Benzylic Thio and Seleno Newman-Kwart Rearrangements.
Eriksen, Kristina; Ulfkjær, Anne; Sølling, Theis I; Pittelkow, Michael; The Journal of organic chemistry 83 (2018) 10786–10797; doi:10.1021/acs.joc.8b01468

data_4035645
_publ_section_title
;
 Benzylic Thio and Seleno Newman-Kwart Rearrangements.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10786
_journal_page_last               10797
_journal_paper_doi               10.1021/acs.joc.8b01468
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C10 H12 Cl N O S'
_chemical_formula_sum            'C10 H12 Cl N O S'
_chemical_formula_weight         229.73
_chemical_name_systematic        'N,N-dimethyl O-(4-chlorobenzyl) thiocarbamate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.31(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.779(7)
_cell_length_b                   16.269(12)
_cell_length_c                   7.242(5)
_cell_measurement_reflns_used    5063
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.375
_cell_measurement_theta_min      2.531
_cell_volume                     1087.3(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.9925
_diffrn_measured_fraction_theta_max 0.9925
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12180
_diffrn_reflns_theta_full        30.6115
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         2.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0846 before and 0.0426 after correction. The Ratio of minimum to maximum transmission is 0.9261. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.4033
_exptl_crystal_description       needle
_exptl_crystal_F_000             481.2475
_exptl_crystal_recrystallization_method 'From ethanol'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.4439
_refine_diff_density_min         -0.3862
_refine_diff_density_rms         0.1082
_refine_ls_d_res_high            0.6979
_refine_ls_d_res_low             8.1343
_refine_ls_goodness_of_fit_ref   1.0346
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     129
_refine_ls_number_reflns         3329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0346
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.5042P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                2522
_reflns_number_total             3329
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b01468_si_001.cif
_cod_data_source_block           mo_D8V3329_0m_a
_cod_original_cell_volume        1087.3(13)
_cod_database_code               4035645
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'