#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025336.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_4025336
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_compound_source        'Local laboratory'
_chemical_formula_moiety         'C17 H19 Cl N2 O S '
_chemical_formula_sum            'C17 H19 Cl N2 O S'
_chemical_formula_weight         334.869
_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_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1213(2)
_cell_length_b                   9.5780(2)
_cell_length_c                   20.1152(6)
_cell_measurement_reflns_used    13074
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1757.34(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.00524
_diffrn_orient_matrix_UB_12      0.04471
_diffrn_orient_matrix_UB_13      0.09996
_diffrn_orient_matrix_UB_21      0.05613
_diffrn_orient_matrix_UB_22      -0.07923
_diffrn_orient_matrix_UB_23      0.03838
_diffrn_orient_matrix_UB_31      0.04185
_diffrn_orient_matrix_UB_32      0.02524
_diffrn_orient_matrix_UB_33      -0.00910
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4999
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.01
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Plate (0.06x0.23x0.27 mm)'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.221
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1197P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1896
_reflns_number_gt                3742
_reflns_number_total             4973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100173f_si_007.cif
_cod_data_source_block           global
_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_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C17 H19 Cl N2 O S '
_cod_database_code               4025336
_cod_database_fobs_code          4025336
loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
'-X+ 1/2,-Y,+Z+ 1/2'
'+X+ 1/2,-Y+ 1/2,-Z'
'-X,+Y+ 1/2,-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
_atom_site_disorder_assembly
_atom_site_disorder_group
S9 S 0.69529(8) 1.24094(8) -0.15001(4) 0.03163(19) Uani 1 1 d . . .
Cl5 Cl 0.84853(11) 0.59398(10) 0.07059(6) 0.0553(3) Uani 1 1 d . . .
O10 O 0.8288(2) 1.3296(3) -0.14965(12) 0.0394(5) Uani 1 1 d . . .
C7 C 0.7317(3) 1.0367(3) -0.06740(15) 0.0279(6) Uani 1 1 d . . .
N8 N 0.6838(3) 1.1650(3) -0.07318(13) 0.0329(5) Uani 1 1 d . . .
N2 N 0.5493(3) 1.1366(3) 0.04425(15) 0.0415(7) Uani 1 1 d . . .
C1 C 0.7123(3) 0.9618(3) -0.00484(14) 0.0294(6) Uani 1 1 d . . .
C6 C 0.7830(3) 0.8320(3) 0.00448(16) 0.0331(6) Uani 1 1 d . . .
C20 C 0.9331(4) 1.0119(3) -0.15198(18) 0.0387(7) Uani 1 1 d . . .
C15 C 0.8028(3) 0.9614(3) -0.12425(15) 0.0304(6) Uani 1 1 d . . .
C2 C 0.6182(3) 1.0125(3) 0.04713(16) 0.0328(6) Uani 1 1 d . . .
C16 C 0.7347(4) 0.8449(4) -0.15202(17) 0.0392(7) Uani 1 1 d . . .
C3 C 0.5995(4) 0.9286(4) 0.10373(17) 0.0421(8) Uani 1 1 d . . .
C5 C 0.7618(3) 0.7549(4) 0.06043(17) 0.0362(7) Uani 1 1 d . . .
C18 C 0.9200(5) 0.8326(4) -0.23642(19) 0.0498(9) Uani 1 1 d . . .
C4 C 0.6703(4) 0.8027(4) 0.11070(18) 0.0429(8) Uani 1 1 d . . .
C19 C 0.9900(4) 0.9468(4) -0.2090(2) 0.0482(9) Uani 1 1 d . . .
C11 C 0.5419(4) 1.3630(4) -0.1399(2) 0.0467(9) Uani 1 1 d . . .
C13 C 0.5724(6) 1.4650(4) -0.0848(3) 0.0680(13) Uani 1 1 d . . .
C12 C 0.4037(4) 1.2756(5) -0.1285(2) 0.0603(11) Uani 1 1 d . . .
C14 C 0.5334(5) 1.4373(5) -0.2073(3) 0.0652(13) Uani 1 1 d . . .
C17 C 0.7924(4) 0.7823(4) -0.2080(2) 0.0493(9) Uani 1 1 d . . .
H2A H 0.4750 1.1618 0.0759 0.050 Uiso 1 1 d R . .
H2B H 0.5601 1.1993 0.0081 0.050 Uiso 1 1 d R . .
H6 H 0.8476 0.7971 -0.0294 0.040 Uiso 1 1 d R . .
H20 H 0.9740 1.0963 -0.1329 0.046 Uiso 1 1 d R . .
H16 H 0.6477 0.8078 -0.1318 0.047 Uiso 1 1 d R . .
H3 H 0.5387 0.9567 0.1409 0.051 Uiso 1 1 d R . .
H18 H 0.9607 0.7889 -0.2752 0.060 Uiso 1 1 d R . .
H4 H 0.6562 0.7483 0.1503 0.051 Uiso 1 1 d R . .
H19 H 1.0775 0.9822 -0.2295 0.058 Uiso 1 1 d R . .
H13A H 0.4907 1.5275 -0.0803 0.082 Uiso 1 1 d R . .
H13B H 0.6589 1.5173 -0.0955 0.082 Uiso 1 1 d R . .
H13C H 0.5872 1.4160 -0.0437 0.082 Uiso 1 1 d R . .
H12A H 0.3214 1.3369 -0.1227 0.072 Uiso 1 1 d R . .
H12B H 0.4153 1.2189 -0.0895 0.072 Uiso 1 1 d R . .
H12C H 0.3872 1.2166 -0.1664 0.072 Uiso 1 1 d R . .
H14A H 0.4556 1.5047 -0.2074 0.078 Uiso 1 1 d R . .
H14B H 0.5152 1.3683 -0.2409 0.078 Uiso 1 1 d R . .
H14C H 0.6248 1.4833 -0.2163 0.078 Uiso 1 1 d R . .
H17 H 0.7452 0.7031 -0.2279 0.059 Uiso 1 1 d 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'
Cl Cl 0.1484 0.1585 '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_
_diffrn_radiation_wavelength
0.71073
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
O10 S9 N8 106.81(13) . . ?
O10 S9 C11 105.11(16) . . ?
N8 S9 C11 97.13(15) . . ?
N8 C7 C1 119.8(3) . . ?
N8 C7 C15 121.9(3) . . ?
C1 C7 C15 118.3(2) . . ?
C7 N8 S9 117.3(2) . . ?
C6 C1 C2 118.3(3) . . ?
C6 C1 C7 119.5(2) . . ?
C2 C1 C7 122.2(3) . . ?
C5 C6 C1 121.5(3) . . ?
C15 C20 C19 119.1(3) . . ?
C16 C15 C20 119.7(3) . . ?
C16 C15 C7 119.8(3) . . ?
C20 C15 C7 120.4(3) . . ?
N2 C2 C3 119.0(3) . . ?
N2 C2 C1 123.1(3) . . ?
C3 C2 C1 118.0(3) . . ?
C17 C16 C15 120.3(3) . . ?
C4 C3 C2 121.9(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 Cl5 120.8(2) . . ?
C4 C5 Cl5 118.6(3) . . ?
C19 C18 C17 120.0(3) . . ?
C3 C4 C5 119.8(3) . . ?
C18 C19 C20 120.4(3) . . ?
C13 C11 C12 113.4(4) . . ?
C13 C11 C14 111.1(4) . . ?
C12 C11 C14 110.2(3) . . ?
C13 C11 S9 110.8(3) . . ?
C12 C11 S9 107.2(3) . . ?
C14 C11 S9 103.7(3) . . ?
C16 C17 C18 120.5(4) . . ?
C2 N2 H2A 121.5 . . ?
C2 N2 H2B 123.0 . . ?
H2A N2 H2B 114.9 . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.5 . . ?
C15 C20 H20 117.2 . . ?
C19 C20 H20 123.4 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 119.7 . . ?
C4 C3 H3 115.7 . . ?
C2 C3 H3 122.4 . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 120.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 120.4 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 120.1 . . ?
C11 C13 H13A 109.3 . . ?
C11 C13 H13B 109.0 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 110.1 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.4 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C14 H14A 110.5 . . ?
C11 C14 H14B 108.2 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.7 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 118.7 . . ?
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
S9 O10 1.485(2) . ?
S9 N8 1.711(3) . ?
S9 C11 1.834(3) . ?
Cl5 C5 1.745(3) . ?
C7 N8 1.309(4) . ?
C7 C1 1.460(4) . ?
C7 C15 1.500(4) . ?
N2 C2 1.346(4) . ?
C1 C6 1.413(4) . ?
C1 C2 1.437(4) . ?
C6 C5 1.360(5) . ?
C20 C15 1.398(4) . ?
C20 C19 1.404(5) . ?
C15 C16 1.394(5) . ?
C2 C3 1.404(5) . ?
C16 C17 1.380(5) . ?
C3 C4 1.375(5) . ?
C5 C4 1.389(5) . ?
C18 C19 1.382(6) . ?
C18 C17 1.383(6) . ?
C11 C13 1.504(6) . ?
C11 C12 1.531(5) . ?
C11 C14 1.533(6) . ?
N2 H2A 0.9608 . ?
N2 H2B 0.9473 . ?
C6 H6 0.9601 . ?
C20 H20 0.9698 . ?
C16 H16 0.9600 . ?
C3 H3 0.9694 . ?
C18 H18 0.9600 . ?
C4 H4 0.9600 . ?
C19 H19 0.9601 . ?
C13 H13A 0.9601 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9599 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9599 . ?
C12 H12C 0.9601 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9601 . ?
C17 H17 0.9599 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 46187443
