Abstract
In the title compound, C17H14I4N2O2, there are two intramolecular O—H⋯N hydrogen bonds, which make S(6) ring motifs. In the crystal, there are no significant intermolecular interactions present.
Related literature
For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to Schiff base ligands, see, for example: Kargar et al. (2011 ▶); Kia et al. (2010 ▶). For a related structure, see: Kargar et al. (2012 ▶).
Experimental
Crystal data
C17H14I4N2O2
M r = 785.90
Monoclinic,
a = 4.5578 (3) Å
b = 16.5095 (11) Å
c = 27.2417 (18) Å
β = 91.736 (4)°
V = 2048.9 (2) Å3
Z = 4
Mo Kα radiation
μ = 6.10 mm−1
T = 291 K
0.30 × 0.14 × 0.14 mm
Data collection
Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.262, T max = 0.482
16049 measured reflections
4458 independent reflections
2832 reflections with I > 2σ(I)
R int = 0.047
Refinement
R[F 2 > 2σ(F 2)] = 0.035
wR(F 2) = 0.059
S = 0.98
4458 reflections
226 parameters
H-atom parameters constrained
Δρmax = 0.61 e Å−3
Δρmin = −0.72 e Å−3
Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203214X/su2471sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203214X/su2471Isup2.hkl
Supplementary material file. DOI: 10.1107/S160053681203214X/su2471Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1—H1⋯N1 | 0.90 | 1.76 | 2.569 (5) | 148 |
| O2—H2⋯N2 | 0.89 | 1.75 | 2.564 (5) | 150 |
Acknowledgments
HK and AAA thank PNU for financial support. MNT thanks the GC University of Sargodha, Pakistan, for the research facility.
supplementary crystallographic information
Comment
In continuation of our work on the crystal structures of Schiff base ligands (Kargar et al., 2011; Kia et al., 2010), we synthesizes and carried out the X-ray structure analysis of the title compound.
In the title compound, Fig. 1, a potential tetradentate Schiff base ligand, there are two intramolecular O—H···N hydrogen bonds (Table 1) that make S(6) ring motifs (Bernstein et al., 1995). The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those reported for a similar structure (Kargar et al., 2012).
In the crystal, there are no significant intermolecular interactions present.
Experimental
The title compound was synthesized by adding 3,5-dibromosalicylaldehyde (2 mmol) to a solution of propylenediamine (1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 30 min. The resultant solution was filtered. Light-yellow prismatic single crystals of the title compound, suitable for X-ray structure determination, were obtained by recrystallization from ethanol by slow evaporation of the solvents at room temperature over several days.
Refinement
The OH H atoms were located in a difference Fourier map and were constrained to ride on the parent O atom with Uiso(H) = 1.5Ueq(O). The C-bound H atoms were included in calculated positions and treated as riding atoms: C-H = 0.93 and 0.97 Å, with Uiso(H) = 1.2Ueq(C).
Figures
Fig. 1.
The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering.
Crystal data
| C17H14I4N2O2 | F(000) = 1432 |
| Mr = 785.90 | Dx = 2.548 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 2453 reflections |
| a = 4.5578 (3) Å | θ = 2.5–27.5° |
| b = 16.5095 (11) Å | µ = 6.10 mm−1 |
| c = 27.2417 (18) Å | T = 291 K |
| β = 91.736 (4)° | Needle, light-yellow |
| V = 2048.9 (2) Å3 | 0.30 × 0.14 × 0.14 mm |
| Z = 4 |
Data collection
| Bruker SMART APEXII CCD area-detector diffractometer | 4458 independent reflections |
| Radiation source: fine-focus sealed tube | 2832 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.047 |
| φ and ω scans | θmax = 27.1°, θmin = 1.4° |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −5→5 |
| Tmin = 0.262, Tmax = 0.482 | k = −21→17 |
| 16049 measured reflections | l = −34→34 |
Refinement
| 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.059 | H-atom parameters constrained |
| S = 0.98 | w = 1/[σ2(Fo2) + (0.0161P)2] where P = (Fo2 + 2Fc2)/3 |
| 4458 reflections | (Δ/σ)max = 0.002 |
| 226 parameters | Δρmax = 0.61 e Å−3 |
| 0 restraints | Δρmin = −0.72 e Å−3 |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
| x | y | z | Uiso*/Ueq | ||
| I1 | −0.84612 (9) | 1.18172 (2) | 0.147565 (15) | 0.05342 (13) | |
| I2 | −0.80900 (9) | 0.88529 (2) | 0.274765 (14) | 0.05293 (13) | |
| I3 | 0.66705 (10) | 0.36716 (2) | 0.091322 (16) | 0.06029 (14) | |
| I4 | 0.86332 (9) | 0.67131 (2) | 0.208721 (14) | 0.05504 (13) | |
| O1 | −0.4461 (7) | 1.0651 (2) | 0.08517 (12) | 0.0406 (9) | |
| H1 | −0.3177 | 1.0345 | 0.0688 | 0.061* | |
| O2 | 0.4376 (7) | 0.7341 (2) | 0.12415 (12) | 0.0446 (9) | |
| H2 | 0.2946 | 0.7497 | 0.1030 | 0.067* | |
| N1 | −0.1123 (8) | 0.9443 (2) | 0.06648 (15) | 0.0350 (10) | |
| N2 | 0.0681 (9) | 0.7303 (3) | 0.05131 (15) | 0.0395 (11) | |
| C1 | −0.5088 (10) | 1.0271 (3) | 0.12709 (18) | 0.0303 (12) | |
| C2 | −0.6977 (10) | 1.0640 (3) | 0.16025 (19) | 0.0322 (12) | |
| C3 | −0.7811 (11) | 1.0236 (3) | 0.20139 (19) | 0.0377 (13) | |
| H3 | −0.9105 | 1.0480 | 0.2226 | 0.045* | |
| C4 | −0.6736 (11) | 0.9465 (3) | 0.21164 (17) | 0.0341 (13) | |
| C5 | −0.4784 (10) | 0.9102 (3) | 0.18129 (18) | 0.0329 (12) | |
| H5 | −0.4028 | 0.8593 | 0.1890 | 0.040* | |
| C6 | −0.3933 (10) | 0.9501 (3) | 0.13875 (18) | 0.0294 (12) | |
| C7 | −0.1787 (10) | 0.9141 (3) | 0.10729 (18) | 0.0342 (13) | |
| H7 | −0.0857 | 0.8666 | 0.1175 | 0.041* | |
| C8 | 0.1172 (11) | 0.9065 (3) | 0.03753 (18) | 0.0378 (13) | |
| H8A | 0.2494 | 0.8767 | 0.0594 | 0.045* | |
| H8B | 0.2299 | 0.9487 | 0.0220 | 0.045* | |
| C9 | −0.0043 (11) | 0.8493 (3) | −0.00185 (18) | 0.0391 (14) | |
| H9A | 0.1530 | 0.8340 | −0.0232 | 0.047* | |
| H9B | −0.1519 | 0.8776 | −0.0217 | 0.047* | |
| C10 | −0.1411 (11) | 0.7724 (3) | 0.01916 (18) | 0.0415 (14) | |
| H10A | −0.3131 | 0.7867 | 0.0374 | 0.050* | |
| H10B | −0.2030 | 0.7368 | −0.0075 | 0.050* | |
| C11 | 0.1244 (10) | 0.6563 (3) | 0.04552 (19) | 0.0375 (13) | |
| H11 | 0.0295 | 0.6283 | 0.0200 | 0.045* | |
| C12 | 0.3351 (10) | 0.6128 (3) | 0.07772 (19) | 0.0351 (13) | |
| C13 | 0.3936 (11) | 0.5311 (3) | 0.07004 (19) | 0.0407 (14) | |
| H13 | 0.3015 | 0.5036 | 0.0441 | 0.049* | |
| C14 | 0.5879 (11) | 0.4914 (3) | 0.1010 (2) | 0.0387 (13) | |
| C15 | 0.7236 (11) | 0.5313 (3) | 0.14057 (19) | 0.0381 (13) | |
| H15 | 0.8510 | 0.5032 | 0.1618 | 0.046* | |
| C16 | 0.6701 (11) | 0.6115 (3) | 0.14830 (18) | 0.0352 (13) | |
| C17 | 0.4795 (11) | 0.6551 (3) | 0.11703 (19) | 0.0347 (13) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| I1 | 0.0713 (3) | 0.0303 (2) | 0.0585 (3) | 0.0101 (2) | −0.0011 (2) | −0.0040 (2) |
| I2 | 0.0675 (3) | 0.0569 (3) | 0.0348 (2) | −0.0083 (2) | 0.00783 (19) | 0.0078 (2) |
| I3 | 0.0820 (3) | 0.0365 (2) | 0.0627 (3) | 0.0121 (2) | 0.0063 (2) | −0.0041 (2) |
| I4 | 0.0633 (3) | 0.0545 (3) | 0.0467 (2) | −0.0014 (2) | −0.0092 (2) | −0.0021 (2) |
| O1 | 0.051 (2) | 0.033 (2) | 0.038 (2) | 0.0030 (17) | 0.0072 (18) | 0.0107 (18) |
| O2 | 0.057 (2) | 0.031 (2) | 0.046 (2) | 0.0008 (18) | −0.0050 (19) | 0.0028 (19) |
| N1 | 0.034 (3) | 0.037 (3) | 0.034 (3) | −0.001 (2) | 0.004 (2) | 0.003 (2) |
| N2 | 0.042 (3) | 0.038 (3) | 0.039 (3) | 0.001 (2) | 0.001 (2) | 0.002 (2) |
| C1 | 0.034 (3) | 0.023 (3) | 0.033 (3) | −0.010 (2) | −0.004 (3) | 0.001 (3) |
| C2 | 0.036 (3) | 0.019 (3) | 0.042 (3) | 0.001 (2) | −0.003 (3) | −0.004 (3) |
| C3 | 0.044 (3) | 0.032 (3) | 0.038 (3) | −0.001 (3) | 0.006 (3) | −0.010 (3) |
| C4 | 0.041 (3) | 0.033 (3) | 0.028 (3) | −0.006 (3) | 0.001 (3) | −0.002 (3) |
| C5 | 0.038 (3) | 0.031 (3) | 0.029 (3) | 0.001 (2) | −0.008 (3) | 0.002 (3) |
| C6 | 0.032 (3) | 0.023 (3) | 0.032 (3) | −0.001 (2) | −0.007 (2) | −0.002 (2) |
| C7 | 0.035 (3) | 0.031 (3) | 0.037 (3) | 0.005 (2) | −0.004 (3) | −0.001 (3) |
| C8 | 0.037 (3) | 0.042 (3) | 0.035 (3) | 0.002 (3) | 0.007 (3) | 0.002 (3) |
| C9 | 0.041 (3) | 0.046 (4) | 0.031 (3) | 0.011 (3) | 0.001 (3) | 0.001 (3) |
| C10 | 0.038 (3) | 0.046 (4) | 0.039 (3) | 0.004 (3) | −0.007 (3) | −0.005 (3) |
| C11 | 0.034 (3) | 0.044 (4) | 0.035 (3) | −0.001 (3) | 0.004 (3) | 0.000 (3) |
| C12 | 0.033 (3) | 0.036 (3) | 0.037 (3) | −0.001 (3) | 0.007 (3) | 0.007 (3) |
| C13 | 0.046 (4) | 0.039 (3) | 0.038 (3) | −0.002 (3) | 0.010 (3) | −0.005 (3) |
| C14 | 0.041 (3) | 0.026 (3) | 0.049 (4) | 0.004 (2) | 0.011 (3) | −0.003 (3) |
| C15 | 0.043 (3) | 0.037 (3) | 0.035 (3) | 0.004 (3) | 0.005 (3) | 0.003 (3) |
| C16 | 0.038 (3) | 0.031 (3) | 0.037 (3) | −0.002 (3) | 0.003 (3) | 0.006 (3) |
| C17 | 0.039 (3) | 0.030 (3) | 0.035 (3) | −0.004 (3) | 0.014 (3) | 0.000 (3) |
Geometric parameters (Å, º)
| I1—C2 | 2.083 (5) | C6—C7 | 1.447 (6) |
| I2—C4 | 2.103 (5) | C7—H7 | 0.9300 |
| I3—C14 | 2.100 (5) | C8—C9 | 1.521 (6) |
| I4—C16 | 2.091 (5) | C8—H8A | 0.9700 |
| O1—C1 | 1.341 (5) | C8—H8B | 0.9700 |
| O1—H1 | 0.9004 | C9—C10 | 1.533 (6) |
| O2—C17 | 1.334 (5) | C9—H9A | 0.9700 |
| O2—H2 | 0.8944 | C9—H9B | 0.9700 |
| N1—C7 | 1.264 (6) | C10—H10A | 0.9700 |
| N1—C8 | 1.468 (6) | C10—H10B | 0.9700 |
| N2—C11 | 1.260 (6) | C11—C12 | 1.468 (7) |
| N2—C10 | 1.452 (6) | C11—H11 | 0.9300 |
| C1—C2 | 1.405 (6) | C12—C13 | 1.392 (6) |
| C1—C6 | 1.409 (6) | C12—C17 | 1.422 (7) |
| C2—C3 | 1.367 (6) | C13—C14 | 1.372 (7) |
| C3—C4 | 1.390 (7) | C13—H13 | 0.9300 |
| C3—H3 | 0.9300 | C14—C15 | 1.392 (7) |
| C4—C5 | 1.370 (6) | C15—C16 | 1.364 (6) |
| C5—C6 | 1.397 (6) | C15—H15 | 0.9300 |
| C5—H5 | 0.9300 | C16—C17 | 1.397 (7) |
| C1—O1—H1 | 108.6 | C8—C9—H9A | 108.9 |
| C17—O2—H2 | 107.0 | C10—C9—H9A | 108.9 |
| C7—N1—C8 | 119.9 (4) | C8—C9—H9B | 108.9 |
| C11—N2—C10 | 121.4 (4) | C10—C9—H9B | 108.9 |
| O1—C1—C2 | 119.7 (4) | H9A—C9—H9B | 107.7 |
| O1—C1—C6 | 121.7 (5) | N2—C10—C9 | 110.7 (4) |
| C2—C1—C6 | 118.5 (5) | N2—C10—H10A | 109.5 |
| C3—C2—C1 | 120.4 (4) | C9—C10—H10A | 109.5 |
| C3—C2—I1 | 119.6 (4) | N2—C10—H10B | 109.5 |
| C1—C2—I1 | 120.0 (4) | C9—C10—H10B | 109.5 |
| C2—C3—C4 | 120.4 (5) | H10A—C10—H10B | 108.1 |
| C2—C3—H3 | 119.8 | N2—C11—C12 | 122.1 (5) |
| C4—C3—H3 | 119.8 | N2—C11—H11 | 118.9 |
| C5—C4—C3 | 120.7 (5) | C12—C11—H11 | 118.9 |
| C5—C4—I2 | 119.7 (4) | C13—C12—C17 | 120.1 (5) |
| C3—C4—I2 | 119.6 (4) | C13—C12—C11 | 120.6 (5) |
| C4—C5—C6 | 119.8 (5) | C17—C12—C11 | 119.3 (5) |
| C4—C5—H5 | 120.1 | C14—C13—C12 | 119.6 (5) |
| C6—C5—H5 | 120.1 | C14—C13—H13 | 120.2 |
| C5—C6—C1 | 120.0 (5) | C12—C13—H13 | 120.2 |
| C5—C6—C7 | 120.5 (4) | C13—C14—C15 | 120.9 (5) |
| C1—C6—C7 | 119.4 (5) | C13—C14—I3 | 120.0 (4) |
| N1—C7—C6 | 122.9 (5) | C15—C14—I3 | 119.1 (4) |
| N1—C7—H7 | 118.6 | C16—C15—C14 | 120.1 (5) |
| C6—C7—H7 | 118.6 | C16—C15—H15 | 119.9 |
| N1—C8—C9 | 113.1 (4) | C14—C15—H15 | 119.9 |
| N1—C8—H8A | 109.0 | C15—C16—C17 | 121.1 (5) |
| C9—C8—H8A | 109.0 | C15—C16—I4 | 120.5 (4) |
| N1—C8—H8B | 109.0 | C17—C16—I4 | 118.4 (4) |
| C9—C8—H8B | 109.0 | O2—C17—C16 | 120.3 (5) |
| H8A—C8—H8B | 107.8 | O2—C17—C12 | 121.6 (5) |
| C8—C9—C10 | 113.3 (4) | C16—C17—C12 | 118.1 (5) |
| O1—C1—C2—C3 | 175.1 (4) | C11—N2—C10—C9 | −127.5 (5) |
| C6—C1—C2—C3 | −3.9 (7) | C8—C9—C10—N2 | −55.5 (6) |
| O1—C1—C2—I1 | −6.0 (6) | C10—N2—C11—C12 | −179.9 (4) |
| C6—C1—C2—I1 | 174.9 (3) | N2—C11—C12—C13 | −179.5 (5) |
| C1—C2—C3—C4 | 1.8 (7) | N2—C11—C12—C17 | 0.5 (8) |
| I1—C2—C3—C4 | −177.0 (4) | C17—C12—C13—C14 | 0.9 (8) |
| C2—C3—C4—C5 | 1.2 (7) | C11—C12—C13—C14 | −179.0 (5) |
| C2—C3—C4—I2 | −179.4 (3) | C12—C13—C14—C15 | 1.1 (8) |
| C3—C4—C5—C6 | −2.0 (7) | C12—C13—C14—I3 | 177.9 (4) |
| I2—C4—C5—C6 | 178.6 (3) | C13—C14—C15—C16 | −1.6 (8) |
| C4—C5—C6—C1 | −0.2 (7) | I3—C14—C15—C16 | −178.4 (4) |
| C4—C5—C6—C7 | 177.6 (4) | C14—C15—C16—C17 | 0.0 (8) |
| O1—C1—C6—C5 | −175.9 (4) | C14—C15—C16—I4 | 178.2 (4) |
| C2—C1—C6—C5 | 3.1 (7) | C15—C16—C17—O2 | −177.7 (5) |
| O1—C1—C6—C7 | 6.3 (7) | I4—C16—C17—O2 | 4.1 (6) |
| C2—C1—C6—C7 | −174.7 (4) | C15—C16—C17—C12 | 2.0 (7) |
| C8—N1—C7—C6 | 177.2 (4) | I4—C16—C17—C12 | −176.3 (3) |
| C5—C6—C7—N1 | 174.0 (4) | C13—C12—C17—O2 | 177.2 (5) |
| C1—C6—C7—N1 | −8.2 (7) | C11—C12—C17—O2 | −2.9 (7) |
| C7—N1—C8—C9 | 96.3 (5) | C13—C12—C17—C16 | −2.5 (7) |
| N1—C8—C9—C10 | −68.6 (5) | C11—C12—C17—C16 | 177.5 (4) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.90 | 1.76 | 2.569 (5) | 148 |
| O2—H2···N2 | 0.89 | 1.75 | 2.564 (5) | 150 |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2471).
References
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- Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
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- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203214X/su2471sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203214X/su2471Isup2.hkl
Supplementary material file. DOI: 10.1107/S160053681203214X/su2471Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report