—C1—C6 | 117.9 (8) | C13—C8—N1 | 115.8 (8) |
C3—C2—C1 | 121.9 (9) | C10—C9—C8 | 121.6 (9) |
C3—C2—Br1 | 120.5 (6) | C10—C9—H9 | 119.2 |
C1—C2—Br1 | 117.6 (7) | C8—C9—H9 | 119.2 |
C2—C3—C4 | 118.0 (8) | C9—C10—C11 | 119.3 (9) |
C2—C3—H3 | 121.0 | C9—C10—H10 | 120.4 |
C4—C3—H3 | 121.0 | C11—C10—H10 | 120.4 |
C5—C4—C3 | 121.9 (9) | C12—C11—C10 | 120.0 (8) |
C5—C4—Br2 | 120.4 (8) | C12—C11—I1 | 121.4 (7) |
C3—C4—Br2 | 117.8 (6) | C10—C11—I1 | 118.6 (7) |
C4—C5—C6 | 120.2 (10) | C11—C12—C13 | 120.0 (9) |
C4—C5—H5 | 119.9 | C11—C12—H12 | 120.0 |
C6—C5—H5 | 119.9 | C13—C12—H12 | 120.0 |
C5—C6—C1 | 120.1 (8) | C12—C13—C8 | 121.0 (9) |
C5—C6—C7 | 119.0 (9) | C12—C13—H13 | 119.5 |
C1—C6—C7 | 120.8 (8) | C8—C13—H13 | 119.5 |
N1—C7—C6 | 121.1 (9) | ||
O1—C1—C2—C3 | 178.1 (8) | C8—N1—C7—C6 | 178.0 (8) |
C6—C1—C2—C3 | −1.9 (13) | C5—C6—C7—N1 | 176.9 (9) |
O1—C1—C2—Br1 | −2.1 (12) | C1—C6—C7—N1 | −3.5 (14) |
C6—C1—C2—Br1 | 177.9 (6) | C7—N1—C8—C9 | 4.3 (14) |
C1—C2—C3—C4 | 1.4 (14) | C7—N1—C8—C13 | −173.3 (9) |
Br1—C2—C3—C4 | −178.3 (7) | C13—C8—C9—C10 | −1.0 (15) |
C2—C3—C4—C5 | −0.2 (14) | N1—C8—C9—C10 | −178.6 (9) |
C2—C3—C4—Br2 | 179.7 (7) | C8—C9—C10—C11 | 1.8 (16) |
C3—C4—C5—C6 | −0.4 (15) | C9—C10—C11—C12 | −1.5 (16) |
Br2—C4—C5—C6 | 179.7 (7) | C9—C10—C11—I1 | −179.4 (8) |
C4—C5—C6—C1 | −0.1 (14) | C10—C11—C12—C13 | 0.4 (15) |
C4—C5—C6—C7 | 179.6 (9) | I1—C11—C12—C13 | 178.2 (8) |
O1—C1—C6—C5 | −178.9 (9) | C11—C12—C13—C8 | 0.5 (16) |
C2—C1—C6—C5 | 1.2 (13) | C9—C8—C13—C12 | −0.2 (15) |
O1—C1—C6—C7 | 1.5 (13) | N1—C8—C13—C12 | 177.7 (9) |
C2—C1—C6—C7 | −178.5 (8) |
Experimental details
Crystal data | |
Chemical formula | C13H8Br2INO |
Mr | 480.92 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 8.0213 (17), 8.5936 (18), 11.290 (2) |
α, β, γ (°) | 87.066 (3), 76.541 (4), 66.203 (3) |
V (Å3) | 691.7 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 8.08 |
Crystal size (mm) | 0.14 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.334, 0.447 |
No. of measured, independent and observed (I > 2σ) reflections | 3478, 2455, 1802 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.197, 1.00 |
No. of reflections | 2455 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.19, −2.26 |
Computer programs: SMART (Bruker 1997), SAINT (Bruker 1997), SHELXTL (Bruker, 2001).
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Schiff bases are important in diverse fields of chemistry and biochemistry owing to their biological activities, photochromism and so on (Yeap et al., 2003). Thus, the chemists are prompted to generate the 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-iodobenzenamine.
In (I), two aromatic substituents lie trans to each other across the C=N bond. The molecule is almost planar, with a dihedral angle of 4.4 (5)° between the aromatic rings. Intramolecular O1—H1···N1 hydrogen bonding generates an S(6) ring motif. The crystal packing exhibits short intermolecular I1···Br2i (d[I1···Br2]=3.7226 (16) Å, symmetry code: (i) -1 + x,1 + y,-1 + z) contacts.