Crystal structure of a 1:1 co-crystal of the anti­cancer drug gefitinib with azelaic acid

In the title co-crystal, C(22)H(24)ClFN(4)O(3)·C(9)H(16)O(4), gefitinib (GTB; systematic name: quinazolin-4-amine) co-crystallizes with azelaic acid (AA; systematic name: nona­nedioic acid). The co-crystal has the monoclinic P2(1)/n centrosymmetric space group, containing one mol­ecule each of GTB and AA in the asymmetric unit. A structure overlay of the GTB mol­ecule in the co-crystal with that of its most stable polymorph revealed a significant difference in the conformation of the morpholine moiety. The significant deviation in the conformation of one of the acidic groups of azelaic acid from its usual linear chain structure could be due to the encapsulation of one acidic group in the pocket formed between the two pincers of GTB namely, the morpholine and phenyl moieties. Both GTB and AA mol­ecules form N—H⋯O, O—H⋯N, C—H⋯O hydrogen bonds with C—H⋯F close contacts along with off-stacked aromatic π–π inter­actions between the GTB mol­ecules.