Crystal forms of 9-hydroxy-risperidone (paliperidone)

Crystalline Paliperidone, designated as Form I, characterized by data selected from the group consisting of:

• (i) X-ray powder diffraction spectrum with peaks at about:
• 5.8, 8.4, 9.5 and 11.6 degrees two theta ±0.2 degrees two theta;
• (ii) a solid-state 13C NMR spectrum with signals at about 163.1, 161.2 and 156.8±0.2 ppm;
• and
• (iii) a solid-state 13C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 115 to 180 ppm of about 45.8, 43.9 and 39.5±0.1 ppm.

A crystalline form of Paliperidone, designated as Form II, characterized by data selected from the group consisting of:

• (i) X-ray powder diffraction spectrum with peaks at about:
• 10.3, 14.6, 22.0, 24.6 and 25.0 degrees two theta ±0.2 degrees two theta;
• (ii) X-ray powder diffraction spectrum with peaks at about:
• 10.3, 13.3, 13.9, 14.6 and 15.1 degrees two theta ±0.2 degrees two theta;
• (iii)a solid-state 13C NMR spectrum with signals at about 163.4, 121.8 and 116.7±0.2 ppm;
• and
• (iv)a solid-state 13C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 95 to 180 ppm of about 65.7, 24.1 and 19.0±0.1 ppm.

A crystalline form of Paliperidone, designated as Form III, characterized by data selected from the group consisting of:

• (i) X-ray powder diffraction spectrum with peaks at about:
• 10.8, 14.1, 15.8 and 16.8 degrees two theta ±0.2 degrees two theta;
• (ii) a solid-state 13C NMR spectrum with signals at about 164.1, 161.3 and 157.9±0.2 ppm;
• and
• (iii)a solid-state 13C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 115 to 180 ppm of about 46.7, 43.9 and 40.5±0.1 ppm.

A crystalline form of Paliperidone, designated as Form IV, characterized by data selected from the group consisting of:

• (i) X-ray powder diffraction spectrum with peaks at about:
• 10.2, 12.2 and 15.5 degrees two theta ±0.2 degrees two theta;
• (ii) a solid-state 13C NMR spectrum with signals at about 162.6, 160.5 and 157.6±0.2 ppm;
• and
• (iii) a solid-state 13C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 115 to 180 ppm of about 45.9, 43.8 and 40.9±0.1.

A crystalline form of Paliperidone, designated as Form V, characterized by data selected from the group consisting of:

• (i) X-ray powder diffraction spectrum with four or more peaks from the list of:
• about 9.8, 10.9, 15.8, 21.2 and 21.6 degrees two theta ±0.2 degrees two theta;
• (ii) a solid-state 13C NMR spectrum with signals at about 163.4, 161.4 and 157.9±0.2 ppm;
• and
• (iii)a solid-state 13C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 100 to 180 ppm of about 51.1, 49.1 and 45.6±0.1 ppm.

A crystalline form of Paliperidone, designated as Form VI, characterized by data selected from the group consisting of

• (i) an X-ray powder diffraction spectrum with four or more peaks from the list of:
• about 8.5, 8.8, 9.7, 11.2 and 11.6 degrees two theta ±0.2 degrees two theta;
• (ii) a solid-state 13C NMR spectrum with signals at about 163.4, 161.4 and 157.9±0.2 ppm;
• (iii)a solid-state 13C NMR spectrum having chemical shifts differences between the signal exhibiting the lowest chemical shift and another in the chemical shift range of 100 to 180 ppm of about 51.1, 49.1 and 45.6±0.1 ppm.