Crystal engineering of multiple-component organic solids: Pharmaceutical cocrystals of tadalafil with persistent hydrogen bonding motifs
Weyna, David R.; Cheney, Miranda L.; Shan, Ning; Hanna, Mazen; Wojtas, Łukasz; Zaworotko, Michael J.; CrystEngComm 14 (2012) 2377–; doi:10.1039/c2ce06574f

data_7207636
_publ_section_title
;
 Crystal engineering of multiple-component organic solids: Pharmaceutical
 cocrystals of tadalafil with persistent hydrogen bonding motifs
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2377
_journal_paper_doi               10.1039/c2ce06574f
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H19 N3 O4, C10 H12 O3'
_chemical_formula_sum            'C32 H31 N3 O7'
_chemical_formula_weight         569.60
_chemical_melting_point          422.21
_chemical_name_common            'tadalafil propylparaben'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.854(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3357(2)
_cell_length_b                   8.3056(2)
_cell_length_c                   17.3542(5)
_cell_measurement_reflns_used    1885
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.2
_cell_measurement_theta_min      2.55
_cell_volume                     1345.47(6)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_publication_material  'APEX2 (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6565
_diffrn_reflns_theta_full        65.81
_diffrn_reflns_theta_max         65.80
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.7961
_exptl_absorpt_correction_T_min  0.7340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorles
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                3434
_reflns_number_total             3847
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06574f.txt
_cod_data_source_block           TDF_PPB_2
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7207636