##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-aminium chloride
;
_chemical_name_common
;
Duloxetine hydrochloride
;
_chemical_formula_moiety     'C18 H20  N O S +, Cl -'
_chemical_formula_sum     'C18 H20 Cl N O S'
_chemical_formula_iupac     'C18 H20  N O S +, Cl -'
_chemical_formula_weight     333.86
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     9.7453(10)
_cell_length_b     6.9227(7)
_cell_length_c     13.4247(16)
_cell_angle_alpha     90.00
_cell_angle_beta     109.432(4)
_cell_angle_gamma     90.00
_cell_volume     854.09(16)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1635
_cell_measurement_theta_min     2.318
_cell_measurement_theta_max     22.077
_cell_measurement_temperature     150(2)
_exptl_crystal_description     'Thin Plates'
_exptl_crystal_colour     'Colourless'
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.298
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     352
_exptl_absorpt_coefficient_mu     0.347
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.8786
_exptl_absorpt_correction_T_max     0.9897
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method     'φ scans, and ω scans with κ offsets'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6386
_diffrn_reflns_av_R_equivalents     0.0575
_diffrn_reflns_av_sigmaI/netI     0.0824
_diffrn_reflns_theta_min     1.61
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2947
_reflns_number_gt     2255
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0681
_refine_ls_R_factor_gt     0.0444
_refine_ls_wR_factor_gt     0.1102
_refine_ls_wR_factor_ref     0.1307
_refine_ls_goodness_of_fit_ref     0.789
_refine_ls_restrained_S_all     0.777
_refine_ls_number_reflns     2947
_refine_ls_number_parameters     237
_refine_ls_number_restraints     110
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'calc w=1/[σ²(Fo²)+(0.1P)²+0.0292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.005
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.167
_refine_diff_density_min     -0.213
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1309 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.05(10)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_reduction
;
sAINT (Bruker, 2007)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.7076(5) 1.0388(6) 0.3732(3) 0.0414(10) Uani d . 1 . .
    H H1 0.6473 1.0546 0.3018 0.050 Uiso calc R 1 . .
    C C2 0.8113(5) 1.1721(7) 0.4181(3) 0.0559(13) Uani d . 1 . .
    H H2 0.8222 1.2804 0.3779 0.067 Uiso calc R 1 . .
    C C3 0.9031(5) 1.1525(7) 0.5234(3) 0.0498(12) Uani d . 1 . .
    H H3 0.9769 1.2456 0.5538 0.060 Uiso calc R 1 . .
    C C4 0.8856(4) 0.9990(6) 0.5818(3) 0.0404(10) Uani d . 1 . .
    H H4 0.9465 0.9877 0.6534 0.048 Uiso calc R 1 . .
    C C5 0.7784(4) 0.8557(6) 0.5376(2) 0.0333(8) Uani d . 1 . .
    C C6 0.7619(5) 0.6944(7) 0.5957(3) 0.0488(12) Uani d . 1 . .
    H H6 0.8217 0.6804 0.6674 0.059 Uiso calc R 1 . .
    C C7 0.6613(5) 0.5596(7) 0.5500(3) 0.0594(14) Uani d . 1 . .
    H H7 0.6518 0.4508 0.5904 0.071 Uiso calc R 1 . .
    C C8 0.5696(5) 0.5748(7) 0.4444(3) 0.0453(11) Uani d . 1 . .
    H H8 0.5007 0.4764 0.4134 0.054 Uiso calc R 1 . .
    C C9 0.5811(4) 0.7331(5) 0.3870(3) 0.0302(9) Uani d . 1 A .
    C C10 0.6874(4) 0.8761(5) 0.4309(3) 0.0285(8) Uani d . 1 . .
    C C11 0.3962(4) 0.6244(5) 0.2248(3) 0.0287(8) Uani d . 1 A .
    H H11 0.3506 0.5543 0.2709 0.034 Uiso calc R 1 . .
    C C16 0.2800(4) 0.7340(5) 0.1395(3) 0.0334(9) Uani d . 1 . .
    H H16A 0.2233 0.6416 0.0851 0.040 Uiso calc R 1 A .
    H H16B 0.3277 0.8263 0.1051 0.040 Uiso calc R 1 . .
    C C17 0.1769(4) 0.8439(7) 0.1826(3) 0.0395(9) Uani d . 1 A .
    H H17A 0.1988 0.8111 0.2581 0.047 Uiso calc R 1 . .
    H H17B 0.1925 0.9844 0.1776 0.047 Uiso calc R 1 . .
    C C18 -0.0810(4) 0.8802(6) 0.1698(3) 0.0449(10) Uani d . 1 A .
    H H18A -0.0634 0.8265 0.2405 0.067 Uiso calc R 1 . .
    H H18B -0.1802 0.8483 0.1246 0.067 Uiso calc R 1 . .
    H H18C -0.0694 1.0209 0.1746 0.067 Uiso calc R 1 . .
    Cl Cl1 0.02776(10) 0.35210(15) 0.11567(7) 0.0385(3) Uani d . 1 . .
    N N1 0.0237(3) 0.7976(4) 0.1242(2) 0.0334(7) Uani d . 1 . .
    H H1A 0.0015 0.8416 0.0560 0.040 Uiso calc R 1 A .
    H H1B 0.0131 0.6655 0.1214 0.040 Uiso calc R 1 . .
    O O1 0.4920(3) 0.7711(3) 0.28494(18) 0.0335(6) Uani d . 1 . .
    C C12 0.4783(4) 0.4840(6) 0.1806(3) 0.0304(9) Uani d D 1 . .
    S S1A 0.4000(4) 0.2836(6) 0.1112(4) 0.0390(8) Uani d PDU 0.580(5) A 1
    C C13A 0.5587(15) 0.220(3) 0.088(2) 0.043(2) Uani d PDU 0.580(5) A 1
    H H13A 0.5703 0.1075 0.0508 0.051 Uiso calc P 0.58 A 1
    C C14A 0.6634(16) 0.353(2) 0.1292(18) 0.045(2) Uani d PDU 0.580(5) A 1
    H H14A 0.7575 0.3491 0.1227 0.054 Uiso calc P 0.58 A 1
    C C15A 0.6158(17) 0.500(3) 0.184(2) 0.042(4) Uani d PDU 0.580(5) A 1
    H H15A 0.6774 0.6027 0.2199 0.051 Uiso calc P 0.58 A 1
    S S1B 0.6515(6) 0.5208(10) 0.1826(7) 0.0410(14) Uani d PDU 0.420(5) A 2
    C C13B 0.656(2) 0.310(3) 0.119(2) 0.042(3) Uani d PDU 0.420(5) A 2
    H H13B 0.7390 0.2624 0.1043 0.051 Uiso calc P 0.42 A 2
    C C14B 0.526(2) 0.221(4) 0.091(3) 0.045(3) Uani d PDU 0.420(5) A 2
    H H14B 0.5030 0.1062 0.0498 0.054 Uiso calc P 0.42 A 2
    C C15B 0.427(2) 0.318(3) 0.131(2) 0.053(5) Uani d PDU 0.420(5) A 2
    H H15B 0.3325 0.2691 0.1237 0.063 Uiso calc P 0.42 A 2
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.353(6) ?
    C1 C10 . 1.418(5) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.406(5) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.364(6) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.420(6) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.402(6) ?
    C5 C10 . 1.418(4) ?
    C6 C7 . 1.344(6) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.406(5) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.365(5) ?
    C8 H8 . 0.9500 ?
    C9 O1 . 1.381(4) ?
    C9 C10 . 1.413(5) ?
    C11 O1 . 1.433(4) ?
    C11 C16 . 1.519(5) ?
    C11 H11 . 1.0000 ?
    C16 C17 . 1.520(5) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 N1 . 1.472(4) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C18 N1 . 1.469(5) ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    N1 H1A . 0.9200 ?
    N1 H1B . 0.9200 ?
    C12 C15A . 1.332(14) ?
    C12 C15B . 1.341(16) ?
    C12 C11 . 1.501(5) ?
    C12 S1B . 1.699(7) ?
    C12 S1A . 1.703(5) ?
    S1A C13A . 1.734(10) ?
    C13A C14A . 1.351(10) ?
    C13A H13A . 0.9500 ?
    C14A C15A . 1.420(14) ?
    C14A H14A . 0.9500 ?
    C15A H15A . 0.9500 ?
    S1B C13B . 1.699(14) ?
    C13B C14B . 1.351(11) ?
    C13B H13B . 0.9500 ?
    C14B C15B . 1.421(15) ?
    C14B H14B . 0.9500 ?
    C15B H15B . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C10 . . 121.2(3) ?
    C2 C1 H1 . . 119.4 ?
    C10 C1 H1 . . 119.4 ?
    C1 C2 C3 . . 120.9(4) ?
    C1 C2 H2 . . 119.5 ?
    C3 C2 H2 . . 119.5 ?
    C4 C3 C2 . . 119.5(4) ?
    C4 C3 H3 . . 120.2 ?
    C2 C3 H3 . . 120.2 ?
    C3 C4 C5 . . 121.3(3) ?
    C3 C4 H4 . . 119.3 ?
    C5 C4 H4 . . 119.3 ?
    C6 C5 C10 . . 119.5(4) ?
    C6 C5 C4 . . 121.9(3) ?
    C10 C5 C4 . . 118.6(3) ?
    C7 C6 C5 . . 120.0(4) ?
    C7 C6 H6 . . 120.0 ?
    C5 C6 H6 . . 120.0 ?
    C6 C7 C8 . . 122.0(4) ?
    C6 C7 H7 . . 119.0 ?
    C8 C7 H7 . . 119.0 ?
    C9 C8 C7 . . 119.0(4) ?
    C9 C8 H8 . . 120.5 ?
    C7 C8 H8 . . 120.5 ?
    C8 C9 O1 . . 124.8(3) ?
    C8 C9 C10 . . 120.9(3) ?
    O1 C9 C10 . . 114.4(3) ?
    C9 C10 C1 . . 123.0(3) ?
    C9 C10 C5 . . 118.5(3) ?
    C1 C10 C5 . . 118.5(3) ?
    O1 C11 C12 . . 110.4(3) ?
    O1 C11 C16 . . 104.7(3) ?
    C12 C11 C16 . . 112.8(3) ?
    O1 C11 H11 . . 109.6 ?
    C12 C11 H11 . . 109.6 ?
    C16 C11 H11 . . 109.6 ?
    C11 C16 C17 . . 112.6(3) ?
    C11 C16 H16A . . 109.1 ?
    C17 C16 H16A . . 109.1 ?
    C11 C16 H16B . . 109.1 ?
    C17 C16 H16B . . 109.1 ?
    H16A C16 H16B . . 107.8 ?
    N1 C17 C16 . . 111.7(3) ?
    N1 C17 H17A . . 109.3 ?
    C16 C17 H17A . . 109.3 ?
    N1 C17 H17B . . 109.3 ?
    C16 C17 H17B . . 109.3 ?
    H17A C17 H17B . . 107.9 ?
    N1 C18 H18A . . 109.5 ?
    N1 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    N1 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C18 N1 C17 . . 114.6(3) ?
    C18 N1 H1A . . 108.6 ?
    C17 N1 H1A . . 108.6 ?
    C18 N1 H1B . . 108.6 ?
    C17 N1 H1B . . 108.6 ?
    H1A N1 H1B . . 107.6 ?
    C9 O1 C11 . . 120.0(3) ?
    C15A C12 C15B . . 107.3(10) ?
    C15A C12 C11 . . 126.5(7) ?
    C15B C12 C11 . . 126.2(8) ?
    C15B C12 S1B . . 110.1(8) ?
    C11 C12 S1B . . 123.7(3) ?
    C15A C12 S1A . . 110.5(7) ?
    C11 C12 S1A . . 122.9(3) ?
    S1B C12 S1A . . 113.1(3) ?
    C12 S1A C13A . . 92.4(4) ?
    C14A C13A S1A . . 110.4(8) ?
    C14A C13A H13A . . 124.8 ?
    S1A C13A H13A . . 124.8 ?
    C13A C14A C15A . . 111.8(10) ?
    C13A C14A H14A . . 124.1 ?
    C15A C14A H14A . . 124.1 ?
    C12 C15A C14A . . 114.8(11) ?
    C12 C15A H15A . . 122.6 ?
    C14A C15A H15A . . 122.6 ?
    C13B S1B C12 . . 93.3(7) ?
    C14B C13B S1B . . 110.6(11) ?
    C14B C13B H13B . . 124.7 ?
    S1B C13B H13B . . 124.7 ?
    C13B C14B C15B . . 112.1(12) ?
    C13B C14B H14B . . 124.0 ?
    C15B C14B H14B . . 124.0 ?
    C12 C15B C14B . . 113.7(12) ?
    C12 C15B H15B . . 123.2 ?
    C14B C15B H15B . . 123.2 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1A Cl1 2 0.92 2.23 3.113(3) 161.4
    N1 H1B Cl1 . 0.92 2.18 3.087(3) 169.8
data_global
_journal_date_recd_electronic     2009-07-31
_journal_date_accepted     2009-08-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      9
_journal_page_first     o2294
_journal_page_last     o2294
_journal_paper_category     QO
_journal_coeditor_code     BG2289
_publ_contact_author_name     'Bhadbhade, Mohan'
_publ_contact_author_address
;
School of Chemistry
The University of New South Wales
Sydney
NSW 2052
Australia
;
_publ_contact_author_email     m.bhadbhade@unsw.edu.au
_publ_contact_author_fax     '+612 9385 9898'
_publ_contact_author_phone     '+612 9385 4663'
_publ_section_title
;
Duloxetine hydrochloride
;
loop_
    _publ_author_name
    _publ_author_address
    'Bhadbhade, Mohan'
;
UNSW Analytical Centre
The University of New South Wales
Sydney
NSW 2052
Australia
;
    'Hook, James'
;
UNSW Analytical Centre
The University of New South Wales
Sydney
NSW 2052
Australia
;
    'Marjo, Chris'
;
UNSW Analytical Centre
The University of New South Wales
Sydney
NSW 2052
Australia
;
    'Rich, Anne'
;
UNSW Analytical Centre
The University of New South Wales
Sydney
NSW 2052
Australia
;
    'Lin, Qinghong'
;
Arrow Laboratories Ltd
Croydon South
Victoria 3136
Australia
;
