Synthesis of Quaternary-Substituted Thiazolines via Halocyclization of S-Allyl Thioimidate Salts
Parker, Patrick D.; Lemercier, Bérénice C.; Pierce, Joshua G.; The Journal of Organic Chemistry  (2017) –; doi:10.1021/acs.joc.7b02299

data_4033017
_publ_section_title
;
 Synthesis of Quaternary-Substituted Thiazolines via Halocyclization of
 S-Allyl Thioimidate Salts
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02299
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H13 Cl N S, Br'
_chemical_formula_sum            'C11 H13 Br Cl N S'
_chemical_formula_weight         306.64
_chemical_name_common            PP0661
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 107.1752(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8230(4)
_cell_length_b                   26.0046(16)
_cell_length_c                   7.2754(5)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      36.3941
_cell_measurement_theta_min      3.0337
_cell_volume                     1233.31(14)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25429
_diffrn_reflns_theta_full        37.61
_diffrn_reflns_theta_max         37.61
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.686
_exptl_absorpt_correction_T_max  0.59
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         4.789
_refine_diff_density_min         -1.611
_refine_ls_abs_structure_details
;

Flack x determined using 3976 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         25429
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+2.9388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1509
_reflns_number_gt                21403
_reflns_number_total             25429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02299_si_002.cif
_cod_data_source_block           rds620
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4033017
_shelx_res_checksum              38854
_shelx_hkl_checksum              33875