#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/51/4025132.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025132
loop_
_publ_author_name
'Soyeong Kang'
'Hyeon-Kyu Lee'
_publ_section_title
;
 Highly Efficient, Enantioselective Syntheses of (S)-(+)- and
 (R)-(-)-Dapoxetine Starting with 3-Phenyl-1-propanol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              237
_journal_page_last               240
_journal_paper_doi               10.1021/jo902176s
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C9 H11 N O3 S'
_chemical_formula_weight         213.25
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.7300(10)
_cell_angle_beta                 103.1540(10)
_cell_angle_gamma                107.3550(10)
_cell_formula_units_Z            2
_cell_length_a                   5.89850(10)
_cell_length_b                   9.6146(2)
_cell_length_c                   10.1578(2)
_cell_measurement_reflns_used    4239
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.25
_cell_volume                     490.554(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8143
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9609
_exptl_absorpt_correction_T_min  0.9183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_coef       0.006(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0385
_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/[σ²(Fo²)+(0.0554P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                3269
_reflns_number_total             3944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902176s_si_001.cif
_cod_data_source_block           20090601a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        490.553(16)
_cod_database_code               4025132
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.92638(11) 0.25020(7) 0.57896(6) 0.04816(19) Uani 1 1 d . . .
O2 O 1.1768(4) 0.3106(3) 0.5484(2) 0.0551(5) Uani 1 1 d . . .
C3 C 1.3813(6) 0.4524(4) 0.6750(3) 0.0533(8) Uani 1 1 d . . .
H3A H 1.3255 0.5392 0.6986 0.064 Uiso 1 1 calc R . .
H3B H 1.5307 0.4861 0.6488 0.064 Uiso 1 1 calc R . .
C4 C 1.4461(5) 0.4118(4) 0.8079(3) 0.0536(7) Uani 1 1 d . . .
H4A H 1.5101 0.3287 0.7852 0.064 Uiso 1 1 calc R . .
H4B H 1.5791 0.5048 0.8900 0.064 Uiso 1 1 calc R . .
C5 C 1.2187(5) 0.3565(3) 0.8523(3) 0.0429(6) Uani 1 1 d . . .
H5A H 1.1607 0.4435 0.8763 0.052 Uiso 1 1 calc R . .
N6 N 1.0077(4) 0.2179(3) 0.7260(2) 0.0452(6) Uani 1 1 d . . .
H6A H 0.9355 0.1286 0.7310 0.054 Uiso 1 1 calc R . .
O7 O 0.8400(4) 0.3747(3) 0.6121(2) 0.0651(6) Uani 1 1 d . . .
O8 O 0.7696(4) 0.1036(3) 0.4573(2) 0.0710(6) Uani 1 1 d . . .
C9 C 1.2684(5) 0.3147(3) 0.9868(3) 0.0429(7) Uani 1 1 d . . .
C10 C 1.1535(7) 0.3566(4) 1.0863(3) 0.0574(8) Uani 1 1 d . . .
H10A H 1.0454 0.4077 1.0697 0.069 Uiso 1 1 calc R . .
C11 C 1.1956(7) 0.3241(5) 1.2124(4) 0.0684(10) Uani 1 1 d . . .
H11A H 1.1149 0.3517 1.2788 0.082 Uiso 1 1 calc R . .
C12 C 1.3578(7) 0.2506(4) 1.2368(4) 0.0628(9) Uani 1 1 d . . .
H12A H 1.3909 0.2309 1.3217 0.075 Uiso 1 1 calc R . .
C13 C 1.4695(7) 0.2069(4) 1.1389(4) 0.0653(9) Uani 1 1 d . . .
H13A H 1.5759 0.1548 1.1556 0.078 Uiso 1 1 calc R . .
C14 C 1.4273(6) 0.2391(4) 1.0126(3) 0.0542(8) Uani 1 1 d . . .
H14A H 1.5066 0.2094 0.9459 0.065 Uiso 1 1 calc R . .
S21 S 0.31898(11) -0.14464(7) 0.56928(7) 0.0495(2) Uani 1 1 d . . .
O22 O 0.1320(4) -0.3118(3) 0.5377(2) 0.0619(6) Uani 1 1 d . . .
C23 C -0.1364(7) -0.3511(4) 0.4560(4) 0.0664(10) Uani 1 1 d . . .
H23A H -0.1943 -0.2763 0.5116 0.080 Uiso 1 1 calc R . .
H23B H -0.2413 -0.4571 0.4427 0.080 Uiso 1 1 calc R . .
C24 C -0.1595(6) -0.3434(4) 0.3068(3) 0.0559(8) Uani 1 1 d . . .
H24A H -0.3341 -0.3646 0.2551 0.067 Uiso 1 1 calc R . .
H24B H -0.1166 -0.4257 0.2486 0.067 Uiso 1 1 calc R . .
C25 C 0.0116(5) -0.1831(3) 0.3195(3) 0.0425(6) Uani 1 1 d . . .
H25A H -0.0369 -0.1006 0.3744 0.051 Uiso 1 1 calc R . .
N26 N 0.2759(4) -0.1519(3) 0.4034(2) 0.0477(6) Uani 1 1 d . . .
H26A H 0.3953 -0.1388 0.3673 0.057 Uiso 1 1 calc R . .
O27 O 0.5644(5) -0.1361(3) 0.6307(3) 0.0785(7) Uani 1 1 d . . .
O28 O 0.2435(5) -0.0319(3) 0.6519(2) 0.0670(6) Uani 1 1 d . . .
C29 C -0.0044(5) -0.1784(3) 0.1705(3) 0.0411(6) Uani 1 1 d . . .
C30 C 0.1337(6) -0.2343(4) 0.0903(3) 0.0490(7) Uani 1 1 d . . .
H30A H 0.2449 -0.2747 0.1293 0.059 Uiso 1 1 calc R . .
C31 C 0.1082(7) -0.2307(4) -0.0470(3) 0.0581(8) Uani 1 1 d . . .
H31A H 0.2024 -0.2685 -0.0998 0.070 Uiso 1 1 calc R . .
C32 C -0.0563(6) -0.1715(4) -0.1063(3) 0.0567(8) Uani 1 1 d . . .
H32A H -0.0729 -0.1688 -0.1986 0.068 Uiso 1 1 calc R . .
C33 C -0.1937(7) -0.1171(4) -0.0289(3) 0.0591(8) Uani 1 1 d . . .
H33A H -0.3059 -0.0781 -0.0693 0.071 Uiso 1 1 calc R . .
C34 C -0.1692(6) -0.1189(4) 0.1088(3) 0.0515(7) Uani 1 1 d . . .
H34A H -0.2635 -0.0802 0.1608 0.062 Uiso 1 1 calc R . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 S1 O8 119.69(15) . . ?
O7 S1 O2 108.44(13) . . ?
O8 S1 O2 105.34(13) . . ?
O7 S1 N6 108.06(12) . . ?
O8 S1 N6 109.46(13) . . ?
O2 S1 N6 104.85(12) . . ?
C3 O2 S1 113.40(17) . . ?
O2 C3 C4 109.7(2) . . ?
O2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
O2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 111.9(2) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N6 C5 C4 110.3(2) . . ?
N6 C5 C9 109.1(2) . . ?
C4 C5 C9 115.2(2) . . ?
N6 C5 H5A 107.3 . . ?
C4 C5 H5A 107.3 . . ?
C9 C5 H5A 107.3 . . ?
C5 N6 S1 113.97(17) . . ?
C5 N6 H6A 123.0 . . ?
S1 N6 H6A 123.0 . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 C5 118.7(3) . . ?
C14 C9 C5 122.4(3) . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10A 119.4 . . ?
C11 C10 H10A 119.4 . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11A 120.5 . . ?
C10 C11 H11A 120.5 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C9 C14 C13 119.9(3) . . ?
C9 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
O27 S21 O28 118.00(15) . . ?
O27 S21 O22 106.95(15) . . ?
O28 S21 O22 108.38(14) . . ?
O27 S21 N26 108.98(14) . . ?
O28 S21 N26 111.88(13) . . ?
O22 S21 N26 101.21(12) . . ?
C23 O22 S21 115.2(2) . . ?
O22 C23 C24 109.2(2) . . ?
O22 C23 H23A 109.8 . . ?
C24 C23 H23A 109.8 . . ?
O22 C23 H23B 109.8 . . ?
C24 C23 H23B 109.8 . . ?
H23A C23 H23B 108.3 . . ?
C23 C24 C25 112.5(3) . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
N26 C25 C29 109.6(2) . . ?
N26 C25 C24 107.7(2) . . ?
C29 C25 C24 112.2(2) . . ?
N26 C25 H25A 109.1 . . ?
C29 C25 H25A 109.1 . . ?
C24 C25 H25A 109.1 . . ?
C25 N26 S21 113.95(18) . . ?
C25 N26 H26A 123.0 . . ?
S21 N26 H26A 123.0 . . ?
C30 C29 C34 118.2(3) . . ?
C30 C29 C25 122.8(3) . . ?
C34 C29 C25 119.0(3) . . ?
C31 C30 C29 120.6(3) . . ?
C31 C30 H30A 119.7 . . ?
C29 C30 H30A 119.7 . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H31A 119.9 . . ?
C30 C31 H31A 119.9 . . ?
C33 C32 C31 119.6(3) . . ?
C33 C32 H32A 120.2 . . ?
C31 C32 H32A 120.2 . . ?
C32 C33 C34 120.9(3) . . ?
C32 C33 H33A 119.6 . . ?
C34 C33 H33A 119.6 . . ?
C33 C34 C29 120.4(3) . . ?
C33 C34 H34A 119.8 . . ?
C29 C34 H34A 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O7 1.415(2) . ?
S1 O8 1.418(2) . ?
S1 O2 1.556(2) . ?
S1 N6 1.613(2) . ?
O2 C3 1.487(4) . ?
C3 C4 1.515(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.510(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N6 1.487(3) . ?
C5 C9 1.529(4) . ?
C5 H5A 0.9800 . ?
N6 H6A 0.8600 . ?
C9 C10 1.368(4) . ?
C9 C14 1.374(4) . ?
C10 C11 1.395(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.370(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.344(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.395(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
S21 O27 1.407(2) . ?
S21 O28 1.408(2) . ?
S21 O22 1.539(2) . ?
S21 N26 1.622(2) . ?
O22 C23 1.481(4) . ?
C23 C24 1.517(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.517(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N26 1.485(3) . ?
C25 C29 1.511(4) . ?
C25 H25A 0.9800 . ?
N26 H26A 0.8600 . ?
C29 C30 1.383(4) . ?
C29 C34 1.392(4) . ?
C30 C31 1.381(4) . ?
C30 H30A 0.9300 . ?
C31 C32 1.379(5) . ?
C31 H31A 0.9300 . ?
C32 C33 1.356(5) . ?
C32 H32A 0.9300 . ?
C33 C34 1.380(4) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O27 0.86 2.53 3.300(4) 150.0 .
N26 H26A O8 0.86 2.42 3.000(3) 125.3 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 S1 O2 C3 59.2(2) . . . . ?
O8 S1 O2 C3 -171.56(18) . . . . ?
N6 S1 O2 C3 -56.1(2) . . . . ?
S1 O2 C3 C4 60.8(3) . . . . ?
O2 C3 C4 C5 -58.7(3) . . . . ?
C3 C4 C5 N6 56.5(3) . . . . ?
C3 C4 C5 C9 -179.4(3) . . . . ?
C4 C5 N6 S1 -55.5(3) . . . . ?
C9 C5 N6 S1 176.92(19) . . . . ?
O7 S1 N6 C5 -61.7(2) . . . . ?
O8 S1 N6 C5 166.4(2) . . . . ?
O2 S1 N6 C5 53.8(2) . . . . ?
N6 C5 C9 C10 -94.6(3) . . . . ?
C4 C5 C9 C10 140.7(3) . . . . ?
N6 C5 C9 C14 86.5(3) . . . . ?
C4 C5 C9 C14 -38.2(4) . . . . ?
C14 C9 C10 C11 0.1(5) . . . . ?
C5 C9 C10 C11 -178.8(3) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C10 C11 C12 C13 -1.7(6) . . . . ?
C11 C12 C13 C14 1.6(6) . . . . ?
C10 C9 C14 C13 -0.2(5) . . . . ?
C5 C9 C14 C13 178.7(3) . . . . ?
C12 C13 C14 C9 -0.6(5) . . . . ?
O27 S21 O22 C23 -173.0(2) . . . . ?
O28 S21 O22 C23 58.8(2) . . . . ?
N26 S21 O22 C23 -59.0(2) . . . . ?
S21 O22 C23 C24 60.8(3) . . . . ?
O22 C23 C24 C25 -56.3(4) . . . . ?
C23 C24 C25 N26 56.9(3) . . . . ?
C23 C24 C25 C29 177.7(3) . . . . ?
C29 C25 N26 S21 176.88(19) . . . . ?
C24 C25 N26 S21 -60.7(2) . . . . ?
O27 S21 N26 C25 172.2(2) . . . . ?
O28 S21 N26 C25 -55.5(2) . . . . ?
O22 S21 N26 C25 59.7(2) . . . . ?
N26 C25 C29 C30 36.3(4) . . . . ?
C24 C25 C29 C30 -83.4(4) . . . . ?
N26 C25 C29 C34 -145.3(3) . . . . ?
C24 C25 C29 C34 95.0(3) . . . . ?
C34 C29 C30 C31 0.1(5) . . . . ?
C25 C29 C30 C31 178.5(3) . . . . ?
C29 C30 C31 C32 -0.2(5) . . . . ?
C30 C31 C32 C33 -0.2(5) . . . . ?
C31 C32 C33 C34 0.6(5) . . . . ?
C32 C33 C34 C29 -0.7(5) . . . . ?
C30 C29 C34 C33 0.3(5) . . . . ?
C25 C29 C34 C33 -178.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091375
