#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025346.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_4025346
loop_
_publ_author_name
'Marina Martjuga'
'Dmitry Shabashov'
'Sergey Belyakov'
'Edvards Liepinsh'
'Edgars Suna'
_publ_section_title
;
 Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of
 Enantiopure N-tert-Butanesulfinylketimines: Unusual Directing Effects of
 the ortho-Substituent
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2357
_journal_page_last               2368
_journal_paper_doi               10.1021/jo100173f
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H20 Br N O S'
_chemical_formula_sum            'C17 H20 Br N O S'
_chemical_formula_weight         366.31
_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   difmap
_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                   9.3092(8)
_cell_length_b                   12.0749(11)
_cell_length_c                   14.8431(14)
_cell_measurement_reflns_used    5230
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.90
_cell_volume                     1668.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      158(2)
_diffrn_detector_area_resol_mean 0.75
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19135
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    2.587
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(7)
_refine_ls_extinction_coef       0.0029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0209
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0276P)²+0.2300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0519
_reflns_number_gt                3861
_reflns_number_total             4153
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100173f_si_017.cif
_cod_data_source_block           lat1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 
;
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4025346
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Br1 Br 0.184182(17) 0.252463(13) 1.000586(11) 0.03018(6) Uani 1 1 d . . .
S1 S 0.48015(4) 0.15320(3) 0.73044(3) 0.01981(8) Uani 1 1 d . . .
O1 O 0.44575(13) 0.27179(9) 0.71494(9) 0.0299(3) Uani 1 1 d . . .
N1 N 0.32982(15) 0.07733(11) 0.74446(9) 0.0215(3) Uani 1 1 d . . .
H1 H 0.279(2) 0.0847(17) 0.7004(15) 0.026(6) Uiso 1 1 d . . .
C1 C 0.31255(15) 0.13088(12) 0.99181(10) 0.0199(3) Uani 1 1 d . . .
C2 C 0.3842(2) 0.10013(15) 1.07030(12) 0.0256(4) Uani 1 1 d . . .
H2 H 0.366(2) 0.1479(18) 1.1217(14) 0.033(5) Uiso 1 1 d . . .
C3 C 0.4786(2) 0.01179(15) 1.06878(12) 0.0289(4) Uani 1 1 d . . .
H3 H 0.525(2) -0.0022(17) 1.1253(14) 0.030(5) Uiso 1 1 d . . .
C4 C 0.49989(18) -0.04531(14) 0.98891(12) 0.0279(3) Uani 1 1 d . . .
H4 H 0.560(2) -0.1028(18) 0.9836(15) 0.033(6) Uiso 1 1 d . . .
C5 C 0.42866(18) -0.01435(15) 0.91130(11) 0.0236(3) Uani 1 1 d . . .
H5 H 0.4532(19) -0.0517(15) 0.8567(12) 0.019(5) Uiso 1 1 d . . .
C6 C 0.33264(17) 0.07404(13) 0.91067(10) 0.0186(3) Uani 1 1 d . . .
C7 C 0.24666(17) 0.10202(14) 0.82665(11) 0.0191(3) Uani 1 1 d . . .
H7 H 0.2188(17) 0.1760(14) 0.8304(11) 0.018(4) Uiso 1 1 d . . .
C8 C 0.10957(16) 0.03277(14) 0.82379(10) 0.0205(3) Uani 1 1 d . . .
C9 C 0.1163(2) -0.08023(15) 0.80632(11) 0.0245(3) Uani 1 1 d . . .
H9 H 0.206(2) -0.1173(15) 0.7961(12) 0.020(5) Uiso 1 1 d . . .
C10 C -0.0091(2) -0.14326(16) 0.80497(11) 0.0300(4) Uani 1 1 d . . .
H10 H -0.001(3) -0.2195(19) 0.7916(14) 0.044(6) Uiso 1 1 d . . .
C11 C -0.1409(2) -0.09413(18) 0.82077(13) 0.0345(4) Uani 1 1 d . . .
H11 H -0.225(2) -0.1399(17) 0.8187(14) 0.030(5) Uiso 1 1 d . . .
C12 C -0.1484(2) 0.01821(19) 0.83918(13) 0.0336(4) Uani 1 1 d . . .
H12 H -0.234(3) 0.0487(19) 0.8457(16) 0.038(6) Uiso 1 1 d . . .
C13 C -0.0237(2) 0.08112(16) 0.84058(12) 0.0272(4) Uani 1 1 d . . .
H13 H -0.038(2) 0.1526(19) 0.8547(14) 0.038(6) Uiso 1 1 d . . .
C14 C 0.52960(18) 0.09642(13) 0.61933(11) 0.0221(3) Uani 1 1 d . . .
C15 C 0.5621(3) -0.02643(17) 0.62934(15) 0.0377(5) Uani 1 1 d . . .
H15A H 0.478(3) -0.0681(17) 0.6474(15) 0.034(6) Uiso 1 1 d . . .
H15B H 0.635(3) -0.028(2) 0.680(2) 0.072(9) Uiso 1 1 d . . .
H15C H 0.605(3) -0.052(2) 0.5773(17) 0.047(7) Uiso 1 1 d . . .
C16 C 0.4123(2) 0.11981(18) 0.55068(12) 0.0299(4) Uani 1 1 d . . .
H16A H 0.453(2) 0.1074(19) 0.4914(16) 0.043(6) Uiso 1 1 d . . .
H16B H 0.380(2) 0.202(2) 0.5526(14) 0.040(6) Uiso 1 1 d . . .
H16C H 0.337(2) 0.078(2) 0.5588(15) 0.037(6) Uiso 1 1 d . . .
C17 C 0.6653(2) 0.16085(19) 0.59461(14) 0.0327(4) Uani 1 1 d . . .
H17A H 0.741(3) 0.143(2) 0.6352(17) 0.052(7) Uiso 1 1 d . . .
H17B H 0.649(2) 0.243(2) 0.5892(17) 0.050(7) Uiso 1 1 d . . .
H17C H 0.697(2) 0.138(2) 0.5414(17) 0.042(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 0.0033 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'
Br Br -0.2901 2.4595 '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
O1 S1 N1 111.35(7) . . ?
O1 S1 C14 105.88(7) . . ?
N1 S1 C14 96.64(7) . . ?
C7 N1 S1 115.34(11) . . ?
C2 C1 C6 121.69(15) . . ?
C2 C1 Br1 116.78(12) . . ?
C6 C1 Br1 121.53(11) . . ?
C3 C2 C1 119.77(16) . . ?
C2 C3 C4 119.28(16) . . ?
C5 C4 C3 120.68(16) . . ?
C4 C5 C6 121.44(16) . . ?
C5 C6 C1 117.15(14) . . ?
C5 C6 C7 120.93(14) . . ?
C1 C6 C7 121.80(14) . . ?
N1 C7 C6 110.93(13) . . ?
N1 C7 C8 107.76(13) . . ?
C6 C7 C8 109.96(13) . . ?
C9 C8 C13 118.98(16) . . ?
C9 C8 C7 120.35(15) . . ?
C13 C8 C7 120.66(16) . . ?
C8 C9 C10 120.07(18) . . ?
C11 C10 C9 120.43(18) . . ?
C10 C11 C12 119.85(17) . . ?
C11 C12 C13 119.80(18) . . ?
C12 C13 C8 120.85(17) . . ?
C16 C14 C15 112.92(16) . . ?
C16 C14 C17 109.77(15) . . ?
C15 C14 C17 110.83(17) . . ?
C16 C14 S1 110.56(12) . . ?
C15 C14 S1 108.95(12) . . ?
C17 C14 S1 103.40(12) . . ?
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
Br1 C1 1.8974(15) . ?
S1 O1 1.4853(12) . ?
S1 N1 1.6855(14) . ?
S1 C14 1.8444(16) . ?
N1 C7 1.475(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.399(2) . ?
C2 C3 1.382(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.381(2) . ?
C5 C6 1.392(2) . ?
C6 C7 1.520(2) . ?
C7 C8 1.526(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.394(2) . ?
C9 C10 1.393(2) . ?
C10 C11 1.383(3) . ?
C11 C12 1.386(3) . ?
C12 C13 1.387(3) . ?
C14 C16 1.520(3) . ?
C14 C15 1.521(3) . ?
C14 C17 1.528(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 46187628
