Nucleophilic Halogenations of Diazo Compounds, a Complementary Principle for the Synthesis of Halodiazo Compounds: Experimental and Theoretical Studies
Christian Schnaars; Martin Hennum; Tore Bonge-Hansen; Journal of Organic Chemistry 78 (2013) 7488–7497; doi:10.1021/jo401050c

data_4028458
_publ_contact_author_email       tore.hansen@kjemi.uio.no
_publ_contact_author_name        'Tore Hansen'
_publ_section_title
;
 Nucleophilic Halogenations of Diazo Compounds, a Complementary Principle
 for the Synthesis of Halodiazo Compounds: Experimental and Theoretical
 Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7488
_journal_page_last               7497
_journal_paper_doi               10.1021/jo401050c
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C6 H11 N2 O2 S, C F3 O3 S'
_chemical_formula_sum            'C7 H11 F3 N2 O5 S2'
_chemical_formula_weight         324.32
_chemical_name_common            'Dimethylsulfonium diazoacetate triflate'
_chemical_name_systematic
;
(1-diazo-2-ethoxy-2-oxoethyl)dimethylsulfonium triflate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_audit_update_record
;
2012-12-07 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.907(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.795(5)
_cell_length_b                   18.924(11)
_cell_length_c                   9.785(6)
_cell_measurement_reflns_used    2993
_cell_measurement_temperature    296(2)
_cell_measurement_theta_min      2.94
_cell_volume                     1373.5(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10787
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         2993
_exptl_absorpt_coefficient_mu    0.439
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       'Dimethylsulfonium diazoacetate triflate'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0431
_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/[\s^2^(Fo^2^)+(0.0623P)^2^+0.2557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                2211
_reflns_number_total             2828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401050c_si_002.cif
_cod_data_source_block           cs_dmsdaa
_cod_database_code               4028458