#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:36:33 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238376 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/51/1555187.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_1555187
loop_
_publ_author_name
'Huang, Ze-Ao'
'Liu, Hui'
'Lu, Chong-Dao'
'Xu, Yan-Jun'
_publ_section_title
;
 Stereoselective Synthesis of Enantioenriched 2-Chloro-2-aroylaziridines
 by Cascade Reaction between Aryl Nitriles, Silyldichloromethanes, and
 tert-Butanesulfinylimines.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4042
_journal_page_last               4045
_journal_paper_doi               10.1021/acs.orglett.5b01954
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_sum            'C19 H21 Cl2 N O2 S'
_chemical_formula_weight         398.33
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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                   6.1472(15)
_cell_length_b                   11.724(3)
_cell_length_c                   27.834(7)
_cell_measurement_reflns_used    5219
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.27
_cell_volume                     2006.0(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            12592
_diffrn_reflns_theta_full        28.06
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6853
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   face-indexed
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.447
_exptl_crystal_size_min          0.298
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0323
_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)+(0.0427P)²+0.2257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                4174
_reflns_number_total             4715
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01954_si_004.cif
_cod_data_source_block           9a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2005.9(9)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1555187
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
S1 S 0.20849(9) 1.00308(4) 0.171154(18) 0.04868(12) Uani 1 1 d .
Cl2 Cl -0.20625(8) 0.70915(4) 0.11126(2) 0.05338(13) Uani 1 1 d .
Cl1 Cl 0.10573(10) 0.69237(4) 0.031865(18) 0.05591(14) Uani 1 1 d .
C1 C 0.0713(3) 0.72325(14) 0.09411(6) 0.0382(4) Uani 1 1 d .
O1 O 0.3467(2) 0.66505(13) 0.14853(7) 0.0640(4) Uani 1 1 d .
C2 C 0.2055(3) 0.63185(15) 0.12151(7) 0.0423(4) Uani 1 1 d .
C9 C 0.1516(3) 0.84703(14) 0.10309(6) 0.0375(4) Uani 1 1 d .
H9 H 0.3056 0.8508 0.0942 0.045 Uiso 1 1 calc R
C3 C 0.1701(3) 0.50651(15) 0.11461(7) 0.0452(4) Uani 1 1 d .
C10 C 0.0298(3) 0.93476(15) 0.07349(6) 0.0382(4) Uani 1 1 d .
N1 N 0.1344(3) 0.87128(13) 0.15493(6) 0.0447(4) Uani 1 1 d .
H1 H 0.0897 0.8214 0.1753 0.054 Uiso 1 1 calc R
C15 C 0.1209(4) 0.97564(16) 0.03125(7) 0.0519(5) Uani 1 1 d .
H15 H 0.2567 0.9496 0.0214 0.062 Uiso 1 1 calc R
C11 C -0.1718(3) 0.97712(16) 0.08778(8) 0.0469(4) Uani 1 1 d .
H11 H -0.2342 0.9516 0.1163 0.056 Uiso 1 1 calc R
O2 O 0.4441(3) 1.01667(18) 0.16742(7) 0.0821(6) Uani 1 1 d .
C13 C -0.1882(5) 1.09490(19) 0.01772(9) 0.0702(7) Uani 1 1 d .
H13 H -0.2617 1.1477 -0.0012 0.084 Uiso 1 1 calc R
C16 C 0.1438(4) 0.9895(3) 0.23540(8) 0.0642(6) Uani 1 1 d .
C12 C -0.2799(4) 1.05677(17) 0.05995(9) 0.0575(5) Uani 1 1 d .
H12 H -0.4145 1.0846 0.0697 0.069 Uiso 1 1 calc R
C4 C 0.3321(4) 0.43593(19) 0.13168(9) 0.0593(6) Uani 1 1 d .
H4 H 0.4543 0.4676 0.1462 0.071 Uiso 1 1 calc R
C5 C 0.3153(6) 0.3184(2) 0.12744(10) 0.0766(8) Uani 1 1 d .
H5 H 0.4271 0.2715 0.1383 0.092 Uiso 1 1 calc R
C6 C 0.1319(6) 0.27173(19) 0.10710(10) 0.0793(8) Uani 1 1 d .
H6 H 0.1182 0.1929 0.1048 0.095 Uiso 1 1 calc R
C14 C 0.0095(5) 1.0554(2) 0.00371(9) 0.0668(7) Uani 1 1 d .
H14 H 0.0712 1.0821 -0.0247 0.080 Uiso 1 1 calc R
C8 C -0.0120(4) 0.45754(17) 0.09327(9) 0.0577(6) Uani 1 1 d .
H8 H -0.1216 0.5038 0.0810 0.069 Uiso 1 1 calc R
C17 C 0.2631(6) 0.8900(3) 0.25807(10) 0.0963(10) Uani 1 1 d .
H17A H 0.2518 0.8950 0.2924 0.144 Uiso 1 1 calc R
H17B H 0.4136 0.8924 0.2489 0.144 Uiso 1 1 calc R
H17C H 0.1996 0.8198 0.2473 0.144 Uiso 1 1 calc R
C7 C -0.0301(5) 0.34044(19) 0.09027(10) 0.0730(7) Uani 1 1 d .
H7 H -0.1537 0.3081 0.0767 0.088 Uiso 1 1 calc R
C19 C 0.2279(7) 1.1026(3) 0.25634(11) 0.1077(12) Uani 1 1 d .
H19A H 0.1885 1.1075 0.2896 0.162 Uiso 1 1 calc R
H19B H 0.1643 1.1652 0.2391 0.162 Uiso 1 1 calc R
H19C H 0.3834 1.1056 0.2533 0.162 Uiso 1 1 calc R
C18 C -0.1000(5) 0.9795(4) 0.23946(12) 0.1197(15) Uani 1 1 d .
H18A H -0.1470 0.9097 0.2247 0.180 Uiso 1 1 calc R
H18B H -0.1672 1.0429 0.2235 0.180 Uiso 1 1 calc R
H18C H -0.1410 0.9794 0.2727 0.180 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'
Cl Cl 0.1484 0.1585 '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
O2 S1 N1 110.57(10)
O2 S1 C16 107.03(11)
N1 S1 C16 97.09(11)
C2 C1 C9 113.38(15)
C2 C1 Cl2 108.28(12)
C9 C1 Cl2 110.39(12)
C2 C1 Cl1 105.90(12)
C9 C1 Cl1 107.96(12)
Cl2 C1 Cl1 110.85(10)
O1 C2 C3 119.89(17)
O1 C2 C1 117.62(16)
C3 C2 C1 122.47(16)
N1 C9 C10 111.47(14)
N1 C9 C1 108.35(14)
C10 C9 C1 112.94(15)
C4 C3 C8 118.72(19)
C4 C3 C2 116.07(18)
C8 C3 C2 125.20(18)
C15 C10 C11 118.55(18)
C15 C10 C9 119.71(17)
C11 C10 C9 121.74(17)
C9 N1 S1 115.01(12)
C10 C15 C14 120.1(2)
C12 C11 C10 120.5(2)
C14 C13 C12 120.0(2)
C18 C16 C17 113.0(3)
C18 C16 C19 111.9(3)
C17 C16 C19 110.1(2)
C18 C16 S1 107.13(19)
C17 C16 S1 111.55(19)
C19 C16 S1 102.8(2)
C13 C12 C11 120.0(2)
C3 C4 C5 120.9(2)
C6 C5 C4 119.4(2)
C7 C6 C5 120.3(2)
C13 C14 C15 120.8(2)
C7 C8 C3 120.1(2)
C6 C7 C8 120.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4607(19)
S1 N1 1.6730(17)
S1 C16 1.839(2)
Cl2 C1 1.7790(19)
Cl1 C1 1.7826(19)
C1 C2 1.553(3)
C1 C9 1.553(2)
O1 C2 1.213(2)
C2 C3 1.498(3)
C9 N1 1.474(2)
C9 C10 1.515(3)
C3 C4 1.379(3)
C3 C8 1.391(3)
C10 C15 1.388(3)
C10 C11 1.393(3)
C15 C14 1.390(3)
C11 C12 1.383(3)
C13 C14 1.358(4)
C13 C12 1.378(4)
C16 C18 1.508(4)
C16 C17 1.515(4)
C16 C19 1.538(4)
C4 C5 1.387(3)
C5 C6 1.375(4)
C6 C7 1.364(4)
C8 C7 1.380(3)
