#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/79/4027971.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_4027971
loop_
_publ_author_name
'Stefan C. Söderman'
'Adrian L. Schwan'
_publ_section_title
;
 Sulfenate Substitution as a Complement and Alternative to Sulfoxidation
 in the Diastereoselective Preparation of Chiral β-Substituted β-Amino
 Sulfoxides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1638
_journal_page_last               1649
_journal_paper_doi               10.1021/jo302769b
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H25 N O3 S'
_chemical_formula_sum            'C17 H25 N O3 S'
_chemical_formula_weight         323.44
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2028(3)
_cell_length_b                   12.2999(7)
_cell_length_c                   27.7966(15)
_cell_measurement_reflns_used    8789
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      65.55
_cell_measurement_theta_min      4.80
_cell_volume                     1778.81(17)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer oprics'
_diffrn_radiation_source         'Bruker microsource'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10754
_diffrn_reflns_theta_full        65.96
_diffrn_reflns_theta_max         65.96
_diffrn_reflns_theta_min         3.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.709
_exptl_absorpt_correction_T_max  0.9194
_exptl_absorpt_correction_T_min  0.8084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.036(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0306
_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)+(0.0445P)²+0.2056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                2845
_reflns_number_total             2966
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo302769b_si_002.cif
_cod_data_source_block           d1242
_cod_database_code               4027971
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
S1 S 0.82435(8) -0.20055(4) 0.886056(15) 0.02620(13) Uani 1 1 d .
O1 O 0.5565(2) -0.19709(12) 0.90548(5) 0.0326(3) Uani 1 1 d .
O2 O 0.4425(2) 0.07395(13) 0.83514(5) 0.0323(3) Uani 1 1 d .
O3 O 0.7436(2) 0.11835(15) 0.77912(5) 0.0385(4) Uani 1 1 d .
N1 N 0.8696(3) 0.04151(13) 0.84652(6) 0.0237(3) Uani 1 1 d .
C1 C 1.0039(4) -0.44287(19) 0.98306(8) 0.0391(5) Uani 1 1 d .
H1A H 0.9264 -0.5141 0.9769 0.059 Uiso 1 1 calc R
H1B H 0.9812 -0.4238 1.0170 0.059 Uiso 1 1 calc R
H1C H 1.1877 -0.4456 0.9755 0.059 Uiso 1 1 calc R
C2 C 0.8764(4) -0.35921(17) 0.95226(7) 0.0310(4) Uani 1 1 d .
H2A H 0.6965 -0.3491 0.9560 0.037 Uiso 1 1 calc R
C3 C 0.9950(3) -0.29879(17) 0.92039(7) 0.0285(4) Uani 1 1 d .
H3A H 1.1745 -0.3076 0.9156 0.034 Uiso 1 1 calc R
C4 C 0.9904(3) -0.08485(16) 0.91118(7) 0.0257(4) Uani 1 1 d .
H4A H 0.9967 -0.0919 0.9466 0.031 Uiso 1 1 calc R
H4B H 1.1693 -0.0835 0.8991 0.031 Uiso 1 1 calc R
C5 C 0.8573(3) 0.02088(15) 0.89793(6) 0.0230(4) Uani 1 1 d .
H5A H 0.6723 0.0150 0.9074 0.028 Uiso 1 1 calc R
C6 C 0.9789(3) 0.11472(17) 0.92669(6) 0.0276(4) Uani 1 1 d .
H6A H 0.9710 0.0972 0.9614 0.033 Uiso 1 1 calc R
H6B H 1.1622 0.1214 0.9176 0.033 Uiso 1 1 calc R
C7 C 0.8478(4) 0.22106(15) 0.91815(6) 0.0264(4) Uani 1 1 d .
C8 C 0.6282(4) 0.25053(18) 0.94400(7) 0.0310(4) Uani 1 1 d .
H8A H 0.5669 0.2043 0.9689 0.037 Uiso 1 1 calc R
C9 C 0.4987(4) 0.34612(19) 0.93391(8) 0.0387(5) Uani 1 1 d .
H9A H 0.3498 0.3650 0.9518 0.046 Uiso 1 1 calc R
C10 C 0.5851(5) 0.41395(19) 0.89788(8) 0.0421(5) Uani 1 1 d .
H10A H 0.4947 0.4791 0.8908 0.051 Uiso 1 1 calc R
C11 C 0.8038(5) 0.38719(18) 0.87208(8) 0.0419(5) Uani 1 1 d .
H11A H 0.8652 0.4344 0.8476 0.050 Uiso 1 1 calc R
C12 C 0.9330(4) 0.29091(17) 0.88219(7) 0.0336(4) Uani 1 1 d .
H12A H 1.0822 0.2725 0.8642 0.040 Uiso 1 1 calc R
C13 C 0.6651(4) 0.07793(16) 0.82144(6) 0.0252(4) Uani 1 1 d .
C14 C 0.5590(4) 0.1626(2) 0.74391(7) 0.0370(5) Uani 1 1 d .
C15 C 0.4027(5) 0.2537(2) 0.76574(9) 0.0487(6) Uani 1 1 d .
H15A H 0.5150 0.3001 0.7852 0.073 Uiso 1 1 calc R
H15B H 0.2674 0.2229 0.7861 0.073 Uiso 1 1 calc R
H15C H 0.3245 0.2970 0.7400 0.073 Uiso 1 1 calc R
C16 C 0.3928(5) 0.0724(2) 0.72483(9) 0.0518(7) Uani 1 1 d .
H16A H 0.5018 0.0129 0.7133 0.078 Uiso 1 1 calc R
H16B H 0.2878 0.0998 0.6982 0.078 Uiso 1 1 calc R
H16C H 0.2803 0.0458 0.7505 0.078 Uiso 1 1 calc R
C17 C 0.7353(5) 0.2062(4) 0.70505(10) 0.0958(16) Uani 1 1 d .
H17A H 0.8357 0.1463 0.6914 0.144 Uiso 1 1 calc R
H17B H 0.8520 0.2602 0.7190 0.144 Uiso 1 1 calc R
H17C H 0.6323 0.2402 0.6797 0.144 Uiso 1 1 calc R
H1N H 1.006(5) 0.0543(19) 0.8353(8) 0.031(6) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 C3 106.92(9)
O1 S1 C4 106.50(8)
C3 S1 C4 95.11(9)
C13 O3 C14 121.37(14)
C13 N1 C5 122.11(16)
C13 N1 H1N 116.0(17)
C5 N1 H1N 117.5(17)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C1 124.67(18)
C3 C2 H2A 117.7
C1 C2 H2A 117.7
C2 C3 S1 120.89(15)
C2 C3 H3A 119.6
S1 C3 H3A 119.6
C5 C4 S1 111.28(12)
C5 C4 H4A 109.4
S1 C4 H4A 109.4
C5 C4 H4B 109.4
S1 C4 H4B 109.4
H4A C4 H4B 108.0
N1 C5 C4 111.59(15)
N1 C5 C6 111.19(15)
C4 C5 C6 109.19(15)
N1 C5 H5A 108.3
C4 C5 H5A 108.3
C6 C5 H5A 108.3
C7 C6 C5 112.73(15)
C7 C6 H6A 109.0
C5 C6 H6A 109.0
C7 C6 H6B 109.0
C5 C6 H6B 109.0
H6A C6 H6B 107.8
C12 C7 C8 118.03(18)
C12 C7 C6 120.63(18)
C8 C7 C6 121.24(17)
C9 C8 C7 120.9(2)
C9 C8 H8A 119.5
C7 C8 H8A 119.5
C10 C9 C8 120.2(2)
C10 C9 H9A 119.9
C8 C9 H9A 119.9
C9 C10 C11 120.0(2)
C9 C10 H10A 120.0
C11 C10 H10A 120.0
C10 C11 C12 119.7(2)
C10 C11 H11A 120.2
C12 C11 H11A 120.2
C11 C12 C7 121.2(2)
C11 C12 H12A 119.4
C7 C12 H12A 119.4
O2 C13 O3 125.30(17)
O2 C13 N1 125.06(17)
O3 C13 N1 109.64(16)
O3 C14 C16 109.65(19)
O3 C14 C15 110.93(17)
C16 C14 C15 112.26(18)
O3 C14 C17 102.09(15)
C16 C14 C17 111.0(2)
C15 C14 C17 110.5(3)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4952(14)
S1 C3 1.777(2)
S1 C4 1.805(2)
O2 C13 1.220(2)
O3 C13 1.341(2)
O3 C14 1.475(2)
N1 C13 1.349(2)
N1 C5 1.453(2)
N1 H1N 0.79(3)
C1 C2 1.494(3)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.310(3)
C2 H2A 0.9500
C3 H3A 0.9500
C4 C5 1.519(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.540(3)
C5 H5A 1.0000
C6 C7 1.494(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C12 1.391(3)
C7 C8 1.398(3)
C8 C9 1.384(3)
C8 H8A 0.9500
C9 C10 1.379(3)
C9 H9A 0.9500
C10 C11 1.385(4)
C10 H10A 0.9500
C11 C12 1.391(3)
C11 H11A 0.9500
C12 H12A 0.9500
C14 C16 1.503(4)
C14 C15 1.511(4)
C14 C17 1.515(3)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
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
N1 H1N O2 0.79(3) 2.28(3) 3.024(2) 156(2) 1_655
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
C1 C2 C3 S1 -179.36(16)
O1 S1 C3 C2 6.31(19)
C4 S1 C3 C2 115.29(18)
O1 S1 C4 C5 -58.64(14)
C3 S1 C4 C5 -167.98(13)
C13 N1 C5 C4 136.78(18)
C13 N1 C5 C6 -101.0(2)
S1 C4 C5 N1 -65.80(17)
S1 C4 C5 C6 170.88(12)
N1 C5 C6 C7 60.1(2)
C4 C5 C6 C7 -176.34(15)
C5 C6 C7 C12 -91.7(2)
C5 C6 C7 C8 84.5(2)
C12 C7 C8 C9 0.3(3)
C6 C7 C8 C9 -176.04(18)
C7 C8 C9 C10 0.1(3)
C8 C9 C10 C11 -0.8(3)
C9 C10 C11 C12 1.0(3)
C10 C11 C12 C7 -0.5(3)
C8 C7 C12 C11 -0.1(3)
C6 C7 C12 C11 176.28(18)
C14 O3 C13 O2 -0.4(3)
C14 O3 C13 N1 179.11(19)
C5 N1 C13 O2 -17.5(3)
C5 N1 C13 O3 162.92(17)
C13 O3 C14 C16 -67.0(3)
C13 O3 C14 C15 57.6(3)
C13 O3 C14 C17 175.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71567617
