Characterization of a conglomerate-forming derivative of (±)-milnacipran and its enantiomeric resolution by preferential crystallization
Sanfilippo, Claudia; Forni, Alessandra; Patti, Angela; RSC Adv.  (2016) –; doi:10.1039/C6RA07745E

data_7225323
_publ_section_title
;
 Characterization of a conglomerate-forming derivative of (+-)-milnacipran
 and its enantiomeric resolution by preferential crystallization
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA07745E
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H28 N2 O2'
_chemical_formula_sum            'C19 H28 N2 O2'
_chemical_formula_weight         316.43
_chemical_name_systematic
'[(+)-(1S,2R)-Z-diethylaminocarbonyl-2-aminomethyl-1-phenyl-cyclopropane]'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-18 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3704(6)
_cell_length_b                   11.6346(6)
_cell_length_c                   15.6401(9)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.896
_cell_measurement_theta_min      2.181
_cell_volume                     1887.06(18)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  'SHELXL-97,PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0095
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31195
_diffrn_reflns_point_group_measured_fraction_full 0.573
_diffrn_reflns_point_group_measured_fraction_max 0.566
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_min         2.182
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   4.6(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.1551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                2469
_reflns_number_total             2687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra07745e1.cif
_cod_data_source_block           1
_cod_database_code               7225323
_solvent_exptl_crystal_recrystallization_method 'methyl tert-butyl ether '