Crystal structure of [propane-1,3-diylbis(piperidine-4,1-diyl)]bis[(pyridin-4-yl)methanone]–isophthalic acid (1/1)

In the co-crystal of isophthalic acid and [propane-1,3-diylbis(piperidine-4,1-diyl)]bis[(pyridin-4-yl)methanone], molecules are connected into supramolecular chains aligned along the c axis by O—H⋯N hydrogen bonding. These aggregate into supramolecular layers oriented parallel to the ac plane by C—H⋯O interactions.


Structural commentary
The asymmetric unit of the title compound contains a complete isophthalic acid molecule, and a complete ppbp ISSN 1600-5368

Figure 1
The formula unit of the title co-crystal, showing 50% probability ellipsoids and the atom-numbering scheme. Most hydrogen atom positions are shown as grey sticks. Color codes: red O, light blue N, black C, pink H.

Figure 2
A single supramolecular chain in the title co-crystal connected by O-HÁ Á ÁN hydrogen bonding between isophthalic acid and ppbp molecules.

Figure 3
A single layer motif within the title co-crystal.

Figure 4
ABCD stacking pattern of supramolecular layers within the title cocrystal.

Refinement
All H atoms bound to C atoms were placed in calculated positions, with C-H = 0.95 Å for aromatic C atoms, with C-H = 0.99 Å for aliphatic secondary C atoms, and with C-H = 1.00 Å for aliphatic tertiary C atoms, All H atoms were refined in riding mode with U iso = 1.2U eq (C Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2007); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).   (Bruker,2012) was used for absorption correction. wR2(int) was 0.1152 before and 0.0538 after correction. The Ratio of minimum to maximum transmission is 0.8627. The λ/2 correction factor is 0.0015. 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 F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.