Crystal Engineering Approach To Forming Cocrystals of Amine Hydrochlorides with Organic Acids. Molecular Complexes of Fluoxetine Hydrochloride with Benzoic, Succinic, and Fumaric Acids
Scott L. Childs; Leonard J. Chyall; Jeanette T. Dunlap; Valeriya N. Smolenskaya; Barbara C. Stahly; G. Patrick Stahly; Journal of the American Chemical Society 126 (2004) 13335–13342; doi:10.1021/ja048114o

data_4113068
_publ_section_title
;
 Crystal Engineering Approach To Forming Cocrystals of Amine
 Hydrochlorides with Organic Acids. Molecular Complexes of Fluoxetine
 Hydrochloride with Benzoic, Succinic, and Fumaric Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13335
_journal_page_last               13342
_journal_paper_doi               10.1021/ja048114o
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         '2 (C17 H19 F3 N O 1+ Cl 1-), C4 H4 O4'
_chemical_formula_sum            'C38 H42 Cl2 F6 N2 O6'
_chemical_formula_weight         807.64
_chemical_melting_point          437
_chemical_name_common
'Fluoxetine hydrochloride:fumaric acid cocrystal (2:1)'
_chemical_name_systematic
; 
 N-Methyl-g-((4-trifluoromethyl)phenoxy)-benzenepropanamine 
 hydrochloride fumaric acid 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.6914(8)
_cell_length_b                   7.1807(3)
_cell_length_c                   20.6546(7)
_cell_measurement_reflns_used    7497
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.19
_cell_measurement_theta_min      3.31
_cell_volume                     3958.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.1693
_diffrn_reflns_av_sigmaI/netI    0.0961
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15698
_diffrn_reflns_theta_full        58.93
_diffrn_reflns_theta_max         58.93
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    2.130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0619P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                1961
_reflns_number_total             2823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja048114osi20040613_103412_2.cif
_cod_data_source_block           a6g41
_cod_database_code               4113068