Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles.
Matlock, Johnathan V.; Fritz, Sven P.; Harrison, Stephen A.; Coe, Diane M.; McGarrigle, Eoghan M.; Aggarwal, Varinder K.; The Journal of organic chemistry 79 (2014) 10226–; doi:10.1021/jo501885z

data_4030047
_publ_section_title
;
 Synthesis of \a-Substituted Vinylsulfonium Salts and Their Application as
 Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused
 Heterocycles.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10226
_journal_paper_doi               10.1021/jo501885z
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C23 H23 N O3 S'
_chemical_formula_sum            'C23 H23 N O3 S'
_chemical_formula_weight         393.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.113(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0302(8)
_cell_length_b                   13.7455(15)
_cell_length_c                   20.332(2)
_cell_measurement_reflns_used    5865
_cell_measurement_temperature    165.00
_cell_measurement_theta_max      66.40
_cell_measurement_theta_min      3.90
_cell_volume                     1940.0(4)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      165.00
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Bruker APEX2 microstar'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9256
_diffrn_reflns_theta_full        66.39
_diffrn_reflns_theta_max         66.39
_diffrn_reflns_theta_min         3.90
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.678
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.5081.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0451
_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/[\s^2^(Fo^2^)+(0.0664P)^2^+1.1672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                2981
_reflns_number_total             3275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501885z_si_005.cif
_cod_data_source_block           n302660mi
_cod_depositor_comments
'Adding full bibliography for 4030047--4030050.cif.'
_cod_original_cell_volume        1939.9(4)
_cod_database_code               4030047
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C5(H5), C6(H6), C2(H2), C21(H21), C17(H17), C3(H3A),
 C16(H16), C20(H20), C15(H15), C14(H14), C13(H13), C19(H19)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'