We report on a new p-type organic semiconductor single crystal, 5,10,15-trimethyl-10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (N-trimethyltriindole). This molecule crystallizes forming a highly ordered columnar structure in which stacked molecules are situated at two alternating distances (3.53 angstrom and 3.68 angstrom) along the column as determined by single crystal X-ray diffraction analysis. These short intermolecular distances between adjacent units, make this system an ideal candidate for charge-transport processes along the stacks. Relevant parameters for transport (i.e. internal reorganization energies, transfer integral) have been estimated by DFT calculations at a 6-311 G(d,p)/B3LYP level of theory. As a double check for the transfer integral, the electronic band structure of a one-dimensional stack of molecules has been computed. The electronic properties of this material have been studied both theoretically and experimentally. Its HOMO value is found to coincide with Au work function (Phi(Au) = 5.1 eV), thus low barriers are expected for hole injection from gold electrodes. The hole mobility of this material has been predicted theoretically considering a hopping-type mechanism for the charge-transport and determined experimentally at the space charge limited current (SCLC) regime of the current-voltage measurements. Both theoretical and experimental values are in good agreement. The high hole mobility (mu(min) = 0.4 cm(2) V(-1) s(-1)) of this material points towards its useful application in the organic electronics arena. N-Trimethyltriindole single crystals constitute an essential model to study transport properties of triindole-based materials and to design new derivatives with improved electronic performance. (C) 2009 Elsevier B.V. All rights reserved.