#------------------------------------------------------------------------------
#$Date: 2019-11-23 23:59:27 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235678 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/71/4037113.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_4037113
loop_
_publ_author_name
'Bhattacharyya, Aditya'
'Kavitha, C. V.'
'Ghorai, Manas K.'
_publ_section_title
;
 Stereospecific Synthesis of 2-Iminothiazolidines via Domino Ring-Opening
 Cyclization of Activated Aziridines with Aryl- and Alkyl Isothiocyanates.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6433
_journal_page_last               6443
_journal_paper_doi               10.1021/acs.joc.6b01551
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H19 Br N2 O2 S2'
_chemical_formula_sum            'C22 H19 Br N2 O2 S2'
_chemical_formula_weight         487.42
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 114.1340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3343(7)
_cell_length_b                   12.9414(6)
_cell_length_c                   12.2133(6)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.2
_cell_volume                     2067.60(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15319
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    2.212
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0306P)²+1.7555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                3217
_reflns_number_total             4049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01551_si_003.cif
_cod_data_source_block           21aprb
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4037113
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
Br1 Br 0.42462(2) -0.21561(2) 0.14311(3) 0.02631(10) Uani 1 1 d .
S1 S 0.30598(5) -0.00113(6) 0.61284(7) 0.01717(17) Uani 1 1 d .
S2 S 0.02603(5) 0.16146(5) 0.47741(6) 0.01269(16) Uani 1 1 d .
O1 O -0.00347(14) 0.15110(14) 0.57503(18) 0.0167(4) Uani 1 1 d .
O2 O -0.04421(14) 0.13194(14) 0.35926(17) 0.0159(4) Uani 1 1 d .
N1 N 0.12745(17) 0.08600(17) 0.5055(2) 0.0129(5) Uani 1 1 d .
N2 N 0.21801(17) 0.15016(17) 0.6984(2) 0.0149(5) Uani 1 1 d .
C1 C 0.3622(2) -0.1640(2) 0.2426(3) 0.0181(6) Uani 1 1 d .
C2 C 0.2825(2) -0.2172(2) 0.2516(3) 0.0204(7) Uani 1 1 d .
H2 H 0.2586 -0.2783 0.2092 0.024 Uiso 1 1 calc R
C3 C 0.2388(2) -0.1784(2) 0.3249(3) 0.0179(6) Uani 1 1 d .
H3 H 0.1844 -0.2136 0.3306 0.021 Uiso 1 1 calc R
C4 C 0.2738(2) -0.0888(2) 0.3898(3) 0.0161(6) Uani 1 1 d .
C5 C 0.3545(2) -0.0361(2) 0.3797(3) 0.0183(6) Uani 1 1 d .
H5 H 0.3790 0.0244 0.4229 0.022 Uiso 1 1 calc R
C6 C 0.3986(2) -0.0736(2) 0.3054(3) 0.0199(7) Uani 1 1 d .
H6 H 0.4521 -0.0380 0.2980 0.024 Uiso 1 1 calc R
C7 C 0.2201(2) -0.0492(2) 0.4651(3) 0.0167(6) Uani 1 1 d .
H7 H 0.1795 -0.1058 0.4765 0.020 Uiso 1 1 calc R
C8 C 0.1489(2) 0.0412(2) 0.4078(3) 0.0153(6) Uani 1 1 d .
H8A H 0.1817 0.0914 0.3762 0.018 Uiso 1 1 calc R
H8B H 0.0864 0.0176 0.3432 0.018 Uiso 1 1 calc R
C9 C 0.2130(2) 0.0896(2) 0.6162(3) 0.0131(6) Uani 1 1 d .
C10 C 0.2962(2) 0.1468(2) 0.8157(3) 0.0153(6) Uani 1 1 d .
C11 C 0.3277(2) 0.0560(2) 0.8806(3) 0.0191(6) Uani 1 1 d .
H11 H 0.3021 -0.0072 0.8444 0.023 Uiso 1 1 calc R
C12 C 0.3971(2) 0.0591(2) 0.9991(3) 0.0242(7) Uani 1 1 d .
H12 H 0.4177 -0.0021 1.0423 0.029 Uiso 1 1 calc R
C13 C 0.4359(2) 0.1520(3) 1.0540(3) 0.0286(8) Uani 1 1 d .
H13 H 0.4829 0.1537 1.1337 0.034 Uiso 1 1 calc R
C14 C 0.4045(2) 0.2420(3) 0.9898(3) 0.0285(8) Uani 1 1 d .
H14 H 0.4306 0.3048 1.0265 0.034 Uiso 1 1 calc R
C15 C 0.3347(2) 0.2404(2) 0.8713(3) 0.0211(7) Uani 1 1 d .
H15 H 0.3135 0.3019 0.8289 0.025 Uiso 1 1 calc R
C16 C 0.0652(2) 0.2896(2) 0.4724(2) 0.0129(6) Uani 1 1 d .
C17 C 0.0593(2) 0.3281(2) 0.3642(3) 0.0146(6) Uani 1 1 d .
H17 H 0.0368 0.2866 0.2961 0.018 Uiso 1 1 calc R
C18 C 0.0876(2) 0.4294(2) 0.3589(3) 0.0150(6) Uani 1 1 d .
H18 H 0.0839 0.4560 0.2865 0.018 Uiso 1 1 calc R
C19 C 0.1214(2) 0.4922(2) 0.4599(3) 0.0155(6) Uani 1 1 d .
C20 C 0.1273(2) 0.4510(2) 0.5681(3) 0.0157(6) Uani 1 1 d .
H20 H 0.1503 0.4922 0.6365 0.019 Uiso 1 1 calc R
C21 C 0.0996(2) 0.3500(2) 0.5751(3) 0.0158(6) Uani 1 1 d .
H21 H 0.1038 0.3229 0.6475 0.019 Uiso 1 1 calc R
C22 C 0.1513(2) 0.6024(2) 0.4528(3) 0.0212(7) Uani 1 1 d .
H22A H 0.2236 0.6063 0.4747 0.032 Uiso 1 1 calc R
H22B H 0.1339 0.6440 0.5069 0.032 Uiso 1 1 calc R
H22C H 0.1154 0.6275 0.3724 0.032 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'
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
C9 S1 C7 92.23(13)
O1 S2 O2 119.39(11)
O1 S2 N1 107.77(11)
O2 S2 N1 104.20(11)
O1 S2 C16 109.00(12)
O2 S2 C16 108.60(12)
N1 S2 C16 107.20(12)
C9 N1 C8 113.9(2)
C9 N1 S2 121.51(18)
C8 N1 S2 121.31(18)
C9 N2 C10 123.7(2)
C2 C1 C6 121.2(3)
C2 C1 Br1 119.9(2)
C6 C1 Br1 118.9(2)
C1 C2 C3 118.8(3)
C4 C3 C2 121.6(3)
C3 C4 C5 118.8(3)
C3 C4 C7 118.7(2)
C5 C4 C7 122.5(3)
C6 C5 C4 120.3(3)
C1 C6 C5 119.3(3)
C4 C7 C8 113.1(2)
C4 C7 S1 114.3(2)
C8 C7 S1 104.27(19)
N1 C8 C7 104.7(2)
N2 C9 N1 122.2(2)
N2 C9 S1 129.1(2)
N1 C9 S1 108.72(19)
C11 C10 C15 119.3(3)
C11 C10 N2 123.0(3)
C15 C10 N2 117.4(3)
C12 C11 C10 120.1(3)
C13 C12 C11 120.6(3)
C14 C13 C12 119.3(3)
C13 C14 C15 120.9(3)
C14 C15 C10 119.8(3)
C17 C16 C21 121.4(3)
C17 C16 S2 118.5(2)
C21 C16 S2 120.0(2)
C18 C17 C16 118.8(3)
C17 C18 C19 121.1(3)
C18 C19 C20 118.8(3)
C18 C19 C22 120.6(3)
C20 C19 C22 120.6(3)
C21 C20 C19 120.9(3)
C20 C21 C16 118.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.900(3)
S1 C9 1.789(3)
S1 C7 1.828(3)
S2 O1 1.4249(19)
S2 O2 1.433(2)
S2 N1 1.667(2)
S2 C16 1.760(3)
N1 C9 1.407(3)
N1 C8 1.468(3)
N2 C9 1.253(3)
N2 C10 1.413(4)
C1 C2 1.376(4)
C1 C6 1.380(4)
C2 C3 1.380(4)
C3 C4 1.379(4)
C4 C5 1.391(4)
C4 C7 1.509(4)
C5 C6 1.389(4)
C7 C8 1.522(4)
C10 C11 1.386(4)
C10 C15 1.388(4)
C11 C12 1.381(4)
C12 C13 1.378(4)
C13 C14 1.373(5)
C14 C15 1.384(4)
C16 C17 1.383(4)
C16 C21 1.387(4)
C17 C18 1.381(4)
C18 C19 1.388(4)
C19 C20 1.395(4)
C19 C22 1.502(4)
C20 C21 1.379(4)
