Structure of racemic duloxetine hydro-chloride.
Bhadbhade, Mohan M.; Gao, Jiabin; Rich, Anne M.; Marjo, Christopher E.; Acta crystallographica. Section E, Crystallographic communications 79 (2023) 488–493; doi:10.1107/S2056989023003353

data_2022750
_publ_section_title
;
 Structure of racemic duloxetine hydro-chloride.
;
_journal_coeditor_code           HB8060
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              488
_journal_page_last               493
_journal_paper_doi               10.1107/S2056989023003353
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C18 H20 N O S +, Cl -'
_chemical_formula_moiety         'C18 H20 N O S +, Cl -'
_chemical_formula_sum            'C18 H20 Cl N O S'
_chemical_formula_weight         333.86
_chemical_name_systematic
;
(<i>S</i>)-<i>N</i>-Methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propylaminium
chloride
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.587(3)
_cell_length_b                   17.250(3)
_cell_length_c                   6.8040(14)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      2.5
_cell_volume                     1712.1(6)
_computing_cell_refinement
;
<i>XDS</i> (Kabsch, 1993)
;
_computing_data_collection
;
<i>BLU-ICE</i> (McPhillips et al, 2002)
;
_computing_data_reduction
;
<i>XDS</i> (Kabsch, 1993)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_structure_refinement
;
<i>SHELXL2013</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>SHELXS97</i> (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.836
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  '3-BM1 Australian Synchrotron'
_diffrn_measurement_method       '\f scans'
_diffrn_radiation_monochromator  Si<111>
_diffrn_radiation_source         'Synchrotron BM'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            18750
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.849
_diffrn_reflns_theta_min         2.744
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       'Thin plates'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.309
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1143 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.048(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2573
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0442P)^2^+0.4827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0660
_reflns_number_gt                2546
_reflns_number_total             2573
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb8060sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022750.cif.'
_cod_database_code               2022750
_cod_database_fobs_code          2022750
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.997
_shelx_hkl_checksum              65175
_shelx_res_checksum              85653
_shelxl_version_number           2.013